Vacation Rentals By Owner In Chatham, MA

Showing 200 Of 327 Vacation Rentals

Exceptional(9)

$3741.8

/ Nightly

Private Vacation Home

Sophisticated Chatham Oasis with Pool & Spa RPAM062

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(5)

$912.74

/ Nightly

Private Vacation Home

Elbow Inn: Private Retreat with Two Master Suites

Chatham, Massachusetts, United States

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Exceptional(4)

$691.85

/ Nightly

Private Vacation Home

Chatham Bliss - Dog Friendly oasis with EV Charging

Chatham, Massachusetts, United States

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Bath

Sleeps

$563.43

/ Nightly

Private Vacation Home

Great location, Dog Friendly, Central AC!

Chatham, Massachusetts, United States

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Exceptional(19)

$652.37

/ Nightly

Private Vacation Home

Walk to Beach: Chatham Gem w/ Ocean-View Sunroom!

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$756.52

/ Nightly

Private Vacation Home

New 3 bdrm/3b near Jackknife Beach/Wequassett/Gameroom

Chatham, Massachusetts, United States

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Bath

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Exceptional(2)

Select Dates for Price

Private Vacation Home

Located in a quiet neighborhood, less than a mile from downtown Chatham

Chatham, Massachusetts, United States

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Sleeps

Exceptional(3)

$1296.77

/ Nightly

Private Vacation Home

Chatham Family Retreat w/ Heated Pool

Chatham, Massachusetts, United States

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Bath

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Exceptional(1)

$900.72

/ Nightly

Private Vacation Home

4-bedroom house in charming Chatham steps from Main Street and the Mill Pond

Chatham, Massachusetts, United States

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Bath

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Exceptional(112)

$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

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Exceptional(23)

$1202.64

/ Nightly

Private Vacation Home

Downtown Chatham Home - Near Oyster Pond - Spacious Patio - Family Friendly

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(1)

Select Dates for Price

Private Vacation Home

Classic Waterfront Chatham Estate

Chatham, Massachusetts, United States

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$1281.92

/ Nightly

Private Vacation Home

Four Bedroom home with Water Views of Saltwater Millpond & Mitchell River -- Close to Town and Oyster Pond Beach.

Chatham, Massachusetts, United States

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Bath

Sleeps

$452.07

/ Nightly

Private Vacation Home

Dog Friendly Chatham 4 Bedroom, A/C

Chatham, Massachusetts, United States

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Bath

Sleeps

Select Dates for Price

Private Vacation Home

3 BR 2 BA Home in Charming Chatham - Close to Beaches, Town and Lobster Rolls!

Chatham, Massachusetts, United States

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Exceptional(7)

$568.45

/ Nightly

Private Vacation Home

Walk to Main St and Oyster Pond in Chatham!

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(3)

$324.85

/ Nightly

Private Vacation Home

Central AC, Game Room, Dog-Friendly!

Chatham, Massachusetts, United States

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Exceptional(17)

$451.95

/ Nightly

Private Vacation Home

Waterfront on Private Lake!

Chatham, Massachusetts, United States

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Bath

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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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Exceptional(5)

$1432.72

/ Nightly

Private Vacation Home

Located in the heart of downtown Chatham, this gem offers an easy walk to everything.

Chatham, Massachusetts, United States

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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(5)

$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(5)

$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(5)

$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(5)

$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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Exceptional(5)

$666.25

/ Nightly

Private vacation home

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

Chatham, Massachusetts, United States

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Exceptional(5)

$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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Exceptional(5)

$657.71

/ Nightly

Cottage

Excellent Chatham Cottage

Chatham, Massachusetts, United States

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Bath

Sleeps

Exceptional(5)

$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(5)

$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(5)

$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 Rentals By Owner In Chatham, MA

$3741.8

$912.74

$691.85

$563.43

$652.37

$756.52

$1296.77

$900.72

$689.57

$1202.64

$1281.92

$452.07

$568.45

$324.85

$451.95

$951.57

$1432.72

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