Home Vacation Home Rentals By Owner In Chatham, MA

Showing 200 Of 276 Vacation Rentals
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Exceptional(8)

$991.93

/ Nightly
Private Vacation Home

Water Views in Chatham!

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(11)

$994.37

/ Nightly
Private Vacation Home

Panoramic Water Views w/ Private Beach!

Chatham, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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$1020.32

/ Nightly
Private Vacation Home

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

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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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

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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$1027.8

/ Nightly
Private Vacation Home

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

Chatham, Massachusetts, United States

Bed 7

Bed

Bath 5

Bath

Sleep 15

Sleeps
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$1039.88

/ Nightly
Private Vacation Home

Beautiful house that is a walk to downtown!

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(1)

$1042.11

/ Nightly
Private Vacation Home

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

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(1)

$1043.21

/ Nightly
Private Vacation Home

Coastal Comfort & Cape Cod Charm Await

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(9)

$1051.51

/ Nightly
Private Vacation Home

Spacious Home on the Loop in Chatham

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 9

Sleeps
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Exceptional(29)

$1054.47

/ Nightly
Private Vacation Home

Family friendly luxury home with heated pool and spa

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(15)

$1062.18

/ Nightly
Private Vacation Home

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

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(1)

$1063.23

/ Nightly
Private Vacation Home

Peaceful Patio near Beach!

South Chatham, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(23)

$1066.31

/ Nightly
Private Vacation Home

5 Bedroom Chatham Charmer RPAM012

Chatham, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(10)

$1069.08

/ Nightly
Private Vacation Home

Beautiful and Spacious, 3BR/3 BR with bonus room - walk to the beach!

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 12

Sleeps
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$1086.02

/ Nightly
Private Vacation Home

Close to kid-friendly Ridgevale Beach!

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(48)

$1089.18

/ Nightly
Private Vacation Home

Historic Waterfront Home with Sweeping Chatham Water Views! Pet Friendly!

West Chatham, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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$1096.68

/ Nightly
Private Vacation Home

Pet friendly and spacious home in quiet neighborhood!

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(14)

$1111.64

/ Nightly
Private Vacation Home

300 Yds on Sidewalk to Hardings Beach; On Private 1.5 Acres.

Chatham, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(2)

$1126.55

/ Nightly
Private Vacation Home

Charming house located in the heart of downtown Chatham!

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(1)

$1139.04

/ Nightly
Private Vacation Home

Waterfront Chatham Escape, Pet Friendly, Pond Views & Beach Nearby

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Home Most popular vacation rentals in Chatham

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Exceptional(1)

$649.31

/ Nightly
Condo

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

Chatham, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(1)

$702.73

/ Nightly
Private vacation home

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

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(1)

$689.57

/ Nightly
Private vacation home

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

Chatham, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 3

Sleeps
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Exceptional(1)

$684.64

/ Nightly
Private vacation home

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

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(1)

$666.25

/ Nightly
Private vacation home

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

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(1)

$661.52

/ Nightly
Private vacation home

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

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(1)

$657.71

/ Nightly
Cottage

Excellent Chatham Cottage

Chatham, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(1)

$657.11

/ Nightly
Private vacation home

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

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(1)

$651.06

/ Nightly
Private vacation home

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

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(1)

$586.56

/ Nightly
Private vacation home

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

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 1

Bath

Sleep 8

Sleeps

Most Popular Cities in Massachusetts