South Chatham, Massachusetts

Vacation Rentals in South Chatham, Massachusetts

Discover 29 vacation rental properties in South Chatham. From 2 to 4 bedrooms. Average $377/night. 100% have pools.

29 verified listings Book securely on VRBO Prices updated March 2026

29 properties available

Fully Updated Home w/ Great Outdoor Space!

Fully Updated Home w/ Great Outdoor Space!

2 beds 1 bath
PoolA/CWiFiBalcony
$352/night
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Beautifully Maintained 3BR Colonial Close to Forrest Beach

Beautifully Maintained 3BR Colonial Close to Forrest Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$316/night
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Charming Beach House ~ Beautifully Updated & Immaculate. Walk to Sandy Beaches

Charming Beach House ~ Beautifully Updated & Immaculate. Walk to Sandy Beaches

2 beds 2 baths
PoolA/CWiFiBalcony
$331/night
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Walk to Private Beach Hot Tub AC Water Views The Sea Mist

Walk to Private Beach Hot Tub AC Water Views The Sea Mist

3 beds 2 baths
PoolA/CWiFiBalcony
$493/night
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Lovely cottage near beach and town - screened porch, outdoor shower, picnic area

Lovely cottage near beach and town - screened porch, outdoor shower, picnic area

2 beds 1 bath
PoolA/CWiFiBalcony
$180/night
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Close to Bike Path 1 Mile to Beaches!

Close to Bike Path 1 Mile to Beaches!

3 beds 2 baths
PoolA/CWiFiBalcony
$243/night
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Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches

Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches

3 beds 2 baths
PoolA/CWiFiBalcony
$271/night
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Wrap-Around Porch Mins. to Beach!

Wrap-Around Porch Mins. to Beach!

2 beds 1 bath
PoolA/CWiFiBalcony
$271/night
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Stunning Water Views, Swim and Kayak in Tidal River, Walk to Beach, AC, Like New

Stunning Water Views, Swim and Kayak in Tidal River, Walk to Beach, AC, Like New

3 beds 3 baths
PoolA/CWiFiBalcony
$610/night
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Sun Room Beaches and Dog Welcome!

Sun Room Beaches and Dog Welcome!

3 beds 2 baths
PoolA/CWiFiBalcony
$310/night
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Newly Built-3 Levels of Living, Central AC, Proximity to Beach and Marsh Views from Every Room!

Newly Built-3 Levels of Living, Central AC, Proximity to Beach and Marsh Views from Every Room!

2 beds 3 baths
PoolA/CWiFiBalcony
$351/night
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Explore Chatham's Nantucket Sound Beaches!

Explore Chatham's Nantucket Sound Beaches!

2 beds 1 bath
PoolA/CWiFiBalcony
$154/night
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Walk to Nantucket Sound Beaches!

Walk to Nantucket Sound Beaches!

3 beds 1 bath
PoolA/CWiFiBalcony
$180/night
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Beautiful and Pristine Rental in South Chatham.. Recently Reduced!

Beautiful and Pristine Rental in South Chatham.. Recently Reduced!

3 beds 2 baths
PoolA/CWiFiBalcony
$688/night
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Updated Beach House Deck Outdoor Shower!

Updated Beach House Deck Outdoor Shower!

2 beds 1 bath
PoolA/CWiFiBalcony
$211/night
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5-Mins to Forest Beach Dog Friendly!

5-Mins to Forest Beach Dog Friendly!

3 beds 2 baths
PoolA/CWiFiBalcony
$260/night
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New Opening July 6-13!! Spacious 3 BR with A-C, Walk to Beach! Pet Friendly!

New Opening July 6-13!! Spacious 3 BR with A-C, Walk to Beach! Pet Friendly!

3 beds 2 baths
PoolA/CWiFiBalcony
$450/night
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Fantastic Rooftop Deck * 3 Min Walk to Ocean Beach

Fantastic Rooftop Deck * 3 Min Walk to Ocean Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$406/night
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Private Beach Access AC Wifi Fire Pit The Blue Hydrangea

Private Beach Access AC Wifi Fire Pit The Blue Hydrangea

3 beds 2 baths
PoolA/CWiFiBalcony
$513/night
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"Cape Escape" Sunny Renovated House - Walk To Beach, Pickleball, Central AC

"Cape Escape" Sunny Renovated House - Walk To Beach, Pickleball, Central AC

3 beds 2 baths
PoolA/CWiFiBalcony
$572/night
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Sophisticated decor with an amazing use of space throughout this two bedroom (1 king and 2 twins) cottage.

Sophisticated decor with an amazing use of space throughout this two bedroom (1 king and 2 twins) cottage.

2 beds 1 bath
PoolA/CWiFiBalcony
$330/night
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9-Min Walk to Water Fire Pit!

9-Min Walk to Water Fire Pit!

4 beds 2 baths
PoolA/CWiFiBalcony
$385/night
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CHATHAM - WALK TO SANDY BEACHES, RESTAURANTS, SHOPS. PRIVATE YARD, LINENS, MINT!

CHATHAM - WALK TO SANDY BEACHES, RESTAURANTS, SHOPS. PRIVATE YARD, LINENS, MINT!

3 beds 2 baths
PoolA/CWiFiBalcony
$500/night
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Newly Renovated Modern Pond Access!

Newly Renovated Modern Pond Access!

4 beds 2 baths
PoolA/CWiFiBalcony
$340/night
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Cape Cod House w/ Deck & Grill: 2 Mi to Beach!

Cape Cod House w/ Deck & Grill: 2 Mi to Beach!

3 beds 2 baths
PoolA/CWiFiBalcony
$274/night
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Game Room Rooftop Deck Fire Pit!!

Game Room Rooftop Deck Fire Pit!!

4 beds 2 baths
PoolA/CWiFiBalcony
$428/night
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Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View

Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View

3 beds 2 baths
PoolA/CWiFiBalcony
$853/night
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Location, Location, Location!

Location, Location, Location!

3 beds 2 baths
PoolA/CWiFiBalcony
$215/night
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Cape Cod Home w/ Fire Pit & Grill: 1 Mi to Beach!

Cape Cod Home w/ Fire Pit & Grill: 1 Mi to Beach!

3 beds 2 baths
PoolA/CWiFiBalcony
$446/night
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More destinations in Massachusetts

Boston (1034) Nantucket (637) Provincetown (428) Falmouth (348) Wellfleet (288) Cambridge (276) Brewster (271) Chatham (258) Plymouth (247) Gloucester (203) Yarmouth (164) Sandwich (163) Rockport (158) Barnstable (155) Eastham (143) Dennis (139) Dennis Port (129) North Truro (126) Hyannis (121) South Yarmouth (115)