Home Vacation Rentals By Owner In Chatham, MA

Showing 140 Of 327 Vacation Rentals
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Exceptional(37)

$2174.74

/ Nightly
Private Vacation Home

Historic Sea Captain's Home in Downtown Chatham

Chatham, Massachusetts, United States

Bed 8

Bed

Bath 5

Bath

Sleep 18

Sleeps
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Exceptional(1)

$1612.61

/ Nightly
Private Vacation Home

Blue water views and coral sunsets from every room in this beautifully appointed home.

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(6)

$606.79

/ Nightly
Condo

This lovely condo location in town, has both a brick patio and deck for you to enjoy your morning coffee on!

Chatham, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 3

Sleeps
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Exceptional(16)

$2435.5

/ Nightly
Private Vacation Home

Sand Simeon - Relax, Unwind, Repeat!!

Chatham, Massachusetts, United States

Bed 6

Bed

Bath 6

Bath

Sleep 14

Sleeps
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Exceptional(9)

Select Dates for Price
Private Vacation Home

Nautical Comfort near Rail Trail

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(5)

Select Dates for Price
Private Vacation Home

School Street in the Old Village!! Charming, new construction with attention to detail!

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(17)

$1914.37

/ Nightly
Private Vacation Home

Walk to Beach and Town, Hot tub, Sleeps 8, Pet Friendly

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 5

Bath

Sleep 8

Sleeps
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Exceptional(6)

$1170.55

/ Nightly
Private Vacation Home

Beautiful home overlooking Emery Pond

Chatham, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(7)

Select Dates for Price
Private Vacation Home

Seaside Serenity Awaits at The Cape House!

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(1)

Select Dates for Price
Private Vacation Home

Upscale Elegance, Steps from Ridgevale Beach!

Chatham, Massachusetts, United States

Bed 2

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(2)

$1120.83

/ 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(4)

$1116.54

/ Nightly
Condo

Captain's Row: Pool, Tennis & Chatham Charm

Chatham, Massachusetts, United States

Bed 2

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(8)

$571.26

/ Nightly
Private Vacation Home

The Cape Escape: Walk to Harding's Beach

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(10)

$695.37

/ Nightly
Private Vacation Home

NEW LISTING Peace and Quiet Pond Front

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(13)

$799.86

/ Nightly
Private Vacation Home

Steps to Oyster Pond Private Dock!

Chatham, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(6)

$2340.09

/ Nightly
Private Vacation Home

Hiawatha: 177-CC Gorgeous Chatham Estate with heated pool, walk to Town or Beach

Chatham, Massachusetts, United States

Bed 7

Bed

Bath 5

Bath

Sleep 15

Sleeps
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Exceptional(25)

$722.87

/ Nightly
Private Vacation Home

Brand New Four Bedroom Home Near Beach and Town

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(6)

$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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$378.93

/ Nightly
Private Vacation Home

THREE BEDROOM--MINUTES TO GOOSE POND, PLEASANT BAY AND TOWN.

Chatham, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(85)

$797.15

/ Nightly
Private Vacation Home

4 Bedrooms, 2 Baths, Sleeps 8-10

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Cottage

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Home Most popular vacation rentals in Chatham

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Exceptional(85)

$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(85)

$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(85)

$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(85)

$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(85)

$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(85)

$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(85)

$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(85)

$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(85)

$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(85)

$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