Home Vacation Home Rentals By Owner In Chatham, MA

Showing 276 Of 276 Vacation Rentals
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Exceptional(1)

$2288.36

/ Nightly
Private Vacation Home

AMAZING NEW HOME, STEPS FROM LIGHTHOUSE BEACH!

Chatham, Massachusetts, United States

Bed 7

Bed

Bath 11

Bath

Sleep 14

Sleeps
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Exceptional(6)

$2306.57

/ Nightly
Private Vacation Home

Spend your quintessential Cape Cod vacation in a beautifully renovated 1862 Farm House on Stage Harbor Road!

Chatham, Massachusetts, United States

Bed 6

Bed

Bath 6

Bath

Sleep 13

Sleeps
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Exceptional(6)

$2322.52

/ Nightly
Private Vacation Home

Pool and large yard!

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 9

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(7)

$2389.43

/ Nightly
Private Vacation Home

Sophisticated Chatham Retreat with Private Pool and Spa RPAM093

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 4

Bath

Sleep 10

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(15)

$2453.58

/ Nightly
Private Vacation Home

Amazing Location Chatham / walk to Town Beaches and CBI

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(7)

$2462.51

/ Nightly
Private Vacation Home

Oceanside Chatham / walk to Town, Beaches and CBI

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(13)

$2532.14

/ Nightly
Private Vacation Home

Elevate Your Cape Stay: Chatham Luxury with Pool & Beach RPAM026

Chatham, Massachusetts, United States

Bed 6

Bed

Bath 6

Bath

Sleep 14

Sleeps
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Exceptional(7)

$3574.89

/ Nightly
Private Vacation Home

Heated pool, hot tub and breathtaking views! RPMS025

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(53)

$3604.48

/ Nightly
Private Vacation Home

Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.

Chatham, Massachusetts, United States

Bed 8

Bed

Bath 5

Bath

Sleep 18

Sleeps
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Exceptional(9)

$3741.8

/ Nightly
Private Vacation Home

Sophisticated Chatham Oasis with Pool & Spa RPAM062

Chatham, Massachusetts, United States

Bed 5

Bed

Bath 8

Bath

Sleep 12

Sleeps
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Exceptional(1)

$3905.03

/ Nightly
Private Vacation Home

Lovely home with heated pool, dock and the best views! RPMS158

Chatham, Massachusetts, United States

Bed 6

Bed

Bath 4

Bath

Sleep 12

Sleeps
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$4854.51

/ Nightly
Private Vacation Home

Stroll to Chatham's Popular Shops & Dining / Or Walk to Andrew Hardings Beach from This NEW Impeccable Compound

Chatham, Massachusetts, United States

Bed 7

Bed

Bath 7

Bath

Sleep 16

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(1)

$11407.16

/ Nightly
Private Vacation Home

Waterfront, Updated 4 Bedroom Home with Views of Stage Harbor & Nantucket Sound

Chatham, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Cottage

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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

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