Chatham Rentals
- From $630 per night (USD)
VRBO
Large, 3 Bedroom Private Home in East Harwich
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Newly renovated ranch home has plenty of room for both groups and individual guests to enjoy. It is ideally located near ...
From $630 per night (USD)VRBO
- From $1239 per night (USD)
Expedia
Alluring, Upscale in Chatham, Striking Water View, Separate Guest House: 081-C
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
This property is professionally managed by Pretty Picky Properties. Alluring, Upscale in Chatham, Striking Water View, ...
From $1239 per night (USD)Expedia
- From $350 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 $350 per night (USD)VRBO
- From $535 per night (USD)
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 ...
From $535 per night (USD)Expedia
- From $972 per night (USD)
VRBO
On the water with amazing views! Dogs welcome! RPMS014
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Michelle Sylvia rental home. Comfort and charm abound in this updated 18th Century seaside farmhouse (four bedrooms and ...
From $972 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $1035 per night (USD)
VRBO
Luxury condo with all amenities. Pool tennis RPMS120
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Michelle Sylvia high end collection. This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in th ...
From $1035 per night (USD)VRBO
- From $1398 per night (USD)
Expedia
Luxury condo with pool, tennis and waterviews! RPMS118
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Michelle Sylvia high end collection. This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond. Beaut ...
From $1398 per night (USD)Expedia
- From $943 per night (USD)
VRBO
Luxury condo in Chatham with amenities! RPMS119
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Michelle Sylvia high end collection. This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in the ...
From $943 per night (USD)VRBO
- From $1620 per night (USD)
Expedia
Chatham Resort Style Quality with Heated Pool, Close to Everything: 364-C
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 16
This property is professionally managed by Pretty Picky Properties Chatham Resort Style Quality with Heated Pool, Close ...
From $1620 per night (USD)Expedia
- From $289 per night (USD)
VRBO
Sunny, Cape-style home with a game room, yard, firepit, & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Chatham Living Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $289 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Charming Chatham home, close to the beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
This lovely cottage is a short distance to South Chatham's breath taking beaches. Newly renovated kitchen and updates th ...
From $425 per night (USD)VRBO
- From $429 per night (USD)
VRBO
Direct Private Beach Access
- 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 $429 per night (USD)VRBO
- From $385 per night (USD)
Expedia
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 $385 per night (USD)Expedia
- Click For Pricing
VRBO
Water view - Chatham house and boathouse
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 17
A beautiful Chatham home on Ryder's Cove. Plenty of space for an extended family. This listing has both a main house and ...
Click For PricingVRBO
- From $360 per night (USD)
VRBO
Short Walk to Beautiful Ridgevale Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Quiet, family neighborhood, a short stroll to the beach. 2 bedroom, 1 bath, outdoor shower, large deck to enjoy your mor ...
From $360 per night (USD)VRBO
- From $505 per night (USD)
VRBO
Updated, family-friendly, close to downtown Chatham & beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Renovated year round 3+ bedroom house with bonus office/bunk room with central AC, walking distance to downtown Chatham. ...
From $505 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Chatham Charm
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our newly renovated 4-bed, 2-bath Cape house close to downtown Chatham and beaches! The house is equipped wit ...
From $350 per night (USD)VRBO
- From $439 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 $439 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Captains Hill - Harwich Port Vacation Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 13
Welcome to Captains Hill in prime time Harwich Port! This property's unique layout boasts 5 bedrooms, 3 bathrooms, an ou ...
From $275 per night (USD)VRBO
- From $143 per night (USD)
VRBO
Townhouse-style condo at The Hammond House located across from Lighthouse Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lighthouse Beach area! Townhouse-style condo at The Hammond House is located right across from Lighthouse Beach. Spend y ...
From $143 per night (USD)VRBO
- From $585 per night (USD)
Expedia
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 $585 per night (USD)Expedia
- From $1150 per night (USD)
VRBO
Great Cockle Cove Home!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Family Retreat Destination! Let this 7 bedroom, 5 1/2 bathroom home serve as your luxurious home base for a multi-gener ...
From $1150 per night (USD)VRBO
- From $775 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 $775 per night (USD)VRBO
- Click For Pricing
VRBO
Walk to beach and breathtaking views of Red River Marsh
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
New 2021 Listing! If you are looking for stunning views on a private deck for optimal outdoor living overlooking a windi ...
Click For PricingVRBO
- From $2000 per night (USD)
Expedia
The Barn at Hardings Beach
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Unique property offering a 4 bed 3 bath main house and a 3 bed 1.5 bath barn. The basement of the barn is set up as a ...
From $2000 per night (USD)Expedia
- From $394 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 $394 per night (USD)VRBO
- From $402 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 $402 per night (USD)VRBO
- From $869 per night (USD)
VRBO
New Listing - Oyster Bay Lookout - Near Downtown Chatham, Private Beach Access
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
This home is represented by Nauset Rental, a local vacation rental management company. Introducing this charming Chath ...
From $869 per night (USD)VRBO
- From $341 per night (USD)
Expedia
Newly Built-3 Levels of Living, Central AC, Proximity to Beach and Marsh Views from Every Room!
- Bedrooms:
- 4
- Bathrooms:
- 2
- 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 $341 per night (USD)Expedia
- From $238 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 $238 per night (USD)VRBO
- From $400 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 $400 per night (USD)Expedia
- Click For Pricing
VRBO
Walk to Beach and Town, newly renovated 4\/BR
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy easy access to everything from this perfectly located home base. Located in historic Chatham Village, this 1850's ...
Click For PricingVRBO
- Click For Pricing
VRBO
Welcome to Daddy's Mink!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Daddy's Mink; a stunning four bedroom home ideally located outside of downtown Chatham. Inside and out, this property ha ...
Click For PricingVRBO
- From $386 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 $386 per night (USD)VRBO
- Click For Pricing
VRBO
AFFORDABLE AND COMFORTABLE. SHORT DRIVE TO NANTUCKET SOUND!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Reasonably Priced, Charming Rental Located on a little side street, and just a short drive to Nantucket Sound beaches ( ...
Click For PricingVRBO
- From $1594 per night (USD)
VRBO
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 $1594 per night (USD)VRBO
- Click For Pricing
Expedia
Stroll Into Downtown Chatham with Ease \/ One-of-a-Kind Shopping & Dining Experiences
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This lovely home is just steps to Chatham Windmill, Chase Park, Chatham Village and Oyster Pond Beach. It offers two liv ...
Click For PricingExpedia
- From $786 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 $786 per night (USD)VRBO
- From $357 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 $357 per night (USD)Expedia
- Click For Pricing
VRBO
Chatham Beach Cottage 2BR - Short walk to beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to my newly renovated cottage in Chatham, Cape Cod! This 2-bedroom home is situated on a private dirt road, with ...
Click For PricingVRBO
- From $1715 per night (USD)
Expedia
Luxury Chatham Home w\/ Heated Pool and Spa RPAM093
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your luxurious vacation rental in the exclusive enclave of Chatham, MA! This brand new construction boasts th ...
From $1715 per night (USD)Expedia
- From $660 per night (USD)
VRBO
Sunny Waterfront Home Perfect for Cape Cod Getaway!
- 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 $660 per night (USD)VRBO
- From $550 per night (USD)
Expedia
Short stroll to Lighthouse Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Highly sought-after Bridge Street vacation rental! Enjoy your summer holiday in this beautiful home where Lighthouse Bea ...
From $550 per night (USD)Expedia
- From $476 per night (USD)
VRBO
0.6 Miles to Beach Great for families!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16677 - Nautical Nest: 0.6 Miles to Beach Great for families! The Space: Seals swim off shore while you soak u ...
From $476 per night (USD)VRBO
- From $557 per night (USD)
Expedia
Gorgeous distant views of Oyster Pond and Oyster River from the large second story deck.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to Sea la Vie! This beautiful, spacious, well-appointed home has lots of extra living space and all the right a ...
From $557 per night (USD)Expedia
- From $603 per night (USD)
VRBO
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 $603 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $1147 per night (USD)
VRBO
Luxury Cape House - 5 minutes to Nantucket Ferry!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to our beautiful renovated Cape house in the lovely town of Harwich! This gorgeous 5-bed/3.5-bath/4k sq ft home ...
From $1147 per night (USD)VRBO
- From $700 per night (USD)
Expedia
This charming rental on Stage Neck offers tons of privacy and outdoor space!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This charming rental on Stage Neck offers tons of privacy and outdoor space for easy entertaining. Relax on the back dec ...
From $700 per night (USD)Expedia
- Click For Pricing
Expedia
Gorgeous, Sprawling Estate Grounds with Private Pool.
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 10
Magnificent Eight Bedroom Home, with 5.5 Bathrooms, in North Chatham, and a Pool! Located on 1.6 acres, Located on 1.6 ...
Click For PricingExpedia
- From $750 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 $750 per night (USD)VRBO
- From $532 per night (USD)
VRBO
Walk to Everything From this Light and Bright Home Near Town!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Take advantage of the quick walk to the Chatham Anglers' Ball Field, the playground and Main Street from this recently u ...
From $532 per night (USD)VRBO
- From $180 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 $180 per night (USD)VRBO
- From $239 per night (USD)
VRBO
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 $239 per night (USD)VRBO
- From $2000 per night (USD)
VRBO
MAGNIFICENT PANORAMIC SALTWATER VIEWS OF THE ATLANTIC OCEAN, NAUSET BEACH, STRONG SLAND, BASSING HARBOR AND PLEASANT BAY WITH PRIVATE BEACH!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 10
Panoramic Saltwater Views of Nauset Beach, Strong Island, Bassing harbor and Pleasant Bay with Private Beach This 4500 ...
From $2000 per night (USD)VRBO
- From $445 per night (USD)
VRBO
Bright & spacious home on cul-de-sac; 3 min walk to Ridgevale Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to “Down the Road Beach House” - a spacious beach retreat on a quiet cul-de-sac just a 3 minute walk to popular ...
From $445 per night (USD)VRBO
- From $360 per night (USD)
Expedia
Great Family location close to beach and rail trail.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bring the family and come enjoy Cape Cod at its best. Our family friendly, well maintained home is located on a quiet, c ...
From $360 per night (USD)Expedia
- From $266 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 $266 per night (USD)VRBO
- From $1013 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 $1013 per night (USD)VRBO
- From $571 per night (USD)
VRBO
Charming and cozy, and right off the Chatham Loop!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming and cozy, and right off the Chatham Loop! Spend your vacation on Cedar Street, a highly sought after location t ...
From $571 per night (USD)VRBO
- From $377 per night (USD)
Expedia
Spacious Deck, Large Yard & Dogs Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16676 - Shore Break: Spacious Deck, Large Yard & Dogs Welcome! The Space: Chatham is known for its delicious f ...
From $377 per night (USD)Expedia
- From $614 per night (USD)
VRBO
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 $614 per night (USD)VRBO
- From $1178 per night (USD)
Expedia
Superb, Upscale Waterfront in North Chatham: 078-C
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This Property is professionally managed by Pretty Picky Properties. Superb, Upscale Waterfront in North Chatham Sleeps ...
From $1178 per night (USD)Expedia
- From $999 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 $999 per night (USD)VRBO
- From $388 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 $388 per night (USD)VRBO
- From $430 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 $430 per night (USD)VRBO
- From $500 per night (USD)
Expedia
Ridgevale Beach Gem!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Ridgevale Beach and the warm waters of Nantucket Sound are calling. Walk to one of Chatham's most popular beach draws w ...
From $500 per night (USD)Expedia
- From $640 per night (USD)
VRBO
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 d�cor of a modern house ...
From $640 per night (USD)VRBO
- From $800 per night (USD)
Expedia
Lovely 5 BR home with Central a\/c, Cose to Downtown, Chatham Bars Inn, the Golf Course and the Beach!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Lovely 5 BR home with Central a/c, Close to Downtown, Chatham Bars Inn, the Golf Course and the Beach! Located on pres ...
From $800 per night (USD)Expedia
- From $765 per night (USD)
VRBO
THE CHATHAM TREEHOUSE 7 minutes from the Village
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the Treehouse, just 7 mins from the village of Chatham! This beautiful, private property is nestled in the wo ...
From $765 per night (USD)VRBO
- From $384 per night (USD)
VRBO
New Listing- Summer Breeze
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This home is represented by Nauset Rental, a local vacation rental management company. Welcome to Summer Breeze, a char ...
From $384 per night (USD)VRBO
- From $386 per night (USD)
VRBO
Enjoy Classic Chatham Charm and Easy Stroll to Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
<p>Located in Chatham, this welcoming vacation home lets you experience it all. Cape Cod Beaches is within an easy 12-mi ...
From $386 per night (USD)VRBO
- From $414 per night (USD)
VRBO
Newly Renovated Upscale Cottage\/Pvt 2 KING BR Ensuite \/1 Mile to Hardings Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $414 per night (USD)VRBO
- From $895 per night (USD)
VRBO
Chatham~Lake Front~Shark Free Swimming!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This phenomenal home has been completely renovated over the past few years down to the addition of central air, wood flo ...
From $895 per night (USD)VRBO
- From $829 per night (USD)
Expedia
Exquisite Chatham Home, Easy Access to Town, Bike Trail: 330-C
- 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 $829 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 PricingVRBO
- From $816 per night (USD)
Expedia
Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated: 021-C
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
This home is professionally managed by Pretty Picky Properties Luxurious Chatham Home, Heated Saltwater Pool, Newly Ren ...
From $816 per night (USD)Expedia
- From $875 per night (USD)
VRBO
Luxury Townhome Steps to Downtown Chatham, with Fabulous Roof Deck!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
In-Town Chatham Living at its Finest! You will totally love to walk to everything and hang out on the awesome Roof Top D ...
From $875 per night (USD)VRBO
- From $267 per night (USD)
Expedia
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 $267 per night (USD)Expedia
- From $517 per night (USD)
VRBO
Bright home with huge yard, patio & Ping-Pong - close to Ridgevale Beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Ridgevale Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $517 per night (USD)VRBO
- From $190 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 $190 per night (USD)Expedia
- From $389 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 $389 per night (USD)VRBO
- From $545 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 $545 per night (USD)VRBO
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Expedia
New to Market ''Weir on Main'' Location! Location! Location!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FRIDAY TO FRIDAY RENTAL ONLY! New to Market! Location! Location! Location! Our downtown apartment is located on Main Str ...
Click For PricingExpedia
- From $866 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 $866 per night (USD)VRBO
- From $520 per night (USD)
VRBO
Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w\/ Pond Views!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
*** New Listing in 2023 *** Marta (my wife) and I are two Canadians who now call Massachusetts our home. Our lovely ...
From $520 per night (USD)VRBO
- From $180 per night (USD)
Expedia
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Riviera Sunset Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $180 per night (USD)Expedia
- From $235 per night (USD)
VRBO
Harwich vacation escape with central air on Cape Cod bike trail
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Centrally-located 2-bedroom (plus cot & pull-out sofa), 1.5 bath Cape in a quiet neighborhood just 1.5 miles to the beac ...
From $235 per night (USD)VRBO
- From $750 per night (USD)
Expedia
Waterfront Renovated Home with Pool and Dock: 560-C
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Waterfront Renovated Home with Pool and Dock Sleeps 8 Rents Friday - Friday during peak season Pets Considered It's r ...
From $750 per night (USD)Expedia
- From $479 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 $479 per night (USD)VRBO
- From $448 per night (USD)
VRBO
Last Minute Alert Save! 3 MINUTES DRIVING TO JACKNIFE BEACH!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Feel the warm embrace of the sun on your skin, listen to the rhythmic symphony of crashing waves, and surrender to the s ...
From $448 per night (USD)VRBO
- From $575 per night (USD)
VRBO
Lovely 3 BR Home in Harbor Coves, North Chatham...Peaceful Setting!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This lovely cape with 3 bedrooms and 2 1/2 baths sits privately on over an acre of land. A classic, antique home filled ...
From $575 per night (USD)VRBO
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Expedia
Walking distance to downtown, CBI, Fish Pier, Veteran's Field, and beaches.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Perfectly positioned within a comfortable walking distance to downtown Chatham, Chatham Bars Inn, the Chatham Fish Pier, ...
Click For PricingExpedia
- From $352 per night (USD)
VRBO
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 $352 per night (USD)VRBO
- From $1500 per night (USD)
Expedia
Amazing Home, Private Pool, Walk to Downtown Chatham!
- Bedrooms:
- 7
- Bathrooms:
- 4
- Sleeps:
- 10
This exceptional property offers ultimate luxury nestled in an exclusive neighborhood steps to Chatham Village. Overlook ...
From $1500 per night (USD)Expedia
- From $300 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 $300 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 PricingExpedia
- From $426 per night (USD)
VRBO
Chatham Home Rental w\/ Sunroom: Walk to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $426 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 PricingExpedia