Home Vacation Rentals By Owner In Chatham, MA

Showing 120 Of 327 Vacation Rentals
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Exceptional(83)

$370.82

/ Nightly
Private Vacation Home

Renovated cottage 1 mile to beach in Chatham!

Chatham, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(9)

$425.37

/ Nightly
Private Vacation Home

Idyllic Cape House Close to Beaches

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps
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Exceptional(23)

$453.16

/ Nightly
Cottage

Waterfront Chatham Retreat w/ WiFi & Privacy

Chatham, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$943.07

/ Nightly
Cottage

Chatham Charm Awaits - Family-Friendly Cottage Near Beaches & Local Attractions

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(11)

$1150.22

/ Nightly
Private Vacation Home

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

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(78)

$1170.83

/ Nightly
Private Vacation Home

Renovated Chatham Coastal Estate with Water Views and Room for Fourteen

Chatham, Massachusetts, United States

Bed 6

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(2)

$2010.7

/ Nightly
Private Vacation Home

Coastal Retreat Minutes from Hardings Beach!

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(2)

$516.33

/ Nightly
Private Vacation Home

The Nook on Nob Hill, The Nook on Nob Hill

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(6)

Select Dates for Price
Private Vacation Home

Slow M'Ocean – A Fresh Take on Cape Calm

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(18)

$583.78

/ Nightly
Private Vacation Home

Your Perfect South Chatham Summer Stay!!

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(11)

$900.51

/ Nightly
Cottage

Wonderful cottage located in the heart of downtown Chatham......steps to everything.

Chatham, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(14)

$771.16

/ Nightly
Private Vacation Home

Pristine Chatham home walkable to town, CBI, Fish Pier and baseball field

Chatham, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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$2091.38

/ Nightly
Private Vacation Home

Large 5-bdrm oceanfront estate on Monomoy National Wildlife Refuge, pet friendly

Chatham, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(6)

Select Dates for Price
Private Vacation Home

Chatham Ranch Retreat Near Hardings Beach

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(8)

$4973.32

/ Nightly
Private Vacation Home

Tennis anyone Beautiful, brand new construction with 8 bedrooms, 8 full baths and 2 half baths, that can sleep up to 20 guests.

Chatham, Massachusetts, United States

Bed 8

Bed

Bath 8

Bath

Sleep 18

Sleeps
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Exceptional(10)

Select Dates for Price
Private Vacation Home

Lake front, Near Beach, AC, WiFi, Pet Friendly near Bike Path

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(2)

$523.83

/ Nightly
Private Vacation Home

CHARMING 4 BEDROOM HISTORIC PROPERTY, WALK TO TOWN AND LIGHTHOUSE BEACH!!

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

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(7)

$792.76

/ Nightly
Private Vacation Home

Chatham Cape Cod Retreat, near boat yards, Harding's Beach, Stage Harbor Light

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(19)

Select Dates for Price
Private Vacation Home

The Heron's Nest - Sea Breezes & Sweet Dreams

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 9

Sleeps
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Home Most popular vacation rentals in Chatham

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Exceptional(19)

$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(19)

$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(19)

$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(19)

$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(19)

$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(19)

$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(19)

$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(19)

$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(19)

$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(19)

$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