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From $695 per night (USD)
VRBO
Sprawling Home With Great Outdoor Space (2288)
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
If you are looking for the perfect getaway to pamper your guests on your next Cape Cod vacation offering easy access to ...
From $695 per night (USD)
VRBO
From $527 per night (USD)
Expedia
Spacious renovated home, close to Chatham Beaches
Bedrooms:
2
Bathrooms:
4
Sleeps:
14
Welcome to your perfect Cape Cod getaway! Nestled right on the Chatham/Harwich line, this spacious home offers the best ...
From $527 per night (USD)
Expedia
From $2173 per night (USD)
VRBO
Hiawatha: 177-CC Gorgeous Chatham Estate with heated pool, walk to Town or Beach
Bedrooms:
6
Bathrooms:
7
Sleeps:
15
This home is professionally managed by Pretty Picky Properties Gorgeous Chatham Estate with heated pool, walk to Town o ...
From $2173 per night (USD)
VRBO
$Heated Pool AC 1\/2 Mile to Beach!$
From $1176 per night (USD)
Expedia
Heated Pool AC 1\/2 Mile to Beach!
Bedrooms:
3
Bathrooms:
8
Sleeps:
20
Summary: 17739 - Deja Blue: Heated Pool AC 1/2 Mile to Beach! The Space: Accommodations for twenty people, a heated poo ...
From $1176 per night (USD)
Expedia
$THREE BEDROOM UPDATED HOME -- JUST 3\/10'S MILE TO PLEASANT STREET BEACH$
From $752 per night (USD)
VRBO
THREE BEDROOM UPDATED HOME -- JUST 3\/10'S MILE TO PLEASANT STREET BEACH
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Beautiful Updated Home with Lots of Living Space, Short distance to Pleasant Street Beach. This pristine 3 bedroom, 3 ...
From $752 per night (USD)
VRBO
From $320 per night (USD)
Expedia
Close to Bike Path 1 Mile to Beaches!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 16673 - Mayflower Retreat: Close to Bike Path 1 Mile to Beaches! The Space: A quick pedal from the Cape Cod Ra ...
From $320 per night (USD)
Expedia
From $420 per night (USD)
VRBO
Updated Beach House Deck Outdoor Shower!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: 16670 - A Touch of Blue: Updated Beach House Deck Outdoor Shower! The Space: Nautical colors and floods of nat ...
From $420 per night (USD)
VRBO
From $486 per night (USD)
Expedia
5 Min Walk to Red River Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: 17740 - Absolute Beach: 5 Min Walk to Red River Beach! The Space: Happiness in Harwich is hard to hide from. A ...
From $486 per night (USD)
Expedia
From $990 per night (USD)
VRBO
5 Bedroom Chatham Charmer RPAM012
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Located in the highly desirable town of Chatham, this five bedroom, three bath rental home will meet all your vacation n ...
From $990 per night (USD)
VRBO
$Large Chatham Rental w\/ 5 Bedrooms w\/ 5 Private Bathrooms RPAM007$
From $1218 per night (USD)
Expedia
Large Chatham Rental w\/ 5 Bedrooms w\/ 5 Private Bathrooms RPAM007
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
This stunning rental home is a vacationer’s dream! Easy and close access to the ponds, bike trails, conservation area a ...
From $1218 per night (USD)
Expedia
From $727 per night (USD)
VRBO
Picture Perfect Hardings Beach Rental RPAM025
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Located just .89 miles away from Harding's Beach this newly renovated 3 bedroom 2 bath home is perfectly set up for a sp ...
From $727 per night (USD)
VRBO
From $652 per night (USD)
VRBO
Large, 3 Bedroom Private Home in East Harwich
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Newly renovated ranch home has plenty of room for both groups and individual guests to enjoy. It is ideally located near ...
From $652 per night (USD)
VRBO
$Large Home w\/ Fire Pit and Dogs Welcome!$
From $389 per night (USD)
VRBO
Large Home w\/ Fire Pit and Dogs Welcome!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: 16674 - Heatherwood Haven: Large Home w/ Fire Pit and Dogs Welcome! The Space: Escape to Chatham, where baysid ...
From $389 per night (USD)
VRBO
Click For Pricing
Expedia
Beautiful 3 bedroom Cape with spacious deck and hot tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Lovely modern 3 bedroom home, located on a quiet cul-de-sac is the perfect place for a family vacation. Hop on the bike ...
Click For Pricing
Expedia
Click For Pricing
VRBO
The Great Escape
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private setting on quiet street on the outskirts of Chatham. Walk to beaches, bike path, local restaurants, short drive ...
Click For Pricing
VRBO
From $1913 per night (USD)
Expedia
The Gables: 364-C Chatham Resort Style Estate with Heated Pool, Close to Everything
Bedrooms:
9
Bathrooms:
8
Sleeps:
16
This property is professionally managed by Pretty Picky Properties Chatham Resort Style Estate with Heated Pool, Close ...
From $1913 per night (USD)
Expedia
$Sunny, Cape-style home with a game room, yard, firepit, & washer\/dryer$
Click For Pricing
VRBO
Sunny, Cape-style home with a game room, yard, firepit, & washer\/dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Chatham Living Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
Click For Pricing
VRBO
From $513 per night (USD)
Expedia
Direct Private Beach Access (2290)
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover the perfect blend of luxury and convenience in this beautiful 2-bedroom, 2-bath waterfront townhouse that offer ...
From $513 per night (USD)
Expedia
$Spacious w\/ Beautiful Yard & Dogs Welcome!$
From $455 per night (USD)
VRBO
Spacious w\/ Beautiful Yard & Dogs Welcome!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 17742 - A Wave From It All: Spacious w/ Beautiful Yard & Dogs Welcome! The Space: The Lower Cape boasts some o ...
From $455 per night (USD)
VRBO
From $442 per night (USD)
Expedia
Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Renovated year round 4 bedroom house with bonus office/bunk room with central AC, walking distance to downtown Chatham. ...
From $442 per night (USD)
Expedia
From $372 per night (USD)
VRBO
Friendly retreat with a deck, AC, and board games - stellar central location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Corner Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $372 per night (USD)
VRBO
From $277 per night (USD)
Expedia
Townhouse-style condo at The Hammond House located across from Lighthouse Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of The Hammond House, a townhouse-style condo in the Lighthouse Beach area, ideally situated across f ...
From $277 per night (USD)
Expedia
From $917 per night (USD)
VRBO
Pet friendly home with large backyard!
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
Enjoy your Chatham vacation at this spacious, 5 bedroom, 2 bath home. Offering 2 queens, a bunk bed and 4 twins, and a t ...
From $917 per night (USD)
VRBO
From $2081 per night (USD)
Expedia
Great Cockle Cove Home!
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
Family Retreat Destination! Let this 7 bedroom offering 2 queens, 4 twin, 2 full beds and 2 sets of bunk beds, spread o ...
From $2081 per night (USD)
Expedia
From $696 per night (USD)
VRBO
LOCATION & VIEW - Water Front Home In Chatham Village
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Fully renovated cottage on little mill pond. Renovation completed may 2016. A 4 minute walk to town of chatham. 3 bedroo ...
From $696 per night (USD)
VRBO
From $2208 per night (USD)
Expedia
The Barn at Hardings Beach
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
Experience the ultimate getaway at this stunning 7-bedroom retreat, just a mile from Cape Cod’s pristine beaches. Enjoy ...
From $2208 per night (USD)
Expedia
From $531 per night (USD)
VRBO
Gorgeous Home with Game Room Dog Welcome!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: 16675 - Summer Stunner: Gorgeous Home with Game Room Dog Welcome! The Space: Another Cape Cod vacation means a ...
From $531 per night (USD)
VRBO
From $722 per night (USD)
VRBO
Chatham Seascape
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This home is represented by Nauset Rental, a local vacation rental management company. The perfect vacation destinatio ...
From $722 per night (USD)
VRBO
From $758 per night (USD)
VRBO
Vacation in the heart of Chatham and walk to everything. Oyster Pond Beach is right around the corner!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Experience downtown Chatham! No need to drive when you can walk to everything. This charming rental features a classic f ...
From $758 per night (USD)
VRBO
From $530 per night (USD)
Expedia
Newly Built-3 Levels of Living, Central AC, Proximity to Beach and Marsh Views from Every Room!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
3 Bedroom - 3.5 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $530 per night (USD)
Expedia
From $363 per night (USD)
VRBO
Steps to Private Association Beach. End Unit Condo at Outermost Harbor.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Updated Condo at Outermost Harbor. Enjoy amazing views of the famous Chatham sandbars or catch a glimpse of playful seal ...
From $363 per night (USD)
VRBO
From $497 per night (USD)
Expedia
Lovely vacation home less than a mile from Chatham beaches!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Traditional Cape Cod home with a large, private yard with a deck, outdoor shower and hammock in a quiet Chatham neighbor ...
From $497 per night (USD)
Expedia
$Awesome Location! Right on the Chatham \Loop\, Perfect for Long Walks!$
From $523 per night (USD)
VRBO
Awesome Location! Right on the Chatham \"Loop\", Perfect for Long Walks!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Awesome Location! Right on the Chatham "Loop", it is Perfect for Long Walks! This 4-bedroom Cape House is close to town ...
From $523 per night (USD)
VRBO
$Spacious Custom Chatham Home w\/Pool, Guest Cottage & Water Views: 051-C$
From $2733 per night (USD)
Expedia
Spacious Custom Chatham Home w\/Pool, Guest Cottage & Water Views: 051-C
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
This property is professionally managed by Pretty Picky Properties. Spacious Custom Chatham Home w/Pool, Guest Cottage ...
From $2733 per night (USD)
Expedia
$Sprawling 5 BR Chatham Escape \/ Endless Outdoor Living & Entertaining Choices$
From $1084 per night (USD)
VRBO
Sprawling 5 BR Chatham Escape \/ Endless Outdoor Living & Entertaining Choices
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Completely renovated in 2017, this classic Cape is the perfect Chatham beach house. Offering an open flow layout with fi ...
From $1084 per night (USD)
VRBO
From $526 per night (USD)
Expedia
Location is Everything! Walk to 3 of North Chatham's Most Scenic Salt Water Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Location is everything! Walk to 3 of North Chatham's most scenic salt water beaches and a short trip to Chatham's covete ...
From $526 per night (USD)
Expedia
From $2024 per night (USD)
VRBO
Prime Chatham Retreat with Pool, Spa & Style RPAM093
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Welcome to your luxurious vacation rental in the exclusive enclave of Chatham, MA! This stunning homes boasts four spaci ...
From $2024 per night (USD)
VRBO
From $659 per night (USD)
Expedia
WATERFRONT home close to Downtown Chatham!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Soak up the sun while enjoying the lush outdoor space at our waterfront home, Queen’s Quarters. Bring or rent a kayak or ...
From $659 per night (USD)
Expedia
From $564 per night (USD)
VRBO
0.6 Miles to Beach Great for families!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: 16677 - Nautical Nest: 0.6 Miles to Beach Great for families! The Space: Seals swim off shore while you soak u ...
From $564 per night (USD)
VRBO
From $600 per night (USD)
Expedia
Game Room Rooftop Deck Fire Pit!!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: 16678 - Jawsome Getaway: Game Room Rooftop Deck Fire Pit!! The Space: Chatham is the hub of entertainment and ...
From $600 per night (USD)
Expedia
Click For Pricing
VRBO
Close to Ridgevale Beach with great outdoor space!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Close to Ridgevale Beach! This spacious 4 bedroom, 3 bath vacation home is well maintained and just under a mile to popu ...
Click For Pricing
VRBO
From $773 per night (USD)
VRBO
Beautiful Chatham home...3 minute walk to salt water ocean beach!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Great location, spacious home and yard, private deck with brand new gas grill and comfy furniture. Beautifully decorated ...
From $773 per night (USD)
VRBO
$Chatham Getaway- Completely Renovated Cape Cottage w\/ Linens Included$
From $544 per night (USD)
VRBO
Chatham Getaway- Completely Renovated Cape Cottage w\/ Linens Included
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
*Contact us for information on long-term booking opportunities!* This home is represented by Nauset Rental, a local vac ...
From $544 per night (USD)
VRBO
From $277 per night (USD)
Expedia
Charming Chatham Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Prepare to be charmed by this quintessential Cape Cod beach cottage, tucked into a quiet residential neighborhood equidi ...
From $277 per night (USD)
Expedia
From $1573 per night (USD)
VRBO
House In The Heart Of Chatham Village
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
The perfect location: in the heart of Chatham Village with outstanding views of Mill Pond, one of Chatham's most scenic ...
From $1573 per night (USD)
VRBO
From $2408 per night (USD)
VRBO
FIVE BEDROOM -- MAGNIFICENT WATER VIEWS OF PLEASANT BAY AND ATLANTIC OCEAN.
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Panoramic Saltwater Views of Nauset Beach, Strong Island, Bassing harbor and Pleasant Bay with Private Beach This 4500 ...
From $2408 per night (USD)
VRBO
$The Wicked Whidah - Pet-friendly, central location, private yard, sleeps 6 - 3bed\/2bath$
From $349 per night (USD)
VRBO
The Wicked Whidah - Pet-friendly, central location, private yard, sleeps 6 - 3bed\/2bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 bedrooms- 2 bathrooms- sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $349 per night (USD)
VRBO
From $1007 per night (USD)
VRBO
Newly Remodeled Seaside Getaway with Forest Beach in your backyard!
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Newly renovated home with ocean views and Forest Beach right in your backyard. Swim, lounge, kayak, hike, or play tennis ...
From $1007 per night (USD)
VRBO
From $1043 per night (USD)
VRBO
Charming and cozy, and right off the Chatham Loop!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover the charm and coziness of Cedar Street, a highly desirable location just off the Chatham Loop! This vacation re ...
From $1043 per night (USD)
VRBO
From $822 per night (USD)
Expedia
Beautiful and Pristine Rental in South Chatham.. Recently Reduced!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Awesome Three Bedroom Home on a Quiet Cul-de-sac in South Chatham! This beautiful home is perfect for your dream Chath ...
From $822 per night (USD)
Expedia
From $1123 per night (USD)
VRBO
Luxurious Home with Pool & Game Room in Cape Cod
Bedrooms:
5
Bathrooms:
4
Sleeps:
11
Welcome to our newly listed vacation home in Chatham, Cape Cod! This spacious 4-bedroom/4.5-bathroom house is a haven fo ...
From $1123 per night (USD)
VRBO
From $446 per night (USD)
VRBO
Great Cape Cod Getaway!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Guests are sure to enjoy a memorable vacation or special occasion in this fully furnished, 3 bedroom/2.5 bath cape home ...
From $446 per night (USD)
VRBO
From $528 per night (USD)
VRBO
Charming Three Plus Bedroom Home Located on a Quiet street in East Harwich, Close to Beaches and Restaurants!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Beautiful Updated Home with 3+ Bedrooms and downstairs sleeping, 2 living areas and 3 full baths with new Outdoor Show ...
From $528 per night (USD)
VRBO
$Stroll Chatham's Historic Downtown \/ Shops, Dining, Galleries, Etc.$
From $770 per night (USD)
Expedia
Stroll Chatham's Historic Downtown \/ Shops, Dining, Galleries, Etc.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Beautiful home located in the heart of Chatham! This lovely home offers all the amenities and decor of a modern house wh ...
From $770 per night (USD)
Expedia
From $938 per night (USD)
VRBO
THE CHATHAM TREEHOUSE 7 minutes from the Village
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to the Treehouse, just 7 mins from the village of Chatham! This beautiful, private property is nestled in the wo ...
From $938 per night (USD)
VRBO
From $569 per night (USD)
Expedia
Enjoy Classic Chatham Charm and Easy Stroll to Downtown!
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
<p>Located in Chatham, this welcoming vacation home brings it all within your reach. There's convenient onsite parking, ...
From $569 per night (USD)
Expedia
$Newly Renovated Upscale Cottage\/Pvt 2 KING BR Ensuite \/1 Mile to Hardings Beach$
From $467 per night (USD)
VRBO
Newly Renovated Upscale Cottage\/Pvt 2 KING BR Ensuite \/1 Mile to Hardings Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oh Buoy Oh Buoy Escape to Oh Buoy Oh Buoy, our tastefully renovated Chatham cottage just one mile from the soft, white ...
From $467 per night (USD)
VRBO
From $865 per night (USD)
Expedia
Barefoot Bungalow: 330-C Exquisite Chatham Home, Easy Access to Town, Bike Trail
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties Exquisite Chatham Home, Easy Access to Town, Bike Tr ...
From $865 per night (USD)
Expedia
Click For Pricing
VRBO
Downtown Chatham 4 Bedroom House
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
4 bedroom house at end of private, dead-end street in Downtown Chatham. 2 decks, views of conservation land. Listen to ...
Click For Pricing
VRBO
From $983 per night (USD)
Expedia
Eileen's Escape: 021-C Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
This home is professionally managed by Pretty Picky Properties Luxurious Chatham Home, Heated Saltwater Pool, Newly Ren ...
From $983 per night (USD)
Expedia
From $382 per night (USD)
VRBO
Bright home walking distance to Main Street with great patio, firepit & bikes
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Queen Anne Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $382 per night (USD)
VRBO
From $274 per night (USD)
Expedia
Inviting apartment with patio, full kitchen, & golf nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Reynard's Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $274 per night (USD)
Expedia
From $471 per night (USD)
VRBO
Refurbished South Orleans Antique Home Close to Pleasant Bay
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
2/10th's a Mile from Pleasant Bay Warm and inviting, this remodeled antique home with marshland views is within 2/10th' ...
From $471 per night (USD)
VRBO
$Newly Renovated \/ Less that 1 Mile to the Beach$
From $686 per night (USD)
VRBO
Newly Renovated \/ Less that 1 Mile to the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Immaculate and beautifully renovated home set on a quiet Harwich Port cul-de-sac. Located within minutes from Red River ...
From $686 per night (USD)
VRBO
From $1138 per night (USD)
VRBO
Gorgeous, Modern, Dog Friendly Chatham 4 Bedroom with Central AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This home is represented by Nauset Rental, a local vacation rental management company. Gorgeous, modern beach house out ...
From $1138 per night (USD)
VRBO
$Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w\/ Pond Views!$
From $520 per night (USD)
Expedia
Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w\/ Pond Views!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Marta (my wife) and I are two Canadians who now call Massachusetts our home. Our lovely place in South Chatham is our ne ...
From $520 per night (USD)
Expedia
From $370 per night (USD)
VRBO
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Riviera Sunset Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $370 per night (USD)
VRBO
From $1396 per night (USD)
Expedia
Stay Salty: 560-C Waterfront Renovated Home with Pool and Dock
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Waterfront Renovated Home with Pool and Dock Sleeps 8 Rents Friday - Friday during peak season Pets Considered Pool ope ...
From $1396 per night (USD)
Expedia
From $796 per night (USD)
VRBO
Contemporary 4bedroom home near beach.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Come relax with the whole family at our peaceful 4 bedroom home. Recently renovated with 2 full baths and 2 living room ...
From $796 per night (USD)
VRBO
From $454 per night (USD)
Expedia
Beautiful Cape home. Minutes from beaches, restaurants, bike paths & shopping.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Spacious and conveniently located. Close to supermarket, gas station, banks, post office, restaurants and more. Central ...
From $454 per night (USD)
Expedia
From $352 per night (USD)
VRBO
Lovely 1-bedroom loft-with an incredible view
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Have fun with the whole family at this stylish place. We are so exited to share this newly completed space whit you! ...
From $352 per night (USD)
VRBO
Click For Pricing
Expedia
Spacious and beautiful home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Beautiful and welcoming property for a group of family or friends looking to have a wonderful time. Quiet and peaceful ...
Click For Pricing
Expedia
$Chatham Getaway w\/ Sunroom: Walk to Beach!$
From $497 per night (USD)
VRBO
Chatham Getaway w\/ Sunroom: Walk to Beach!
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
You’ll be able to hear the crashing waves from every corner of this Chatham, MA, vacation rental. This 3-bedroom, 2-bath ...
From $497 per night (USD)
VRBO
Click For Pricing
Expedia
Brand New Home & 5 Minute Walk to Ridgevale Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to our brand new 4-bedroom house in Chatham! Our 2250 square foot home sleeps up to 8 guests and is perfect for ...
Click For Pricing
Expedia
From $645 per night (USD)
VRBO
Updated 6 Bedroom Home Close to Everything!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Cranberry Corners is the perfect house for your extended family vacation! DOGS WELCOME! Plenty of space to spread out, ...
From $645 per night (USD)
VRBO
From $461 per night (USD)
Expedia
Chatham Bliss - Dog Friendly oasis with EV Charging
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our recently updated getaway in charming Chatham, MA! Our pet-friendly retreat is the perfect destination for ...
From $461 per night (USD)
Expedia
From $1766 per night (USD)
VRBO
Pool and large yard!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
North Chatham home with a large yard and a lovely pool. The large front room is perfect for reading or watching TV, pla ...
From $1766 per night (USD)
VRBO
From $3490 per night (USD)
Expedia
Sophisticated Chatham Oasis with Pool & Spa RPAM062
Bedrooms:
9
Bathrooms:
6
Sleeps:
12
Welcome to 84 Doane Road in Chatham, MA, where opulence meets comfort and convenience. Nestled in a prime location just ...
From $3490 per night (USD)
Expedia
From $782 per night (USD)
VRBO
Jean's Dream - Newly Renovated Cape House .9Miles from the Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Escape to Jean's Dream a charming Cape house in South Chatham, MA. This delightful newly renovated rental features 2 bed ...
From $782 per night (USD)
VRBO
From $382 per night (USD)
VRBO
Cockle Cottage - Renovated Chatham Cape House .9 Miles from Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Indulge in a memorable stay at Cockle Cottage in Chatham, MA. This inviting rental boasts 2 bedrooms, 1 bathroom and com ...
From $382 per night (USD)
VRBO
From $731 per night (USD)
VRBO
Newly Renovated Guest House For 10 Near The Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to our charming vacation house located in Harwich, Massachusetts! Our property is perfectly located near the bea ...
From $731 per night (USD)
VRBO
From $849 per night (USD)
VRBO
Enjoy a relaxing retreat. Easy access: Beaches, Bike Path, & Great restaurants.
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
This charming, tastefully decorated, and bright home includes a cheerful yellow fully equipped kitchen with a unique isl ...
From $849 per night (USD)
VRBO
From $1083 per night (USD)
VRBO
Located in quiet Riverbay directly on the river; kayak to Jacknife Beach
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Located in quiet Riverbay neighborhood. This 5 bedroom, 4 bath home that sleeps 10. Plenty of room to spread out with ...
From $1083 per night (USD)
VRBO
From $864 per night (USD)
Expedia
Views of Eastward Ho Golf Course from the backyard!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
North Chatham gem offers views of Eastward Ho Golf Course from the backyard! Antique Cape style home that sleeps 8 peopl ...
From $864 per night (USD)
Expedia
From $997 per night (USD)
VRBO
KAYAK TO PLEASANT BAY FROM YOUR BACK YARD! KAYAKS PROVIDED!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
***KAYAK TO PLEASANT BAY FROM YOUR BACK YARD! KAYAKS PROVIDED! OPEN YEAR ROUND Spacious five bedroom, four bath ho ...
From $997 per night (USD)
VRBO
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Expedia
Lovely cottage near beach and town - screened porch, outdoor shower, picnic area
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Chatham Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
Click For Pricing
Expedia
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VRBO
Spacious Waterfront Home on Ryder's Cove! Pet Friendly too!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Contemporary 4 bedroom home located on Ryder's Cove in North Chatham. Plenty of space to spread out, with different liv ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Chatham pond access with view
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy our large back yard and private road that leads to the Pond behind the house, for fishing, non-motor boating, padd ...
Click For Pricing
Expedia
From $459 per night (USD)
VRBO
Cozy Chatham Cottage walk to Hardings ⛱️ , Restaurants & downtown.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Newly remodeled 1950's era cottage with all the comforts for a great visit. Just off the living room and thru French do ...
From $459 per night (USD)
VRBO
From $447 per night (USD)
Expedia
Cape Escape - Two Bedroom, Two Bathroom Near Beaches and Cycling
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
2 Bedroom- 2 Bath- Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of ...
From $447 per night (USD)
Expedia
From $395 per night (USD)
VRBO
Classic Cape House Walking Distance to the Beach - Many recent upgrades
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Recent upgrades: Complete interior painted (March 2025); Main dining table refinished (April 2025); Downstairs bathroom ...
From $395 per night (USD)
VRBO
From $873 per night (USD)
Expedia
Hot Tub! Steps to Oyster Pond Beach and Downtown Chatham.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover this beautifully landscaped, contemporary three-bedroom home, ideally situated on a quiet cul-de-sac, just a sh ...
From $873 per night (USD)
Expedia
From $1694 per night (USD)
VRBO
Steps from Ridgevale Beach!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Steps from Ridgevale Beach! Enjoy spectacular and expansive water views in this beautifully appointed 2 bedroom (king, 2 ...
From $1694 per night (USD)
VRBO
From $892 per night (USD)
VRBO
Beautifully renovated home, outdoor space, pet considered
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Sea~a~Bella - Your perfect Chatham family vacation is here. You will find three beautiful, scenic beaches within walking ...
From $892 per night (USD)
VRBO
From $374 per night (USD)
VRBO
Cute ranch style house on quiet road.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This sunny, cozy Cape-style ranch is a short driving distance to both Harding's and Oyster Pond beaches and the quaint v ...
From $374 per night (USD)
VRBO
$Short walk to beach, A\/C, pets okay, large yard$
From $524 per night (USD)
Expedia
Short walk to beach, A\/C, pets okay, large yard
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 Bedrooms - 1 Bathroom - Sleeps 4 A 3-night midweek stay - Monday to Wednesday - is offered at this home during the pea ...
From $524 per night (USD)
Expedia
From $1167 per night (USD)
VRBO
Enjoy a Cape Cod beach vacation on the beach in picturesque Chatham.
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Have the vacation of your dreams in this oceanfront beach cottage with beautiful water views, located on Morris Island i ...
From $1167 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Chatham Cape Cod Near Bike Trail, 1 Mile to Beach!
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Welcome to a classic coastal getaway at this charming Chatham vacation rental. Located 1 mile from the shore and steps f ...
From $402 per night (USD)
Expedia
From $270 per night (USD)
VRBO
Beautifully Renovated Cape on Bike Trail, 1 mile to Downtown Chatham and Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Charming Cape house recently renovated less than a mile to Downtown Chatham for shopping and restaurants. Located on a q ...
From $270 per night (USD)
VRBO
From $2458 per night (USD)
Expedia
PRIVATE HEATED POOL!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Private Heated pool! Vacation near the beach in this charming 4 bedroom (4 kings) and 3.5 bath home with private pool. C ...
From $2458 per night (USD)
Expedia

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