Vacation Home Rentals By Owner In Chatham, MA

New heated gunite pool. 18X40 with automatic pool cover, and completely fenced in for safety. Design includes many plantings and grass to complete this idyllic garden. The space also includes an outdoor shower, and rinsing station, plus multiple patios and seating areas for hours of outdoor sun and entertaining. brbrPerfect for large groups, families traveling together, family reunions, or anyone looking for a little more space! Bring your extended family, au pair, or a vacation with multiple families at this expansive 6,000 sq ft home that sits privately on a fenced 1-acre yard. brbrHave your morning coffee atop the widow’s walk with 180-degree views of Nantucket Sound, Monomoy Island, Stage Harbor Lighthouse, and the Atlantic Ocean. Relax or sunbathe on the roof deck. Eat, visit, and entertain on the screened-in porch. Go back to the widow’s walk to see the sunset. There are so many choices to take in the sea air and sunshine on this property. brbrThis large estate is perfectly situated to comfortably sleep 16+ while maintaining space and privacy. The bedrooms are clustered in pairings of 2, with a shared bathroom. These sleeping quarters are completely separate from one another. The first floor has one BR with an en-suite bathroom and an additional 2 BR that share a bath. Upstairs includes 2 private quarters, each with 2 BRs and 1 bathroom. brbrThe Caboose is the epicenter of this home. It is a historic, vast open space with high ceilings and beautiful natural light. It has 3 couches, a fireplace, and multiple tables set up for games, checkers, and cards. brbrThe Living Room is a cozy alternate space for sitting and watching the 55-inch TV. The Dining Room has a long mahogany table that sits 12 comfortably. The kitchen is fully equipped, with top-line appliances, 2 sinks, and an island to sit at for morning coffee, afternoon tea, and nighttime cocktails. brbrIn addition, there is a separate carriage house, featuring a king bed, living room, galley kitchen, and bathroom. The carriage house is equipped with another 55-inch TV, a perfect place for the kids' movie night while the parents enjoy an adult dinner in the main house. This estate has so much to offer!brbrThe Sears Point neighborhood is teeming with other families and children, and the quiet lanes and cul-de-sacs make it a perfect place to safely walk, and ride bikes. Let the kids run and play in the grassy, expansive 1-acre yard. The property is completely fenced-in. brbrThis property offers privacy and space, with easy proximity to all Chatham has to offer.brTake a 10-minute bike ride to the center of Chatham - or a 1.3-mile walk/run to the center of town. Take a two-minute stroll and drop your kayaks & paddle boards into Stage Harbor from the landings on Sears Point. Drive 5 minutes to Oyster Pond - easy parking, clean bathrooms, and shallow water make this Chatham’s best beach for young families. If you desire the bigger beaches, it is only a 5-10 minute drive to Lighthouse Beach, Ridgevale Beach, or Hardings Beach.brbrPlease note that we do not allow wedding receptions or any events on the property out of respect for our fellow neighbors and community. Sunday to Sunday rental. 1-week minimum peak season.brbrNo pets, no exceptions.brbrbrbr

Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$306.32

This 2500sq ft house is 8yrs old and offers all the toys including a hot tub, sauna, bikes and kayaks for guest use. From the glassed in observation deck to the fire pit in the back yard, the property offers solitude in a quiet neighborhood only 200yds from West Pond(Goose Pond), playground with skateboarding facility and the bike path. An open floor plan is perfect for a large gathering, meals or family game times. The kitchen is complete with all cooking utensils, pantry and an island with seating. The large dining table is perfect for large groups with a grill steps away on the deck. The loft provides a sleeping area for 4 and access to the observation bubble and upper deck. This rental is pet friendly so you can bring the dog. Renters supply own linens and towels.brbrWIFI, TV and phone are included. Cell phone signals are good here. There are air conditioners in the bedrooms and fans throughout.brbrThe first floor bedroom has 1 queen bed. The second floor bedroom has a queen bed and a twin day bed with a trundle that is also a twin. Together they make a King size.brbrIn the loft there is a queen futon and a couch that pulls out to queen bed and a twin day bed.brbrIn the basement there isa queen futon.brbrIn the office (no door) there is a day bed with a trundle that is twin alone or a king with the trundle pulled out.brbrThere is air conditioning only in the two bedrooms. The basement stays cool so can be a good choice.

Walk to School House Pond in Chatham.

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$389.13

Get ready to relax in this 2-bedroom townhome in Chatham. This awesome property features 2 queen beds and 1 twin bed, perfect for a small group of guests. Enjoy the convenience of amenities like WiFi, a washing machine, and AC during your stay. Easy picturesque 1 mile walk to town. Explore our private beach with walking paths to Lighthouse beach or Monomoy. brTownhouse is configured with first floor living room with full size sofa and love seat, Roku TV, dining table, full Kitchen, full bath, queen bedroom with slider and deck with counter height table and umbrella and grill. Second floor loft with work station, queen bed and twin bed which has a privacy curtain. brEnjoy coffee in the morning with it’s beautiful sunrise on two Adirondack chairs and a view of the ocean and sand bars or sunset on the deck with the same views. brBath and bed linens included

Charming 2 bedroom condo on Private Beach by Outer Most Marina

Chatham, Massachusetts, United States

Bed

1

Bath

Sleeps

$834.74

3 Bedroom-3 Bathroom- Sleeps 8brDuring peak summer weeks it is typical for our properties to require a 7-night stay, either Friday-Friday or Saturday-Saturday, but if you have unique dates please reach out to our Reservation Specialist. Most of our homes offer a 3-night stay minimum in the off-season.brComplimentary Linens Service Provided: This includes bedsheets, bath, beach, and dish towels for every bed home sleeps and total home occupancy.brWe offer a 4 pm Check-In and 10 am Check-OutbrbrRelax, recharge, and reconnect in this Chatham home, nestled in a quiet, nature-filled setting. Spacious living areas, a fully equipped kitchen, and a deck overlooking the serene backyard make it perfect for family and friends. Experience comfort, charm, and the calming beauty of Cape Cod all in one stay.brbrLet Us Tell You About This Home:brDiscover the charm of beautiful Chatham in this welcoming home tucked away in a quiet, picturesque neighborhood. As you arrive, a lovely walkway guides you to the front entrance, where you step into a cozy, welcoming foyer that immediately makes you feel at home. To the left, you'll find the spacious living room, a warm and comfortable space perfect for relaxing after a day on the Cape. This room flows effortlessly into the dining area, which offers generous seating for meals, game nights, and memorable gatherings with family and friends.brbrJust beyond the dining area is the fully equipped kitchen, featuring modern stainless-steel appliances and ample counter space, with everything you need to prepare anything from quick morning breakfasts to full seafood feasts.brThe main level of the home includes three comfortable bedrooms and two full bathrooms, offering convenience and relaxation for guests of all ages. The lower level provides two additional sleeping options along with a full bathroom and a secondary living room. This creates a flexible space that works well for larger families or groups traveling together.brbrBedroom 1- Queen- Main LevelbrBathroom 1- Shower and tub combination- Ensuite to bedroom 1brBedroom 2- Queen- Main LevelbrBathroom 1- Shower and tub combination- Main LevelbrBedroom 3- 2 Twins- Main LevelbrAdditional sleeping area 1- 2 twin- Lower LevelbrBathroom 3- Shower stall- Lower LevelbrAdditional sleeping area 2- Queen- Lower LevelbrbrStep outside to experience the true appeal of Cape Cod living. A deck off the dining area provides the perfect spot for outdoor meals or evening cocktails, while the patio offers additional seating surrounded by nature. Guests also have access to bikes, kayaks with life vests, and paddles, perfect for exploring the area's scenic trails and waterways. Enjoy the gas grill, rinse off after the beach in the classic outdoor shower, or simply unwind in the peaceful backyard oasis with tranquil views of the surrounding landscape.brbrWhether you're seeking relaxing mornings with a cup of coffee, fun-filled days at the beach, or cozy evenings under the stars, this Chatham retreat offers the perfect blend of comfort, charm, and Cape Cod living. Your ideal home away from home.brbrFree Tickets and Complimentary Activities! Create unforgettable memories and experience Cape Cod like a local! Enjoy $750 worth of daily exclusive free tickets to exciting local attractions through our partnership with Xplorie. Your amenities include activities such as Island Cruises, Whale Watch, Bike Rentals and admission to Whydah Pirate Museum. When you're not soaking up the sun on the beach, enjoy daily rounds of golf at Cranberry Valley or Chequessett Golf Courses and mini-golf for family fun.brbrWith all NEVR properties, we think of the little things to make your vacation special. Our Guest Welcome Bag, compliments of the homeowner, contains starter quantities of kitchen and bathroom essentials, with a few locally sourced snacks as well (subject to change based marketplace availability).brbrThis home has Keyless Entry for your convenience.brNo smoking of anything containing tobacco, any other substance, and e-cigarettes, inside or outside of the home.brDog-Friendly Homes are for a Dog only. This home allows 1 dog with a $25 per night fee. A Pet Registration form must be completed upon reservation confirmation. brMax parking of cars at property: 4 - No parking on lawn anytime.brbrAdditional Information to Assist You:brSimply follow our basic check-out instructions at your departure. brState and local taxes are charged if applicable. brFor Reservations made over 60 days away, you will make two payments - 50% initial payment with reservation and the final balance will be auto billed to your credit card 60 days prior to arrival. We accept American Express, Mastercard and Visa for payments.brA confirmed reservation is non-refundable--please consider purchasing trip cancellation insurance. Ask our guest specialist for more details regarding cancel options and trip insurance. brOwners provide paddle boards and kayaks for guests' usagebr***Linens - bed sheets, bath/dish/beach towels and bath mats are included with this homebrPlease ask our guest specialist for details. Our NEVR Homes come with mattress covers, pillows and a bed cover such as blanket, quilt, bedspread etc.brYou must be 25+ years old unless accompanied by a parent or guardian to book one of our Vacation Rental Homes. An ID must be furnished upon request. brbrArea Info: *Mileage is approximatebrCape Shark clothing Store 0.7 MilebrChatham Village Market 0.8 MilebrOyster Pond Beach 1.3 Miles brHarding Beach 2.2 MilesbrLighthouse Beach 2.2 MilesbrStop & Shop 3.0 Miles

Spacious Dog-Friendly Retreat in Chatham

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$1482.56

Your family or group of friends will be close to everything when you stay at this centrally-located home. This cozy home is perfect for those looking to be walking distance to restaurants, boutiques, movie theater, baseball field, beach, & more! Enjoy 5 bedrooms, two decks, a spacious outdoor shower, & a finished basement filled with two seating areas & games. brbrIn Downtown Chathambr.4 Miles to Oyster Pond Beachbr.3 Miles to Seaside Links Golf CoursebrbrExperience Chatham with us & learn more below!brbrKEY FEATURES:brbr☀ Located downtown Chatham, walk to restaurants and boutiquesbr☀ Walking distance to Oyster Pond Beach, Seaside Links Golf Course, Chatham Band Stand, Chatham A's baseball games at Veteran's Field & more!br☀ Sleeps 8: 4 bedrooms + bonus room in the basementbr☀ 2.5 Bathrooms br☀ 1 Dedicated workspacebr☀ Dining table with seating for 8 guestsbr☀ Modern amenities and well-equipped kitchenbr☀ Top deck includes dining table with seating for 10 guests, outdoor sectional, 2 lounge chairs, fire table, and grillbr ☀ Bottom deck includes two seating areas and spacious outdoor shower br☀ Finished basement with large sectional, seating area, ping pong table, and sliders to deck br☀ 3 Smart TVsbr☀ Ping pong table, board games & puzzles br☀ Beach towels, beach chairs, umbrella & beach toys brbrHere Are A Few Kind Words From Our Past Guests:brbrThis house was without a doubt perfect in every way and surpassed our expectations! The Location was awesome, bedding and towels were great with well stocked appliances to use in the kitchen. With Six adults we all had plenty of room and everyone had space. The office came in quite handy for my son-in-law as well!... - JeannebrbrLucia was a perfect host! She was so kind, and responsive. We loved the house. The location couldn’t have been better! So close to town! We will be back! - EmmelebrbrBeautiful home in a beautiful location. Four teens and four adults fit quite comfortably with room to spare. Basement was a great place for the kids to watch movies and play ping pong . Warm and cozy with all the comforts of home . Flexible with check out time was a real plus for us . Grazie Lucia !brLook forward - Adrianabrbr☆☆ BEDROOMS ☆☆brbrThis beautiful home accommodates 8 guests in 4 bedrooms + bonus room in the basement. brbrThe first floor has one bedroom with a queen size bed. brbrThe second floor has three bedrooms. One bedroom with a queen size bed, one bedroom with a full size bed, and one bedroom with two twin beds. brbrThe basement has one king size bed. brbrAir conditioning details + fan details:br- First floor: The bedroom with queen bed has a window A/C unit + floor fan. br- Second floor: There is a mini split in the hallway that cools down the second floor. The queen + full bedrooms also have window A/C units + floor fans. The twin bedroom does not have a window A/C unit but has a stand up fan. br- Basement: The basement with a king bed has a mini split, but not specifically in the bedroom. There is a stand up fan in the bedroom. brbr☆☆ BATHROOMS ☆☆brbrThere are two full bathrooms and one half bathroom. brbrOn the first floor, there is a half bathroom. On the second floor, there is a full bathroom, and in the basement there is a full bathroom. In addition, there is a spacious outdoor shower on the lower level deck that you can access from the basement. brbrEach bathroom is stocked with all the essentials you need for the duration of your stay. brbr☆☆ KITCHEN & LOUNGE ☆☆brbrThe beautiful kitchen is fully equipped with all the appliances, cookware, and utensils you need to feel at home including a coffee machine and more. brbrThe dining area is in between the kitchen and living room with sliders that go to the deck. The outdoor dining table has seats for 10 guests. brbrThe living room is equipped with a couch, chairs, and smart TV with a door opening to the front porch. brbrThere is a spacious finished basement with a large sectional, bench seating area against the wall, smart TV, bedroom, full bathroom, ping pong table, and sliders that open to the lower level deck. brbrIn the basement is a washer + dryer, equipped with laundry detergent and dryer sheets. brbrOn the first level, there is an office space with a desk, chair, smart TV, and futon. brbrThe home does not have central air, but there are two ductless HVAC AC units (second level and basement) that works well to cool down the areas. There is also a Black and Decker AC unit in the living room. brbr☆☆ OUTSIDE SPACE ☆☆brbrThere is a deck off of the dining room including a dining table with seating for 10 guests, a large sectional + chairs with seating for 8 guests, 2 lounge chairs, a fire table, and Weber grill. The deck overlooks the backyard. Enjoy a cookout or soak up some warm sunshine on the roof deck. brbrThe lower level deck includes two seating areas and spacious outdoor shower. brbrThere is a lovely porch on the front of the house with seating for four guests and a coffee table. brbrThe driveway has parking for 4 vehicles. brbr☆☆ PROXIMITY TO CHATHAM BEACHES ☆☆brbr- Oyster Pond Beach: .4 miles br- Lighthouse Beach: 1.1 miles br- Harding Beach: 3.3 miles brbr☆☆ NEARBY PLACES IN CHATHAM ☆☆brbr- Downtown Chatham br- Chatham Bars Inn br- Chatham Seaside Link Golf Course br- Orpheum Theatre br- Chatham Band Stand br- Veterans Field (catch a summer Chatham A's baseball game!)br- Chatham Village Market Grocery Store br- The Chatham Squire br- Lighthouse Beachbr- Oyster Pond Beach br- Chatham Filling Station br- Delmar Bar & Bistro br- Impudent Oyster br- Viera on Mainbr- Sweet Tomatoes Pizza br- Bluefins Sushi & Sake Bar br- Wequassett Resort & Golf Club brbr& so much more! brbr★★★ Book Today & Let Us Take Care Of You In Chatham! ★★★

Downtown Chatham Family Retreat - Spacious Deck, Games & Firepit - Walk to town

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$2557.41

Welcome to your private Chatham retreat, where modern luxury meets classic Cape Cod charm. This stunning four bedroom, four and a half bath home spans almost 3,300 square feet of beautifully designed living space. Every detail has been thoughtfully crafted for comfort, style, and effortless relaxation.brbrAs you step inside, you'll be greeted by stunning finishes and tasteful decor that exude a sense of coastal elegance. The main level features an open concept living area with high ceilings, where natural light pours in through the expansive windows. The living room provides a cozy spot for relaxing, while the adjacent gourmet kitchen is fully equipped to satisfy any culinary craving. The butler’s pantry is stocked with everything you need to entertain and the dining area is perfect for hosting meals.brbrThe main level primary bedroom features a luxurious king bed, walk-in closet and a private en-suite bathroom with an oversized shower, heated floor, dual vanity sinks and a private water closet. The first upper level area houses two more bedrooms, each thoughtfully designed to offer a peaceful retreat. These two guest bedrooms are equally comfortable: one has a queen bed and one has a queen bed and single day bed. Guests on this level will share a hallway bathroom. The second upper level area has the fourth bedroom all by itself at the top of an open staircase (there is a door in the mud room that separates this wing from the kitchen/living areas) and has a king bed and a sitting area with a queen pull out sofa bed, as well as a private en-suite bathroom.brbrThe lower level is an oversized oasis of entertainment and relaxation. There is a large workout area with a Ping-Pong table, Peloton Bike and all the equipment you need to stay in shape while on vacation, along with another full bathroom. The spacious gathering area with a large sectional sofa offers a great spot for movie nights or game nights with the whole family.brbrStep outside and this is where the true magic happens! Enjoy your private backyard oasis, complete with an outdoor shower and heated saltwater pool and spa. Lounge in the sun or take a refreshing dip in the pool, then unwind in the spa as you relax after a day of enjoying the stunning scenery of Chatham. In addition to its backyard oasis - this magical home is just a short drive from both Hardings Beach and Ridgevale Beach - two of the most beautiful local beaches on Nantucket Sound. This vacation rental property truly has it all - luxury, comfort, and endless opportunities for relaxation and recreation. Book your stay today and make unforgettable memories. brbrThe pool and spa are open and heated from 5/16/26 to 10/3/26. All linens and towels are provided. Subject to applicable taxes and fees. Please call for additional details. No pets or smoking allowed. Sat. to Sat., 7 night minimum rentals during the peak season. 4 night stays at reduced rates are available in the shoulder season. All Robert Paul Vacation Rental bookings include a non-refundable $250 fee that includes administrative fee and damage waiver insurance for self-reported incidental damage up to $1,000.00. Upon receipt of a booking request, an agent will reach out to discuss additional damage protection which may be required at this property.

Sophisticated Chatham Retreat with Private Pool and Spa RPAM093

Chatham, Massachusetts, United States

Bed

Bath

10

Sleeps

$1382.94

Recently updated waterfront home overlooking Snake River, Stage Harbor & Nantucket Sound on Stage Island. 4+ bedroom, 3 bath home with open floor plan with oversized windows to take advantage of views. With four levels of living space including a loft and walk-out lower level there is room for all. Take the paddle boards and multiple kayaks over to a sandy beach. Outdoor shower, three exterior decks and outside seating areas. Fall asleep to the smell and sound of the ocean!

Waterfront, Updated 4 Bedroom Home with Views of Stage Harbor & Nantucket Sound

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$355.01

Summary:brbrDog friendly, patio and fire pit, walk to Stage Harbor and Lighthouse BeachbrbrbrbrThe Space:brbrThis home is represented by Nauset Rental, a local vacation rental management company. brbrbrbrBeautiful recently renovated Chatham getaway with water views, walking distance to both Stage Harbor, Lighthouse Beach and Main Street! This gorgeous home has been fully renovated from the ground up, and everything in the house is brand new. Located on a quiet dead end off of Stage Harbor Road, the house is set on a small, beautiful saltwater pond. You'll enjoy nice water views from the house and outdoors on the oversized patio. There is a fire pit and grill on the patio which makes for the perfect way to end the day and watch the sunset over the water in the front yard. Listen to the sound of crickets and peeps while you toast marshmallows and clink glasses. Well-behaved dogs are allowed and will love playing on the lawn. brbrbrbrThe main level of the house features a bright and open living space that flows from living to dining to kitchen. The living area has a comfy couch (converts to full size sleeper sofa), large wall mounted smart TV and working fireplace. The gorgeous modern kitchen is well-appointed with high-end appliances and fixtures - there is a gas range, pot filler, French door fridge with ice maker and large basin stainless steel farmhouse sink. A center island offers prep space and/or work space. High speed WiFi allows for seamless remote work. Modern industrial farmhouse style wood floors, recessed lighting and a neutral decor palette make the entire space warm and inviting, while a new mini split AC keeps it cool. brbrbrbrThe first floor also features a large primary suite with queen size bed and full bathroom with stand up shower. There is also a half bath with stacked washer and dryer on this level. Upstairs, there are two more bedrooms (one with a full bed and one with two twins), a full bathroom with tub/shower combo and double vanity. There are quiet and efficient mini split AC units in all bedrooms for comfortable sleeping. brbrbrbrPast guests rave about the location, and you'll see why! Picturesque Stage Harbor is just a short stroll - under half a mile/about a 7 minute walk. You can also walk down to Bridge Street and cross the historic wooden bridge while taking in beautiful scenery. If you follow Bridge Street all the way down (about 1 mile/20 minute walk) you'll find yourself at gorgeous Lighthouse Beach on the Atlantic. Stunning and serene Morris Island is a short 5 minute drive - great for solitary walks along the sand, saltwater fishing or just plain sunbathing. brbrbrbrDowntown Chatham is within easy reach, approximately 1 mile/20 minute walk to the heart of Main Street. Chatham is home to many delicious eateries featuring local cuisine, unique gift shops, galleries and more. This house is in a great setting just close enough the action but far enough that you'll enjoy peace and quiet. This spot on the pond is such a tranquil setting! brbrbrbrLayout of Bedrooms & Bathrooms:brbrMain LevelbrbrBedroom 1 - queen brbrFull bathroom with stand up shower brbrHalf bath with stacked washer and dryerbrbrUpper LevelbrbrBedroom 2 - double/full bed brbrBedroom 3 - two twins brbrFull bathroom with tub/shower combo brbrbrbr***We welcome approved low-impact DOGS - TENANT must reach out to Nauset Rental with dog details for approval either before making reservation or within 48 hours of submitting online reservation. The owner also requests the respectful use of furniture coverings to ensure a clean experience for everyone :)brbrbrbrWe will need to know the following information:brbr*Any shedding brbr*Any issues with accidents - urination or throwing up brbr*Any issues with chewing furnishings brbr*Barking while unattended or while attended brbr*Does your dog receive flea and tick preventative brbr*Are you confident you can leave property with no sign of your dog when you check out brbr*Do you accept full responsibility for the behavior and impact of dogs in your group during your stay brbrbrbr*Please note: as is standard in the area, guests are asked to provide their own linens and towels. We are happy to refer you to a local linen rental company if needed.*brbrbrbrOther Things to Note:brbr-

Fully Renovated Chatham 3 Bedroom with Water Views

Chatham, Massachusetts, United States

Bed

Bath

6

Sleeps

$511.36

Escape to this cozy three-bedroom, two-bath cottage nestled in a peaceful countryside neighborhood. With central air, high-speed wireless internet, and plenty of amenities, you will feel right at home from the moment you arrive. Sleep comfortably with a queen bed, a double bed, a twin, and fun bunk beds, perfect for families or a group of friends. Step outside to enjoy the privacy of a wooded lot, relax on the spacious deck, or rinse off in the refreshing outdoor shower after a day at the beach. To make your stay even more enjoyable, we've included a welcome bag with essentials, courtesy of the owner. Let us help you plan the perfect getaway, call Chatham Rentals today!

Cozy cottage in delightful country side neighborhood!

Chatham, Massachusetts, United States

Bed

Bath

6

Sleeps

$845.34

Discover this beautifully landscaped, contemporary three-bedroom home, ideally situated on a quiet cul-de-sac, just a short walk from Oyster Pond Beach and downtown Chatham. This spacious home features two master suites, including one on the main level with a queen bed, and a second upstairs with a king bed. The third bedroom, also located upstairs, offers a queen bed. Enjoy the private backyard, complete with a deck, patio, and new hot tub. The open floor plan is perfect for entertaining, and a separate family room with a TV and Wi-Fi provides additional space for relaxation. For your comfort, window A/C units are installed in all bedrooms and living areas. After a day at the beach across the street, rinse off in the enclosed outdoor shower. Grill dinner and then take a leisurely walk into town for ice cream or a movie, and experience the beautiful sunsets over Oyster Pond. This lovely home and excellent location provide the perfect vacation setting. A welcome bag with paper and cleaning products, courtesy of the owner, is provided upon check in to help you get settled in. Contact us at Chatham Rentals, and let us help you plan your stay.

Hot Tub! Steps to Oyster Pond Beach and Downtown Chatham.

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$781.16

Experience your summer vacation in this bright and airy 2-bedroom, 3-bath beach house. It features two queen bedrooms upstairs and two twin beds in the den. Imagine barbecuing and unwinding on the private back deck as the sun dips below the horizon, or sipping your morning coffee while greeting the sunrise. A leisurely walk will take you to the beach, where warm sands and salty waves invite you for a day of seaside bliss. If you're in the mood for exploration, a short bike ride will lead you to the village, brimming with shops and ice cream parlors. Inside, you'll find comfortable, open spaces and AC units in each bedroom, ensuring a cool and relaxing atmosphere. For entertainment, we offer Wi-Fi and a large flat-screen TV, perfect for keeping everyone connected and amused. This is the ultimate spot to savor the ocean breezes, breathtaking sunsets, and the laid-back rhythm of summer days at Little Beach! Contact an agent at Chatham Rentals today, and let us help you create unforgettable vacation memories.

Perfect beach house to spend your summer days in!

Chatham, Massachusetts, United States

Bed

Bath

6

Sleeps

$588.66

Located just off the Chatham loop, this two bedroom home is the perfect spot for your family vacation. It features a queen bed, two twin beds, and two baths, plus a large yard ideal for family entertaining; from barbecues to flag football and Frisbee! Enjoy relaxing on the deck with your morning coffee or an afternoon lemonade after a day at the beach. After a day at the beach, rinse off the sand and salt in the enclosed outdoor shower, then grill up some dinner while the stars start to come out. For more fun, walk a bit further to Oyster Pond for amazing sunsets, or head into downtown Chatham for shopping, dining, a baseball game, or a movie. And don’t forget to bring home the seashells you collect on the beach! Private parking is also available. This comfortable and cozy home is a wonderful place to start your Cape Cod vacation memories, year after year! Call us at Chatham Rentals, and let us help you plan your stay.

Just off the Chatham bike loop... a perfect location for your family vacation.

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$1223.47

Welcome to our newly listed vacation home in Chatham, Cape Cod! This spacious 4-bedroom/4.5-bathroom house is a haven for relaxation and entertainment, making it the perfect choice for your getaway. With its stunning backyard overlooking a heated pool and conservation area, you'll find yourself surrounded by lush greenery and the soothing sounds of nature.brbrWake up to the harmonious melodies of chirping birds as you savor your morning coffee on the deck. The backyard oasis beckons with a heated swimming pool, complete with floats and comfortable lounge chairs, inviting you to take a refreshing dip or simply bask in the sun. Unwind in the outdoor shower after a day of exploration or fire up the outdoor grill for a delectable barbeque feast.brbrStep inside and discover the epitome of comfort and luxury. The gourmet kitchen is a chef's dream, equipped with top-of-the-line appliances and ample space to unleash your culinary creativity. Share meals with loved ones in the spacious dining area, or gather in the cozy living room to relax and enjoy quality time together.brbrEntertainment options abound in our home. Indulge in a cinematic experience in the home theatre, boasting a 70-inch TV for immersive viewing pleasure. The dedicated kids' video game area ensures endless fun for the younger guests. For friendly competition, challenge your family and friends to basketball, foosball, cornhole, or ping pong. And when you're in the mood for a quiet evening, our extensive collection of board games promises hours of laughter and bonding.brbrBeyond the comforts of our vacation home, you'll find yourself in the enchanting town of Chatham. Immerse yourself in its vibrant atmosphere, with great shopping and dining options that cater to all tastes. Explore the picturesque beaches and indulge in the tranquility of the ocean. Embark on a biking adventure along the scenic trails, allowing you to soak in the natural beauty that Cape Cod is renowned for.brbrBook your stay at our new vacation home in Chatham and experience a memorable getaway filled with relaxation, entertainment, and the charm of this fantastic town. Don't miss out on this exclusive opportunity to create cherished memories with your loved ones. We can't wait to welcome you!brbrPlease note: Amenities and availability may vary depending on the season. Additional fees and restrictions may apply. Please check the listing details for more information.brbrMain Level/1st Floor:brElegant family room with wood-burning fireplace and a formal 8-person dining tablebrFully Stocked New Kitchen, Stainless Steel Appliances, Breakfast bar, 6-seater Dining Table and Gas FireplacebrMaster Suite: Queen Bed and ensuite bathroombrLaundry room with washer and dryerbrbr2nd Floor:brMaster bedroom: 4-post king bed with full bath and walk-in closetbr3rd Bedroom: Two twin bedsbr4th Bedroom: Twin-over-full bunk bed and a twin bed with trundle brFull BathroombrbrLower level:brEntertainment/Home theater with 70-inch TVbrBar, 40-bottle wine cooler and refrigeratorbrKids' game room with 65-inch TVbrQueen-size sofa bedbrFoosball tablebrPing Pong tablebrFull BathroombrbrOutdoor Living: brSprawling DeckbrOutdoor 8-seater dining table with UmbrellabrWeber Gas GrillbrRattan Furniture seatingbrGas FirepitbrSecluded Heated Swimming Pool - The pool is set against the lush backdrop of the conservation landbrPool basketball hoopbrPool Floats and TubesbrPool Lounge Chairs with UmbrellabrOutdoor ShowerbrFenced yard (back)brBasketball HoopbrbrGeneral: brWifi to access the internetbrSmart TVs (access to Netflix, Amazon Prime, etc.)brCable TVbrBoard GamesbrLinens and Towels includedbrBorrow Beach Chairs (8) and Beach Umbrella for usebrBorrow Beach sand toys for usebrCentral Cooling and HeatingbrParking: Driveway for 4 vehiclesbrbrPlease note that for security purposes, this property has security cameras that record or transmit video, images, or audio. Camera 1 is over the leading garage door, Camera 2 is over the front door, and Camera 3 is inside the garage.

Luxurious Home with Pool & Game Room in Cape Cod

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$1663.3

This lovely home is the perfect getaway for families or a group of friends looking for a home filled with entertainment that is close to downtown Chatham, beaches, and much more. This cozy home has an open concept living area, kitchen/dining room space, a large outdoor space equipped with a massive deck, yard, grill, and fire pit, as well as a fully furnished basement with a game room.brbr2 Min Drive to Downtown Chathambr6 Min Drive to Lighthouse Beach brbrExperience Chatham with us & Learn More Below! brbrKEY FEATURES:br☀ Sleeps 8; 4 bedrooms, 2 king, 1 queen, 2 twin br☀ 3.5 Bathrooms; 3 full (2 full baths have combined tub + shower) + half bathroom br☀ Top of the line mattresses, 100% beautiful cotton linens and fluffy blankets br☀ Open concept living room, kitchen, and dining area with cathedral ceilings and fireplace br☀ Dining room table seating for 6 guests, with 4 bar stool seats at the kitchen counterbr☀ Modern amenities and well-equipped kitchen with wine cooler br☀ Large, brand new deck inclusive of a dining table with seating for 8 guests + umbrella, couch + seating area, 2 reclining lounge chairs, and Weber gill br☀ Yard with a fire pit and seating br☀ Finished Basement with Pool Table, Foosball Table, and Board gamesbr☀ Bikes, Helmets, Beach Chairs, Beach toys, Beach balls, Cooler, Boogie Boards, Cornhole, Bocce, Beach Towels, and Basketball Hoop br☀ Walking or a short dive to many shops, restaurants, and markets br☀ Newly renovated with comfortable and stylish furniture throughout br☀ At the end of a quiet road, nestled into conservation land, surrounded by hydrangeas br☀ Outdoor shower br☀ 4 Smart TVsbr☀ Clean as can be! We pride ourselves on the cleanliness of our home br☀ Bonus Room! Above the garage 1 bedroom + full bath for an additional charge (Available - late May-early Nov)brbrHere Are A Few Kind Words From Our Past Guests:brbr“This is a beautiful home. The beds are all very comfortable; the whole house very clean and the property beautiful and quiet. My son loved the pool table. I enjoyed the peaceful backyard and the sound of birds in the morning.” - Christine S.brbr“House was fantastic and just as described. We could walk to many places but had our private paradise in the backyard. Communication with the host was excellent. Highly recommend the home.” - Michael J. brbr“Everything about this well appointed house makes it an ideal Cape Cod experience for quiet, clean, and spacious days right near beaches and shops. We are already booked for next summer.” - Tara S. brbr“This was an amazing property and so well equipped and centrally located. Lois has thought of everything and the place is super clean with tons of beach stuff, towels, supplies, etc. We loved the property and it was perfect for our kids and the location to town was awesome. Would definitely come back!” - Angela S. brbr☆☆ BEDROOMS ☆☆brbrThis gorgeous home accommodates 8 guests in 4 bedrooms. brbrOn the main level of the home, there is one master bedroom, fitted with a king-size bed and a private full bathroom. Also on the main floor is a bedroom fitted with a queen-size bed, across from a half-bathroom. brbrThe upper level accommodates another four guests. One master bedroom is fitted with a king-size bed and ensuite, the other bedroom has two twin beds. brbr☆☆ BATHROOMS ☆☆brbrThere are three full bathrooms and one-half bathroom in this home, each of them stocked with all the essentials you need for the duration of your stay including shampoo, conditioner, soap, two blow dryers, and two hair straighteners. brbrThe main level of the home has a full bathroom in the master bedroom, and a half bathroom close to the kitchen and second bedroom on the first floor. The second level of the home has a full bathroom with a large combination shower and tub. There are two doors to the bathroom - one off of the master bedroom, and another one off of the hallway for easy access from both bedrooms. Worry about nothing with these thoughtfully stocked bathrooms that provide everything you need and more. brbrThe finished basement has a full travertine bathroom. There is also an outdoor shower. brbr☆☆ KITCHEN & LOUNGE ☆☆brbrLiving Room: The living room is cozy with a couch two large chairs around a fire place and smart TV. brbrKitchen: The bright and airy kitchen is fully stocked with all the appliances, cookware, and utensils you need to feel at home including a coffee machine + coffee. There are also 4 counter stools. brbrDining area: The dining area seats 6 guests surrounded by stunning nautical decor. There are slider doors next to the dining area that go out to the deck. brbrFinished basement: Couch, TV, pool table, foosball table, board games, puzzles, beautiful travertine bathroom with shower, and walk-out sliding door to the back yard and outdoor shower. Perfect place to unwind and have some fun! Please know there is no heat in the basement. brbrThere is a washer + dryer, equipped with laundry detergent in the hallway close to the first-floor bedrooms. brbrOriginal paintings of Chatham throughout the house by local Chatham Artist, Lois Castellana. brbr☆☆ OUTSIDE SPACE ☆☆brbrThis home is at the end of a quiet street, nestled in conservation land. There is a long driveway leading to the house with a basketball hoop at the top. The backyard has a large mahogany deck equipped with a dining room table with seating for 8 guests + umbrella, couch/seating area, 2 reclining lounge chairs, and Weber gill. Below the deck is a large yard perfect for lawn games, with a fire pit and seating. There are sliding doors leading to the deck off of the kitchen, and also off of the living area in the basement making it accessible to go in and out. brbr☆☆ NEED AN EXTRA BEDROOM ☆☆brbrFor an additional rental fee, there is a room above the detached garage with king king-size bed, sitting area with TV, window A/C unit, and bathroom. Please inquire if interested. Please know this space is only offered to whomever is renting the house.brbrPricing: br- June-Sept: $295/night br- Oct-May: $250/night brbrPlus $200 cleaning brbrAvailability: br- April through early November brbr☆☆ HOUSE RULES ☆☆brbr- No events or parties.br- No more than 8 guests max allowed at the home or 10 if you also book the apartment above the garage.br- No pets.br- No smoking.br- Quiet hours: 10pm-8ambr- No food or drink other than water in the living areas or bedrooms.br- Must be 25+ years old to book.br- This is a private family home, please be respectful.brbr☆☆ WHEN REQUESTING TO BOOK ☆☆brbrPlease share a bit about yourself - what brings you to Chatham, who you are traveling with, and how many people will be staying at the property.brbr☆☆ A NOTE FROM US ☆☆brbrOur family and friends have always enjoyed the comforts of this family home, we know you will too! There is a lot of space to relax and enjoy your Cape Cod vacation at Chatham Breeze. You can enjoy the sweet sound of birds while sipping morning coffee on the deck, or cook your favorite fish on the grill with family & friends, relax in the sun with a good book, or watch the kids play basketball, foosball or the many other activities all over the property, everyone has a piece of vacation heaven at Chatham Breeze.brbr★★★ Book Today & Let Us Take Care Of You In Chatham! ★★★

Cozy Family Home in Chatham - Firepit, Game Room, Large Deck, Yard + More

Chatham, Massachusetts, United States

Bed

Bath

8

Sleeps

$1148.49

Views, views, views! Charming 3 bedroom, 3 bath cottage right on Mill Pond. Classic Cape Cod furnishings. Window A/C units in bedrooms for those hot summer nights. Access to shared dock for swimming and boating; and Wi-Fi make for a great vacation. Walk to town for shopping, dining, ice cream and the movies. Stroll to Lighthouse Beach for a day of sun and surf in the salty Atlantic Ocean. Use of shared tennis court. Water Access: DOCK. And possible boat accommodations: Mooring available for $300/week. Parking is in front of garage -100 feet from house. This waterfront property has a large flat lawn on the banks of the Mill Pond, and is available for wedding rentals during the shoulder seasons (June, September & October only) for $10,500 per week. Dog (2) friendly, too; pet fee of $150 will be added to the lease. Please park in driveway and walk down to the rental. (You may drive down to load and unload). Call us at Chatham Rentals and let us help you plan your stay.

Pet friendly, water views and lush lawns!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$672.4

Location, Location, Location – New to the rental market, this fully renovated centrally located cape home checks all the boxes. Within minutes you can walk to some of Chatham's top attractions including Downtown, Chatham Bars Inn, Oyster Pond, Chatham A's baseball games and the Fish Pier. brbrThis well-appointed home features a new chef’s kitchen with a 20' vaulted ceiling open to sunroom/seating area. Sliding doors take guests from the sunroom to a patio with outdoor seating or you may enjoy your meal in a separate dining room just off the kitchen. Kitchen features stainless steel appliances, white cabinets, white quartz countertops and a large island with seating. Also downstairs is a new laundry room and full bath. Rounding out the first floor is a comfortable living room, a perfect place to gather with family and friends and enjoy the Red Sox games on the new 55 inch flat screen TV. brbrUpstairs is three bedrooms and one full bath. All have been repainted, and the wide pine floors have been restored to their original beauty. The bedrooms have new furniture and new bedding. Two bedrooms with queen beds and the third bedroom, the “kid’s room”, features bunk beds and a twin bed. brbrAfter a day at the beach, rinse off the sand in the new outdoor shower while your kids enjoy playing whiffle ball in the large, private side yard. brbrEnjoy the comforts of your own home in this well-equipped Chatham rental. There is no need to pack up two cars to go on a family vacation anymore. This inviting home is stocked with new linens, towels, beach towels and blankets, beach toys, back pack beach chairs, adult bikes, Double & Single BOB Jogging Strollers, McLaren stroller, red wagon, Graco Pack ‘n Play, high chair, board games and many other items to make you feel right at home. brbrWhether you are a family looking to enjoy the sand and surf or a couple looking to explore all that Chatham has to offer, this newly renovated home is the perfect place for your next vacation. brbrbrAmenities: br-New amenities include Central Air Conditioning in entire house, Outdoor Shower, Weber Gas Grill, Sonos, 55 inch Samsung Cable TV, and much more.brbrbrLess than 10 minute walk to the following landmarks/attractions:br-Downtown Shopping/Restaurants br-Chatham Bars Inn via a walking path at end of streetbr-Oyster Pondbr-Chatham Anglers Games/Children's Playgroundbr-Chatham Fish Pier brbrbrbr

In Town Newly Renovated Cape

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$572.33

Experience the beauty of Cape Cod at Chatham Shenanigans. This beautiful, well-appointed, bright home is centrally located to all that Chatham has to offer. It’s the ideal spot for discerning guests looking to be close to the hubbub of town but in a serene, private, and quiet setting. brbr~Just a 5 min drive or mile walk to enjoy downtown Main Street restaurants, shops, and Cape-league baseball br~Less than 5 min drive to Hardings Beachbr~4 great restaurants within walking distancebrbrThe spacebrKEY FEATURES:br☀ 3 luxurious bedrooms; 1 king, 1 queen, 2 twinsbr☀ Private den/office with additional queen pull out sleepingbr☀ 2 full bathrooms + 1 half bathbr☀ Full kitchen stocked with all your cooking needsbr☀ Cozy living room w/ indoor fireplace + flat-screen TVbr☀ Lower-level living/game room w/ an additional TV, ping pong table + card game tablebr☀ Outdoor living area w/ a solo stovebr☀ Full washer + dryerbr☀ Quiet and private location only minutes from all that Chatham has to offerbr☀ Free parkingbrbr☆☆ BEDROOMS + BATHROOMS ☆☆brEach of the three bedrooms is designed with guest comfort in mind. brbrThe primary bedroom with king-sized bed and en-suite is on the main level. The second floor boasts two additional bedrooms - one queen-sized bed and another with two twin-sized beds perfect for both kiddos and adults!brbrThe main level has one half-bath off the garage entry. There is a full-bath with walk-in shower and double sinks ensuite to the primary bedroom on the main floor. The second full bathroom is on the second floor and includes a shower/tub and is shared with the bedrooms on this level. brNOTE: As is common on Cape Cod, Guests are responsible for providing their own linens, including sheets and towels, at this property.br☆☆ KITCHEN & DINING ☆☆brThe open-concept main level of the home boasts soaring ceilings and views of the private backyard. The kitchen and dining area offer plenty of room to comfortably host family dinners and are outfitted with all the cookware, dishes, utensils, dishwasher pods, and appliances you will need to cook delicious meals. The farmhouse dining table can seat up to eight.brbr☆☆ LIVING SPACES ☆☆brThere are three separate indoor living spaces around the home: one first floor living area, one comfortable den/office on the main floor, and one in the basement lower level. Each of the bedrooms also has a small seating nook if you’re looking for a little more privacy from the rest of the group.brbrThe main living area boasts floor-to-ceiling windows, which allow you to enjoy the secluded and private views of the backyard from the comfort of the sofa or plush chair. There’s also a large flat-screen Smart TV for movie night.brbrThe den/office is a relaxing space where you can fully immerse yourself into the pages of your next read or work from anywhere at the desk with beautiful views of the conservation land across the street.brbrThe lower-level is a bright and open space with a big-screen TV, a quality ping pong table, and a game table with a small collection of fun games for the family.brbr☆☆ OUTSIDE SPACE ☆☆brWhile there are plenty of outdoor activities nearby, the house also provides its own outdoor sanctuary for guests to enjoy. We invite you to enjoy a competitive game of corn hole, relax on our private patio or settle in for a quiet evening by the solo stove. There are plenty of seating areas for guests to sip morning coffee in or enjoy a happy hour drink as the sun goes down. String lights provide ambient lighting and there is a large outdoor dining table for al fresco meals.brbr☆☆ ADDITIONAL INFO ☆☆brThis home also offers first-floor laundry and a 2 car garage to store all your beach gear. brbrWe provide many household staples to get you started – Paper Towels, Toilet Paper, Soap, Laundry Detergent, etc. As is customary on Cape Cod, linens and towels are not provided but may be provided to guests through a third party. This is not included in the rental price. Please inquire about pricing and referrals. brbrGuest accessbrGuest have private access to the full property with the exception of the storage room in the basement. There is free parking available in the driveway.brbrImportant NotesbrNo pets allowed.brNo smoking or parties allowed on the property.brPrimary renter must be at least 25 years old to book. A valid photo ID is required prior to check-in.brAs is common on Cape Cod, Guests are responsible for providing their own linens, including sheets and towels, at this property. Pillows, blankets and covers are provided. Guests can bring their own or we refer to Chatham Concierge for linen services where you can rent from their online store. They can deliver linens to the property on your arrival date and pick them up on your departure date. The cost for linen rentals varies depending on your needs and planned occupancy.brA rental contract must be agreed to during the booking process. The Guest is responsible to read and understand the rental rules prior to booking. By clicking Request to book the Guest is accepting all of the terms and conditions.brThis home is on a septic system so occupancy is strictly enforced to avoid a septic backup of sewage in to the house. Your max occupancy during your booking is what you submit in your booking. Additional guests must be approved.brCheck-out time is strict, and if our cleaners arrive while you're still at the house, we may incur extra charges, which will be passed on to our guests.brWe are not responsible for any injuries, illnesses, or accidents that may occur during your stay, nor for the loss of personal belongings or valuables.brA Trust + Safety Fee is applied per night in lieu of a security deposit.br ★☆ Book Now & Let Us Take Care Of You at Chatham Shenanigans! ☆★br Follow & tag us on Instagram: @pleasantchathamcapes

Chatham Shenanigans, Chatham Shenanigans

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$1104.16

This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in the heart of Chatham, Cape Cod, Massachusetts. Fresh and new, the Townhome also includes access to a swimming pool and tennis courts. brbrTownhome 31 features a well-appointed master bedroom with king bed. Second bedroom has 2 full beds. An amazing loft has an additional two twin beds, plus a beautiful den has a Queen Sleeper sofa. Ideal for two or four people, and can accommodate up to eight people when using lofts. Also boasts a fully-equipped kitchen and water views. Beautifully decorated with charming interior decor.brbrEach has picturesque views of Oyster Pond and plenty of open space. Townhome 31 may be rented with Townhome 32 for approximately 4,250 SF of living area (contact Owner for more details).brbrOyster Pond Condominium Complex includes free tennis court, swimming pool, shuffle board, acres of lawn for kite flying, playing catch, and family fun. Wide range of excellent nearby restaurants from super casual on up. Restaurant listings available as are brochures on activities for adults and kids. All summer take your family to the famous Chatham Band Concert, Cape League baseball, and Summer Theatre. Sightseeing, whale watching, seals, cycling, beaches, golf, movies are all nearby. Small kids activities in Chatham also include a huge playground and a train museum, both right near a real fire station. Oyster Pond’s great location is nearby Chatham Main Street’s strolling and shopping.brbrConvenient walk to downtown Chatham location. Close to Atlantic Ocean, Nantucket Sound and Oyster Pond beaches, as well as golf and all the best Cape Cod has to offer.brbrBring your canoe, kayak or Sunfish and use private dock on Oyster Pond providing access to the pond, Oyster River, Stage Harbor, Nantucket Sound, South beach, Monomoy Island and the Atlantic Ocean. Nearby Oyster River Boatyard offers power boat rentals.brbrAmenities include: Heated swimming pool, tennis; shuffleboard, patios, fully appointed kitchens, washer & dryer, gas grill, cable TV, full central air conditioning and heating, wireless internet, and morebrbr See other units we have available: VRBO #3926813 and #4209584 brbrTown of Chatham permit STR-323.

Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks

Chatham, Massachusetts, United States

Bed

Bath

8

Sleeps

$4341.83