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

Chatham Rentals

From $751 per night (USD)
VRBO
Heated Plunge Pool, Game Barn, AC, 5 Min to Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Summary: 16683 - Cherry Blossom: Plunge Pool, Game Barn, AC, 5 Min to Beach! The Space: Experience the charm of Cha ...
From $751 per night (USD)
VRBO
From $920 per night (USD)
Expedia
Rail Trail Access: Home 2 Mi to Lighthouse Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your next Cape Cod adventure awaits at this cozy Chatham vacation rental. Perfect for a memorable family getaway on the ...
From $920 per night (USD)
Expedia
From $754 per night (USD)
VRBO
Newly Renovated Chatham Home overlooking Cranberry Bog.
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Beautiful classic cape house with huge back deck overlooking a quintessential Cape Cod cranberry bog. The house has been ...
From $754 per night (USD)
VRBO
From $2183 per night (USD)
VRBO
Water views, private beach and spectacular sunsets from highest point in town.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This large, beautiful home is the perfect place to stay for your next beach vacation: whether you’re hosting a big group ...
From $2183 per night (USD)
VRBO
From $406 per night (USD)
VRBO
Relaxing 3br, private yard, walk to beach, close to bike trail and shopping!
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Relax and unwind at this charming South Chatham cottage, just a short 0.4-mile walk to Pleasant Street Beach. Set on a l ...
From $406 per night (USD)
VRBO
From $1001 per night (USD)
Expedia
Panoramic Water Views w/ Private Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Summary: 16684 - Deja View: Panoramic Water Views w/ Private Beach! The Space: Find yourself on island time at this ...
From $1001 per night (USD)
Expedia
From $223 per night (USD)
VRBO
Newly renovated house 3 minutes to Wequassett Resort and 7 minutes to CBI.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Relax with the whole family at this peaceful place to stay. A stunning, fresh, contemporary home in Chatham! Perched upo ...
From $223 per night (USD)
VRBO
From $581 per night (USD)
Expedia
Ping-Pong & Backyard: Spacious Chatham Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Experience beachside bliss when you stay at this 3-bedroom, 3-bath South Chatham vacation rental! The home also features ...
From $581 per night (USD)
Expedia
From $553 per night (USD)
VRBO
Walk to Pleasant St Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Special Pricing Offered for Remaining In-Season Weeks - Book and Save10% Off, $2925 per week, plus fees and taxes ...
From $553 per night (USD)
VRBO
Click For Pricing
Expedia
Chatham Tails & Trails!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Charming three-bedroom home in quiet neighborhood! One floor living, this home offers a queen bed in each of the three ...
Click For Pricing
Expedia
From $1554 per night (USD)
VRBO
Private and pet friendly with expansive back deck
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Private and pet friendly. The bright, open living and dining area features a large slider that leads directly to the bac ...
From $1554 per night (USD)
VRBO
From $4793 per night (USD)
Expedia
Stroll to Chatham's Popular Shops & Dining / Or Walk to Andrew Hardings Beach from This NEW Impeccable Compound
Bedrooms:
7
Bathrooms:
7
Sleeps:
16
Stroll to Chatham's Popular Shops & Dining / Or Walk to Andrew Hardings Beach from This NEW Impeccable Compound Rece ...
From $4793 per night (USD)
Expedia
From $521 per night (USD)
VRBO
Chatham EsCAPE: Pet Friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This charming 3-bedroom, 2-bathroom home is ideally situated between the tranquil Ridgevale Beach and the vibrant Chatha ...
From $521 per night (USD)
VRBO
From $541 per night (USD)
Expedia
Close to Beach Renovated Dog Friendly Cape Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
4 minutes from the beach and nestled on a spacious half acre set back more than 250 feet on a private road, this newly r ...
From $541 per night (USD)
Expedia
From $809 per night (USD)
VRBO
New! Chatham Cottage- 1 Mile to Downtown & Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to our charming 2 bed/1 bath North Chatham cottage! A short walk to Chatham`s best beaches and downtown shops an ...
From $809 per night (USD)
VRBO
Click For Pricing
Expedia
Steps to Chatham's Historic Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Luxury Retreat on Popular Main Street Chatham. This unique hide-a-way is a spacious 2 bedroom 2nd floor condo in the he ...
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Expedia
From $667 per night (USD)
VRBO
Stroll To Lighthouse Beach or Chatham's Charming Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Best location to spend your days in Chatham! This comfortable condominium overlooks the peaceful marshland in the back a ...
From $667 per night (USD)
VRBO
From $572 per night (USD)
Expedia
Walk to Main St and Oyster Pond in Chatham!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: 16685 - Slack Tide : Walk to Main St and Oyster Pond in Chatham! The Space: Discover the epitome of Cape C ...
From $572 per night (USD)
Expedia
From $1771 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 $1771 per night (USD)
VRBO
From $753 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 $753 per night (USD)
VRBO
From $664 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 ...
From $664 per night (USD)
VRBO
From $607 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 $607 per night (USD)
Expedia
From $502 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 $502 per night (USD)
VRBO
From $1069 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 $1069 per night (USD)
Expedia
From $540 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 encl ...
From $540 per night (USD)
VRBO
From $1033 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 $1033 per night (USD)
Expedia
From $1448 per night (USD)
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 ...
From $1448 per night (USD)
VRBO
From $1399 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 $1399 per night (USD)
VRBO
From $830 per night (USD)
VRBO
Cozy Chatham Getaway- minutes to all things Cape Cod!
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 $830 per night (USD)
VRBO
From $719 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 $719 per night (USD)
Expedia
From $800 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 $800 per night (USD)
VRBO
From $1120 per night (USD)
Expedia
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 $1120 per night (USD)
Expedia
From $995 per night (USD)
VRBO
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 $995 per night (USD)
VRBO
From $772 per night (USD)
Expedia
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 $772 per night (USD)
Expedia
From $683 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 $683 per night (USD)
VRBO
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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- ...
Click For Pricing
Expedia
From $11024 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 $11024 per night (USD)
VRBO
From $884 per night (USD)
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 ...
From $884 per night (USD)
Expedia
From $1189 per night (USD)
VRBO
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 $1189 per night (USD)
VRBO
From $1528 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 $1528 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 ...
Click For Pricing
VRBO
From $357 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 $357 per night (USD)
Expedia
From $632 per night (USD)
VRBO
Half Mile Walk to Beach, Dog Friendly!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: 16691 - Seaside: Half Mile Walk to Beach, Dog Friendly! The Space: Located in the coveted Ridgevale Beach ...
From $632 per night (USD)
VRBO
From $491 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 ...
From $491 per night (USD)
Expedia
From $463 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 Hideaw ...
From $463 per night (USD)
VRBO
From $915 per night (USD)
VRBO
Marsh and Nantucket Sound Views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Booking Special - Reduced Rates for Remaining 2026 September Nights - Reduced from $800 to $500 per night (3 Night Min. ...
From $915 per night (USD)
VRBO
From $3860 per night (USD)
VRBO
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 s ...
From $3860 per night (USD)
VRBO
From $2017 per night (USD)
Expedia
Great Location Steps to Chatham Lighthouse & Town
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
PRICE RECENTLY REDUCED BY $2500! Stunning four-bedroom home located in the heart of Chatham...tucked away in the Old ...
From $2017 per night (USD)
Expedia
From $995 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 $995 per night (USD)
VRBO
From $880 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 wate ...
From $880 per night (USD)
Expedia
From $908 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 $908 per night (USD)
VRBO
From $1211 per night (USD)
VRBO
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 $1211 per night (USD)
VRBO
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VRBO
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 ...
Click For Pricing
VRBO
From $744 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 $744 per night (USD)
VRBO
From $529 per night (USD)
VRBO
Golf, Shop & Beach-Hop! Cape Cod Gem Steps to Sand
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 $529 per night (USD)
VRBO
From $409 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 char ...
From $409 per night (USD)
Expedia
From $885 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 $885 per night (USD)
VRBO
From $1283 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 $1283 per night (USD)
VRBO
Click For Pricing
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 ...
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VRBO
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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 ...
Click For Pricing
Expedia
From $488 per night (USD)
VRBO
Quintessential Cape Cod Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
. Escape to our cozy Cape Cod cottage in Chatham! This charming, eclectic retreat is perfect for couples, solo adventure ...
From $488 per night (USD)
VRBO
From $503 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 Enthusiast ...
From $503 per night (USD)
VRBO
From $1107 per night (USD)
VRBO
.5 miles to the Beach. Close to Wequasset. Foosball & Kid Friendly Amenities!
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 $1107 per night (USD)
VRBO
From $723 per night (USD)
Expedia
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 Deli ...
From $723 per night (USD)
Expedia
From $348 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 $348 per night (USD)
VRBO
From $1992 per night (USD)
Expedia
Coastal Retreat Minutes from Hardings Beach!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Coastal retreat in West Chatham - Minutes from Hardings Beach! Escape to this stunning, recently renovated beach house n ...
From $1992 per night (USD)
Expedia
From $1000 per night (USD)
VRBO
Chatham Charm Awaits - Family-Friendly Cottage Near Beaches & Local Attractions
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Escape to this delightful cottage nestled in picturesque Chatham—your perfect home base for Cape adventures! With 3 comf ...
From $1000 per night (USD)
VRBO
From $1595 per night (USD)
VRBO
Spacious Lakefront Escape - Perfect for Families
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
Welcome to our spacious lakefront home, perfect for families and large groups! With two master suites, four additional b ...
From $1595 per night (USD)
VRBO
From $938 per night (USD)
VRBO
Mooncusser Cottage – A Charming Waterfront Escape
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Mooncusser Cottage – A Charming Waterfront Escape Welcome to Mooncusser, a delightful vintage waterfront cottage where l ...
From $938 per night (USD)
VRBO
From $582 per night (USD)
Expedia
Renovated Chatham Cottage – Steps to Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
The Space Newly renovated and ready for your best Cape Cod summer. This charming 3-bedroom, 1.5-bath home in South Chath ...
From $582 per night (USD)
Expedia
From $813 per night (USD)
VRBO
Private Beach, Water Views, Incredible Location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: 16695 - Tide's Edge: Private Beach, Water Views, Incredible Location! The Space: Welcome to Tide's Edge, a ...
From $813 per night (USD)
VRBO
From $1648 per night (USD)
Expedia
Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Welcome to your dream Cape Cod getaway! Our brand-new, fully renovated 4-bedroom, 5-bath luxury home offers breathtaking ...
From $1648 per night (USD)
Expedia
From $1596 per night (USD)
VRBO
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Charming 5-Bedroom Home in the Heart of Downtown Chatham – Walk to Beach, Shops & More Welcome to your perfect Cape Cod ...
From $1596 per night (USD)
VRBO
From $724 per night (USD)
Expedia
Pet Friendly Waterfront Overlooking Oyster River
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Special Off-Season Pricing Offered for Remaining In-Season June and July Weeks - Book and Save Breezes and Views ...
From $724 per night (USD)
Expedia
From $1704 per night (USD)
VRBO
All-New Coastal Luxury Near CBI & Beaches, Dog-Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Spacious, newly renovated home off Shore Rd. Steps to Chatham Bars Inn, Fish Pier, Cow Yard Beach, Veterans Field, and ...
From $1704 per night (USD)
VRBO
From $1789 per night (USD)
Expedia
Experience a relaxing vacation at this beautifully maintained estate!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Experience a relaxing vacation at this beautifully maintained estate, featuring lush gardens and mature trees. This brig ...
From $1789 per night (USD)
Expedia
From $1581 per night (USD)
VRBO
Experience the charm of a beautiful seaside cottage just steps from Ridgevale Beach!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Experience the charm of a beautiful seaside cottage just steps from Ridgevale Beach! Available as a new rental for 2026, ...
From $1581 per night (USD)
VRBO
From $686 per night (USD)
Expedia
Spacious Dog-Friendly Retreat in Chatham
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
3 Bedroom-3 Bathroom- Sleeps 8 During peak summer weeks it is typical for our properties to require a 7-night stay, eith ...
From $686 per night (USD)
Expedia
From $1321 per night (USD)
VRBO
NEW! Spacious, Deck, Ping Pong, Foosball & Firepit - Luxurious Chatham Vacation!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Chatham Vacation, a newly renovated Cape Cod retreat perfect for families, two families traveling together & ...
From $1321 per night (USD)
VRBO
From $596 per night (USD)
VRBO
3BR Retreat Near Forest Beach & the Cape Cod Rail Trail
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Enjoy outdoor fun and easy access to Chatham`s vibrant town center. Easily explore local beaches, restaurants, ...
From $596 per night (USD)
VRBO
From $1506 per night (USD)
VRBO
Pet friendly, water views and lush lawns!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Views, views, views! Charming 3 bedroom, 3 bath cottage right on Mill Pond. Classic Cape Cod furnishings. Window A/C un ...
From $1506 per night (USD)
VRBO
From $973 per night (USD)
Expedia
Luxury Chatham Escape w/ Stunning Waterfront Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Wake up to stunning waterfront views at this beautifully designed Chatham retreat. The main level features an open livin ...
From $973 per night (USD)
Expedia
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VRBO
Beautiful and Spacious, 3BR/3 BR with bonus room - walk to the beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Lovely 4-bedroom, 3.5-bath beach rental on a quiet side street, just steps from Harding’s Beach. Light and bright with b ...
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VRBO
From $1547 per night (USD)
Expedia
Walk to Famous Chatham Lighthouse Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Ideally situated in one of Chatham's most sought-after areas, just steps from Lighthouse Beach, this vacation home is ri ...
From $1547 per night (USD)
Expedia
From $654 per night (USD)
VRBO
New construction. Short Walk to Beautiful Ridegevale Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
New construction, more photos to come. Quiet neighborhood. Short stroll to Ridgevale Beach, sleeps 6. First floor maste ...
From $654 per night (USD)
VRBO
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VRBO
Four Bedroom - Just 6/10's of a Mile to Nantucket Sound Forest Beach
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Charming Four Bedroom, 1.5 Bath Cottage that is just 6/10's of a mile to beautiful Forest Beach. * * * * See en ...
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VRBO
From $344 per night (USD)
VRBO
Central AC, Game Room, Dog-Friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 16701 - Happy Ours: Central AC, Game Room, Dog-Friendly! The Space: Welcome to Happy Ours, where your Cape ...
From $344 per night (USD)
VRBO
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Expedia
3 BR 2 BA Home in Charming Chatham - Close to Beaches, Town and Lobster Rolls!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This 3 BR 2 BA home is perfect for your vacation in delightful Chatham. From June 20th to September 12th 2026, there is ...
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Expedia
From $732 per night (USD)
VRBO
Coastal Fun in Chatham – Your Cape Cod Escape
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Stunning Chatham Home near Beach & Rail Trail Three levels of spacious, updated accommodations. Enjoy the grill, expan ...
From $732 per night (USD)
VRBO
From $733 per night (USD)
Expedia
Relaxing Cape Escape • Family Retreat • Walk to Beach • 6 beds • Sleeps 8
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Tucked between Forest Beach and Pleasant Street Beach, Stone’s Throw is a light-filled 4-bedroom, 3-bath South Chatham r ...
From $733 per night (USD)
Expedia
From $1318 per night (USD)
VRBO
North Chatham Beachwalk -Spacious 6 bedroom walk to beach sprawling private yard
Bedrooms:
3
Bathrooms:
6
Sleeps:
13
Sprawling Family home 3-minute walk to the beautiful Chatham Beach Relax and enjoy your summer family vacation in this s ...
From $1318 per night (USD)
VRBO
From $1168 per night (USD)
Expedia
Chatham Family Retreat w/ Heated Pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Beautiful 5BR Chatham home with Pool Chatham Retreat with Heated Pool, Spacious Deck & Direct Rail Trail Access Welcom ...
From $1168 per night (USD)
Expedia
From $783 per night (USD)
VRBO
New 3 bdrm/3b near Jackknife Beach/Wequassett/Gameroom
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to The Caper's Mate, a charming 3 bedroom, 3 full bath house located near Jackknife Cove, Wequassett Resort, clo ...
From $783 per night (USD)
VRBO
From $567 per night (USD)
Expedia
Great location, Dog Friendly, Central AC!
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Summary: 16699 - Cranberry Haus: Great location, Dog Friendly, Central AC! The Space: Get ready for your next Cape ...
From $567 per night (USD)
Expedia
From $961 per night (USD)
VRBO
Gorgeous, Dog Friendly, Central AC
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: Dog friendly, beautiful private yard, close to downtown Chatham and beaches The Space: This home is repres ...
From $961 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Sea House The Space: Tucked away among the trees at the end of a quiet lane, this light-filled cottage pro ...
From $351 per night (USD)
Expedia
From $894 per night (USD)
VRBO
Serene home near downtown with furnished deck - walk to Ridgevale Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Cozy Cape Time The Space: Classically Cape Cod in its style and appeal, this cozy, four-bedroom retreat in ...
From $894 per night (USD)
VRBO
From $397 per night (USD)
Expedia
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: A Chatham Pearl on Oyster River The Space: Experience a glimpse of Cape Cod waterfront living at this thre ...
From $397 per night (USD)
Expedia
From $533 per night (USD)
VRBO
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Lucky Number Seven The Space: This immaculate, sun-lit home features a spacious living room with a comfort ...
From $533 per night (USD)
VRBO
From $486 per night (USD)
Expedia
Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: South Chatham Sunshine The Space: Beach-going families will find a welcoming retreat at this three-bedroom ...
From $486 per night (USD)
Expedia

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Results: 439 Rentals