Vacation Rentals in Chatham, Massachusetts

50 Properties Available

Chatham Seaside home and walk to the beach and even a water view! Private vacation home
Chatham Seaside home and walk to the beach and even a water view!
$11445 / night
View Details
Sophisticated Chatham Oasis with Pool & Spa RPAM062 Private vacation home
Sophisticated Chatham Oasis with Pool & Spa RPAM062
$3742 / night
View Details
New for 2025! Lovely home with heated pool, dock and the best views! RPMS158 Private vacation home
New for 2025! Lovely home with heated pool, dock and the best views! RPMS158
$3122 / night
View Details
Hiawatha: 177-CC Gorgeous Chatham Estate with heated pool, walk to Town or Beach Private vacation home
Hiawatha: 177-CC Gorgeous Chatham Estate with heated pool, walk to Town or Beach
$2340 / night
View Details
Historic Chatham house was moved from Water Street to present location in 1872 to avoid destruction by the salty tides. Private vacation home
Historic Chatham house was moved from Water Street to present location in 1872 to avoid destruction by the salty tides.
$2199 / night
View Details
Booking for Summer 2024! Private vacation home
Booking for Summer 2024!
$2160 / night
View Details
Water views, private beach and spectacular sunsets from highest point in town. Private vacation home
Water views, private beach and spectacular sunsets from highest point in town.
$2021 / night
View Details
Walk to Beach and Town, Hot tub, Sleeps 8, Pet Friendly Private vacation home
Walk to Beach and Town, Hot tub, Sleeps 8, Pet Friendly
$1981 / night
View Details
Luxury Chatham Home w\/ Heated Pool and Spa RPAM093 Private vacation home
Luxury Chatham Home w\/ Heated Pool and Spa RPAM093
$1715 / night
View Details
Luxury Family Fun - Heated Pool, Hot Tub, Game Room, Walk to Beach Private vacation home
Luxury Family Fun - Heated Pool, Hot Tub, Game Room, Walk to Beach
$1613 / night
View Details
2 Adjacent Homes on 6-acre Chatham Estate. Water views and access. Tennis & more Private vacation home
2 Adjacent Homes on 6-acre Chatham Estate. Water views and access. Tennis & more
$1602 / night
View Details
Spacious, Deck, Ping Pong, Foosball & Firepit - Luxurious Chatham Vacation! Private vacation home
Spacious, Deck, Ping Pong, Foosball & Firepit - Luxurious Chatham Vacation!
$1391 / night
View Details
Location and Luxury Private vacation home
Location and Luxury
$1357 / night
View Details
Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated: 021-C Private vacation home
Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated: 021-C
$1353 / night
View Details
Enjoy a Cape Cod beach vacation on the beach in picturesque Chatham. Private vacation home
Enjoy a Cape Cod beach vacation on the beach in picturesque Chatham.
$1317 / night
View Details
Apres Sea - Chatham 4 Bedroom w\/ Central AC Private vacation home
Apres Sea - Chatham 4 Bedroom w\/ Central AC
$1221 / night
View Details
Alluring Chatham in-town home with pool, walk to it all: 052-CS Private vacation home
Alluring Chatham in-town home with pool, walk to it all: 052-CS
$1206 / night
View Details
Luxurious Chatham Home with Expansive Water Views: 048-CS Private vacation home
Luxurious Chatham Home with Expansive Water Views: 048-CS
$1127 / night
View Details
Waterfront Pet Friendly Home, with best views in Chatham! Private vacation home
Waterfront Pet Friendly Home, with best views in Chatham!
$1094 / night
View Details
Waterfront house on Cape Cod in Chatham, MA. Private vacation home
Waterfront house on Cape Cod in Chatham, MA.
$1000 / night
View Details
Chatham Ocean View Home, Beach Accesso, 3 Decks, Pets Considered, Sleeps 10 Private vacation home
Chatham Ocean View Home, Beach Accesso, 3 Decks, Pets Considered, Sleeps 10
$977 / night
View Details
Walk to private beach, central air, wifi, 3 bedrooms. Cottage
Walk to private beach, central air, wifi, 3 bedrooms.
$975 / night
View Details
Elbow Inn: Private Retreat with Two Master Suites Private vacation home
Elbow Inn: Private Retreat with Two Master Suites
$910 / night
View Details
Home Plate Nestled in Downtown Chatham! Private vacation home
Home Plate Nestled in Downtown Chatham!
$909 / night
View Details
Chatham Compound + Carriage House - Huge yard, Game Room, Kayaks, Sleeps 10 Private vacation home
Chatham Compound + Carriage House - Huge yard, Game Room, Kayaks, Sleeps 10
$879 / night
View Details
New Waterfront Townhome Private vacation home
New Waterfront Townhome
$864 / night
View Details
Great location, Dog Friendly, Central AC! Private vacation home
Great location, Dog Friendly, Central AC!
$856 / night
View Details
Shore Road, Chatham – Just Renovated, Walk to Beach and Town, Superb Elevated Ocean Views: 568-C Private vacation home
Shore Road, Chatham – Just Renovated, Walk to Beach and Town, Superb Elevated Ocean Views: 568-C
$791 / night
View Details
Stroll To Lighthouse Beach or Chatham's Charming Downtown Private vacation home
Stroll To Lighthouse Beach or Chatham's Charming Downtown
$791 / night
View Details
Perfectly located, with central AC. 3BR, sleeps 6-8 Private vacation home
Perfectly located, with central AC. 3BR, sleeps 6-8
$777 / night
View Details
LOCATION & VIEW - Water Front Home In Chatham Village Private vacation home
LOCATION & VIEW - Water Front Home In Chatham Village
$775 / night
View Details
Beautiful Chatham Private vacation home
Beautiful Chatham
$760 / night
View Details
Contemporary 4bedroom home near beach. Private vacation home
Contemporary 4bedroom home near beach.
$755 / night
View Details
Pure Cape Cod Bliss around the corner from Pleasant Street Beach! Private vacation home
Pure Cape Cod Bliss around the corner from Pleasant Street Beach!
$733 / night
View Details
Cozy Family Home in Chatham - Firepit, Game Room, Large Deck, Yard + More Private vacation home
Cozy Family Home in Chatham - Firepit, Game Room, Large Deck, Yard + More
$731 / night
View Details
Star of the Sea - Newly Renovated Cape House .9Miles from the Beach Private vacation home
Star of the Sea - Newly Renovated Cape House .9Miles from the Beach
$727 / night
View Details
Located in the heart of downtown Chatham, this gem offers an easy walk to everything. Private vacation home
Located in the heart of downtown Chatham, this gem offers an easy walk to everything.
$713 / night
View Details
Walk to the beach! The Salty Breeze sleeps 10; updated house, bikes, beach toys! Private vacation home
Walk to the beach! The Salty Breeze sleeps 10; updated house, bikes, beach toys!
$711 / night
View Details
BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort. Private vacation home
BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort.
$708 / night
View Details
Chatham-Walk to Town\/Beach-Multi Family Friendly Private vacation home
Chatham-Walk to Town\/Beach-Multi Family Friendly
$679 / night
View Details
Stunning Water Views 2 Decks! By Beach! Private vacation home
Stunning Water Views 2 Decks! By Beach!
$674 / night
View Details
Awesome Location! Right on the Chatham \"Loop\", Perfect for Long Walks! Private vacation home
Awesome Location! Right on the Chatham \"Loop\", Perfect for Long Walks!
$666 / night
View Details
Walk to downtown Chatham! Private vacation home
Walk to downtown Chatham!
$643 / night
View Details
Central AC Close to Beach Dog Friendly! Private vacation home
Central AC Close to Beach Dog Friendly!
$633 / night
View Details
Chatham Bars Inn Hotel resort
Chatham Bars Inn
$633 / night
View Details
This lovely condo location in town, has both a brick patio and deck for you to enjoy your morning coffee on! Condo
This lovely condo location in town, has both a brick patio and deck for you to enjoy your morning coffee on!
$620 / night
View Details
Air Conditioned, King bed Comfort .Dog friendly Private vacation home
Air Conditioned, King bed Comfort .Dog friendly
$616 / night
View Details
Spacious Home with Direct Pond Access! Private vacation home
Spacious Home with Direct Pond Access!
$614 / night
View Details
Chatham rental ~ 4 bed\/3ba ~ walk to the beach Private vacation home
Chatham rental ~ 4 bed\/3ba ~ walk to the beach
$600 / night
View Details
Charming Family Cape, Impeccably Landscaped With Water Views Near The Beach! Private vacation home
Charming Family Cape, Impeccably Landscaped With Water Views Near The Beach!
$597 / night
View Details