Vacation Rentals By Owner In Chatham, MA

This property offers travelers an experience like no other property in Chatham. Set back deep off of Barn Hill rd on over 1.25 acres of park like grounds. Complete privacy yet minutes to all the activities Chatham has to offer. Immaculate interior completely renovated, with a backyard like no other. Located on the beach access road with sidewalks at the end of driveway, No road crossings. 15 minute stroll, or 2 minute drive to Hardings beach and 5 minute drive to downtown Chatham. Home features a large deck with natural gas weber grill, Teak dining set for 8 people. Deck leads to a 20x20 large patio with additional high bar table and chairs for 4. An additional couch and chairs for 6 people. There is a horse shoe pit and a large fire pit with seating for 6. Cafe style lighting and outdoor speakers surround the outdoor space. Spacious cedar outdoor shower. Interior of home has large kitchen with granite countertops, maple cabinets fully stocked with all kitchen utilities needed to prepare meals. Kitchen also includes a built in wine fridge. Large dining room table that seats 8 with double glass sliders leading to deck. Living room has gas fireplace, large sectional couch, 50 flat screen TV with sound bar, along with air conditioning for relaxing after a hard day at the beach. brPrimary suite with private bath, 42 flat screen TV and air conditioning. 2nd bedroom has a Queen size bed, 42 flat screen TV and air conditioning. brIn-law suite has 2 queen beds, 42 Flat screen TV, full bath, air conditioning and separate area with couch, and 50 Flat screen TV for watching or gaming.br*All 3 full baths have showers, no bathtub in home*

Away from it all, secluded getaway 1 mile from beach , 5 minutes to Town Center

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$397.14

. Escape to our cozy Cape Cod cottage in Chatham! This charming, eclectic retreat is perfect for couples, solo adventurer'sbrand small families. Harding's & Ridgevale beaches only a mile from the cottage. Features are a private patio, deck, outdoor enclosed shower, fire pit ,lots of flowers and birds.br A simple, shabby-chic getaway with modern comforts like Wi-Fibrand AC, just 3 miles from downtown Chatham. Your perfect beach vacation awaits.My partner Michael and I live in a separate cottage on the property and are available for any questions you may have otherwise we will respect your privacy . Having lived in Chatham for forty years I can make lots of recommendations of “must do” while you are here.

Quintessential Cape Cod Cottage

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$730.84

Very secluded 3br family friendly (pets considered) full Cape at the end of a cul-de-sac. Located in rural Stage Harbor section of Chatham this house allows our renters to adhere to the current Mass State Covid-19 Guidelines, while enjoying walking & biking attractions the backside of Chatham offers. A short walk to beautiful (dog friendly) Stage Harbor Beach, less than a mile from Chatham light house and downtown you are afforded many options during these challenging times.brbr* Longer stays are available and will be discounted appropriately and is currently activated on the listing. brbrLocated in the Historic Stage Harbor area of Chatham, minutes from beach, less then a mile from Chatham light house and downtown. House is situated on 1 acre of property at the end of a cul-de-sac with one side adjacent to conservation land, very quiet area. brbrTwo working fireplaces, full eat in kitchen with dining room and living room. One bedroom upstairs with King & Twin beds, second bedroom with Full & twin beds. Full bath on second floor, tons of closet space in both bedrooms. Master suite located on the 1st level with a King Size Tempur-Pedic bed, flat screen w/ cable & full bath. Plenty of closet space on both floors and a 1st floor laundry space.

Secluded Chatham Cape Cod House Stage Harbor Area

Chatham, Massachusetts, United States

3

Bed

Bath

6

Sleeps

$977.95

Summary:brbr16700 - The Wind Drifter: Waterfront Escape, Game Room, Dog Friendly!brbrbrbrThe Space:brbrThe Wind Drifter awaits your next Cape Cod escape. This spacious, waterfront home is convenient located in Chatham, MA, offering the perfect setting for a relaxing family getaway or a fun trip with friends, accommodating up to 12 guests.brbrStart your mornings with coffee on the back deck, taking in sweeping water views, with only the calls of shorebirds in the background. Inside, a bright, open kitchen flows seamlessly into the dining and living areas—perfect for gathering, sharing meals, and enjoying time together. Open the windows to enjoy fresh breezes off the water. The home features 6 bedrooms and 4 bathrooms with flexible sleeping arrangements designed for groups of all sizes. On the first floor, you’ll find a king bedroom with easy access to a nearby walk-in shower. Upstairs offers four additional bedrooms—including 3 queens, a kids room (with 2 twin trundle beds), while a private king suite above the garage provides extra space and privacy. brbrThe basement game room with a pool table is perfect for friendly competition or to catch up your favorite TV show on the 75 TV, while the deck invites cookouts on the grill or relaxed evenings dining al fresco under the Cape Cod sky. Unwind with s’mores by the wood fire pit or sip your favorite cocktail as the fire crackles and the sun sets. Lounge on any of the plush couches on the first floor and taken in the breathtaking water views, rain or shine.brbrLocated just a short drive (about 6 minutes) from Harding’s Beach and Ridgevale Beach—and with Lighthouse Beach also nearby—you’ll have easy access to some of Chatham’s most beloved spots. You’re also minutes away from local favorites like Mac’s Chatham Fish & Lobster, Del Mar Bar & Bistro, Mom & Pops Burgers, Hey Joe’s, and Jam Coffee Shop. Spend your days exploring charming downtown Chatham, browsing boutiques, visiting local museums, spotting seals at Chatham Fish Pier, or biking along the Cape Cod Rail Trail. For nature lovers, the Monomoy National Wildlife Refuge is a must.brbrWhether you’re here to reconnect, explore, or simply relax by the water, The Wind Drifter captures the essence of a perfect Cape Cod vacation. Book your stay and experience Chatham at its best.brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog) br-Sleeps 12brBedroomsbr-Total 6br-1st Floor Bedroom: 1 King Bed (ensuite)br-2nd Floor Bedroom: 1 Queen Bed br-2nd Floor Bedroom: 1 Queen Bedbr-2nd Floor Bedroom: 1 Queen Bedbr-2nd Floor Bedroom: 2 Twin Trundle Bedsbr2nd Floor Bedroom: 1 King Bed (ensuite)brBathroomsbr-Total 4br-1st Floor: Full Bathroom, Shower (ensuite to King Bed, 1st Floor)br-1st Floor: Full Bathroom, Showerbr-2nd Floor: Full Bathroom, Shower (ensuite to King Bed, 2nd Floor)br-2nd Floor: Full Bathroom, Shower/Tub CombobrOther Amenities br-Mini Split in dining roombr-Floor/Window Unit ACs in Bedroomsbr-Game Roombr-Pool Tablebr-WiFibr-Smart TV br-Washer/Dryer br-Propane Grillbr-Wood Fire Pitbr-Please note outdoor amenities are available seasonallybr-Please note there is a ring doorbell camera at the front door that faces the drivewaybr-Indoor Fireplaces are not for guest use (fines remitted)br-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-Parking for 5 cars maximumbr-C0579370550brbrbrbrOther Things to Note:brbrPlease note there is a ring doorbell camera at the front door that faces the driveway

Waterfront Escape, Game Room, Dog Friendly!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$1219.75

This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in the heart of Chatham, Cape Cod, Massachusetts. Fresh and new, the Townhouse also includes access to a swimming pool and tennis courts. brbrThis beautiful Townhome can also be rented and combined with Oyster Pond Townhome 31 for approximately 4,250 SF of living space. For prices and availability contact owner directly. brbrTownhome 32 features a well-appointed master bedroom with king bed. Spacious master balcony has a spectacular water view. The additional bedroom has two full beds and a private bath. The twin bedroom also has an amazing loft that can sleep additional people in two twin beds (children love it!). The den has a queen sleeper sofa. Boasts a fully-equipped kitchen and living room with TV/DVD.brbrBeautiful ground floor sun-room has incredible views and a large wrap-around brick patio, complete with expansive water views, a great gas barbecue grill, chaise lounges, tables, and plenty of chairs. Perfect for eating/entertaining outdoors. Convenient washer/dryer is inside the unit.brbr See other units we have available: VRBO #3926813 and #4208842brbrThis picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in the heart of Chatham, Cape Cod, Massachusetts. Fresh and new, the Townhome also includes access to a swimming pool and tennis courts. brbrTownhome 31 features a well-appointed master bedroom with king bed. Second bedroom has 2 full beds. An amazing loft has an additional two twin beds, plus a beautiful den has a Queen Sleeper sofa. Ideal for two or four people, and can accommodate up to eight people when using lofts. Also boasts a fully-equipped kitchen and water views. Beautifully decorated with charming interior decor.brbrEach has picturesque views of Oyster Pond and plenty of open space. Townhome 31 may be rented with Townhome 32 for approximately 4,250 SF of living area (contact Owner for more details).brbrOyster Pond Condominium Complex includes free tennis court, swimming pool, shuffle board, acres of lawn for kite flying, playing catch, and family fun. Wide range of excellent nearby restaurants from super casual on up. Restaurant listings available as are brochures on activities for adults and kids. All summer take your family to the famous Chatham Band Concert, Cape League baseball, and Summer Theatre. Sightseeing, whale watching, seals, cycling, beaches, golf, movies are all nearby. Small kids activities in Chatham also include a huge playground and a train museum, both right near a real fire station. Oyster Pond’s great location is nearby Chatham Main Street’s strolling and shopping.brbrConvenient walk to downtown Chatham location. Close to Atlantic Ocean, Nantucket Sound and Oyster Pond beaches, as well as golf and all the best Cape Cod has to offer.brbrBring your canoe, kayak or Sunfish and use private dock on Oyster Pond providing access to the pond, Oyster River, Stage Harbor, Nantucket Sound, South beach, Monomoy Island and the Atlantic Ocean. Nearby Oyster River Boatyard offers power boat rentals.brbrAmenities include: Heated swimming pool, tennis; shuffleboard, patios, fully appointed kitchens, washer & dryer, gas grill, cable TV, full central air conditioning and heating, wireless internet, and morebrbr See other units we have available: VRBO #3926813 and #4209584 brbrTown of Chatham permit STR-325.

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

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$529.23

No need to drive into Town-- this home is located right in the heart of the Town's activities, Chatham Angler ballgames, Town playground and Oyster Pond Beach Area. Oyster Pond Beach is a saltwater inlet with sandy beach, bathhouse and lifeguards - one mile from the house. Head over to the Chatham Fish Pier and watch the fishing boats come in or buy fresh seafood or a meal - only 7/10's of a mile away.brbrThis immaculate three bedroom/two bath home is perfect for you; quaint little neighborhood on a quiet side street with a great location. brbrThe property is light, bright and spacious and boasts a master bedroom with a comfortable Queen size bed and flat screen television. Second Bedroom has two Double Beds and the Third Bedroom has a Bunkbed with Double on the bottom and Twin bed on top. There are two baths one with tub and shower and the other has a shower only. Bath with tub/shower was recently updated.brbrProperty offers wireless internet and expanded cable. The enclosed outdoor shower is perfect at the end of a hot summer day. If that doesn't cool you down, be sure to enjoy the four window unit air conditioners throughout the house. There is a combined open dining room, living room and sunlit kitchen which overlooks the deck, gas grill and backyard, perfect for outdoor games and barbecues. You'll find the property is also nicely furnished and very comfortable. brbr* Additional fees:br- $220 non-refundable reservation fee br-Damage Protection Fee - $30br-Guest Services Fee - 3.5%br- Cleaning Fee - $280br- All applicable taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO SMOKINGbr* OCCUPANCY: 7 (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.

THREE BEDROOM -- SHORT DISTANCE TO TOWN, FISH PIER AND OYSTER POND BEACH.

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$1214.32

Amazing views! Enjoy the views of Pleasant Bay out to the ocean and the Outer Beach! This 4 bedroom 3 bath home is spacious and comfortable. Open kitchen and sitting area for family to enjoy together.A beautiful patio overlooking the water for coffee in the morning or sunset watching in the evening, as well as a deck off of the main level primary bedroom. There is water and beach access directly from the house, as well as access to the private association beach which is a 5 minute walk. Mini-Split ACs. 2 kayaks available for usebrbrThe house is located in a private association at the and of quiet street.

North Chatham Waterfront Oasis

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$917.36

Perfect vacation spot. Enjoy your vacation on this 3 bedroom 2 bath, Central air conditioned house bordering Emery Lake. Beautiful views of the pond and adjacent cranberry farm. Enjoy the pond for kayaking, swimming, and fishing(2 kayaks are provided). Relax on the 40' deck facing the pond and barbecue on Weber stainless steel grill. Inside the house, there are two 65, 4K TV's, one on each floor with multi channel cable and Wi Fi, a competition quality Ping Pong table, PS4 Pro for gaming and entertainment, and variety of old fashioned board games. There are two bedrooms on upper floor each with a queen size bed and a family room and kitchen and a full bathroom. On the lower floor, there is a bedroom with queen size bed, a family room with a sectional and sleeping couch, a full bathroom, and a den with sleeping coach. Both floors have sliding doors to outside with views of the pond. Two bedrooms have water views and one bedroom has cranberry farm views.brYou can walk, bike, or drive a few minutes to all the attraction Chatham has to offer.The house is only 1.5 mile to town center (mostly side walks) for shopping, restaurants, galleries, etc. It is a short walk away from the Cape Cod Biking Trail. Oyster Pond Beach is about 1.5 miles away. Other beaches including Light House Beach, Harding Beach, Ridge vale beach are about 2.7 miles away.

CHATHAM WATER FRONT/VIEW HOUSE FIRST TIME RENTAL

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$2975.62

This property is professionally managed by Pretty Picky PropertiesbrbrSleeps 16brEight Bedrooms, Nine BathsbrRents Friday to Friday during Peak SeasonbrLinens Included, beds madebrPool is open from Memorial Day through Columbus Day weekendbrbrThis totally renovated former Bed & Breakfast, known as the Chatham Gables Inn, brings a new level of luxury and comfort to a Chatham vacation for your group of up to 16. brbrNot that you will ever feel the need to leave the property, but should you choose to venture out, it's good to know you're close to everything you love about Chatham. Bring or rent bikes! That's all you'll need with so much, so close. Bike five minutes to Lighthouse Beach, Chatham's biggest and best. Or ride two minutes to Oyster Pond Beach (aka Children's Beach), a smaller, more sheltered beach. Or walk down to the Chatham Pier Fish Market, where you can take home the catch of the day, fresh off the boat. And it's only a few-minutes' walk to Main Street, Chatham Village, for shops, restaurants, galleries, concerts, Cape League baseball, playground, tennis courts, ice cream parlors and much more.brbrThe 4,200+ square foot house presents the perfect intersection of classic New England charm and leading-edge creature comforts and convenience. Exposed beam ceilings, heated wide plank wood floors and tasteful choices of furnishings, fabrics, paint and wallpaper all combine to create a one-of-a-kind living experience. The home's centerpiece is the gleaming white farmhouse kitchen with its expansive center island with second sink. All appliances are new and commercial grade. The kitchen flows into the charming conservatory, which in turn, opens to the patio beyond.brbrYour outdoor living will, of course, center on the beautiful, heated pool and adjacent hot tub. There is also a gas fueled fire pit, so your outdoor pleasure extends beyond sunset. The gas grill lives out here, as well, and you're likely to prepare and serve most meals using the outdoor kitchen-area and patio dining table and chairs.brbrThis home offers multiple inviting lounge areas, each as comfortable and appealing as the next. Sleeping accommodations include eight bedrooms, each with its own name such as “Surfside,” “Nantucket” or “Great Point.' Each has bedding for two. There are five kings, one queen and two bedrooms each with two twins. Each bedroom has its own private full bath en suite, and each has a smart TV. brbrThe lower level includes an oversized laundry with two washers and two dryers plus an additional refrigerator. And to complete its resort-like amenities, there is a game room down here as well. There is cable/smart TV and high-speed Wi-Fi, of course.brbrThe home is cooled via an ultra quiet system, which allows customized climate control for each bedroom. It also features Lutron Lighting® allowing guests to automatically or manually adjust the level and even the color of the LED light to create the ideal environment for any living space.brbrPlease enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%.brbrBe sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod.brbrIt's your vacation. Get Picky! ®brbrTown of Chatham Registration #152

The Gables: 364-C Chatham Resort Style Estate with Heated Pool, Close to Everything

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$1272.75

Located in quiet Riverbay neighborhood. This 5 bedroom, 4 bath home that sleeps 10. Plenty of room to spread out with a living room, and a family room and entertainment downstairs. The main floor has a king bedroom, queen and 2 twins with 2 full baths. Upstairs there is a queen bed and 2 twins with a full bath. Slimline units are in each of these bedrooms. The finished basement has a full entertainment center for the kids to enjoy and watch tv. Enjoy the outdoor space with the large expansive deck. Tenants can access the river via the conservation commission path offered where you can put the kayaks in and go to Pleasant Bay. Shower in the enclosed outdoor shower after a day at the beach. Dog friendly too! 1 dog allowed. Ask your agent for details-$150 fee will apply. Welcome bag included-reusable tote with paper and cleaning products compliments of the owner. Call us at Chatham Rentals and let us help you plan your stay.

Located in quiet Riverbay directly on the river; kayak to Jackknife Beach

Chatham, Massachusetts, United States

5

Bed

4

Bath

10

Sleeps

$761.51

Sparkling Updated Home With Wonderful Views of Oyster River and Stetson Cove brbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrThis spacious, immaculate home boasts a large kitchen with double ovens and updated stainless steel appliances. You'll also enjoy the enclosed outdoor shower, central air conditioning, and queen size futon in the family room. This rental is nicely furnished and quite comfortable with lots of living space. House has open floor plan in the living room/dining space/kitchen; the living room and family room offer extra living spaces as well. Two cable televisions available in alcove off the living room and second floor family room area. You'll find it is very light and bright with all of the comforts of home. This home offers a first floor laundry room, wireless internet, as well as a peaceful setting on quiet side street in the Stage Neck area. brbrThere are two bedrooms on the first floor, one with a king bed with doors that access the back yard area. The second bedroom across the hall has two twin beds. There is a shared bath with tub and shower on the first floor. On the second floor there is a bedroom with a queen that overlooks the back yard with views of Stetson Cove and another bedroom with two twin beds. There is another shared bath with tub and shower located on the second floor.brbrThe setting is serene as you sit out on the patio and enjoy the lovely water views of Stetson Cove; and another added plus, it is just 1.5 miles to town and Oyster Pond beach with sandy beach, bathhouse, lifeguard and parking. brbrBedroom #1 - King, Bedroom #2 - Two Twins, Bedroom #3 - Queen, Bedroom #4 - Two Twinsbrbr* Additional fees:br- $175 non-refundable reservation fee (no security deposit required)br- Cleaning Fee - $350br- All applicable taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO SMOKINGbr* 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.

WATER VIEW OF STETSON COVE! UPDATED HOME WITH SO MUCH TO OFFER!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$466.57

This inviting South Chatham home offers a comfortable and convenient setting for a classic Cape Cod getaway. Located in a peaceful residential area, the property provides easy access to Chatham’s beautiful beaches, scenic shoreline, and charming downtown filled with local shops, restaurants, and summer activities.brbrInside, the home is thoughtfully arranged to accommodate families or small groups. The primary bedroom features a king bed, while two additional bedrooms each offer two twin beds, ideal for kids or flexible sleeping arrangements. Two full bathrooms ensure convenience for everyone during your stay.brbrThe main living space is designed for relaxation, with a comfortable living room centered around a 40 TV. The fully equipped kitchen makes it easy to prepare meals at home, whether you're cooking a fresh seafood dinner or enjoying a casual breakfast before heading out for the day. A lobster pot is included for those looking to experience a true Cape Cod tradition.brbrStep outside and enjoy the home’s spacious backyard, perfect for yard games, outdoor dining, or simply unwinding after a day at the beach. The deck and gas grill create an ideal setup for summer evenings, and the outdoor shower makes rinsing off after sandy beach days quick and easy.brbrWith central air conditioning, a large yard, and a location that keeps you close to everything Chatham has to offer, this home continues to be a great choice for a relaxed and memorable stay on Cape Cod.brbrDriveway parking is available for two vehicles. Administrative fees and applicable taxes may apply. Linens are not provided; guests may bring their own or arrange for a rental.brbrAmenities Include:brCentral air conditioning, WiFi, washer and dryer, fully equipped kitchen, dishwasher, microwave, coffee maker, toaster oven, television, deck with furniture, gas grill, outdoor shower, and private yard.brbrNo pets allowed.

Cozy Retreat in South Chatham (2374)

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$646.08

Chatham retreat CLOSE to EVERYTHING, walk to CBI, fish pier, town, baseball field etc.brCompletely remodeled to perfection with a new kitchen, bathroom and Central Air along with furnishings by Serena & Lily and a Sonos entertainment system. brPlus 4 additional beds in the lower level. Outdoor gas fire pit and built in BBQ for easy entertaining and outdoor shower. 2 full bedrooms with a king and queen size bed along with a completely finished lower level with 4 additional beds.

Pristine Chatham home walkable to town, CBI, Fish Pier and baseball field

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$768.83

Get ready to relax in this 3-bedroom riverfront property featuring a 7-person hot tub and expansive deck. With water views and private access to the Monomoy River (aka Muddy Creek), guests can enjoy the riverside fire pit or take a paddle in the kayak or canoe up river to Pleasant Bay. Set in a quiet neighborhood, this house is perfect for a family or friend group looking for a peaceful vacation. With amenities like central A/C, washer/dryer, gas grill, WiFi, and the best outdoor shower in Chatham, guests can enjoy a comfortable stay after a day at the beach. The principle bedroom has a private deck and private 3/4 bathroom, and the other two bedrooms share a full bathroom. Our place is equipped for both long or short stays to make your vacation one to remember.

Cozy Riverfront retreat w hot tub, deck, fire pit. Kayak to Pleasant Bay!

Chatham, Massachusetts, United States

3

Bed

Bath

6

Sleeps

$759.73

Experience a true Cape Cod getaway in this charming coastal home, perfectly set on the tranquil waters of Taylor’s Pond. Step out onto the spacious, water-facing deck to enjoy morning coffee or watch the sunset over the pond, or take advantage of direct pond access for kayaking or paddleboarding. After a day at the beach, rinse off in the refreshing outdoor shower.brbrJust a short 1/3 mile brings you to Cockle Cove Beach or chose the wooded path near the home to access the private association beach. You’ll find restaurants, shopping, dining, and fishing just moments away. Experience everything that makes Chatham so special moments from your doorstep.brbrInside, the home is bright and welcoming, with an open-concept layout that showcases the pond views throughout. The shiplap kitchen blends classic coastal charm with modern convenience, complete with a breakfast bar for four. Adjacent, the dining area seats eight and opens seamlessly to a comfortable family room, all offering serene water views.brbrThe primary bedroom features a queen bed and a private en suite bath with a tub/shower combination. Two additional bedrooms on this level (one with a queen and one with two twins) share a full bath with tub/shower combo. Downstairs, a waterfront bedroom with two twin beds opens via sliding glass doors directly to the backyard, creating a peaceful retreat for guests. A washer and dryer on this level add convenience, and driveway parking for three cars makes coming and going easy.brbrShort getaways available with an added cleaning fee. Save the cleaning fee by booking 7 or more consecutive days. brDogs considered with added fee. An administrative fee and applicable taxes may apply. Linens are not provided. Guests may either bring their own or rent linens.

Waterfront Home Overlooking Taylor's pond (2417)

Chatham, Massachusetts, United States

4

Bed

Bath

8

Sleeps

$547.46

Breezes and Views on Oyster River! Relax in the sun and enjoy the views of the water from the deck of this quintessential 4 bedroom home. Watch boats sail by and sunsets fall from this lovely spot in Chatham. Walk down your private stairs to the water's edge and go kayaking or rent a slip at the Oyster River Marina and bring your own boat. Window A/C units in all of the bedrooms, WiFi and flat screen TV keeps you connected. Dog friendly $100 fee will be added to the lease.

Pet Friendly Waterfront Overlooking Oyster River

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$1115.89

This is a 5* Exceptional property but all its past reviews did not convey when it was recently relisted. Highwood Cottage is an owner-managed home offering lovely outdoor amenities such as a large yard for outdoor activities, a coveted private beach shared with 3 other families at the end of the street (a short walk (not the 11 minutes that the headline says on listing), and a beautiful neighborhood with water views all around for unforgettable morning / evening walks. This part of Chatham is the most sought after neighborhood of all, offering privacy, elegant homes and just the perfect summer feel. A coffee shop, post office and restaurants are within walking distance, and Chatham's famous downtown is a straight shot down Old Harbor Road. Enjoy cooking out in the evening, eating on the screened porch or at the large dining table if it is misty out. Making memories is easy here at Highwood Cottage.

Private Beach, Beautiful Location, Well-Behaved Pet Friendly

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$501.59

Summary:brbr16674 - Heatherwood Haven: Large Home w/ Fire Pit and Dogs Welcome!brbrbrbrThe Space:brbrEscape to Chatham, where bayside beaches are ready for your sunbathing and saltwater swims this summer. brbrBring the whole family, pup included, to Heatherwood Haven, a charming split level home. Pushing open the front door, you’re greeted by the home’s ground floor living room, a great spot for a late night movie or card games on the card table towards the back of the room. Head upstairs to the home’s TV room, complete with wall-mounted TV and vaulted ceilings, or whip up something to eat in the kitchen, just adjacent to the living room and dining room. brbrWhen it’s time to retire for the night, choose one of four bedrooms in this sleeps 10 home. Split evenly between both floors, you will find the primary bedroom with king bed and a second bedroom with queen bed on the first floor, while the remaining two bedrooms can be found on the ground floor, one with a queen bed and the final bedroom housing two full size beds. brbrOutside, the entertainment options of this incredible home continue. Eat under the stars on the back deck, or enjoy some s’mores around the fire pit as you watch your pup run around the spacious backyard. New hardscaping and landscaping will be completed for the 2025 rental season. Other amenities include a washer and dryer, propane grill, and an outdoor shower. This home is also 0.7 miles from Goose Pond! With plenty of space, an incredible location, and no shortage of entertainment options Heatherwood Haven has something for everyone. brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 10br-Floors (1st Floor + Ground Floor)br-1,764 sq. ft. br-4 Bedroomsbr-1st Floor Bedroom: 1 King Bedbr-1st Floor Bedroom: 1 Queen Bedbr-Ground Floor Bedroom: 1 Queen Bedbr-Ground Floor Bedroom: 2 Full BedsbrBathroomsbr-Total 3br-1st Floor: Shower/ Tub Combobr-Ground Floor: Showerbr-Ground Floor: Shower/ Tub Combobr-Fully Equipped Kitchenbr-Mini-Split A/Cbr-Smart Lock/Self Check-Inbr-WiFibr-Smart TVbr-Propane Grillbr-Deck with Outdoor Diningbr-Outdoor Showerbr-Fire Pitbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0294290550brbrbrbrThe Neighborhood:brbrOceanside

Large Home w/ Fire Pit and Dogs Welcome!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$599.05

Welcome to your serene waterfront retreat on Taylors Pond, offering direct access to Cockle Cove and the vast expanse of the Atlantic Ocean. This two-story abode boasts unparalleled water views from both floors, each adorned with expansive decks perfect for soaking in the coastal ambiance. The top floor welcomes you with a charming walk-through kitchen, leading seamlessly to a cozy family room complete with a TV for relaxing evenings in. Adjacent is a spacious dining area, ideal for enjoying meals with loved ones while overlooking the tranquil waters. A full bath and a queen-sized bedroom complete this level, providing comfort and convenience.brbrDescending to the lower floor, you'll find a captivating game room facing the water, featuring a ping pong table and a cozy sitting area for entertainment and relaxation. Additional sleeping accommodations are provided by bunk beds, ensuring ample space for family and guests. Two more bedrooms offer cozy retreats, while another full bath and a washer-dryer setup add practicality to your stay. After a day of coastal adventures, rinse off in the outdoor shower before settling in for a peaceful evening.brbrOutside, a private dock awaits, perfect for launching paddle sports or simply enjoying the mesmerizing views. With saltwater just steps away, aquatic adventures abound, while proximity to Cockle Cove Beach and Ridgevale Beach ensures endless days of seaside bliss. Situated minutes from downtown Chatham and Harwich, you'll have easy access to shopping, dining, and entertainment. Parking for two cars in the driveway ensures convenience for your coastal escapes. Whether you're seeking relaxation or adventure, This idyllic renal home offers the perfect setting for your Cape Cod getaway. 3 night minimums available! Dogs considered for an added fee. BOOK NOW!!! An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

Waterfront Home With Dock and Two Water Facing Decks! (2372)

Chatham, Massachusetts, United States

3

Bed