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From $525 per night (USD)
VRBO
BOATHOUSE on Pleasant Bay - swim, fish, kayak, etc. right off your front porch.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Like living on a yacht without the rocking - originally built to house boats, the Boathouse is cozy like a ship with wat ...
From $525 per night (USD)
VRBO
From $566 per night (USD)
Expedia
Charming Chatham Abode with Sunroom!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 16686 - Chatham Life: Charming Chatham Abode with Sunroom! The Space: Embark on a journey into the quintessent ...
From $566 per night (USD)
Expedia
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VRBO
Bright, sunny condo in North Chatham!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This two bedroom two bathroom sunny condo is located in the quiet neighborhood of North Chatham. A 10 minute bike ride t ...
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VRBO
From $816 per night (USD)
Expedia
Walk to Oyster Pond and Main Street Chatham!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: 16687 - Starboard Stay: Walk to Oyster Pond and Main Street Chatham! The Space: Just a steps from the tranquil ...
From $816 per night (USD)
Expedia
From $2113 per night (USD)
VRBO
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
About this space Welcome to a beautiful Coastal retreat! — a spacious seaside escape perfect for families or groups. St ...
From $2113 per night (USD)
VRBO
From $643 per night (USD)
VRBO
Walk to downtown Chatham!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your Chatham adventure begins at this lovely 3-bedroom house. With 2 queen beds and 1 full bed, it's the perfect retreat ...
From $643 per night (USD)
VRBO
From $826 per night (USD)
VRBO
Walk to Downtown Chatham, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: 16688: Sand Bar - Walk to Downtown Chatham, Steps to Beach! The Space: Introducing Sand Bar: Your Private Have ...
From $826 per night (USD)
VRBO
From $529 per night (USD)
Expedia
Waterfront Home With Dock and Two Water Facing Decks! (2372)
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your serene waterfront retreat on Taylors Pond, offering direct access to Cockle Cove and the vast expanse of ...
From $529 per night (USD)
Expedia
From $422 per night (USD)
VRBO
Beach Bag Ready & Friday to Friday Rental!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
FRIDAY TO FRIDAY RENTAL.... Cozy beach house sleeps 9 with 4 bedrooms (2 queen, double, 2 twins) and 2 baths, hardwood f ...
From $422 per night (USD)
VRBO
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Expedia
Cottage on freshwater lake with short walk to town beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Our three bedroom 1 bathroom cottage was completely renovated in 2019. A beautiful 4 acre private property with a short ...
Click For Pricing
Expedia
From $318 per night (USD)
VRBO
Water-view house near golf with firepit, grill, deck, central AC & washer/dryer
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Chatham Charmer Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $318 per night (USD)
VRBO
From $579 per night (USD)
Expedia
Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Stunning 4-Bedroom Oasis in a great location with Pool, Hot tub, and outdoor kitchen.. Your comfort and enjoyment are ...
From $579 per night (USD)
Expedia
From $665 per night (USD)
VRBO
Stunning Marsh Views, Near Pleasant Street Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16689: Lady Slipper - Stunning Marsh Views, Near Pleasant St. Beach! The Space: Nestled in the serene enclave ...
From $665 per night (USD)
VRBO
From $678 per night (USD)
Expedia
A short drive brings you to Jackknife Cove!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy your vacation at this charming and cozy, 3 bedroom, 2 bath home. Offering 2 queens, 2 twins, and a king. Enjoy you ...
From $678 per night (USD)
Expedia
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VRBO
Peaceful Patio near Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Great for two families and near Ridgevale Beach! This house is located in a quiet neighborhood on a cul-du-sac. A perf ...
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VRBO
From $1022 per night (USD)
VRBO
Renovated Chatham Compound on Bike Path, Less Than a Mile to the Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
This newly designed charming Chatham compound can sleep over 10 guests with 2 bedrooms in the main house, 2 bedrooms in ...
From $1022 per night (USD)
VRBO
From $535 per night (USD)
VRBO
Cozy Chatham Getaway- minutes to all things Cape Cod- New listing!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to your perfect beach getaway in beautiful Chatham! This charming four-bedroom, two-bathroom cottage is just 2 m ...
From $535 per night (USD)
VRBO
From $513 per night (USD)
Expedia
Brand New Four Bedroom Home Near Beach and Town
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Brand new 4 bedroom, 2 bath North Chatham home near town and beach. On the first floor, the home boasts a designer kitch ...
From $513 per night (USD)
Expedia
From $629 per night (USD)
VRBO
Chatham Cape Cod Retreat, near boat yards, Harding's Beach, Stage Harbor Light
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
This modern Chatham home, filled with books and art, and surrounded by nature, is a peaceful retreat for those who appre ...
From $629 per night (USD)
VRBO
From $1259 per night (USD)
VRBO
Private Beach, Beautiful Neighborhood, Well-Behaved Pet Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
The perfect spot, offering lovely outdoor amenities such as a large, beautiful hedged yard for outdoor activities, a cov ...
From $1259 per night (USD)
VRBO
From $1277 per night (USD)
VRBO
Private Beach, Beautiful Location, Well-Behaved Pet Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This is a 5* "Exceptional" property but all its past reviews did not convey when it was recently relisted. Highwood Co ...
From $1277 per night (USD)
VRBO
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Expedia
3 Bedroom Sea-Side Cottage w/ Beach Access RPAM083
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled at the end of Little Beach Road in Chatham, this charming 3-bedroom, 2-bathroom cottage invites you to indulge i ...
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Expedia
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VRBO
2 Bedroom Sea-Side Cottage w/ Beach Access RPAM085
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled at the end of Little Beach Road in Chatham, this charming 2-bedroom, 1-bathroom cottage invites you to indulge i ...
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VRBO
From $412 per night (USD)
Expedia
Charming house with patio, Washer/Dryer, & central location
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Dreamcatcher Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $412 per night (USD)
Expedia
From $537 per night (USD)
VRBO
Beautiful Chatham, Sun Sand & Surf. 8/10 mile to beaches ,pet friendly home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Island view is a beautiful Chatham beach house Located in a quite cul- de- sac , think about the warm tranquil mornings ...
From $537 per night (USD)
VRBO
From $907 per night (USD)
Expedia
Slow M'Ocean – A Fresh Take on Cape Calm
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
3 Bedroom - 3.5 Baths - Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $907 per night (USD)
Expedia
From $605 per night (USD)
VRBO
Rhododendron Cottage – Walk to Cockle Cove
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedroom - 2 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $605 per night (USD)
VRBO
From $605 per night (USD)
VRBO
Downtown Chatham Luxurious & Spacious Condo w/ Roof Deck - Close to Oyster Pond
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy easy access to everything from this centrally located condo in the heart of downtown Chatham. This luxury condo is ...
From $605 per night (USD)
VRBO
From $293 per night (USD)
VRBO
Dog-Friendly Cape Cottage Near Beach & Towns
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
2 Bedroom - 2 Baths - Sleeps 5 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $293 per night (USD)
VRBO
From $409 per night (USD)
Expedia
Cape Cod Cottage Near Beaches & Bike Trail
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Summary: Welcome to Harwich—your ideal Cape Cod getaway. This delightful home sleeps 6 and features 4 bedrooms: 2 with q ...
From $409 per night (USD)
Expedia
From $514 per night (USD)
VRBO
Poppy's Place: Cape Escape for Family & Friends
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
3 Bedroom - 3 Bath - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $514 per night (USD)
VRBO
From $979 per night (USD)
Expedia
Coastal Escape: Steps to Red River Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
4 Bedroom - 3 Baths - Sleeps 10 Complimentary Linens Service Provided: This includes bedsheets, bath, beach, and dish to ...
From $979 per night (USD)
Expedia
From $807 per night (USD)
VRBO
Chatham Shenanigans, Chatham Shenanigans
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Experience the beauty of Cape Cod at Chatham Shenanigans. This beautiful, well-appointed, bright home is centrally locat ...
From $807 per night (USD)
VRBO
From $699 per night (USD)
Expedia
Saltaire: Coastal Getaway Near Hardings Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 Bedroom - 2 Baths - Sleeps 6 During peak summer weeks, our properties typically require a 7-night stay, either Friday- ...
From $699 per night (USD)
Expedia
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VRBO
3-bedroom house in charming Chatham with WiFi, fitness room, AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This 3-bedroom house in Chatham is perfect for your escape to relaxation. With 1 king bed, 1 queen bed, and 4 twin beds, ...
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VRBO
From $419 per night (USD)
Expedia
“Mermaid’s Rest” Quiet South Chatham 2-Bedroom House, Close To Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
“Mermaid’s Rest” is a well kept 2 bedroom Chatham home just a short drive from popular Rigdevale, Cockle Cove, and Hardi ...
From $419 per night (USD)
Expedia
From $1488 per night (USD)
VRBO
Waterfront, Updated 4 Bedroom Home with Views of Stage Harbor & Nantucket Sound
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Recently updated waterfront home overlooking Snake River, Stage Harbor & Nantucket Sound on Stage Island. 4+ bedroom, 3 ...
From $1488 per night (USD)
VRBO
From $739 per night (USD)
VRBO
New 2025 Chatham Hideaway - Peaceful Woodland Overlooking Minister's Pond
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Welcome to Chatham Hideaway! This sprawling estate, surrounded by woodland and lush gardens, offers a private setting fo ...
From $739 per night (USD)
VRBO
From $609 per night (USD)
VRBO
Summerwind - Ocean views and walk to beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Beautiful well maintained home with fabulous views of Nantucket Sound and a short walk from driveway to beach. ...
From $609 per night (USD)
VRBO
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Expedia
Chatham Gem with Pool & High-End Style RPAM104
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
NEW FOR THE 2025 SEASON! Welcome to your perfect Cape Cod getaway in the heart of Chatham! This stunning 4-bedroom, 3.5- ...
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Expedia
From $409 per night (USD)
VRBO
Secluded, Walk to Rail Trail, Dog-Friendly Oasis
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Escape to a secluded Cape Cod oasis we call the Hidden Hollow. This beautiful, family-friendly home features a cozy fire ...
From $409 per night (USD)
VRBO
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Expedia
Charming Guest House, with Waterviews & Private Beach! Perfect for Fun Weekends!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in South Orleans, this pet-friendly sun-filled Guest House offers 2 large bedrooms and 2 full baths. Located in ...
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Expedia
From $466 per night (USD)
VRBO
Cozy Retreat in South Chatham (2374)
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our cozy single-family home located in beautiful South Chatham. This property features 3 comfortable bedrooms ...
From $466 per night (USD)
VRBO
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Expedia
Perfect beach house to spend your summer days in!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Experience your summer vacation in this bright and airy 2-bedroom, 3-bath beach house. It features two queen bedrooms up ...
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Expedia
From $1678 per night (USD)
VRBO
Rambling 9 bedroom within walking distance to Red River Beach.
Bedrooms:
6
Bathrooms:
9
Sleeps:
14
Rambling 9 bedroom, updated home with layout flexibility (3 living rooms, 2 kitchens!). Perfect for families traveling t ...
From $1678 per night (USD)
VRBO
From $595 per night (USD)
Expedia
Nautical Comfort near Rail Trail
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Modern nautical-themed decor abounds in this newly renovated, freshly painted Cape located in West Chatham. On a quiet ...
From $595 per night (USD)
Expedia
From $890 per night (USD)
VRBO
Steps to Red River Beach!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Steps to Red River Beach, a lifeguarded, groomed sand beach with restrooms and food trucks! Enjoy long walks, sunbathing ...
From $890 per night (USD)
VRBO
From $695 per night (USD)
VRBO
Downtown Chatham Family Retreat - Spacious Deck, Games & Firepit - Walk to town
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Your family or group of friends will be close to everything when you stay at this centrally-located home. This cozy home ...
From $695 per night (USD)
VRBO
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VRBO
Cozy cottage in delightful country side neighborhood!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this cozy three-bedroom, two-bath cottage nestled in a peaceful countryside neighborhood. With central air, hi ...
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VRBO
From $680 per night (USD)
Expedia
Woods Edge: Walk to Red River Beach, Pet Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 Bedrooms - 2 Baths - Sleeps 6 During peak summer weeks, our properties typically require a 7-night stay, either Friday ...
From $680 per night (USD)
Expedia
From $267 per night (USD)
VRBO
Charming 2 bedroom condo on Private Beach by Outer Most Marina
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Get ready to relax in this 2-bedroom townhome in Chatham. This awesome property features 2 queen beds and 1 twin bed, pe ...
From $267 per night (USD)
VRBO
From $713 per night (USD)
Expedia
Beautiful house that is a walk to downtown!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This quiet, charming home is in a highly sought-after location. You can leave your car parked and walk to breakfast, Oys ...
From $713 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Half Mile Walk to Beach, Dog Friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: 16691 - Seaside: Half Mile Walk to Beach, Dog Friendly! The Space: Located in the coveted Ridgevale Beach area ...
From $368 per night (USD)
VRBO
From $521 per night (USD)
Expedia
Walk to Beach, Private Patio and Backyard!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: 16690 - Chatham Haven: Walk to Beach, Private Patio and Backyard! The Space: Discover the charm of Chatham at ...
From $521 per night (USD)
Expedia
From $419 per night (USD)
VRBO
Minutes to Red River Beach, Dog Friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 17755 - Deer Run Hideaway: Minutes to Red River Beach, Dog Friendly! The Space: Welcome to Deer Run Hideaway, ...
From $419 per night (USD)
VRBO
From $512 per night (USD)
Expedia
HarwichPort 4 bdr 3 bath - Walk to Red River Beach - next to Wychmere
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Amazing family vacation house! All 5-star reviews! Comes with all linens, towels! 0.3 mi walk to Red River Beach! Short ...
From $512 per night (USD)
Expedia
From $307 per night (USD)
VRBO
Charming 3-bedroom house in fabulous Harwich 1 mile from Red River Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Consider this house your home away from home while you visit Harwich. With 3 bedrooms, 2 bathrooms, and essential amenit ...
From $307 per night (USD)
VRBO
From $751 per night (USD)
VRBO
Marsh and Nantucket Sound Views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
PETS ALLOWED WITH OWNER APPROVAL If you love the beach, views of the water and a beautiful home with every amenity, ...
From $751 per night (USD)
VRBO
From $3161 per night (USD)
VRBO
New for 2025! Lovely home with heated pool, dock and the best views! RPMS158
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Michelle Sylvia coastal collection. Nestled on its own exclusive point within the private Stage Island enclave, this ...
From $3161 per night (USD)
VRBO
From $571 per night (USD)
Expedia
Chatterbox: 032-CB Chatham Charm in the Heart of Town
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This property is professionally managed by Pretty Picky Properties Chatham Charm in the Heart of Town NEW Listing for ...
From $571 per night (USD)
Expedia
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VRBO
Great Location Steps to Chatham Lighthouse & Town
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Stunning four-bedroom home located in the heart of Chatham...tucked away in the Old Village section of town, you can w ...
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VRBO
From $726 per night (USD)
VRBO
4-bedroom house in charming Chatham steps from Main Street and the Mill Pond
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Nestled in Chatham, this charming house offers 4 bedrooms - 2 queen beds, 1 full bed, and 1 twin bed. With 2.5 bathrooms ...
From $726 per night (USD)
VRBO
From $682 per night (USD)
VRBO
3BR - Large Yard and Patio, Near Beaches
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Location: Located on a dead-end road near the head of Pleasant Bay. This 3 bedroom home offers a large fenced in yard wi ...
From $682 per night (USD)
VRBO
From $921 per night (USD)
Expedia
Malabar: 407-CB Chatham Charm, Walk to Beach and Town
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
This property is professionally managed by Pretty Picky Properties. Chatham Charm, Walk to Beach and Town NEW Listing ...
From $921 per night (USD)
Expedia
From $988 per night (USD)
VRBO
Cape Escape: 048-CS Luxurious Chatham Home with Expansive Water Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties Luxurious Chatham Home with Expansive Water Views S ...
From $988 per night (USD)
VRBO
From $619 per night (USD)
VRBO
Beautifully Renovated Cape Cod Retreat near Pleasant Bay & Top Attractions
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
*Cancellation policy at end of property description.* Nestled in the picturesque town of Harwich, Mooncusser is a beau ...
From $619 per night (USD)
VRBO
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VRBO
Coastal Comfort at Red River Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Experience the warm sand, cool waters, and coral-colored sunsets with a walk to Red River Beach! This beautifully update ...
Click For Pricing
VRBO
From $332 per night (USD)
Expedia
NEW 2025! Family friendly cabin in Harwich, water peek & walk to private beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Located in a quiet, walkable neighborhood, this one floor, three-bedroom two bath home is a five-minute stroll from two ...
From $332 per night (USD)
Expedia
From $487 per night (USD)
VRBO
Pool, Half Mile to Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Summary: 17759 - Blue Lagoon: Pool, Half Mile to Beach! The Space: Perched atop a hill, this Harwich home is your gatew ...
From $487 per night (USD)
VRBO
From $842 per night (USD)
Expedia
Luxury Waterfront with Game Room!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Summary: 16693 - Chatham Homecoming: Luxury Waterfront with Game Room! The Space: Perched above the shimmering waters o ...
From $842 per night (USD)
Expedia
From $506 per night (USD)
VRBO
Harbor View House: 094-H Modern Harwich Port Home with Water Views
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This property is professionally managed by Pretty Picky Properties Modern Harwich Port Home with Water Views NEW LISTI ...
From $506 per night (USD)
VRBO
From $687 per night (USD)
Expedia
Elbow Inn: Private Retreat with Two Master Suites
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This spacious Chatham beach house comfortably sleeps 8, making it the perfect retreat for families or friends. With 4 be ...
From $687 per night (USD)
Expedia
From $595 per night (USD)
VRBO
NEW LISTING! Northside Dennis 4BD--A/C, Close to Popular Dennis Beaches
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
NEW LISTING! Large 4 Bedroom, 3 Bath Northside Dennis home. A comfortable Cape escape offering spacious rooms and a conv ...
From $595 per night (USD)
VRBO
From $787 per night (USD)
VRBO
NEW! Luxury Family Fun - Heated Pool, Hot Tub, Game Room, Walk to Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to The Tide Watch - our luxurious retreat, perfect for families or a group of friends! This stunning home featur ...
From $787 per night (USD)
VRBO
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VRBO
Near Wequassett Resort and Golf Club in Harwich, overlooking a cranberry bog!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this spacious and inviting Harwich rental, perfectly situated near the Wequassett Resort and Golf Club, with b ...
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VRBO
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Expedia
Beautiful sunsets and saltwater views from every room
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Magnificent, wraparound saltwater views of the Atlantic Ocean, Nauset Beach, Strong Island, Bassing Harbor and north to ...
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Expedia
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VRBO
Charming 4-bedroom house with AC and WiFi steps from Wequassett Resort
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Escape to your perfect Cape Cod summer with this stunning rental property located steps away from the beauty of Pleasant ...
Click For Pricing
VRBO
From $1019 per night (USD)
Expedia
Waterfront on Pleasant Bay!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 17711 - Island Views: Waterfront on Pleasant Bay! The Space: Wake up to sweeping views of Pleasant Bay, where ...
From $1019 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Great location with Water Views!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: 17710 - Captains Cottage: Great location with Water Views! The Space: Escape to the charm of Harwich, where th ...
From $357 per night (USD)
VRBO
From $434 per night (USD)
VRBO
Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Book your Cape Cod escape where location, historic charm, and value unite! Our beautifully preserved and updated 1930s h ...
From $434 per night (USD)
VRBO
From $617 per night (USD)
VRBO
South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus!
Bedrooms:
3
Bathrooms:
6
Sleeps:
11
This home is professionally managed by Pretty Picky Properties Waterfront, Six Bedrooms, Free Boating Bonus! NEW Listi ...
From $617 per night (USD)
VRBO
From $643 per night (USD)
Expedia
Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This home is professionally managed by Pretty Picky Properties Spectacular Pleasant Bay Views, Free Boating Bonus! NEW ...
From $643 per night (USD)
Expedia
From $337 per night (USD)
VRBO
Walk to Beach: South Chatham Home
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Close to Golf Courses | 9 Mi to Nickerson State Park Discover where East Coast beaches meet small-town charm at this 2- ...
From $337 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Walk to Water, near Downtown Chatham!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16692 - Coastal Escape: Walk to Water, Near Downtown Chatham! The Space: Welcome to Coastal Escape, a charming ...
From $292 per night (USD)
Expedia
From $447 per night (USD)
VRBO
Harwich Home with Sunroom near Red River Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Perfect Vacation Spot for Family Gatherings Escape to this charming vacation home, nestled in a peaceful neighborhood w ...
From $447 per night (USD)
VRBO
From $989 per night (USD)
VRBO
Spacious 4-bedroom house in Chatham - Walkable to Oyster Bay Pond & Downtown.
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Enjoy the wonders of Chatham in our family's summer home. Located a 2 minute walk from Oyster Bay Pond and 8 minutes fr ...
From $989 per night (USD)
VRBO
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VRBO
Family Tides Ridgevale Beach Getaway!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Short walk to Ridgevale Beach! This 3 bedroom house (king, 4 twins) and 2 full baths allows plenty of space for the enti ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Porch, Paws and Sandy Beaches
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Spacious Farmer's Porch and close to Forest Beach!! Cozy 4BR (Queen, King, 4 Twins) 1.5 Bath in South Chatham! Grab the ...
Click For Pricing
Expedia
From $474 per night (USD)
VRBO
The perfect cozy Chatham getaway awaits you!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Your ideal Chatham getaway awaits in this cozy home, featuring 2 bedrooms, 1 bathroom, and within walking distance of do ...
From $474 per night (USD)
VRBO
From $611 per night (USD)
VRBO
Pondside Retreat - Beach Access, Game Room, Firepit, Spacious Yard & Water Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to your perfect Cape Cod getaway for families or a group of friends! This beautiful retreat offers stunning pond ...
From $611 per night (USD)
VRBO
From $371 per night (USD)
VRBO
The Osprey Nest on Main!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Fantastic Location!! This charming one-bedroom studio, upstairs apartment with a queen bed and futon is light, bright, a ...
From $371 per night (USD)
VRBO
From $369 per night (USD)
VRBO
THREE BEDROOM--MINUTES TO GOOSE POND, PLEASANT BAY AND TOWN.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Comfortable home with quiet setting, just short drive to Downtown Chatham, Two Ponds and Beaches. * * * * See e ...
From $369 per night (USD)
VRBO
From $480 per night (USD)
VRBO
Coastal Comforts Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Create unforgettable memories with your loved ones at this peaceful and private retreat in West Chatham. This spacious t ...
From $480 per night (USD)
VRBO
From $527 per night (USD)
Expedia
41 Poolside: 041-CS Coastal Retreat in Chatham – Modern Comfort & New Heated Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This property is professionally managed by Pretty Picky Properties. Sleeps 6 Linens included beds made Rents ...
From $527 per night (USD)
Expedia
Click For Pricing
VRBO
Vintage 1730 Farmhouse
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This vintage farm style home built in 1730 has 4 bedrooms (3 kings, 1 queen) and 4 bathrooms and a den that has a trundl ...
Click For Pricing
VRBO
From $258 per night (USD)
Expedia
Comfortable, Spacious North Chatham Condo!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This fabulous second-floor condo is centrally located in Nickerson Corners in North Chatham, close to downtown and Light ...
From $258 per night (USD)
Expedia
From $3483 per night (USD)
VRBO
ON PLEASANT BAY - TOPSIDE MAIN HOUSE
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
<p>Located in Orleans, this 4-bedroom, 3.5-bathroom vacation home lets you experience it all. Fans of nature and the out ...
From $3483 per night (USD)
VRBO
From $336 per night (USD)
VRBO
Quintessential Cape Cod Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
My cottage is close to Harding's & Ridgevale beach, Chatham farmer market, convenience stores, restaurants and sandwich ...
From $336 per night (USD)
VRBO
From $502 per night (USD)
VRBO
The Nook on Nob Hill, The Nook on Nob Hill
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
<h1><strong>Walk to Downtown Chatham & Cape Cod Rail Trail</strong> </h1> <p><strong>The Perfect Cape Cod Vacation Rent ...
From $502 per night (USD)
VRBO
From $568 per night (USD)
Expedia
Relax Close to Chatham & Orleans (2401)
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Nestled in a quiet neighborhood just off Route 28, this inviting Harwich home is perfectly situated for your Cape Cod es ...
From $568 per night (USD)
Expedia

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