Chatham, Massachusetts

Vacation Rentals in Chatham, Massachusetts

Discover 258 vacation rental properties in Chatham. From 1 to 9 bedrooms. Average $501/night. 100% have pools.

258 verified listings Book securely on VRBO Prices updated March 2026

258 properties available

Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!

Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!

2 beds 2 baths
PoolA/CWiFiBalcony
$456/night
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New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach

New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach

1 bed 1 bath
PoolA/CWiFiBalcony
$329/night
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Newly Renovated Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach

Newly Renovated Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach

2 beds 2 baths
PoolA/CWiFiBalcony
$347/night
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Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

2 beds 1 bath
PoolA/CWiFiBalcony
$293/night
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Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!

Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!

2 beds 2 baths
PoolA/CWiFiBalcony
$532/night
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Steps to Chatham Center & Lighthouse Beach - charming home with central AC

Steps to Chatham Center & Lighthouse Beach - charming home with central AC

3 beds 4 baths
PoolA/CWiFiBalcony
$584/night
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Charming 3b/2ba House Close to Downtown/Pier/Beach

Charming 3b/2ba House Close to Downtown/Pier/Beach

2 beds 2 baths
PoolA/CWiFiBalcony
$490/night
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Cozy Cape near Chatham Center

Cozy Cape near Chatham Center

4 beds 2 baths
PoolA/CWiFiBalcony
$417/night
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Cute clapboard cottage on the hill off Stage Island Road!

Cute clapboard cottage on the hill off Stage Island Road!

1 bed 1 bath
PoolA/CWiFiBalcony
$130/night
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Sweet clapboard cottage that is walk to the beach and downtown!

Sweet clapboard cottage that is walk to the beach and downtown!

1 bed 1 bath
PoolA/CWiFiBalcony
$141/night
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Renovated cottage 1 mile to beach in Chatham!

Renovated cottage 1 mile to beach in Chatham!

2 beds 1 bath
PoolA/CWiFiBalcony
$240/night
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Outermost Waterfront Chatham Home w/ Wraparound Views

Outermost Waterfront Chatham Home w/ Wraparound Views

2 beds
PoolA/CWiFiBalcony
$592/night
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Charming Downtown Chatham

Charming Downtown Chatham

1 bed 1 bath
PoolA/CWiFiBalcony
$241/night
View Details → Book on VRBO
This lovely condo location in town, has both a brick patio and deck for you to enjoy your morning coffee on!

This lovely condo location in town, has both a brick patio and deck for you to enjoy your morning coffee on!

1 bed 1 bath
PoolA/CWiFiBalcony
$208/night
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Carriage House with Beautiful Water View, Steps to Beach & Main Street

Carriage House with Beautiful Water View, Steps to Beach & Main Street

2 beds 1 bath
PoolA/CWiFiBalcony
$396/night
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Charming Chatham Cottage

Charming Chatham Cottage

2 beds 1 bath
PoolA/CWiFiBalcony
$173/night
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Delightful Cottage for Two

Delightful Cottage for Two

1 bed 1 bath
PoolA/CWiFiBalcony
$130/night
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Dog-Friendly Home w/Yard, Deck, Free WiFi, New Gas Grill - Walk to the Beach

Dog-Friendly Home w/Yard, Deck, Free WiFi, New Gas Grill - Walk to the Beach

2 beds 1 bath
PoolA/CWiFiBalcony
$201/night
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Classic Cape House Walking Distance to the Beach

Classic Cape House Walking Distance to the Beach

3 beds 3 baths
PoolA/CWiFiBalcony
$251/night
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Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views

Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views

2 beds 1 bath
PoolA/CWiFiBalcony
$311/night
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Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

1 bed 1 bath
PoolA/CWiFiBalcony
$173/night
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Convenient to all amenities and beaches in Chatham

Convenient to all amenities and beaches in Chatham

1 bath
PoolA/CWiFiBalcony
$211/night
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Chatham Home ~1 Mi to Downtown & Oyster Pond Beach

Chatham Home ~1 Mi to Downtown & Oyster Pond Beach

2 beds 2 baths
PoolA/CWiFiBalcony
$257/night
View Details → Book on VRBO
New! Chatham Cottage- 1 Mile to Downtown & Beaches

New! Chatham Cottage- 1 Mile to Downtown & Beaches

2 beds 1 bath
PoolA/CWiFiBalcony
$331/night
View Details → Book on VRBO
Stay in a Chatham Windmill! Beautiful Water View, Steps to Beach & Main Street

Stay in a Chatham Windmill! Beautiful Water View, Steps to Beach & Main Street

1 bed 1 bath
PoolA/CWiFiBalcony
$304/night
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Cape Cod Chatham Water View Retreat

Cape Cod Chatham Water View Retreat

1 bed 1 bath
PoolA/CWiFiBalcony
$227/night
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Peaceful, Charming, Quiet, Airy, Cozy - Take A Look!

Peaceful, Charming, Quiet, Airy, Cozy - Take A Look!

3 beds 2 baths
PoolA/CWiFiBalcony
$276/night
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WALK TO RESTAURANTS, SHOPS & LIQUOR STORE!! CLOSE TO DOWNTOWN CHATHAM!!

WALK TO RESTAURANTS, SHOPS & LIQUOR STORE!! CLOSE TO DOWNTOWN CHATHAM!!

3 beds 1 bath
PoolA/CWiFiBalcony
$215/night
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On Goose Pond Pet Friendly Wifi Water Views Private

On Goose Pond Pet Friendly Wifi Water Views Private

1 bed 1 bath
PoolA/CWiFiBalcony
$271/night
View Details → Book on VRBO
Chatham Cottage on the Big Pond One Mile to Ocean Beaches

Chatham Cottage on the Big Pond One Mile to Ocean Beaches

2 beds 1 bath
PoolA/CWiFiBalcony
$155/night
View Details → Book on VRBO
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

2 beds 1 bath
PoolA/CWiFiBalcony
$307/night
View Details → Book on VRBO
Lovely Stage Harbor Estate Guest House W/Private Beach to Use

Lovely Stage Harbor Estate Guest House W/Private Beach to Use

2 beds 2 baths
PoolA/CWiFiBalcony
$326/night
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Chatham walk to Cape Cod beach

Chatham walk to Cape Cod beach

3 beds 2 baths
PoolA/CWiFiBalcony
$452/night
View Details → Book on VRBO
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

1 bed 1 bath
PoolA/CWiFiBalcony
$192/night
View Details → Book on VRBO
Walk to Main St and Oyster Pond in Chatham!

Walk to Main St and Oyster Pond in Chatham!

3 beds 2 baths
PoolA/CWiFiBalcony
$215/night
View Details → Book on VRBO
Beautiful Downtown Chatham 1 Bed, Close to the Beach - Newly renovated + Patio

Beautiful Downtown Chatham 1 Bed, Close to the Beach - Newly renovated + Patio

1 bed 1 bath
PoolA/CWiFiBalcony
$276/night
View Details → Book on VRBO
Pet Friendly on Oyster Pond River!

Pet Friendly on Oyster Pond River!

4 beds 2 baths
PoolA/CWiFiBalcony
$395/night
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Hidden Gem - Captain's Haven

Hidden Gem - Captain's Haven

1 bed 1 bath
PoolA/CWiFiBalcony
$136/night
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Chatham Escape!

Chatham Escape!

3 beds 1 bath
PoolA/CWiFiBalcony
$201/night
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Quintessential Cape directly on the Cape Cod Rail, Dog Friendly!

Quintessential Cape directly on the Cape Cod Rail, Dog Friendly!

4 beds 2 baths
PoolA/CWiFiBalcony
$174/night
View Details → Book on VRBO
Steps to Private Association Beach. End Unit Condo at Outermost Harbor.

Steps to Private Association Beach. End Unit Condo at Outermost Harbor.

2 beds 1 bath
PoolA/CWiFiBalcony
$236/night
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Full Renovation! Amazing Spot with Views!

Full Renovation! Amazing Spot with Views!

2 beds 1 bath
PoolA/CWiFiBalcony
$318/night
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Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6.

Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6.

3 beds 2 baths
PoolA/CWiFiBalcony
$335/night
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Charming/Great Location/Walk to town/baseball field

Charming/Great Location/Walk to town/baseball field

2 beds 1 bath
PoolA/CWiFiBalcony
$452/night
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Excellent Chatham Cottage

Excellent Chatham Cottage

1 bed 1 bath
PoolA/CWiFiBalcony
$452/night
View Details → Book on VRBO
Luxury 9 BR Home w/ Pool in Downtown Chatham

Luxury 9 BR Home w/ Pool in Downtown Chatham

9 beds 10 baths
PoolA/CWiFiBalcony
$2,738/night
View Details → Book on VRBO
Chatham Beach Facing 2 Bedroom Condo With Private Beach Access

Chatham Beach Facing 2 Bedroom Condo With Private Beach Access

2 beds 2 baths
PoolA/CWiFiBalcony
$361/night
View Details → Book on VRBO
Quaint 2 Bedroom Cottage Overlooking White Pond

Quaint 2 Bedroom Cottage Overlooking White Pond

2 beds 1 bath
PoolA/CWiFiBalcony
$243/night
View Details → Book on VRBO

Showing 48 of 258 properties

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