Chatham Vacation Rentals - HolidayHomes base64Hash Chatham Vacation Rentals - HolidayHomes

Chatham Vacation Rentals

Browse 799 available vacation homes and compared across 7 trusted partners

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Top-Rated Vacation rentals in Chatham

Book the highest-rated Chatham vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

We use AI to generate the short summary in each offer below, check full description before booking.
House Chatham

5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet

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House Chatham

Coastal Charm in South Chatham โ€“ Walk to Beach & Bike Trail!

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House Chatham

Vacation home with BBQ & patio | Perfect for remote work

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House Chatham

Beautiful Retreat / Hot tub/ Walk to Ridgevale Beach

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House Chatham

Chatham-Walk to Town/Beach-Multi Family Friendly

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House Chatham

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

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House Chatham

Children-friendly pleasant house with patio, yard & grill | Nature view | Next to the beach | Perfect for remote work

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House Chatham

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

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House Chatham

Children-friendly spacious house with grill & patio | City view | Dogs allowed

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House Chatham

Child-friendly house with barbecue, yard & patio | Nature view | Beach nearby

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Cabin Chatham

Family-oriented beautiful cottage with barbeque | Water view | Pets allowed

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House Chatham

BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort.

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Condo Chatham

Children-friendly condo with grill & patio | City view

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House Chatham

Beachfront Nantucket style home with amazing views on 3 acre estate setting

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House Chatham

Classic 5Br Cape Cod Home In Exclusive N. Chatham- Steps To The Private Beach

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Top 15 most Recommended Vacation Rentals in Chatham

Discover your ideal Chatham vacation rental with real-time comparisons of 799 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

We use AI to generate the short summary in each offer below, check full description before booking.
House Chatham
House โˆ™ 8 guests โˆ™ 3 bedrooms

Children-friendly charming house with barbeque & patio | City view | Close to the beach | Pets are welcome

Chatham, Barnstable County, Massachusetts, United States
This spacious house rental in Chatham accommodates 8 guests and features a family-friendly kitchen for memorable gatherings.
from $911
per night
(10)
View deal
Cabin Chatham
Cabin โˆ™ 6 guests โˆ™ 3 bedrooms

Cottage with patio, yard & BBQ

Chatham, Barnstable County, Massachusetts, United States
This cozy cabin in West Chatham accommodates 6 guests and features a family-friendly yard perfect for outdoor fun.
from $373
per night
(101)
View deal
House Chatham
House โˆ™ 8 guests โˆ™ 4 bedrooms

Fully equipped spacious house with garden, terrace & barbecue | Perfect for remote work | Pet-friendly

Chatham, Barnstable County, Massachusetts, United States
This house rental in North Chatham accommodates 8 guests and features a spacious yard perfect for outdoor activities.
from $321
per night
(8)
View deal
House Chatham
House โˆ™ 8 guests โˆ™ 4 bedrooms

House | Dogs allowed

Chatham, Barnstable County, Massachusetts, United States
This house rental in West Chatham accommodates 8 guests and features convenient parking for your stay.
from $601
per night
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House Chatham
House โˆ™ 6 guests โˆ™ 3 bedrooms

Family-oriented beautiful house with BBQ, patio & yard | Nature view | Beach nearby

Chatham, Barnstable County, Massachusetts, United States
This house rental in Chatham accommodates 6 guests and features a family-friendly yard perfect for outdoor activities.
from $603
per night
(49)
View deal
House Chatham
House โˆ™ 6 guests โˆ™ 3 bedrooms

Pleasant vacation home with terrace, garden & grill

Chatham, Barnstable County, Massachusetts, United States
Charming house rental in Chatham for 6 guests featuring a spacious yard perfect for outdoor activities.
from $334
per night
(39)
View deal
House Chatham
House โˆ™ 8 guests โˆ™ 4 bedrooms

Vacation home with barbecue, patio & garden

Chatham, Barnstable County, Massachusetts, United States
This spacious house rental in Chatham accommodates 8 guests and features a family-friendly kitchen and a large yard.
from $649
per night
(2)
View deal
House Chatham
House โˆ™ 12 guests โˆ™ 5 bedrooms

Children-friendly big vacation home with barbeque, private pool & patio | Good for workation

Chatham, Barnstable County, Massachusetts, United States
This spacious house rental in Chatham accommodates 12 guests and features a private pool for a relaxing getaway.
from $1,151
per night
(2)
View deal
House Chatham
House โˆ™ 10 guests โˆ™ 4 bedrooms

Family-oriented vacation home with patio, BBQ & yard | Nature view | Pets are welcome

Chatham, Barnstable County, Massachusetts, United States
Spacious house rental in Chatham for 10 guests featuring a family-friendly yard and ample parking.
from $390
per night
(135)
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