Vacation Rentals By Owner In Chatham, MA

$915.6

Little Queen - 3 Bedroom Renovated Cottage in Chatham

Chatham, Massachusetts, United States

Come relax at this beautiful and chic retreat. The property is a completely renovated 1860 cottage on nearly an acre of land. It has all the modern comforts like central AC, crisp new bathrooms, and a chef's kitchen, while keeping ye olde New England charm. The home is light and airy, with wide plank original wood floors, pane over pane windows, a large kitchen, comfy beds, and a cushy sectional sofa in the living room. Everything is brand-new - all systems, appliances, furniture, and household items - with some curated vintage accents. The new organic cotton bed linens and fluffy white towels are from Quince, and the kitchen is well-equipped with a Breville espresso maker, Breville air fryer/toaster oven, Kitchenaid stand mixer, Breville electric kettle, and All-Clad pans. There are two bedrooms on the main floor with queen size beds in each, and there is a sweet little sleeping loft above the kitchen with a twin bed for a child or smaller adult. The second floor is the master bedroom, also with a queen size bed, and with an en suite bathroom that has a soaking tub and hand held shower. The second bathroom is downstairs and has a shower and there is - of course! - an outdoor shower, with a private changing area. The home also has a dining room and sun porch, and an outdoor table table and chairs, as well as an outdoor seating set. The location is fantastic - Goose pond for swimming and fishing is less than a mile away, and the iconic Corner Store is walking distance. It is close to downtown Chatham and also Harwichport, and has easy access to Bay and Oceanside beaches, as well as to Route 6 to head to the National Seashore and other Cape spots.

3

Bed

2

Bath

7

Sleeps

$616.67

/ Nightly

Private Vacation Home

Coastal Fun in Chatham – Your Cape Cod Escape

Chatham, Massachusetts, United States

Stunning Chatham Home near Beach & Rail TrailbrbrThree levels of spacious, updated accommodations. Enjoy the grill, expansive deck, and game room with foosball & darts!brbrWelcome to your cozy Cape Cod retreat! This bright and inviting spot in Chatham has everything you need for a laid-back getaway—plenty of space to unwind, lots of natural light, and easy access to beaches, shops, and great local eats.brbrStep inside to a sunny sitting room that flows right into the updated kitchen, complete with stainless steel appliances and a cute breakfast nook for morning coffee or pancakes with the family. Off the kitchen, there’s a formal dining room for shared meals and a spacious living room with a big TV—perfect for movie nights after a day at the beach.brbrSliding doors open to a huge back deck, where you can grill, lounge, or just soak up the Cape Cod air. It’s the ideal setup for easy indoor-outdoor living.brbrUpstairs, you’ll find comfortable bedrooms designed for a good night’s sleep, including a peaceful primary suite and rooms that are great for kids or extra guests. Downstairs, the finished basement is all about fun—with a TV, foosball table, and dartboard ready for family game nights.brbrWhen you’re ready to explore, Chatham has something for everyone. Stroll along Main Street for shopping and ice cream, catch a Chatham Anglers baseball game, or visit the lighthouse for incredible ocean views and enjoy Lighthouse Beach. Don’t miss the Fish Pier—it’s always a hit to watch the seals waiting for scraps from the fishing boats! And if you love the outdoors, grab your bike and hit the Cape Cod Rail Trail, just down the street. Forest Beach on Nantucket Sound is just 1.5 miles away for some quiet sun and sand.brbrWhether you’re here to relax, explore, or just spend time together, this is the perfect home for making Cape Cod memories.

3

Bed

2

Bath

7

Sleeps

$665.02

/ Nightly

Private Vacation Home

New construction. Short Walk to Beautiful Ridegevale Beach

Chatham, Massachusetts, United States

New construction, more photos to come. brQuiet neighborhood. Short stroll to Ridgevale Beach, sleeps 6. First floor master bedroom with king bed, bureau, walk in closet. Full bath with walk in shower. Laundry room on the first floor. Front to back, fully stocked kitchen/dinning area opens to the living room with a cathedral ceiling, gas fireplace and sliders to a large patio. Upstairs is a second bedroom with a queen bed, bureau, and closet. Across the hall is a bonus room with a trundle bed that can be used as 2 twins or an over-sized queen bed, bureau and closet. Full bathroom on the second floor with a tub. Large patio to enjoy morning coffee or evening barbecue. Outdoor shower and shed with beach chairs and pails/shovels for the little ones. Beach is family friendly and about a 3 minute walk. Shallow inlet for toddlers, ocean side has kayak & sailboat rentals. Snack bar/beach shop serves lunch on their patio. Picturesque town of Chatham is a 3 mile drive. Variety of restaurants, shops, take in a Chatham A's game Veteran's Field, or Friday night concert at the bandstand downtown, Kate Gould Park.

2

Bed

2

Bath

6

Sleeps

$1128.57

/ Nightly

Private Vacation Home

Four Bedroom home with Water Views of Saltwater Millpond & Mitchell River -- Close to Town and Oyster Pond Beach.

Chatham, Massachusetts, United States

3200 Square Foot Cape with Spectacular Water Views of Millpond, the Mitchell River and Stage Harbor in the Distance.brbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrThe perfect spot for kayaking and canoeing! Just drop your canoe or kayak in front of the house. Enjoy a cocktail or cup of coffee on the magnificent deck with water views; relax in this home's quiet setting at the end of a cul-de-sac. brbrThis home boasts air conditioning (ductless a/c units) throughout the house as well as wireless internet access. There is room for everyone in this rental with lots of living space, expansive deck facing the water, comfortable sunroom, and open family room/kitchen. brbrYou can also enjoy your privacy in the master bedroom with King bed, private bath with shower, deck with outdoor furniture and water views, and a television on the first floor. Also on the first floor there is a bedroom with a Double bed across from bath with tub and shower. Upstairs there are two bedrooms and a bath with a tub and shower. The first bedroom has two Twins and second bedroom has a Queen bed. All four bedrooms have wonderful water views. Property also offers updated bathrooms.brbrA Convection oven, front loading washer/dryer (located on the first floor), and two flat screen televisions add to this property. Make sure to jump in the enclosed outdoor shower after a day on the pond or at the beach. Just a short distance to town and Oyster Pond Beach, you can wander down from the house straight to the Fourth of July parade and other activities in town. This is well maintained home in an exquisite location with amazing water views, truly a wonderful opportunity you won't want to pass up.brbrFirst Floor: Bedroom #1 - King, Bedroom #2 - DoublebrSecond Floor: Bedroom #3 - Queen, Bedroom #4 - Two Twinsbrbr* Additional fees:br- $175 non-refundable reservation fee (no security deposit required)br- Cleaning Fee - $420br- all applicable taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO SMOKINGbr* NO PETS ALLOWEDbr* OCCUPANCY: 8 (Adults and children)br* PARKING FOR 4 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.

Bed

Bath

Sleeps

$418.08

/ Nightly

Private Vacation Home

Walk to the warm waters of Nantucket sound 3B/2B home CA, W & D, all amenities

Chatham, Massachusetts, United States

Three bedroom, two bath home 1/2 mile walk to Ridgevale Beach. Home includes central air, color cable, wi-fi, washer and dryer, whirlpool, outdoor shower, deck, gas grill, fireplace, large yard, beach chairs and full kitchen. Bedrooms include master with queen bed, upstairs bedroom has an additional queen bed and downstairs has two twin beds..The house has everything you might need. Ridgevale is a premier beach, with the warm waters of Nantucket Sound and an inlet called Buck's Creek, making it one of the best beaches for children and adults. Chatham is an especially great town and considered a destination because of all it has to offer. There is a public golf course, tennis, movie theater, baseball league games, plays, boating, fishing, hiking, biking trails and more. Enjoy all Chatham has to offer in a comfortable home.

Bed

Bath

Sleeps

$679.55

/ Nightly

Condo

Outermost Waterfront Chatham Home w/ Wraparound Views

Chatham, Massachusetts, United States

Right down the hill from the famous Chatham Light House, this one-floor living, 2 bedroom, 2 full bath end unit with wraparound views is as close to the ocean as you get!brbrThis open floor plan home is steps away from the condo association’s private beach, and offers gorgeous views from almost every room. Imagine sipping your coffee early in the morning, sitting on your private deck to watch the sun rise and the tide come in.brbrClamming and fishing are plentiful and this location has a protected harbor and the fastest access out to Nantucket Sound and the Atlantic. Outermost Harbor Marine Harbor is right next door. Downtown Chatham, with its restaurants and shopping, is just a walk or bike ride away. The nearby Monomoy National Wild Life Refuge offers plentiful birding and opportunities for exploring!brbrThe living room features plenty of cozy seating and flat-screen TV. The master bedroom with queen bed and large, attached bathroom also has a flat-screen TV. The second bedroom has one queen and one twin, and a large closet. brbrThe spacious and bright kitchen has a dishwasher and all amenities you could want. Unit also includes a stacked washer/dryer, central A/C and free wifi. There are two private decks, a small one at the front of the unit, and a large deck with picnic table and umbrella, and seating-with-a-view for many friends and family.brbrInside, a large dining table seats 6-8.brbrThis is the Cape Cod lifestyle at its finest!brbrNo smoking and no pets, please! brbrOur home has two parking spots in the property lot.brbrNOTE: We supply bedding blankets and pillows, mattress protectors, toilet paper, paper towels, laundry detergent, dish/hand soap.brbrDuring peak summer dates (June through mid September) a minimum one-week rental is required. Three-night rentals may be available at other times of year.brbrHave a larger group Please check out our other unit right downstairs: https://www.homeaway.com/vacation-rental/p7414776

Bed

Bath

Sleeps

$522.71

/ Nightly

Private Vacation Home

New! Chatham Cottage- 1 Mile to Downtown & Beaches

Chatham, Massachusetts, United States

Escape to our charming 2 bed/1 bath North Chatham cottage!brbrA short walk to Chatham's best beaches and downtown shops and restaurants. Nearby attractions include Ryders Cove & Marina, Oyster Pond, downtown Chatham, bike path, Chatham Bars Inn, Chatham A's Baseball Field, and Wequassett Resort & Golf Club.brbrOur home is a great fit for families, couples, or small groups who want to explore all that Chatham has to offer.brbrOur charming Cape Cod cottage, will make you feel right at home! brbrCharming 2 bedroom, 1 bathroom home is nestled perfectly on a gorgeous corner lot in North Chatham. Bright & inviting living room with hardwood floors, decorative fireplace, built ins & door to side patio. Our cozy eat-in kitchen is fully stocked with all necessary appliances and items, and can be accessed via a set of stairs up the back from the driveway. You will find a complete bathroom with a bathtub and shower, followed by a tastefully furnished living room that features a decorative fireplace, a large smart TV, a couch that can be converted into a queen-size bed, a love seat, and an oversized comfortable chair. To the right of the fireplace is a beautiful built-in bookshelf stocked with our favorite beach reads and board games. There are two bedrooms off the living room, each with a queen bed and a smart TV. During the summer, you can enjoy the sunny Cape Cod weather on the patio which features an outdoor shower, seating area, and dining table. Our property also features a lush green lawn, ideal for playing outdoor games and basking in the sun.brbrInside you'll find: brThe living room features a smart TV, a built-in bookshelf stocked with great beach reads, two couches, a lounger chair, and a full-size pull-out sleeper sofa. There is also a decorative fireplace. brbrFully equipped kitchen with oven, stove, dishwasher, blender, fridge, toaster, drip coffee maker (with complimentary coffee & filters), tea kettle, cookware, serveware, and dinnerware.brbrGuest bedroom 1 and 2 each have a queen size bed and a smart TV. The full bathroom includes a shower and tub, hair dryer, shampoo, and conditioner.brbrThe garage/basement is equipped with a washer, dryer, laundry supplies, and complimentary beach items that you can use during your stay.brbrOutside Features: brOur garage on the driveway level serves as storage for outdoor and beach gear, as well as laundry facilities, all complimentary for our guests. brbrThere is a private driveway that can accommodate up to 3-4 carsbrbrLarge patio with a seating area and dining table for intimate meals. brbrGrassy backyard with lawn games, outdoor shower, beach chairs, and a cooler for summer days.brbrYou are welcome to use all of our home's amenities, except for one supply closet located in the kitchen!brbrPlease don't hesitate to reach out to us via Airbnb chat, with any questions or concerns! We're happy to accommodate and should get back to you as soon as possible!brbrChatham's best beaches and vibrant downtown filled with some of our favorite shops and restaurants are just minutes away. Ryders Cove, The Chatham Bars Inn, The Chatham A's Baseball Field, Oyster Pond, and Wequassett Resort & Golf Club are also nearby attractions.brbrIt is highly recommended to have a personal vehicle to fully explore the area's attractions.brbrEnjoy complimentary high-speed Wi-Fi, which is perfect for remote work!brbrYou'll be delighted to know that we provide fresh linens, including soft sheets and plush bath, hand, and wash towels for your ultimate comfort during your stay.brbrWe have a pack and play available in the second bedroom closet for your little one. We also have crib sheets, but feel free to bring your own preferred baby sheets.brbrIn the summer, we use two window AC units to cool the house effectively. Portable fans are also available.brbrOur private driveway can comfortably accommodate 3-4 vehicles for parking.brbrWe are huge dog lovers and would be delighted to have your furry friend stay with us! However, please let us know in advance if you plan to bring your pup. As a responsible pet owner, you are expected to clean up after your dog and inform us immediately if there are any accidents inside the premises, so that we can take care of it promptly. Please note that the absolute maximum number of pets allowed per stay is one. Any violation of this rule will result in the loss of your security deposit. Additionally, there is a non-refundable pet fee of $125 per stay, which does not cover any potential damages caused by your pets. If anything happens during your stay, please inform us immediately, and we will work with you to resolve the issue.brbrFor the safety of our guests and property, we have installed exterior-only security cameras. These cameras are actively recording both audio and video outside all entrances and side doors. Please note that any tampering with the cameras, including but not limited to covering or disabling them, will result in the early termination of your reservation with no refunds whatsoever.

Bed

Bath

Sleeps

$751.22

/ Nightly

Cottage

Ocean & Marina Views From This Charming Cottage! Walk To Beach & Town.

Chatham, Massachusetts, United States

Charming cottage right next to Outermost Marina with views of the boats & water. The quintessential beach house! If you want granite counter tops & new construction this is not the vacation home for you. This is a classic Cape Cod summer cottage that will remind you of summers past. An incredible spot to build some new family memories while enjoying all Chatham has to offer. You are able to walk to the famous Lighthouse in minutes and downtown Chatham is close by. Features 3 bedrooms (sleeps 7): brBedroom 1: queenbrBedroom 2: two twins and one queenbrBedroom 3: kingbrAlso has two bathrooms. More pictures to come (we are just moving in!). brPlease note, in July & August, we only rent by the week (Fri.-Fri). In the off-season we are open to shorter rentals.

3

Bed

2

Bath

7

Sleeps

$6834.3

/ Nightly

Private Vacation Home

Your Ultimate Vacation Destination!

Chatham, Massachusetts, United States

This is your ultimate vacation destination! Simply stunning, custom built home with a grand farmer's porch! Sit and sip a cool drink while rocking in the shade, catching up with friends and family, and admiring the colorful gardens. Brand new water front home in North Chatham, has everything and more. Professionally decorated with a Cape Cod charm, and all new beds and furniture. Gourmet kitchen, lounge and bar area with panoramic views of the water, spacious back porch with hot tub and grill leads to your own private dock, mooring and beach area, patio with fire pit and Adirondack chairs overlooking the blue water. A widow's walk deck offers tables and chairs and an incredible expansive view of Bassing Harbor and Ryder's Cove. This is outdoor living at it's best. Bright and airy finished lower level boasts an exercise room with a bar, wine fridge, large flat screen TV and a ping pong table; all allowing for indoor fun. Every custom bedroom has an en suite bath, and large flat screen TV. The master bedroom wing offers a private office, lounge area, dressing room with built ins, private deck and spa like bathroom with soaking tub. Barn door bunk room with custom built in bunk beds, private bath and flat screen TV, is just perfect for kids. There are 4 king beds and 2 bunk beds.This home also comes with a Welcome Bag while in season. This reusable tote is filled with all of your paper and cleaning products needed for your visit; compliments of the owner. Beautiful grounds, gorgeous views and an absolutely magnificent home is where you can begin making your vacation memories.

Bed

Bath

Sleeps

$512.6

/ Nightly

Private Vacation Home

Three Bedroom Updated Home -- Just Minutes to Pleasant Bay, Town and Bike Path!

CHATHAM, Massachusetts, United States

Sun Filled, Completely Renovated 3 Bedroom, 2 Bath. Minutes from Pleasant Bay or Downtown, Perfect for your Cape Adventure.brbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * *brbrThis sparkling home is open, bright and spacious and offers 1800 square feet of completely renovated, newly furnished, one-floor living.br brThere are three large bedrooms that are very comfortable. The master bedroom is located on the right side of the house with a walk in closest and en-suite with two sinks and shower. On the left side of the house there are two bedrooms, one with a queen and the other with two twins. The second bath with tub and shower is located next to these bedrooms.brbrYou'll find a new and well-equipped kitchen which opens to a dramatic, chandeliered dining area. A large air conditioned sunporch with wraparound windows offers an outdoor dining option where you can relax while overlooking conserved woods and private backyard. Property has a back patio with outdoor seating and gas grill. Five skylights and large windows flood the home with light. This property also includes the following amenities: central air, brand new first floor laundry center, HD cable TV and high-speed wi-fi, and off street parking for up to four cars. Use of the garage is not allowed.brbrIt's an easy trip to two local ponds, a quick drive to downtown Chatham or the Pleasant Bay beaches, or seven minutes by bike to the CC Rail Trail. You're in the center of it all in a great family neighborhood.brbrOne Level: Bedroom #1 - Queen Bedroom #2 - Two Twins Bedroom# 3 - Queenbrbr* Additional fees:br- Non-refundable reservation fee - $220br- Guest Services Fee 3.5%br-Damage Protection Fee - $30br- Cleaning Fee - $280br- all applicable taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO SMOKINGbr* OCCUPANCY: 6 (Adults and children)br* PARKING FOR 4 VEHICLES br* 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.

Bed

Bath

Sleeps

$1344.43

/ Nightly

Private Vacation Home

Chatham Vacation Rental With Pool and Charm to Spare! RPAM096

Chatham, Massachusetts, United States

Located in one of Cape Cod’s premier resort towns, 764 Riverview Drive offers everything a discerning vacationer is looking for! Featuring 4 bedrooms and 3 full bathrooms, the home can sleep 8 people comfortably in beds. Complimenting the excellent location of the home is the star of the show: a private, heated pool. Spend your summer days exploring the amazing coastline, shopping and dining at the world class options on Main Street, and come home to relax in your backyard oasis. As for beaches, you have your pick: Jackknife Beach is .6 miles away, Oyster Pond Beach is 3 miles, Ridgevale Beach is 3.1 miles, Hardings Beach is 3.6 miles, Chatham Lighthouse Beach is 4.2 miles and our own National Park, the Cape Cod National Seashore is just 9.8 miles away. Take a day and explore two more excellent towns with amazing cultural centers: both Harwich Port Village and Orleans Village are a short drive. brbrThe home has a thoughtful layout with a great flow for entertaining and relaxing. You enter in the main floor great room which leads into the dining/kitchen area to the left and the living room to the right. The kitchen is fully stocked with everything you need for home cooking and grilling (and has the laundry area tucked neatly next door). The living room has cable TV, large sectional, additional seating nooks and large slider leading to the pool area. Off of the living room is the first bedroom, which has an en-suite private bathroom and a queen bed. And if you aren’t careful, you may miss the primary bedroom which is discretely tucked behind a secret door next to the fireplace and features an en-suite private bathroom and a king bed. Upstairs there are the final two sleeping spaces (one with a queen bed and one with 2 single beds) plus a full bathroom between them to share. Central AC throughout the house will keep you cool on those balmy summer nights. All bedroom have cable TV.brbrThe backyard features the pool, outdoor dining table, seating areas, a pool cabana for relaxing out of the sun, a gas grill and a truly exceptional oversized outdoor shower enclosure. The grounds have plenty of lawn space for games.brbrThis property is available as a winter rental from 10/1/25 to 5/1/26 for $3500 / month plus utilities. If interested please inquire.brbrPool open and heated from 5/16/26 to 10/9/26. Bookings outside that time frame in 2026 will not have access to the pool. Seven night minimum rentals in the peak season, Sat. to Sat. only. Four night minimum rentals in shoulder and off seasons at reduced rates, check in and out on any day. No pets, please. All linens and towels are provided. Subject to applicable taxes and fees. 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 security protection which may be required at this property.

Bed

Bath

Sleeps

$1394.06

/ Nightly

Private Vacation Home

Large Chatham Rental w/ 5 Bedrooms w/ 5 Private Bathrooms RPAM007

Chatham, Massachusetts, United States

This stunning rental home is a vacationer’s dream! Easy and close access to the ponds, bike trails, conservation area and town! Featuring 4,100 sq. ft. of luxury living, you and your guests will enjoy every moment of your time here. Featuring five bedrooms each with their own private bathroom, you will find it difficult to find another home that offers such a perfect set-up.brbrThe Main floor of the home features a large great room with the kitchen, dining area and living room. An additional tv area is next to the great room as well as a half bathroom. Down the hall on the main floor are two bedrooms, both with queens beds and private en-suite baths. brbrThere are two separate second floor bedrooms, each accessed by their own staircase. The primary bedroom has a king bed with a large en-suite bathroom with a separate soaker tub and shower. The primary bedroom has a private balcony as well overlooking the side patio. The other second floor bedroom features a queen bed and a private en-suite bathroom.brbrThe lower level of the home is a large walkout space with two additional seating areas, laundry room, a bedroom with a queen bed which is a private bathroom next door.brbrThe outdoor space has a wood burning fire-pit surrounded by chairs, two outdoor dining tables, a gas grill and an outdoor shower.brbrEnjoy the Chatham lifestyle and create a place for you and yours to return year after year. All linens and towels are included. Dogs are considered on a case by case basis. 7 night minimum, Sat. to Sat. during the season. Subject to applicable taxes and fees. All Robert Paul Vacation Rental bookings include a non-refundable $250 fee that includes administrative fee and damage waiver assurance for self-reported incidental damage up to $1,000.00. Upon receipt of a booking request, an agent will reach out to discuss additional security protection which may be required at this property.

Bed

Bath

Sleeps

$978.1

/ Nightly

Private Vacation Home

SHORT WALK TO LIGHTHOUSE BEACH AND TOWN....WATERFRONT ON MILLPOND WITH PATH TO WATER!!

Chatham, Massachusetts, United States

Fabulous Old Village Location, Minutes to Lighthouse Beach and Townbrbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrLarge, rustic waterfront historic property on saltwater Millpond. The property is 4/10 mile to Lighthouse Beach and 1/2 mile to downtown. Walk to restaurants, shops, coffee shops, and ice cream. Wireless internet and cable television provided along with gas grill and enclosed outdoor shower. This property is full of Cape Cod charm. brbr Antique home that offers first floor master bedroom with a queen and a private bath, and on the second floor there are three additional bedrooms each with two twin beds side by side, and a bunk room with two twins and three built in bunks. There are two baths on the second floor at each end of the house. There are portable fans available for each bedroom. Property does not provide air conditioning. Please keep in mind there is a steep stairway to the second floor in case you are traveling with younger children.brbrYou're sure to enjoy the outdoor space-- a beautiful large patio that faces Millpond, spacious yard, and plenty of parking. Path from back yard leads down to the water. Great spot for kayaks! Enjoy your breakfast on the terrace on a beautiful summer morning or read a great book in the afternoon. With truly picturesque water views and a private setting, the well maintained yard is great for outdoor games or outdoor dining!. There are two outdoor dining tables and a large umbrella along with ample outdoor seating. brbr* Additional fees:br- $220 non-refundable reservation fee; $30 damage protection fee (no security deposit required); guest services feebr- $490 cleaning feebr- All applicable taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO SMOKINGbr* OCCUPANCY: 11 (Adults and children)br* PARKING FOR 5 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. Activities and availability are subject to change. Not available on stays over 28 days.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.brbrKGC CDEAN

Bed

Bath

Sleeps

$596.7

/ Nightly

Private Vacation Home

Sea views steps to Ridgevale Beach - Airy Cottage. Modern Amenities. Pet.linen

Chatham, Massachusetts, United States

Pet ok with approval first. Bright and airy cottage sleeps max 5 (2 BR - 1Q, 2T) plus single pull out sofa bed in hi living room. A block by footpath from Ridgevale Beach. Linens included. No pets permitted. Classic beach cottage with original pine interior, now bright and freshly painted with updated modern conveniences (including a/c, WiFi, washer, dryer, dishwasher, smart TVs with cable). Water views and beautiful sunsets from large second-story sun deck (accessed via exterior stairs at back of house) with seating/dining table. Living room plus separate family room with dining area. Well-equipped kitchen. Bathroom has shower (no tub) plus a fully-enclosed outdoor shower at back of house to enjoy with hot/cold water. brbrThis traditional but updated Cape Cod beach cottage is steps to the warm, safe waters of Nantucket Sound on the south side of the beautiful, unspoiled town of Chatham on the elbow of Cape Cod. Ridgevale Beach is Chatham's most popular warm-water family beach. It's a long, wide sandy beach with tidal inlets perfect for exploring. Safe, gradual sloping sandy bottom ocean swimming with small waves. brbrLots of activities at your doorstep: fish, swim, build sand castles, windsurf, sail, canoe. You can get food, equipment and boat rentals at the Ridgevale Beach Snack Bar - just two minutes walk from the cottage. And just a five-minute drive to all that downtown Chatham has to offer.brbrPast guest book comments have been ' perfect romantic getaway ' , ' Beach access is big plus' 'gorgeous views' ' would recommend to anyone' 'We had a great time- the kids met so many friends on the beach. brbrParking for max two cars in driveway - no parking allowed on lawn or in street. brbrThe cottage is in a safe, upscale beachfront neighborhood on a dead-end street. Access to beach footpath is diagonally across street from cottage.

Bed

Bath

Sleeps

$2042.93

/ Nightly

Private Vacation Home

Best Location / Oceanside near Chatham Bar's Inn

Chatham, Massachusetts, United States

brbrOUR LOCATION:brOur home sits on a double-lot, just a few hundred feet from the Atlantic Ocean, with just a few minutes-walk to Town, Beaches, Fish Pier, Chatham Bars Inn, fine restaurants, golf, spa, tennis, shopping and attractions. The neighborhood is both exclusive and very private. brbrSETTING:brThis exquisitely furnished Antique Cape home has 4 bedrooms and 3 baths (more details below). Well maintained, this property was built in 1950. It's a short walk to the Atlantic Ocean via our private path which starts at the ocean-end of our property. brbrACCOMMODATIONS:brThe 1st floor master suite has a split-king bed. There's a private bath with air-tub / shower. The suite also includes a private sitting room with closet. brbrAlso on the 1st floor is a smaller bedroom with private bathroom and shower. This room has a private door to the outside. This room has trundle-twins.brbrOn the 2nd floor, there are two bedrooms. the larger one has oversized twins, with the smaller one having trundle-twins. brbrLANDSCAPING:brThe landscaping is all Organic including lawn, vegetable garden, trees and flower beds. Help yourself to our vegetable garden. It's a stunning Oceanside location. brbrWHAT'S NEARBY (easy walking distance):br 4 of Chatham's swimming beaches, Fish Pier, Lighthouse Beach, Town Center, Friday night Band Concerts, fine restaurants, shopping and cultural venues. brbrAlso, we are just minutes' walk from the world-class Chatham Bars Inn, offering golf, spa, tennis facilities, beach bar and fine dining. Their specialty is Beachside clam-bakes and lobster dinners. Easy walk to Oceanside lunch. Fine dining is inside at the Sacred Cod and STARS restaurant. brbrPOPULAR VISIT:brInclude whale-watching, day visits to Nantucket and Martha's Vineyard via ferry. There are numerous historical venues all over Cape Cod including Plymouth Plantation and Mayflower Museum and/or Plantation (Plymouth), the Whaling Museum (New Bedford) and so many more on-Cape adventures.brbrREVIEWS:brOur guest book contains all 5-star reviews. We have photographed and videoed the property and rooms extensively, so there can be no disappointment upon arrival.

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$425.35

/ Nightly

Private Vacation Home

Peaceful, Charming, Quiet, Airy, Cozy - Take A Look!

Chatham, Massachusetts, United States

This 3 bedroom 2 bathroom two-story cape is private, quiet, and overlooks a lovely cranberry bog. Inside it's airy and open with rustic, European charm. Living room, dining room table and kitchen are in one large wood-paneled open space. Game room with TV and ping pong table in basement.brEasy to get to, the house is conveniently located off Route 28, at the end of a quiet cul-de-sac. On the large deck behind the house, you can enjoy a cup of tea in the morning, a sun-drenched tanning mid-day, or an evening cocktail, all with nothing but nature as backdrop. Walk down the short path leading to a lovely walk around the peaceful cranberry bog, where you'll often spot an egret or a great blue heron.brChoose among several nearby beaches and ponds to swim, sunbathe, sail, windsurf or walk - all within a mile or two. The Cape Cod Bike Trail is within walking (or bike riding) distance and you can pick up home-baked muffins and pies at Marion's Pie Shop on the way back.brChatham Center, just five minutes away by car, (2.5 miles)is known for its enticing shops, weekly band concerts in the gazebo, a charming historic little library, and a selection of restaurants ranging from casual to fine dining. (And baseball fans will NOT want to miss the opportunity to attend a Chatham A’s game at Veteran’s Field, also just 5 minutes away.)

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$786.64

/ Nightly

Private Vacation Home

Waterfront on Private Lake!

Chatham, Massachusetts, United States

Summary:brbr16644 - Lover's Lookout: Waterfront on Private Lake!brbrbrbrThe Space:brbrEnjoy your best days of summer at our waterfront home located on the private Lover’s Lake in central Chatham! Bring or rent kayaks/SUP boards (Chatham Kayak Company is close by!) and cast away on the water soaking up the Cape Cod sun! Craving a little salt Not to worry, Jackknife Beach and Harding’s Beach are both just a 5-10 minute drive away. brbrWhen you are all watered out, come back to the house to grill dinner on the gas grill and enjoy a meal on either the 2nd-floor deck or covered patio. Head back towards the water and relax in an Adirondack chair and watch the sunset paint the sky over the lake! Alternatively, brighten up a rainy night by making a homemade meal in the newly renovated kitchen, bright and clean with glistening white subway tiles and Stainless Steel Samsung Appliances. Enjoy an appetizer in the living area then share a meal around the formal dining table and admire the gleam of the steel art and decorative fireplace in the light. After dinner, retreat downstairs to the TV/Game Room for some late-night fun. Play a game of foosball, eat some popcorn and watch a movie on the couch, or indulge in a classic board game like Trivial Pursuit or Scrabble.brbrWhen you’re finally tuckered out from the day, head your separate ways to one of our home’s 4 bedrooms that sleeps up to 9 people. The main bedroom sits on the backside of the house on the first floor and features a King size bed-- where you can overlook the lake from a wall of windows that wraps around the back corner of the room. It also boasts a King bed, private Full Bathroom, TV, and a closet and dresser for ample storage. The second bedroom awaits across the home and struts a Queen Bed, TV, Full Bathroom, and large closet. The final two bedrooms are off of the Game Room on the ground floor. The third bedroom has one Queen and one Twin bed, closet and dresser, and its own door to the shared full bathroom-- which makes bedtime a breeze with two sinks! The fourth bedroom is across the floor and has two twin beds, a dresser, and a slider that goes out to the Patio. Central A/C on the 1st floor and mini-splits on the ground floor will keep you cool on the most feverish days of summer! Other top amenities include WiFi, cable TV, gas grill, and sheets and bath towels provided for each guest.brbrIf you’re up for exploring the town, stroll down Main Street Chatham, or catch the Chatham Angler’s (of the Cape Cod Baseball League) play at Veteran’s Field. While you're out and about, be sure to check out some of our favorite eateries too like Hangar B (serving the best brunch around!), Mom & Pop’s (grilling the best veggie burger you’ll ever have), or Mac’s Chatham Fish & Lobster (broiling/frying all the best of Cape Cod seafood). Our waterfront home is bound to leave you with everlasting memories of summer and steal your heart forever!brbrHome Details:br-Sleeps 9br-2 Floors (Ground Floor and 1st Floor)brBedroomsbr-Total 4br-1st Floor Master Bedroom: 1 King Bed w/ en suite Full Bathroombr-1st Floor Bedroom #2: 1 Queen Bed w/ en suite Full Bathroombr-Ground Floor Bedroom #3: 1 Queen Bed and 1 Twin Bed w/ en suite Full Bathroombr-Ground Floor Bedroom #4: 2 Twin BedsbrBathroomsbr-Total 3br- 1st Floor: Full Bathroom w/ Shower (en suite King Bedroom)br-1st Floor: Full Bathroom w/ Shower/Tub combo (en suite Queen Bedroom)br-Ground Floor: Full Bathroom w/ ShowerbrOther Amenitiesbr-Central A/C on 1st Floorbr-Mini-Split A/C System on Ground Floorbr-Cable TV br-WiFibr-Fireplace NOT for guest usebr-Game Room (Foosball Table)br-Board Games/Gamesbr-Washer/Dryer br-Gas Grillbr-Deck with Furniturebr-Patio with Furniturebr-Private Backyardbr-Waterfront on Private Lakebr-NO pets (fines remitted)br-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0408780550brbrbrbrThe Neighborhood:brbrGeneral

4

Bed

3

Bath

9

Sleeps

$366.71

/ Nightly

Private Vacation Home

Central AC, Game Room, Dog-Friendly!

Chatham, Massachusetts, United States

Summary:brbr16701 - Chatham Bliss: Central AC, Game Room, Dog-Friendly!brbrbrbrThe Space:brbrWelcome to Chatham Bliss, where your Cape Cod dreams come to life. This inviting 3-bedroom, dog-friendly retreat comfortably hosts up to 6 guests and offers the perfect blend of charm, comfort, and coastal living in beautiful Chatham.brbrbrbrSettle into the bright, welcoming living room, where sliding doors open onto the deck and fill the space with natural light. The fully equipped kitchen makes it easy to gather and prepare meals with family and friends. When it’s time to unwind, you’ll rest comfortably in two plush queen bedrooms—one featuring a full bathroom with a shower—while the kids’ room, equipped with a twin bed and trundle, offers flexible sleeping arrangements.brbrbrbrOn the ground floor, a game room awaits, perfect for friendly competition around the pool table or cozy movie nights with your party. No matter the weather, it’s an ideal space to have fun.brbrbrbrA washer and dryer provide added convenience, making it easy to refresh after a day at the beach. A half bathroom on the ground floor and a full bathroom on the first floor, combined with WiFi, streaming TV, and central air conditioning, ensure comfort and ease throughout your stay.brbrbrbrStep outside and enjoy classic Cape Cod living. Fire up the BBQ grill for an easy family meal, then dine al fresco in the outdoor seating area. As the evening winds down, gather around the wood-burning firepit for cozy nights under the stars, sipping a glass of your favorite cocktail.brbrbrbrSpend your days exploring some of Chatham’s best beaches—Hardings Beach, Ridgevale Beach, and Cockle Cove are all less than a 10-minute drive away. For nature lovers, the Monomoy National Wildlife Refuge offers beautiful trails and coastal scenery. Just a short drive away, Chatham’s charming Main Street invites you to browse boutiques, art galleries, and local shops. Enjoy brunch at Pain D’Avignon, fresh seafood at The Impudent Oyster, casual bites at Mom & Pops Burgers, or sushi at Bluefins. Don’t miss the iconic Chatham Squire for a lively night out, and be sure to stop by the Chatham Pier Fish Market for the freshest local catch and a true Cape Cod experience.brbrbrbrWhether you're here for sun-soaked beach days, unforgettable dining, or pure relaxation, Chatham Bliss is your ideal home base. Book your stay and experience the very best of Cape Cod living.brbrbrbrHome Details:brbr-Dogs Welcomed (w/fee of $45/night per dog)brbr-Sleeps 6brbrBedroomsbrbr-Total 3brbr-1st Floor Bedroom: 1 Queen Bed (Ensuite)brbr-1st Floor Bedroom: 1 Queen Bedbrbr-1st Floor Bedroom: 1 Twin Bed w/ TrundlebrbrBathroomsbrbr-Total 2.5brbr-Ground Floor: Half Bathroombrbr-1st Floor: Full Bathroom, with Tub/Shower Combobrbr-1st Floor: Full Bathroom, with Shower (Ensuite w/ Queen Bedroom)brbrOther Amenities brbr-Central A/C brbr-WiFibrbr-Smart TV brbr-Streaming Service brbr-Game Roombrbr-Pool Tablebrbr-Washer/Dryerbrbr-Propane Grillbrbr-Wood Firepitbrbr-Please note outdoor amenities are available seasonallybrbr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbrbr-Cleaned with Hospital Grade Disinfectantbrbr-Parking for 2 cars maximumbrbr-C0569530550

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$868.68

/ Nightly

Private Vacation Home

5 Bedroom Chatham Charmer RPAM012

Chatham, Massachusetts, United States

Located in the highly desirable town of Chatham, this five bedroom, three bath rental home will meet all your vacation needs. Sleeping twelve people comfortably, you will have plenty of room to enjoy your stay in the large living room while the kids hang out in the adjoining family room. Featuring a first floor king master bedroom plus 2 queen bedrooms, 1 king bedroom, and bunk room with 4 single beds upstairs, there are plenty of options for sleeping arrangements. Charmingly appointed, everything you need to enjoy your time here is accounted for: an outdoor shower to rinse off after a day at the beach, gas grill on the spacious deck, plenty of parking, great location and a quick walk down the neighborhood path to Emery Pond for kayaking and swimming! Plus, air hockey and ping pong in the basement for those rainy days and corn hole boards for the sunny ones! Located just 1.4 miles to Main Street (a 15-minute ride on the bike path), you and your guests will have an easy time experiencing the outstanding dining and shopping that Chatham has to offer, or bring your tennis rackets and play a match at one of the several public courts. Be sure to stop by the famous Chatham Squire Restaurant and have some of the best fried seafood on Cape Cod, or head over to the world-renowned Chatham Bars Inn and enjoy a drink at their beach bar. You have easy drives to some of the best beaches around like Lighthouse Beach, Hardings Beach, or Ridgevale Beach. This home is also perfectly suited for weekend retreats in the spring or fall. Getting married Spend time with your wedding party in this expansive home and enjoy getting ready under one roof together! Central AC throughout the home will keep you cool on those balmy summer days. brTenants provide their own linens and towels. No pets please. Seven night minimum in the peak season, Sat. to Sat. Four night minimum the rest of the year. Subject to applicable taxes and fees. All Robert Paul Vacation Rental bookings include a non-refundable $250 fee that includes administrative fee and damage waiver assurance for self-reported incidental damage up to $1,000.00. Upon receipt of a booking request, an agent will reach out to discuss additional security protection which may be required at this property.

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$3826.83

/ Nightly

Private Vacation Home

Elevate Your Cape Stay: Chatham Luxury with Pool & Beach RPAM026

Chatham, Massachusetts, United States

Located just .9 miles from the Chatham Bars Inn and 1.3 Miles from Main Street, this 6 bedroom 6 full bath luxury home sleeps 14 comfortably. Featuring a heated salt water pool and spa, this home is the definition of a Chatham luxury property with 5400 sq ft of living space. Across the street is the home's path to the beach with its ever changing views of Aunt Lydias Cove, Chatham Harbor and Tern Island.brbrAs you enter the home you walk up a set of stairs to a covered porch. Inside, the home is split into two separate wings connected by a breezeway. The main wing features a gourmet kitchen with an oversized island, multiple sitting/living areas, dining room with a table that sits 14, access to the decks with outdoor dining table and natural gas grill and a lovely screened in porch. Also in this wing are three ensuite bedrooms. The first floor bedroom has a king bed; upstairs you will find a queen bedroom and a bedroom w/ 2 single beds.brbrThe second wing of the home has a truly grand TV room, with a cloud couch for tons of seating. In this wing are the other three bedrooms. The first floor bedroom is a bunk room with 3 sets of twin bunks beds. There is a full bathroom off of the TV room for people sleeping here to use. Upstairs in this wing are two more ensuite bedrooms: one w/ a queen bed and one w/ a king bed.brbrThe back deck has a staircase that leads down to the pool area which is enclosed in decking and features plenty of seating and lounging options. The pool is heated, salt water based and gets plenty of sunlight. The spa is next to the pool, with controls for heating, jets and lights! The pool and the spa are professional maintained and cleaned weekly for tenants.brbrFrom the moment you step in the home, you will notice the amount of care and craftsmanship that went into the construction and renovation of this property. Bespoke details and thoughtful touches are around every corner. If you are looking for a premier rental in Chatham to make your stay to Cape Cod unforgettable, look no further...brbrThe home is available for year round bookings. Please see below for minimum stay requirements based on the time of year. Please note, off season bookings do not include the pool or spa.brbrSubject to applicable taxes and fees. No pets please. All linens and towels are provided. All Robert Paul Vacation Rental bookings include a non-refundable $250 fee that includes administrative fee and damage waiver assurance for self-reported incidental damage up to $1,000.00. Upon receipt of a booking request, an agent will reach out to discuss additional security protection which may be required at this property.brbrSTAY REQUIREMENTS:br8/30/25- 10/3/25- 4 night minimum stays (Pool and Spa are Open)br10/4/25 - 5/15/26 - 3 night minimum stays (Pool and Spa are Closed)br5/16/26 - 6/26/26 - 4 night minimum stays (Pool and Spa are Open) br6/27/26 - 9/4/26 - 7 night minimum stays, Sat. to Sat. only (Pool and Spa are Open) br9/5/26 - 10/2/26- 4 night minimum stays (Pool and Spa are Open) br10/3/26 - 12/31/26 - 3 night minimum stays (Pool and Spa are Closed)brbrBEDROOM CONFIGURATION:brFirst Floor-brBedroom 1- 1 king bed w/ ensuite bathroombrBedroom 2- 6 twins beds in 3 bunk bed formation (bathroom in hallway)brSecond Floor Wing 1-brBedroom 3- 1 queen bed w/ ensuite bathroombrBedroom 4- 2 twin beds w/ ensuite bathroom brSecond Floor Wing 2-brBedroom 5- 1 queen bed w/ ensuite bathroombrBedroom 6- 1 king bed w/ ensuite bathroom

6

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6

Bath

14

Sleeps

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