Chatham, Massachusetts Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Chatham, Massachusetts on RentalSaver.com!

Chatham Rentals

Filter

Popular Areas

From $644 per night (USD)
VRBO
Like new with nautical theme!
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 $644 per night (USD)
VRBO
From $890 per night (USD)
Expedia
Steps to Red River Beach!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Steps to Red River Beach, a lifeguarded, groomed sand beach with restrooms and food trucks! Enjoy long walks, sunbathing ...
From $890 per night (USD)
Expedia
From $1089 per night (USD)
VRBO
Downtown Chatham Family Retreat - Spacious Deck, Games & Firepit - Walk to town
Bedrooms:
3
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 $1089 per night (USD)
VRBO
From $473 per night (USD)
Expedia
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 ...
From $473 per night (USD)
Expedia
From $599 per night (USD)
VRBO
3bd 2bth Dog Friendly .3 miles to Red River Beach
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 $599 per night (USD)
VRBO
From $315 per night (USD)
Expedia
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 $315 per night (USD)
Expedia
From $849 per night (USD)
VRBO
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 $849 per night (USD)
VRBO
From $424 per night (USD)
Expedia
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 $424 per night (USD)
Expedia
From $477 per night (USD)
VRBO
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 $477 per night (USD)
VRBO
From $319 per night (USD)
Expedia
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 $319 per night (USD)
Expedia
From $528 per night (USD)
VRBO
HarwichPort 4 bdr 3 bath - Walk to Red River Beach - next to Wychmere
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
0.3 mi walk to Red River Beach! Short drive to downtown Harwichport and the Freedom Ferry to Nantucket! Great house for ...
From $528 per night (USD)
VRBO
$Spacious home located steps to the beach with patio, W\/D, AC, & kayaks$
From $427 per night (USD)
Expedia
Spacious home located steps to the beach with patio, W\/D, AC, & kayaks
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Crows Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $427 per night (USD)
Expedia
From $320 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 $320 per night (USD)
VRBO
From $783 per night (USD)
VRBO
Marsh and Nantucket Sound Views!
Bedrooms:
4
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 $783 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:
5
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 $1356 per night (USD)
Expedia
Chatterbox: 032-CB Chatham Charm in the Heart of Town
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
This property is professionally managed by Pretty Picky Properties Chatham Charm in the Heart of Town NEW Listing for ...
From $1356 per night (USD)
Expedia
From $300 per night (USD)
VRBO
Bright cape cod retreat; steps to White pond, bike path, CAC & fire pit
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunny-Side Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $300 per night (USD)
VRBO
Click For Pricing
Expedia
Great Location Steps to Chatham Lighthouse & Town
Bedrooms:
5
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 ...
Click For Pricing
Expedia
From $715 per night (USD)
VRBO
4-bedroom house in charming Chatham steps from Main Street and the Mill Pond
Bedrooms:
3
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 $715 per night (USD)
VRBO
From $576 per night (USD)
VRBO
3BR - Large Fenced In Yard, Patio, Near Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Location: Located on a dead-end road near the head of Pleasant Bay, this 3 bedroom house offers a large fenced in yard w ...
From $576 per night (USD)
VRBO
From $960 per night (USD)
VRBO
Malabar: 407-CB Chatham Charm, Walk to Beach and Town
Bedrooms:
5
Bathrooms:
3
Sleeps:
8
This property is professionally managed by Pretty Picky Properties. Chatham Charm, Walk to Beach and Town NEW Listing ...
From $960 per night (USD)
VRBO
From $895 per night (USD)
Expedia
Cape Escape: 048-CS Luxurious Chatham Home with Expansive Water Views
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties Luxurious Chatham Home with Expansive Water Views N ...
From $895 per night (USD)
Expedia
From $702 per night (USD)
VRBO
Beautifully Renovated Cape Cod Retreat near Pleasant Bay & Top Attractions
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
*Cancellation policy at end of property description.* Nestled in the picturesque town of Harwich, Mooncusser is a beau ...
From $702 per night (USD)
VRBO
From $1159 per night (USD)
Expedia
Walk to 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 ...
From $1159 per night (USD)
Expedia
From $332 per night (USD)
VRBO
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)
VRBO
From $821 per night (USD)
Expedia
Pool, Half Mile to Beach!
Bedrooms:
4
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 $821 per night (USD)
Expedia
From $1122 per night (USD)
VRBO
Luxury Waterfront with Game Room!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: 16693 - Chatham Homecoming: Luxury Waterfront with Game Room! The Space: Perched above the shimmering waters o ...
From $1122 per night (USD)
VRBO
From $604 per night (USD)
Expedia
Harbor View House: 094-H Modern Harwich Port Home with Water Views
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
This property is professionally managed by Pretty Picky Properties Modern Harwich Port Home with Water Views NEW LISTI ...
From $604 per night (USD)
Expedia
From $495 per night (USD)
VRBO
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 $495 per night (USD)
VRBO
$NEW LISTING! Northside Dennis 4BD--A\/C, Close to Popular Dennis Beaches$
From $612 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 $612 per night (USD)
VRBO
From $1460 per night (USD)
VRBO
Luxury Family Fun - Heated Pool, Hot Tub, Game Room, Walk to Small Beach - 5BR
Bedrooms:
4
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 $1460 per night (USD)
VRBO
From $838 per night (USD)
Expedia
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 ...
From $838 per night (USD)
Expedia
From $684 per night (USD)
VRBO
Soundside Sanctuary - Chatham Home Close to Forest Beach & The Rail Trail
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to Soundside Sanctuary! Nestled in a quiet Chatham neighborhood, this peaceful retreat offers spacious, updated ...
From $684 per night (USD)
VRBO
From $2719 per night (USD)
Expedia
Sunsets and saltwater views of The Atlantic Ocean, Nauset Beach, Strong Island and Bassing Harbor
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Magnificent, wraparound saltwater views of the Atlantic Ocean, Nauset Beach, Strong Island, Bassing Harbor and north to ...
From $2719 per night (USD)
Expedia
From $840 per night (USD)
VRBO
Charming 4-bedroom house with AC and WiFi steps from Wequassett Resort
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Escape to your perfect Cape Cod summer with this stunning rental property located steps away from the beauty of Pleasant ...
From $840 per night (USD)
VRBO
From $844 per night (USD)
Expedia
Waterfront on Pleasant Bay!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: 17711 - Island Views: Waterfront on Pleasant Bay! The Space: Wake up to sweeping views of Pleasant Bay, where ...
From $844 per night (USD)
Expedia
From $563 per night (USD)
VRBO
Great location with Water Views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 17710 - Captains Cottage: Great location with Water Views! The Space: Escape to the charm of Harwich, where th ...
From $563 per night (USD)
VRBO
From $728 per night (USD)
Expedia
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 $728 per night (USD)
Expedia
From $911 per night (USD)
VRBO
South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus!
Bedrooms:
4
Bathrooms:
6
Sleeps:
11
This home is professionally managed by Pretty Picky Properties Waterfront, Six Bedrooms, Free Boating Bonus! NEW Listi ...
From $911 per night (USD)
VRBO
From $755 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 $755 per night (USD)
Expedia
From $346 per night (USD)
VRBO
Walk to Beach: South Chatham Home
Bedrooms:
1
Bathrooms:
3
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 $346 per night (USD)
VRBO
From $434 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 $434 per night (USD)
Expedia
From $482 per night (USD)
VRBO
Harwich Home with Sunroom near Red River Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A perfect vacation spot for family gatherings. The house is located in a quiet neighborhood that is walking distance to ...
From $482 per night (USD)
VRBO
From $989 per night (USD)
VRBO
Spacious 4-bedroom house in Chatham - Walkable to Oyster Bay Pond & Downtown.
Bedrooms:
5
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
From $246 per night (USD)
VRBO
Charming antique cottage walk to everything downtown Chatham !
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Your cozy getaway awaits in Chatham at this adorable Main Stret in town antique cottage ! One block walk to the Squire ...
From $246 per night (USD)
VRBO
From $668 per night (USD)
Expedia
Close to Ridgevale Beach!
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 ...
From $668 per night (USD)
Expedia
From $479 per night (USD)
VRBO
Close to Forest Beach!!
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 ...
From $479 per night (USD)
VRBO
From $558 per night (USD)
Expedia
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 $558 per night (USD)
Expedia
From $1250 per night (USD)
VRBO
Pondside Retreat - Beach Access, Game Room, Firepit, Spacious Yard & Water Views
Bedrooms:
4
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 $1250 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Fantastic Main Street location!!
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 $385 per night (USD)
Expedia
From $369 per night (USD)
VRBO
THREE BEDROOM--MINUTES TO GOOSE POND, PLEASANT BAY AND TOWN.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cozy, comfortable home just short drive to town and beaches. This Chatham 3 bedroom, 2 bath offers central air conditio ...
From $369 per night (USD)
VRBO
From $536 per night (USD)
Expedia
Peaceful and private retreat in West Chatham.
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 $536 per night (USD)
Expedia
From $1014 per night (USD)
VRBO
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. NEW Listing for 2025! Sleeps 6 Linens i ...
From $1014 per night (USD)
VRBO
From $1530 per night (USD)
Expedia
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 ...
From $1530 per night (USD)
Expedia
From $278 per night (USD)
VRBO
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 $278 per night (USD)
VRBO
From $2350 per night (USD)
Expedia
ON PLEASANT BAY - TOPSIDE MAIN HOUSE
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
<p>Located in Orleans, this vacation home lets you experience it all. Fans of nature and the outdoors will love being wi ...
From $2350 per night (USD)
Expedia
From $344 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 $344 per night (USD)
VRBO
From $591 per night (USD)
VRBO
The Nook on Nob Hill, The Nook on Nob Hill
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Walk to Downtown Chatham & Cape Cod Rail Trail The Perfect Cape Cod Vacation Rental for Families & Outdoor Enthusiasts ...
From $591 per night (USD)
VRBO
From $593 per night (USD)
VRBO
Relax Close to Chatham & Orleans (2401)
Bedrooms:
3
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 $593 per night (USD)
VRBO
From $953 per night (USD)
VRBO
Family Friendly Home. Kid Amenities. Beach Nearby!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Perfect for families, this cozy vacation home is packed with kid-friendly amenities! Enjoy a lovely deck, two spacious l ...
From $953 per night (USD)
VRBO
From $744 per night (USD)
VRBO
Sweeping Views, 150 Yards to Private Beach!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: 16694 - Oceanside Delight: Sweeping Views, 150 Yards to Private Beach! The Space: Escape to Oceanside Delight, ...
From $744 per night (USD)
VRBO
From $1001 per night (USD)
Expedia
Shore Daze: 096-C Luxury Living in Chatham with Pool and Hot Tub
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
This property is professionally managed by Pretty Picky Properties Luxury Living in Chatham with Pool and Hot Tub Pool ...
From $1001 per night (USD)
Expedia
From $259 per night (USD)
VRBO
New listing! Cozy, fresh and clean 1-bedroom cottage with Pond access in Chatham
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This cozy 1-bedroom cottage in Chatham is the perfect retreat for a couple’s or solo getaway. 2 occupants only please. S ...
From $259 per night (USD)
VRBO
$Waterfront 3-BR House w Hot tub: kayak\/canoe up the tidal river to Pleasant Bay!$
From $676 per night (USD)
Expedia
Waterfront 3-BR House w Hot tub: kayak\/canoe up the tidal river to Pleasant Bay!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Get ready to relax in this 3-bedroom house in Chatham. This wonderful riverfront property features a 7-person hot tub wi ...
From $676 per night (USD)
Expedia

Search Your Destination Now!

Chatham Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 664 Rentals