Chatham Vacation Rentals - HolidayHomes base64Hash Chatham Vacation Rentals - HolidayHomes

Chatham Vacation Rentals

Browse 864 available vacation homes and compared across 8 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

House Chatham
Near Harding's Beach, 4 min walk to Oyster River. 3BR, 2Bath, enclosed deck area
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House Chatham
See the World Cup AND Enjoy a Chatham Vacation June 2026
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House Chatham
5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet
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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
Renovated, modern Chatham beach house with lots of cozy charm
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House Chatham
Vacation home with yard, private pool & grill | City view
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House Chatham
Historic Waterfront Home with Sweeping Chatham Water Views! Pet Friendly!
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House Chatham
Child-friendly house with barbecue, yard & patio | Nature view | Beach nearby
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House Chatham
Peaceful, Charming, Quiet, Airy, Cozy - Take A Look!
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House Chatham
House with private pool, patio & barbeque
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Condo Chatham
Chatham Luxury! WALK to beach
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Cabin Chatham
Ocean & Marina Views From This Charming Cottage! Walk To Beach & Town.
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House Chatham
Fully equipped wonderful vacation home with barbeque, garden & terrace | Beach nearby | Suitable for remote work | Dogs allowed
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House Chatham
Fully equipped house with BBQ, patio & garden | Pets allowed
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Top 15 most Recommended Vacation Rentals in Chatham

Discover your ideal Chatham vacation rental with real-time comparisons of 864 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Chatham
House ∙ 6 guests ∙ 3 bedrooms

100 m² House

Chatham, Barnstable County, Massachusetts, United States
This house rental in West Chatham accommodates 6 guests and features a family-friendly kitchen for convenient meal preparation.
from $372
per night
(84)
View deal
Cabin Chatham
Cabin ∙ 6 guests ∙ 3 bedrooms

157 m² Cabin

Chatham, Barnstable County, Massachusetts, United States
This cozy cabin in West Chatham accommodates 6 guests and features a welcoming fireplace for a perfect getaway.
from $345
per night
(16)
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House Chatham
House ∙ 10 guests ∙ 4 bedrooms

323 m² House

Chatham, Barnstable County, Massachusetts, United States
This house rental in Chatham accommodates 10 guests and features a private pool for a relaxing vacation experience.
from $884
per night
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House Chatham
House ∙ 12 guests ∙ 5 bedrooms

232 m² House

Chatham, Barnstable County, Massachusetts, United States
Spacious house rental in North Chatham for 12 guests featuring a beautiful yard and ample parking.
from $855
per night
(2)
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Condo Chatham
Condo ∙ 5 guests ∙ 2 bedrooms

102 m² Condo

Chatham, Barnstable County, Massachusetts, United States
This Chatham condo accommodates 5 and features beach access for enjoyable seaside living.
from $531
per night
(77)
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House Chatham
House ∙ 8 guests ∙ 4 bedrooms

164 m² House

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 $342
per night
(1)
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House Chatham
House ∙ 12 guests ∙ 5 bedrooms

446 m² House

Chatham, Barnstable County, Massachusetts, United States
Spacious house rental in Chatham accommodates 12 guests and features a family-friendly yard for outdoor activities.
from $469
per night
(67)
View deal
House Chatham
House ∙ 6 guests ∙ 3 bedrooms

107 m² House

Chatham, Barnstable County, Massachusetts, United States
Charming house rental in Chatham for 6 guests featuring a spacious yard perfect for outdoor activities.
from $327
per night
(38)
View deal
House Chatham
House ∙ 8 guests ∙ 5 bedrooms

155 m² House

Chatham, Barnstable County, Massachusetts, United States
This house rental in Chatham accommodates 8 guests and features a spacious yard for outdoor relaxation.
from $486
per night
(16)
View deal

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