Vacation Home Rentals By Owner In Chatham, MA

Showing 20 Of 276 Vacation Rentals

Exceptional(15)

$1062.18

/ Nightly

Private Vacation Home

Hardings Hideaway: 020-C Renovated Chatham Beach House with Views

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(12)

$915.22

/ Nightly

Private Vacation Home

Charming two year old 3Bd Rm 4 bath home .6mi to Ridgevale Beach

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(45)

$941.11

/ Nightly

Private Vacation Home

Ocean views, path to beach, short walk to lighthouse and town, sleeps 12

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(38)

$951.57

/ Nightly

Private Vacation Home

BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort.

Chatham, Massachusetts, United States

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Bath

Sleeps

$964

/ Nightly

Private Vacation Home

Hot Tub! Steps to Oyster Pond Beach and Downtown Chatham.

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$977.25

/ Nightly

Private Vacation Home

Waterfront Escape, Game Room, Dog Friendly!

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(79)

$986.56

/ Nightly

Private Vacation Home

GREAT LOCATION - Water View, Walk to beach & Town!

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(123)

$991.52

/ Nightly

Private Vacation Home

Water View-Walk town/beach, pets considered, Linen Option

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(8)

$991.93

/ Nightly

Private Vacation Home

Water Views in Chatham!

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(11)

$994.37

/ Nightly

Private Vacation Home

Panoramic Water Views w/ Private Beach!

Chatham, Massachusetts, United States

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Bath

Sleeps

$1020.32

/ Nightly

Private Vacation Home

Sweeping Water Views, Deeded Beach Access, Pet Friendly and AC

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(26)

$1024.9

/ Nightly

Private Vacation Home

Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond

Chatham, Massachusetts, United States

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Bath

Sleeps

$1027.8

/ Nightly

Private Vacation Home

Bring Fido! Spacious 2 family home 7-bedroom 5 bathroom in charming Chatham.

Chatham, Massachusetts, United States

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Bath

Sleeps

$1039.88

/ Nightly

Private Vacation Home

Beautiful house that is a walk to downtown!

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(1)

$1042.11

/ Nightly

Private Vacation Home

Stroll Chatham's Historic Downtown / Shops, Dining, Galleries, Etc.

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(1)

$1043.21

/ Nightly

Private Vacation Home

Coastal Comfort & Cape Cod Charm Await

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(9)

$1051.51

/ Nightly

Private Vacation Home

Spacious Home on the Loop in Chatham

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(29)

$1054.47

/ Nightly

Private Vacation Home

Family friendly luxury home with heated pool and spa

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(11)

$1150.22

/ Nightly

Private Vacation Home

.5 miles to the Beach. Close to Wequasset. Foosball & Kid Friendly Amenities!

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(78)

$1170.83

/ Nightly

Private Vacation Home

Renovated Chatham Coastal Estate with Water Views and Room for Fourteen

Chatham, Massachusetts, United States

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Bath

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Rent a place that suits your needs

Private vacation home

View 276 Private vacation home

Cottage

View 27 Cottage

Most popular vacation rentals in Chatham

Exceptional(78)

$649.31

/ Nightly

Condo

Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(78)

$702.73

/ Nightly

Private vacation home

Visit Chatham this winter—nominated one of Hallmark Channel’s merriest towns!

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(78)

$689.57

/ Nightly

Private vacation home

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

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(78)

$684.64

/ Nightly

Private vacation home

Cozy Riverfront retreat w hot tub, deck, fire pit. Kayak to Pleasant Bay!

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(78)

$666.25

/ Nightly

Private vacation home

A well-appointed getaway near beach, Wifi, Gas grill, Fireplace

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(78)

$661.52

/ Nightly

Private vacation home

Unique Oyster Pond 3bd-2ba home in private setting close to downtown.

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(78)

$657.71

/ Nightly

Cottage

Excellent Chatham Cottage

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(78)

$657.11

/ Nightly

Private vacation home

FOUR BEDROOM-- CLOSE TO TOWN AND TWO SALTWATER BEACH AREAS!

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(78)

$651.06

/ Nightly

Private vacation home

Charming Walk to Beach Chatham-Bayview Cottage 3 BR--Central A/C; Wi-Fi

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(78)

$586.56

/ Nightly

Private vacation home

Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball

Chatham, Massachusetts, United States

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Bath

Sleeps

Vacation Home Rentals By Owner In Chatham, MA

$1062.18

$915.22

$941.11

$951.57

$964

$977.25

$986.56

$991.52

$991.93

$994.37

$1020.32

$1024.9

$1027.8

$1039.88

$1042.11

$1043.21

$1051.51

$1054.47

$1150.22

$1170.83

Rent a place that suits your needs

Most popular vacation rentals in Chatham

$649.31

$702.73

$689.57

$684.64

$666.25

$661.52

$657.71

$657.11

$651.06

$586.56

Most Popular Cities in Massachusetts