Vacation Home Rentals By Owner In Chatham, MA

Sea~a~Bella - Your perfect Chatham family vacation is here. You will find three beautiful, scenic beaches within walking distance providing the perfect summer Chatham day. Minutes away from restaurants, shopping and Cape Cod Baseball, there is something for everyone in the family.brbrThis modern home with plenty of space will ensure a wonderful stay. The backyard has plenty of room for games in addition to a new Outdoor kitchen and natural gas fire pit to relax comfortably on those cooler nights.brThe spacebrThis newly renovated and inviting home in quintessential Chatham is perfect for your next family vacation.brbrYou can enjoy beautiful sunsets from either the front or the back yard on comfortable Adirondack chairs, surrounded by music from the Sonos speaker system. The outdoor area also has a brand-new kitchen and natural gas firepit to complete this backyard retreat, inclusive of atmosphere lighting and lush landscaping.brbrOnce inside, you will find an open concept coastal space, with a newly renovated kitchen and thoughtfully designed living space.brbrThe elegant ensuite primary bedroom, has a king size bed, a newly renovated bathroom with a walk-in shower and a Smart TV. Adjacent to the primary bedroom, you'll find another room with a twin bed and desk perfect for additional guests and privacy for work, if needed.brThe family room houses a large screen smart TV with plenty of comfortable seating for all. The spacious sofa bed provides extra sleeping space.brbrOn the second level, there are two more bedrooms. A queen bedroom and a room with three twin beds, all recently renovated, along with an ample size full bath.brbrYou will also find an outside shower perfect for after a day at the beach. To ensure the most comfortable outdoor experience we have also sprayed the entire property for mosquitoes and ticks.brbrWe hope you come and experience the perfect blend of Coastal living and comfort in this North Chatham retreat.brGuest accessbrGuests have access to the entire property.brOther things to notebrAdditionally, there is a brand new samsung washer and dryer in the first floor mudroom. Beach chairs are provided.brbrTotal of 3 smart TVs. 1 family room, 1 in th e primary bedroom and 1 in one of the upstairs bedroom.brbrThree beaches nearby: Scatteree Beach(.65Miles), Cotchpincut(.70Miles) and Cow yard (.68Miles). Nauset beach is also a short drive away.

Beautifully renovated home, outdoor space, pet considered

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$718.96

Summary:brbr16658 - Home Base: Centrally Located Home w/ Patio Fire Pit!brbrbrbrThe Space:brbrConveniently situated in the middle of Chatham Village, a mere 3 minute (.2 mile) walk from downtown Chatham, is Home Base--the perfect location for your next Cape Cod getaway! Enjoy all that Chatham has to offer within easy reach of this house’s convenient central location. This unique home features a comfortable front patio and side deck with plenty of room to make the most of beautiful Cape Cod weather Chatham’s downtown area has a variety of dining, bars, shopping and even a movie theatre all within easy walking distance. The charming downtown area is sure to captivate you like so many others who have fallen in love with Chatham. You don’t even need to go downtown for a delicious meal though! Home Base is directly across the street from the Chatham Filling Station which is a favorite breakfast and lunch destination of locals and visitors alike. brbrOnly a 100 feet away from the private front patio of Home Base sits Veteran’s Field which is home field of the Cape Cod Baseball League’s Chatham Anglers. Catching an Anglers game is the perfect way to spend a warm summer night enjoying a slice of small town America reminiscent of a simpler time. If relaxing under the stars instead of the lights of Veteran’s Field is more your style, don’t worry! There is a side deck at Home Base with a propane grill for barbequing and a fire pit for relaxing with a cocktail or making s'mores with the kids.brbrUpon entering Home Base you are greeted by a spacious and well equipped kitchen and beautiful wood floors which run throughout the home. Through the dining room you will find a hallway leading to a bathroom, laundry, and master bedroom with Queen size bed and private bathroom. Walking in the other direction through the living room leads you to the upstairs of the house. brbrUpstairs there are three bedrooms, two with a queen size bed and one with a bunk bed that is a twin on top and a full on the bottom. There is also a beautifully refinished bathroom with tasteful subway tile for a sleek and modern look. Between the central location, spacious accommodation and unique charm we are confident Home Base will be a Grand Slam when it comes to a location for your next Cape Vacation.brbr*NOTE - This is an antique home and stairs to second-floor bedrooms are steep (not appropriate for young children or elderly adults)!brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 9br-2 Floorsbr-1st Floor Master Bedroom: 1 Queen Bedbr-2nd Floor Bedroom #2: 1 Queen Bedbr-2nd Floor Bedroom #3: 1 Queen Bedbr-2nd Floor Bedroom #4: 1 Full bed & 1 Twin Bed (Bunk)br-Central A/Cbr-WiFibr-Cable TVbr-Washer/Dryer br-Gas Grill br-Outdoor Showerbr-Firepitbr-Deck with Furniturebr-Patio with Furniturebr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0422690550brbrbrbrThe Neighborhood:brbrGeneral

Centrally Located Home w/ Patio Fire Pit!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$650.94

Location! Location! Location! brThe “Woodford Reserve” for fun and respite!brThis is classic cape cod home with four bedrooms, 2 bathrooms and an outdoor shower. The bedrooms are 2 queen bedrooms located on the second floor and 1 twin bedroom also located on the second floor. The full bedroom is located adjacent to the bathroom on the first floor. Two families often find this home ideal for sharing as there are 2 good sized queen bedrooms. brbrThe kitchen is fully stocked for all your cooking and entertaining needs.brAdditional seating in the cool breezeway and seating for eight around the large dining room table for all your entertaining needs and family fun.brThere is a grand 70 foot wrap around deck on the back of the house with a large fenced yard. A new weber gas grill awaits you on the back deck and there is plenty of seating for all.brThere is a beautiful patio with fire pit overlooking a large lawn.brThe house has deeded rights to Lovers lake, 5-6 minute walk and is a short walk (200 yards) to the Cape Cod Bike Trail. Also, walk to tennis, pickle ball, and basketball courts. Chatham, voted one of America's prettiest downtown's Main Street, is a five minute drive or a lovely 20 minute walk. (1.2 miles)brbrDrive to beach 1-2 miles away.

4 Bedrooms, 2 Baths, Sleeps 8-10

Chatham, Massachusetts, United States

4

Bed

Bath

8

Sleeps

$382.3

Comfortable home with quiet setting, just short drive to Downtown Chatham, Two Ponds and Beaches.brbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrThis cozy home offers 3 bedrooms and 2 baths along with Central Air Conditioning and wireless internet , Enjoy peace and tranquility in this quiet residential neighborhood of Chatham. This home is centrally located, just a short distance to Town, bike path, ponds and beaches. brbrOn the right side of the house there is a master bedroom with a Queen bed and private bath with shower. Across the hall there is a bedroom with Double bed and one Twin and a third bedroom with a Bunkbed (2 Twins). There is second bath with tub and shower near the kitchen and livingroom area. The livingroom has plenty of comfortable seating with cable television.brbrFrom the dining area step out to a nice sunny rear deck with outdoor dining table and charcoal grill along with an enclosed outdoor shower. Enjoy the spotless kitchen which was recently updated with stainless steel appliances.brbrBedroom #1 - Queen, Bedroom #2 - One Twin and One Double Bed, Bedroom #3 - Twin Bunk Bedbrbr* Additional fees:br- $175 non-refundable reservation fee (no security deposit required)br- Cleaning Fee - $210br- all applicable taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO SMOKINGbr* NO PETS ALLOWEDbr* OCCUPANCY: 6 (Adults and children)br* PARKING FOR 3 VEHICLESbr* SHEETS AND TOWELS ARE NOT PROVIDED. WE CAN PROVIDE INFORMATION FOR A LINEN RENTAL SERVICE.brbr*** FREE ACTIVITIES INCLUDED ****brTo enhance your vacation experience, Kinlin Grover Compass includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area. brbrAs a guest of Kinlin Grover Compass, you'll receive free tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities! Activities and availability are subject to change.brbr**** CANCELLATION/REFUND POLICY ****brUpon cancellation for ANY reason, money will be refunded less a 20% service fee of the total rental amount due, ONLY if the property is re-rented for the same terms and conditions of the original Agreement. Tenant further acknowledges and agrees that where Kinlin Grover Compass undertakes to re-let the property, the rental fee to be charged to the substitute tenant shall be in an amount to be determined in the reasonable discretion of Kinlin Grover Compass and Owner. Tenant agrees that any cancellation of the reservation, undertaken at any time, shall not be effective unless in writing and delivered to Kinlin Grover Compass.

THREE BEDROOM--MINUTES TO GOOSE POND, PLEASANT BAY AND TOWN.

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$503.79

2 Bedroom- 2 Bath- Sleeps 4brA 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of our homes offer flexible stays with a 3 night minimum in the off season - ask our Reservation Specialists for more details.brGuests can bring their own linens or rent from our Linen Service for an extra fee (Bed Sheets, Bath, Beach and Kitchen Towels)brWe offer a 4 pm Check-In and 10 am Check-OutbrbrWelcome to Cape Escape! Enjoy this Cape Cod Vacation Rental nestled in Chatham offering 2 bedrooms and 2 bathrooms with dedicated TV room, Wifi and AC. Whether you're enjoying a family dinner on the patio, watching the kids play in the yard, cycling on the bike trail or visiting one of the nearby ponds, great memories are sure to be made in this home. brbrOwners Share Why I Love My Home:brThis little house has been enjoyed by four generations of our family, as a getaway, a place for leisure and relaxation, a sanctuary from the stresses of everyday life. You'll find this house to be very well-situated. Nothing is very far away, and a lot is very nearby. You can walk to Schoolhouse Pond. Hardings Beach, downtown Chatham, Coastguard Light Beach and the fish pier are all within a short drive, and the famous Cape Cod Rail Trail (a bike trail) stretching from Hyannis to Wellfleet and the Cape Cod National Seashore is easily accessed. If you're here during summer months, the weekly Chatham Band Concerts and the college all-star Cape Summer Baseball League are not to be missed. So welcome to our Cape Escape! We hope it will be yours too.brbrLet Us Tell You About This Home:brFollow the path from the driveway to the front door of this home and you will be transported to a classic Cape Cod experience - from the plantings lining the path to the easy one floor living of this ranch style home - Cape Escape reflects generations of one family coveting their space on our island and creating their own oasis. You will immediately feel welcome when entering this home as the open floorplan doused in crisp white and bold blue hues sets the scene.brbrThe living area adorned by local artwork and plenty of seating invites you to enjoy some time with loved ones. The nearby dining space over looks the backyard and offers seating for six - perfect for gathering family or friends around the table for a shared meal. If the weather or shady privacy of the outdoor patio is enticing, you can also dine al fresco before moving from the picnic table to the Adirondack chairs beside the patio for an evening libation. All of these plans are made possible by the fully stocked and recently renovated kitchen, featuring ample counter space for preparation as well as peninsula - perfect for serving meals or presenting charcuterie to your guests.brbrDown the hallway, you will encounter Bathroom #1 with tub/shower combination and modern appointments from recent updating. Nearby is Bedroom #1 offering plenty of storage and two Twin sized beds. brbrAt the end of the hall is a wonderful TV room with flat screen TV, cable and streaming capacity and a comfortable sleeper sofa on which to view you favorite content. Across from the TV room is the primary bedroom with Queen sized bed and full en suite bathroom featuring a tub/shower combination.brbrAdditional hospitable appointments offered in this home are a washer and dryer located in the unfinished lower level and a traditional Cape Cod outdoor shower tucked against the side of the home.brbrCome to this home to have everything you need for a comfortable vacation along with an ideal location from which to explore the area and facilitate a perfect Cape Escape!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 offers Keyless Entry for your convenience.brNO SMOKING of anything containing tobacco, any other substance, and e-cigarettes, inside or outside of the home.brNO PETS are allowed inside or outside the home! brMax parking of cars at property: 2. No parking on Lawn anytime. brFireplace is not functional.brTown of Chatham Rental Certificate: STR-396 brbrAdditional Information to Assist You:brOur calendars are updated in real-time and are accurate.brDeparture cleaning is included with your reservation at no additional charge. Simply 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 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. br***Linens - bed sheets, bath/dish/beach towels and bath mats are not included with this home but can be rented at time of booking or at a later date through our linen rental partner. Please 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 approximatebr0.25 Mile to Goose Pondbr0.6 Mile to Schoolhouse Pondbr1 Mile to the Corner Store (best burrito's in town, maybe on the Cape for that matter! Also a good cup of coffee offered)br1.2 Miles to the bike path on Sam Ryder Road - More info on The Rail Trail can be found here: Info on Cape Cod bike trailsbr1.8 Mile to East Harwich - Stop & Shop grocery store, Liquor Store, Shopping, Restaurantbr2.1 Miles to Jacknife Harbor Beachbr2.2 Miles to Ridgevale Beachbr3.2 Miles to Hardings Beachbr3.4 Miles to Forest Street Beach (an ocean beach on Nantucket Sound with warmer water and gentle waves)brbrShort drive (2.6 miles) into the town of Chatham where you will find :brThe Orpheum movie theaterbrSeal toursbrShoppingbrRestaurantsbrFriday night Band stand concertsbrThe Monomoy TheaterbrPlaygroundbrPublic TennisbrChatham A's Baseballbr*Mileage is approximate

Cape Escape - Family-Friendly Chatham Retreat

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$4501.7

This wonderfully renovated 1877 home, winner of the 2025 Building & Remodeling Industry of Cape Code Best Rennovation award, nestled in downtown Chatham is centrally located within walking distance from everything Chatham has to offer! Bring the whole family and create new memories together. After a long day exploring Cape Cod, you'll be hard-pressed to choose between relaxing by the brand-new pool and hot tub, gathering around the fire pit and cooking out poolside, or simply sitting on the screened-in porch and enjoying the refreshing evening breeze. Should you ever feel the need to venture outside the home, downtown Chatham and all its restaurants and shops are only a few minutes' walk from the front door. Our favorite is Emack & Bolio’s Ice Cream!brbrThe house has 9 bedrooms, all with ensuite bathrooms. A king bedroom with shower and bathtub on the first floor, 4 king bedrooms as well as a queen/full bunk bedroom on the second floor, 4 twin beds on the third floor, plus two king bedrooms in the carriage house makes sure there is room for everyone in the family. brbrThis expansive grassy lot, unique in downtown Chatham, has plenty of room for outdoor games. Our brand-new patio provides guests with access to a 15’x45’ heated pool and hot tub, as well as a gas grill for delicious cookouts, and a gas fire pit provides a cozy gathering spot for the telling of well-worn ghost stories.brbrAlthough this unique Chatham property is perfect for bringing family together, it also provides room for family members to spread out and do their own thing. The new gourmet kitchen is a chef's dream, with excellent appliances and granite countertops. Two refrigerators, a dedicated wine refrigerator, and an ice maker will ensure that your family get togethers are well-supported. On the first floor you will find a huge family room that opens onto the large screened-in porch; fully foldable doors allow the family room to be open to the outside with countless amenities such as a 65” TV. For those looking for a little privacy, there is a separate den with a 65” TV for the sports and movie fanatics and a game table for that game of Monopoly or for the puzzle enthusiast. On the second floor there is a room with a 65” TV and bubble hockey table to let give the kids their own hang out space. And don't forget our adorable, secret hiding spot for the little pirates in your family!brbrIf you feel like venturing out then this home is a perfectly situated launching pad. Oyster Pond Beach (child-friendly) is an 8 minute walk while Lighthouse Beach (Atlantic facing) is about a 18 minute walk from the house. Restaurants like The Captain's Table and Bluefin Sushi, along with shops like Yellow Umbrella Books and Fisherman's Daughter, are less than a 2 minute walk from the house. brbrThere is nothing overlooked at this luxury Cape Cod vacation property which is uniquely equipped to entertain large groups. Linens, towels, and basic supplies are provided with your rental. Beach chairs, towels, and cooler are provided as well, freeing up room in the car and making packing for your trip stress-free.brbrPlease enter your travel dates on the right of this page for up-to-date pricing. As is customary in vacation rentals, there may be fees in addition to the base rates listed, including a reservation fee, a non-refundable Accidental Damage Protection (ADP) fee, and a refundable security deposit. As required by law, there are also state and local taxes, totaling 14.45%, applied to all reservations of fewer than 31 days in length. brbrThis home offers a 3-night minimum stay during select weeks in January – June & September – December. During the summer we have a 7 night minimum Sunday to Sunday. brbrThe pool and hot tub are closed from mid-October to early May.brbrWe require our lease agreement to be signed to stay in our home. We do not allow on site weddings, tents and party setups are not allowed, and no large parties. brbrDogs may be allowed - but must be discussed to complete booking. We reserve the right to say no to your request for your pet. We charge an extra fee for the pet stay.brbrWe have security cameras at each corner of the house and Ring doorbells on each door.brbrhttps://www.capecodbuilders.org/2025-bricc-award-winners/brbrhttps://chathamlivingmag.com/2023-spring-digital-issue/

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$1018.95

Relaxed Cape Escape near Bucks Creek & Ridgevale BeachbrbrWelcome to your Cape Cod getaway in Chatham. This two-story home sits in a peaceful neighborhood within walking distance of the scenic Bucks Creek Marsh area and less than a mile from beloved Ridgevale Beach. Whether you're here for sunny beach days, bike rides, or seafood feasts around the grill, this is a spot made for easy living.brbrStep inside to a bright and comfy living room perfect for movie nights, rainy-day lounging, or board game battles around the coffee table. The kitchen has everything you need to whip up vacation meals, from pancake breakfasts to fresh-off-the-grill dinners. There’s also a dining table for eight so the whole crew can gather together.brbrOutdoors, you have choices: lounge on the farmhouse front porch to enjoy a good book or conversation, or slide open the back door to enjoy refreshing breezes and meals outdoors on the backyard private deck. Fire up the gas grill and toast to another perfect Chatham evening.brbrThe first floor has a large bedroom with a king bed, and also offers a full bathroom and convenient washer/dryer. Head upstairs to find three relaxing bedrooms and two more full baths. The primary suite includes its own seating area, TV, and en suite with a tub/shower combo. The additional bedrooms share a full bath along with a cozy reading / play area. All have plenty of natural light.brbrAdventure is never far. The Cape Cod Rail Trail is just a mile away for biking and exploring, the downtown Chatham shops and restaurants and numerous beaches are all within an easy drive. Chatham is perfectly situated mid-Cape to explore the beauty of the cape, from state parks to local conservation lands to the national seashore. Summer nights offer the opportunity to take in a Cape Cod League game at the local Chatham Anglers ballpark or concerts at the Chatham bandstand. brbrPack your flip-flops, bring the family (including the board games), and settle into a carefree Cape Cod vacation.

Stevie, The Cape Farmhouse

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$547.79

Welcome to our recently updated getaway in charming Chatham, MA! Our pet-friendly retreat is the perfect destination for both you and your furry friend, offering a seamless blend of comfort and convenience. With the added bonus of an EV charger, you can recharge both yourself and your electric vehicle.brbrStep inside our thoughtfully designed space, where modern aesthetics meet coastal charm. The interior has undergone a recent transformation, boasting fresh updates and a contemporary ambiance that will make you feel right at home. Every detail has been carefully curated to ensure your utmost comfort and relaxation during your stay.brbrOur pet-friendly policy means that your four-legged companion is more than welcome to join you on your vacation. We understand that pets are family too, and we provide amenities and accommodations to ensure their comfort. Whether it's exploring the nearby dog-friendly beaches or simply enjoying the spacious backyard, your furry friend will have a blast!brbrSpeaking of convenience, the addition of an EV charger is a game-changer for eco-conscious travelers. You can now seamlessly explore the Cape Cod area, knowing that your vehicle will be fully charged and ready for your next adventure. Say goodbye to range anxiety and hello to hassle-free exploration.brbrLocated in the picturesque town of Chatham, you'll find an array of activities and attractions just moments away. From strolling along the quaint streets lined with boutique shops to indulging in fresh seafood at local restaurants, there's something for everyone here. The nearby beaches offer the perfect backdrop for leisurely walks or basking in the sun.brbrBook your stay at our pet-friendly, recently updated retreat with an EV charger, and experience the best of Chatham. We can't wait to welcome you and your furry friend to our coastal haven!

Chatham Bliss - Dog Friendly oasis with EV Charging

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$509.01

brbr Just off of Barnhill Rd on the way to popular Harding's Beach, this air conditioned, updated three bedroom house offers a relaxed and comfortable atmosphere perfect for families or couples. Nestled down a private road in a quiet neighborhood of mostly seasonal homes,you will be only a short 4-5 minute stroll to Barn Hill town landing on the beautiful Oyster River. Although there is no swimming beach here, it does have a public boat ramp and is a nice place to just wander to and appreciate the scenery and tranquility. Kids will love going back day after day to poke around the shore looking for horseshoe crabs or watching the local shell fishermen bring in their day's catch.brAbout a 15 minute walk, short bike ride or quick drive in the other direction is beautiful Harding's Beach with public facilities, lifeguards and a canteen truck. Other popular beaches, including fresh water ponds, are also close by.brThe home has a nice enclosed private deck with tables and chairs and a gas grill. And the adjacent brick patio offers some shade surrounded by a flowering cherry tree and perennial plantings.brThe house features a cozy living room with Roku TV and a DVD player. The updated kitchen with adjoining dining area also serves as additional living space with a spacious dining room table perfect for night time board games. The kitchen is fully equipped and has a nice island with bar stool seating. The first floor has two bedrooms, one with twin beds, the other with a queen. The first floor bathroom was recently fully renovated brUpstairs is a master bedroom with a queen size bed, TV , small deck overlooking the patio, and full bath featuring a jacuzzi tub!!brAll bedrooms have ceiling fans. The livingroom also has a ceiling fan.brBesides all of the various beaches, Chatham has plenty of other activities to offer....A couple of small museums, seal watching, fishing, public tennis, pickleball and basketball courts, great bike trails, golf, beach yoga, health and fitness club, kayaking, sailing ..........brAt night we have many restaurants from casual pizza or fried clams to fine dining. Chatham Anglers baseball under the lights at Veteran's Field, several summer concert series and the famous friday night Chatham Band concerts in Kate Gould Park.brPossible day trips from Chatham might include the JFK Museum in Hyannis, Heritage Plantatioin Sandwich, Provincetown on the very tip of Cape Cod, Boston and all it's historical sights,(and Red Sox games), or take the ferry in neighboring Harwich to Nantucket. Owners are avid pickle ball players and would be happy to have you join us in a game!!

Near Harding's Beach, 4 min walk to Oyster River. 3BR, 2Bath, enclosed deck area

Chatham, Massachusetts, United States

3

Bed

Bath

6

Sleeps

$653.12

Your ideal Chatham getaway awaits in this cozy home, featuring 2 bedrooms, 1 bathroom, and within walking distance of downtown. Beautifully updated kitchen! The house sleeps five, with one queen bed and one bunk bed (twin over full). Relax and enjoy the backyard, where you can play lawn games or rinse off in the outdoor shower after a day at the beach. Additional amenities include AC (3 slimline units in the living room and each bedroom) and wireless internet to ensure a comfortable and entertaining vacation. The property's location makes it easy to walk to everything. It is a short stroll to Veteran's Field for an Anglers game, as well as a playground for children. You'll also be just a half-mile from the downtown village, perfect for an afternoon of shopping, a night out, or a band concert. Oyster Pond, where you can spend a day at the beach with the kids, is also nearby. On the premises, there is parking for up to three cars ( this rental sometimes shares the driveway with another rental - no worries, there is plenty of room!) . As a special touch, this home includes a Welcome Bag—a reusable tote filled with a starter pack of paper and cleaning products, courtesy of the owner. It's all here, waiting for you! Contact us at Chatham Rentals, and we'll help you plan your stay.

The perfect cozy Chatham getaway awaits you!

Chatham, Massachusetts, United States

Bed

1

Bath

5

Sleeps

$524.54

Summary:brbr16699 - Cranberry Haus: Great location, Dog Friendly, Central AC!brbrbrbrThe Space:brbrGet ready for your next Cape Cod adventure at Cranberry Haus — a dog-friendly 6-bedroom, 4-bathroom home overlooking a tranquil cranberry bog in coveted Chatham, MA.brbrbrbrWake up to soft morning sunlight streaming through airy windows and the peaceful beauty of nature just outside. The home’s spacious living areas and sun-drenched sunroom create a serene, seaside-inspired atmosphere—perfect for relaxing with family and friends. The open-concept kitchen and living space is designed for connection, whether you're preparing fresh local meals, streaming your favorite shows on the Smart TV, or gathering around the table to share stories and laughter.brbrbrbrAccommodating up to 12 guests, the home features six bedrooms. On the main floor, you'll find two bedrooms, each with a king bed, both with TVs. The ground floor offers four additional bedrooms, including two with a king bed and two kids' bedrooms—each with two twin beds—providing plenty of space and privacy for everyone. With four full bathrooms (two on each level), there’s no waiting—whether you're rinsing off after the beach or getting ready for a night out. Stay cool and comfortable with central AC on the main floor and a split system on the ground floor. A washer and dryer add convenience, making post-beach cleanups effortless and helping you settle right back into vacation mode. Step outside onto the first-floor deck, complete with seating and a grill—perfect for laid-back cookouts and evening gatherings.brbrbrbrLocated less than 10 minutes from some of Cape Cod’s most beautiful beaches, including Harding’s Beach, Lighthouse Beach (where you might even spot seals), and Cockle Cove Beach, you have your pick of seaside adventures. A visit to the iconic Chatham Lighthouse is a must for breathtaking ocean views and memorable photos. For dining, you’re minutes from top local favorites like Del Mar, Pain D’Avignon Restaurant & Boulangerie, and Mac’s Chatham Fish & Lobster for fresh seafood. Spend your afternoons strolling along Chatham Main Street, exploring charming boutiques and shops, or visit the Chatham Fish Pier for a true local experience. In the evening, enjoy live music at the famous Chatham Squire or indulge in sushi at Bluefins. Looking for adventure Rent bikes and explore nearby trails, walk the scenic paths of Monomoy National Wildlife Refuge, or visit the Shark Center for a fun and educational outing.brbrbrbrBack at home, unwind on the upper deck with your favorite drink under the star-filled Cape Cod sky.brbrbrbrExperience the summer rhythm of Chatham, and book your getaway today.brbrbrbrHome Details:brbr-Dogs Welcomed (w/fee of $45/night per dog)brbr-Sleeps 12brbrBedroomsbrbr-Total 6brbr-Ground Floor: 1 King Bedbrbr-Ground Floor: 1 King Bedbrbr-Ground Floor: 2 Twin Bedsbrbr-Ground Floor: 2 Twin Bedsbrbr-1st Floor: 1 King Bedbrbr-1st Floor: 1 King BedbrbrBathroomsbrbr-Total 4brbr-Ground Floor: Showerbrbr-Ground Floor: Shower/Tub Combobrbr-1st Floor: Full Bathroom, Showerbrbr-1st Floor: Full Bathroom, Shower/Tub CombobrbrOther Amenities brbr-Central AC on the main floor, Split System in all downstairs bedroomsbrbr-WiFibrbr-Smart TVbrbr-Streaming Servicebrbr-Washer/Dryer brbr-Propane Gas Grillbrbr-Gas Stove (ground floor, for guest use)brbr-Please note outdoor amenities are available seasonallybrbr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbrbr-Cleaned with Hospital Grade Disinfectantbrbr-Parking for 5 cars maximumbrbr-C0426600550

Great location, Dog Friendly, Central AC!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$503.58

NEWLY RENOVATED CHATHAM WINDMILL for your special Cape Cod vacation experience!brbrLocated overlooking Chatham's beautiful Oyster Pond, enjoy the opportunity to stay in this classic Chatham Windmill for a cozy and memorable vacation! This windmill retreat is the perfect location for your Chatham vacation. Take advantage of the beach just outside your door or wander down the street into Chatham center! Enjoy so much of Chatham - without even getting in your car! brbrThis unique Windmill vacation rental has one bedroom with king sized bed on the second floor, with small full kitchen and dining area, two sitting/TV areas and a full bathroom on the first floor. The Windmill also has a private patio with BBQ grill, dining table and chairs. Enjoy the beautiful water view from Adirondack chairs, just outside your door. brbrLinens (bed and bath) are included. This property has two adjacent units (the Sea Captain's House and the Carriage House) that share the driveway and parking. If you are interested in booking these units as well, for a larger group, please inquire.

Stay in a Chatham Windmill! Beautiful Water View, Steps to Beach & Main Street

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$671.46

Summary:brbr16637 - The Driftwood: Spacious w/ Large Outdoor Area Fire Pit!brbrbrbrThe Space:brbrOur beautifully decorated, spacious, and impeccably clean home is the perfect choice for a large family, two smaller families traveling together or a group of friends. brbrDownstairs you will find a large living area complete with flat screen TV, large eat-in kitchen, and full bathroom and bedroom with Queen bed. The second floor of this home has three bedrooms, and a full bathroom. On the basement level of our home, you will find not only a ping pong table, but a foosball table as well where kids can hang out for hours. The lofted 2nd floor Master Bedroom boasts a King bed with private balcony for enjoying morning coffee in peace before others awake for the day. brbrEnjoy whipping up breakfast at home or try heading to Hangar B restaurant (just down the road at charming Chatham airport) for the best breakfast and lunch on Cape Cod (seriously!) After breakfast, hop on a Stick’n Rudder Aero Tour to see the amazing views of the Cape and ocean from the friendly skies! After a day spent adventuring, soaking up some sun at the beach or shopping the beautiful boutiques of Chatham, return home to grill up a feast on our home’s large back patio while enjoying your favorite cocktail. Wind down the evening sitting around the fire pit with friends, sharing stories and making Cape memories to last a lifetime!brbrHome Details:br-No Pets(Fines Remitted)br-Sleeps 8br-2 FloorsbrBedroomsbr-1st Floor Bedroom: 1 Queen Bedbr-2nd Floor Bedroom: 1 Queen Bedbr-2nd Floor Bedroom: 1 Full Bedbr-2nd Floor Loft Bedroom: 1 King Bed (with window overlooking living room)brBathrooms:br-1st Floor: Full Bathroom w/ Shower/Tub combobr-2nd Floor: Full Bathroom w/ ShowerbrOther Amenitiesbr-A/C Units in Bedroomsbr-Cable TVbr-WiFibr-Washer/Dryerbr-Wood fireplace is NOT for guest usebr-Gas Grillbr-No Petsbr-Game Room with Ping Pong and Foosball Tablesbr-Large Private Deck and Patiobr-Fire Pitbr-Outdoor Showerbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0136270550brbrbrbrThe Neighborhood:brbrGeneral

Spacious w/ Large Outdoor Area Fire Pit!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$651.62

You’ll be able to hear the crashing waves from every corner of this Chatham, MA, vacation rental. This 3-bedroom, 2-bathroom home sits just a short walk from Harding’s Beach and a quick drive from all of Cape Cod’s top attractions! Spend some time at the beach, then rinse off in the outdoor shower before relaxing in the sunroom. Head out to shop the day’s catch at Chatham Pier Fish Market, go on a cranberry bog tour, or take the family for a day of fun at Whydah Pirate Museum.brbr-- THE PROPERTY --brbrC0395230550 | Outdoor Shower | RV/Trailer Parking (30’ Max) | Fireplace | 1,700 Sq FtbrbrBedroom 1: King Bed | Bedroom 2: King Bed (New Photos Coming Soon) | Bedroom 3: 2 Twin BedsbrbrINDOOR LIVING: Flat-screen TV, DVD player, board games, books, dining table, walk-in closetbrOUTDOOR LIVING: Private yard, deckbrKITCHEN: Cooking basics, dishware/flatware, dishwasher, refrigerator, stove, microwave, coffee maker, coffee grinder, kettle, toaster, garbage disposalbrGENERAL: Free WiFi, keyless entry, central A/C, ceiling fans, complimentary toiletries, linens/towels, washer/dryer, laundry detergent, hangers, hair dryer, trash bags/paper towelsbrSUITABILITY: Stairs required to access, bedroom/full bathroom on 1st floorbrPARKING: Driveway (3 vehicles), street (first-come, first-served)brbr-- THE LOCATION --brbrSUN & SAND: Harding’s Beach (0.2 miles), Ridgevale Beach (3 miles), Cape Cod National Seashore (5 miles)brCOASTAL LIVING: Chatham Lighthouse (4 miles), Chatham Pier Fish Market (4 miles), Shark Center Chatham (4 miles)brFAMILY FUN: Pirate's Cove Adventure Golf (14 miles), Whydah Pirate Museum (15 miles), Cape Codder Water Park (23 miles)brAIRPORT: Cape Cod Gateway Airport (20 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to access

Walk to Beach: Chatham Gem w/ Ocean-View Sunroom!

Chatham, Massachusetts, United States

3

Bed

Bath

6

Sleeps

$761.02

Welcome to The Caper's Mate, a charming 3 bedroom, 3 full bath house located near Jackknife Cove, Wequassett Resort, close to downtown, Chatham Bars Inn, Lighthouse beach! brbrBeautiful home, featuring coastal classic interior with all of the modern amenities to make your vacation that much more enjoyable. Enjoy abundant outdoor space for lawn games, basement game room, a fire pit with seating, patio with dining table, outdoor shower, appointed chef's kitchen, full linens, towels, beach chairs and more.brbrThis home is well appointed with bed linens, blankets, quilts, pillows and towels all provided with beds made upon arrival. brbrThe home is equipped with central air, wifi, 3 smart TV's, washer/dryer, lawn games, beach chairs, umbrella, towels, cooler and more.brbrThe home has an open and airy kitchen and dining room area. The dining room has direct access to a private backyard with patio table and chairs, gas fire pit with Adirondack chairs, Weber gas grill and an outdoor shower. brbrAdditionally, the house has a spacious back and side yard great for outdoor activities, like bocce and crochet. The 3 season sunporch also provides access to the backyard.brbrThe fully finished basement provides a cozy and relaxing place to play games, shoot pool, play ping pong and watch movies!brbrLocated in a neighborhood of Riverbay Estates, this home is close to all the destinations that make Chatham so amazing; jump on the many bike trails, watch the Chatham A's play, Stroll downtown Main Street, visit Jackknife Cove Beach, Lighthouse Beach, and Oyster Pond. brbrOnce inside, you’ll discover coastal classic interior with all of the modern amenities to make your vacation that much more enjoyable. This is a perfect place to call home while you’re here on Cape Cod!brbrHome Details:brbrMain Level:br-Sleeps 8br-Bedroom #1: Queen Bedbr-Bedroom #2: Queen Bed, Twin bunkbedbr-Bedroom #3: Queen Bed, Desk, Smart TV, Ensuite full Bathbr-Bathroom #1: Full bath, Tub and shower, dual sinksbr-Bathroom#2: Full bath, Walk in Shower, Ensuite to Bedroom #3br-Laundry Closet- Washer and Dryerbr-Living Room- Gas Fireplacebr-Dining Room: Seating for 8br-Kitchen: stocked with all kitchen essentialsbr-Den: Smart TVbr-Sunporch 3 season enclosed porch with access to backyardbrbrLower Level:br-Fully finished basement: Open and airy space for relaxing and fun, play games, pool and ping pong, Smart TVbr-Bathroom #3- Full bath, Walk in ShowerbrbrGarage:br- Beach Supplies and Lawn Games storagebr- Cleaning supplies and High chairbrbrOutdoor Living: br-Outdoor shower, Weber gas grill, patio table and chairs, gas fire-pit with Adirondack chairs and large yard (back and side) brbrAccess to:br-Trout Pond and Pickeral Pond within the Riverbay Estates Neighborhoodbr- Quiet streets for strolling, jogging and bikingbrbrGeneral: brWifi, Central Air, 3 Smart TV, gas living room fireplacebrbrDistance to:brJackknife Cove- .9 miles brWequassett Resort- 1.8 milesbrChatham Main Street- 3 milesbrRidgevale Beach- 3 milesbrChatham Bars Inn- 3.4 milebrLighthouse Beach- 4.3milesbrbrBest and most beautiful town on the Cape. Come enjoy our piece of heaven and make yourselves at home!

New 3 bdrm/3b near Jackknife Beach/Wequassett/Gameroom

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$519.29

Summary:brbr16636 - Canoe Club: Pond Front Home w/ Game Room Dog Friendly!brbrbrbrThe Space:brbrAwake to water views and enjoy your morning coffee on the back deck as you take in the landscape of the pond and let the kids (dog included!) run in the fenced-in yard below. Spend your day canoeing, paddle boarding or kayaking in Mill Pond or head to one of the various area beaches for a day spent with your toes in the sand. Return home to our impeccably clean and cheerful home to cool down in the air conditioning, and whip up some favorite summertime snacks in the brand new kitchen. brbrOn the first floor of this home, you will find two bedrooms, one with a king bed, and one with two Twin beds. You’ll also find the kitchen, living room and full bathroom. Upstairs there’s a full bathroom and private sitting area with a Chess Board and other table game classics! The finished basement has a bedroom with 2 sets of bunk beds (4 twin beds) and a half bath -- AND a pool table, ping pong table, foosball table, and other fun amenities for kids of all ages. brbrEnjoy warm evenings grilling on the back deck -- maybe before heading out to the famous weekly Chatham Band Concert or taking in a movie at the deluxe Orpheum theater downtown. Other Chatham favorites not to be missed are Chatham Corner Store (for fast and fresh Mexican food), Hangar B Eatery (for the best breakfast of your life), and Mac’s Chatham Fish & Lobster (delicious local seafood). brbrThis home offers something for everyone in your party - the chef, the water sport enthusiast, the gamer, and even the dog! Don’t miss out on your opportunity to make great Chatham memories! brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 8brBedroomsbr-Total: 3br-1st Floor Bedroom: 1 King Bedbr-1st Floor Bedroom: 2 Twin BedsbrBathroomsbr -2nd Floor Bedroom: Queen Bed -Total: 2.5br-1st Floor: Full Bath w/ Tub/Shower Combobr-2nd Floor: Full Bath w/ Showerbr-Ground Floor: 1/2 Bathbr-Central A/Cbr-Window A/C in Upstairs Bedroomsbr-TVbr-WiFibr-Washer/Dryerbr-Outdoor Shower br-Fire Pit (wood)br-Foosball Tablebr-Ping Pong Tablebr-Pool Tablebr-Chess Boardbr-Table Gamesbr-Gas Grillbr-Water Viewsbr-Waterfrontbr-Walk to Waterbr-Parking is available in the driveway for a maximum of 2 cars. There is no street parking available or allowed.br-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-C0406140550brbrbrbrThe Neighborhood:brbrGeneral

Pond Front Home w/ Game Room Dog Friendly!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$666.41

Summary:brbr16638 - The Flying Fish: Perfect for Group w/ Kids & Dogs w/ Hot TubbrbrbrbrThe Space:brbrAre you searching for a recently renovated home with a hot tub and room for the whole family for your vacation Look no further than The Flying Fish! The hot tub on the back deck is the perfect place to take your vacation relaxation to the next level, whatever the season! Located in a quiet neighborhood within walking distance of Forest Beach this house is also a short drive away from some of the best restaurants and shops both Harwich Port and Downtown Chatham have to offer! brbrbrbrThe interior redesign features new flooring, paint, appliances, fixtures, and countertops done in a sophisticated coastal style. The Flying Fish features an open concept eat-in kitchen and large living room. Also on the first floor is a bedroom with a Queen bed, half bath, and laundry room. On the second floor you’ll find two Queen bedrooms, one with an en-suite full bathroom. There is another full bathroom upstairs as well as the “bunk” room which has five bunk beds! The home is also equipped with WiFi, a YouTube TV streaming subscription, and A/C to make sure you spend your vacation in comfort.brbrbrbrOn the outside, this home offers a large semi-fenced private yard with a gas grill, an outdoor shower, and a welcoming deck with plenty of seating–a great spot from which to enjoy those beautiful summer evenings! Don’t forget that your pups are welcome to join in on the fun too! Up to 2 dogs are allowed at the Flying Fish (with an additional fee). brbrbrbrUnder half a mile away, you will find Forest Beach–one of Chatham’s best-known and most beautiful bayside beaches. What could be better than taking a short walk to the beach just down the street brbrbrbrThe Flying Fish is also convenient to local favorite restaurants like The Talkative Pig, Bucca’s Tuscan Roadhouse, Brax Landing. If you are feeling adventurous the Freedom Ferry to Nantucket also departs from nearby Saquatucket Harbor. brbrbrbrHome Details:brbr-Dogs Welcomed (w/fee of $45/night per dog)brbr-Sleeps 10brbr-2 FloorsbrbrBedroomsbrbr-Total 4brbr-1st Floor Bedroom: 1 Queen Bedbrbr-2nd Floor Master Bedroom: 1 Queen Bed with en suite Full Bathroombrbr-2nd Floor Bedroom: 1 Queen Bedbrbr-2nd Floor Bedroom: 5 Twin BedsbrbrBathroomsbrbr-Total 2.5brbr-1st floor: Half Bathroombrbr-2nd Floor: Full Bathroom w/ Shower/Tub combobrbr-2nd Floor: Full Bathroom w/ Shower (en-suite Queen Bedroom)brbrOther Amenitiesbrbr-Central A/Cbrbr-TVbrbr-WiFibrbr-Washer/Dryerbrbr-Hot Tubbrbr-Outdoor Shower brbr-Ping Pong Tablebrbr-Foosball Tablebrbr-Propane Grillbrbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbrbr-Cleaned with Hospital Grade DisinfectantbrbrC0416360550brbrbrbrThe Neighborhood:brbrOceanside

Perfect for Group w/ Kids & Dogs w/ Hot Tub

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$383.57

Cute Chatham Getaway - Just 6/10's of a Mile to Chatham Fish Pier and 8/10's of a mile into Town center.brbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrThis amazing Chatham property has everything you are looking for. Immaculate 3 bedroom, 2 bath home with central air conditioning. Kick back in the fantastic screened sun porch. Perfect for reading a good book or having a cup of coffee or cocktails. Prepare a relaxing meal in the eat in kitchen with updated appliances, cabinets and counter tops. Comfort abounds in the living room with large sectional sofa and flat screen television with expanded cable and wireless internet access.brbrThe master bedroom has a queen bed and boasts a private bath with luxurious separate tub and shower. The second bedroom also has a Queen bed and the third bedroom has two sets of Bunkbeds - sleeping 4. There is a second bath with tub and shower as well. brbrThe open backyard is perfect for outdoor sports and yard games. Wash off that sand from the beach in the enclosed outdoor shower. Cook dinner on the gas grill and enjoy your meal on the outdoor dining table with umbrella. brbrGo to the Chatham Fish Pier-- watch the fishing boats come in and enjoy fresh seafood straight from the fish market. You'll also be just a short distance to town activities, restaurants, playground, Chatham Angler's Baseball field and Oyster Pond beach-- a great saltwater inlet with a sandy beach and lifeguards. You don't want to pass up this amazing summer vacation opportunity.brbrBedroom #1 - Queen, Bedroom#2 - Queen, Bedroom #3 - Two Bunk beds with 4 Twinsbrbr* Additional fees:br- $175 non-refundable reservation fee (no security deposit required)br- Cleaning Fee - $280br- All applicable taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO SMOKINGbr* NO PETS ALLOWED.br* OCCUPANCY: 8 (Adults and children)br* PARKING FOR 2 VEHICLESbr* SHEETS AND TOWELS ARE NOT PROVIDED. WE CAN PROVIDE INFORMATION FOR A LINEN RENTAL SERVICE.brbr**** FREE ACTIVITIES INCLUDED ****brTo enhance your vacation experience, Kinlin Grover Compass includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area. brbrAs a guest of Kinlin Grover Compass, you'll receive free tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities! Activities and availability are subject to change.brbr**** CANCELLATION/REFUND POLICY ****brUpon cancellation for ANY reason, money will be refunded less a 20% service fee of the total rental amount due, ONLY if the property is re-rented for the same terms and conditions of the original Agreement. Tenant further acknowledges and agrees that where Kinlin Grover Compass undertakes to re-let the property, the rental fee to be charged to the substitute tenant shall be in an amount to be determined in the reasonable discretion of Kinlin Grover Compass and Owner. Tenant agrees that any cancellation of the reservation, undertaken at any time, shall not be effective unless in writing and delivered to Kinlin Grover Compass.

THREE BEDROOM UPDATED HOME--CLOSE TO FISH PIER AND TOWN.

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$255.6