Chatham vacation rentals

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Recommended by KAYAK

Best Chatham vacation rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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$181 - $704$704 - $1,226$1,226 - $1,748$1,748 - $2,270$2,270+ per night

Property Types

ApartmentCondoCottageHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Chatham

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Perfect couples escape. Close to beaches, great biking & walking & pet friendly. - Chatham - Outdoors view
Perfect couples escape. Close to beaches, great biking & walking & pet friendly.
Chatham, MA
Free Wi-Fi
Pet friendly
$683+
Check availability
Lucky Number Seven - Chatham - Living room
Lucky Number Seven
Chatham, MA
9.4Wonderful(45)
Pet friendly
$767+
Check availability
Riviera Sunset - Chatham - Living room
Riviera Sunset
Chatham, MA
8.5Very good(14)
$725+
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Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach - Chatham - Living room
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
Chatham, MA
$539+
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Corner Cottage - Chatham - Building
Corner Cottage
Chatham, MA
7.8Good(9)
$535+
Check availability
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham - Chatham - Living room
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham
Chatham, MA
7.7Good(14)
$339+
Check availability
Seashell Wishes-Salty Kisses - Chatham - Balcony
Seashell Wishes-Salty Kisses
Chatham, MA
9.1Wonderful(12)
Pet friendly
$450+
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\'Chatham Up\' - Come Stay, Relax, Have Fun! - Chatham - Restaurant
\'Chatham Up\' - Come Stay, Relax, Have Fun!
Chatham, MA
Pet friendly
$414+
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Updated Beach House Deck Outdoor Shower! - Chatham - Patio
Updated Beach House Deck Outdoor Shower!
Chatham, MA
9.4Wonderful(10)
Parking
Free Wi-Fi
Pet friendly
$301+
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Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches - Chatham - Building
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Chatham, MA
$803+
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Delightful Cottage for Two - Chatham - Living room
Delightful Cottage for Two
Chatham, MA
Free Wi-Fi
$279+
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Lovely Home Near Bike Path Dog Welcome! - Chatham - Living room
Lovely Home Near Bike Path Dog Welcome!
Chatham, MA
8.3Very good(6)
Parking
Free Wi-Fi
Pet friendly
$363+
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Sea House - Chatham
Sea House
Chatham, MA
8.8Very good(10)
$556+
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A Chatham Pearl on Oyster River - Chatham
A Chatham Pearl on Oyster River
Chatham, MA
7.2Good(13)
Pet friendly
$584+
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33 Marcus - Chatham
33 Marcus
Chatham, MA
$1,147+
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#604: Great Location - Private, Secluded Near Downtown & Beach! Dog Friendly! - Chatham
#604: Great Location - Private, Secluded Near Downtown & Beach! Dog Friendly!
Chatham, MA
5.0Fair(1)
$238+
Check availability
Useful Info

KAYAK’s insights for vacation rentals in Chatham

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Chatham with confidence.

Which month has the cheapest vacation rental rates in Chatham?

Vacation rentals are cheapest in Chatham in February, with average rates of $247. In comparison, April is the most expensive month, with prices at $1,851.

What is the cheapest day of the week to book a vacation rental in Chatham?

Monday offers the lowest rates in Chatham, with an average nightly price of $248. The highest prices are found on Friday, with average rates at $975.

How early should you book a vacation rental in Chatham?

Book at least 59 days before your stay begins to get the best price for your Chatham vacation rental.
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Good to know

Low season

February

High season

April

Average price (weeknight)

$458

Average price (weekend night)

$929
Cheapest month to stay with an average 64% drop in price.
Most expensive month to stay with an average 172% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Chatham vacation rental deals

  • Pet friendly is the most popular vacation rental property amenity in Chatham
  • Vacation rentals in Chatham are around 50% more expensive than hotels on average. Search here to compare prices for all accommodation types in Chatham.
  • The best vacation rental property in Chatham is Lucky Number Seven (9.4, 45 reviews), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Chatham, you should consider visiting during the low season. The cheapest vacation homes in Chatham can be found in February and November.
  • The cheapest night for renting a vacation home in Chatham is Monday. In contrast, the most expensive is Friday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Chatham for 10 days.
  • The cheapest Chatham vacation rental found on KAYAK in the last 2 weeks was $372, while the most expensive was $1,265.

FAQs when booking a vacation home in Chatham

  • How much is a vacation rental for a week in Chatham?

    The average price for a weekly Chatham vacation rental found by KAYAK users in the last 2 weeks is $3,820.

  • How much is a vacation rental for a month in Chatham?

    The average price for a monthly Chatham vacation rental found by KAYAK users in the last 2 weeks is $16,372.

  • What types of vacation rentals are available in Chatham?

    There are loads of different property types that you can make your vacation home in Chatham. You’ll find apartments, condos, cottages, houses and villas.

  • Are there any pet-friendly vacation rentals in Chatham?

    There are a number of dog and pet-friendly Chatham vacation rentals, with around 18% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Chatham?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Chatham?

Our map will help you find the perfect place to stay in Chatham by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Chatham

Chatham vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Chatham. Find cheap vacation homes to rent in Chatham. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Chatham that suits you best.

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