Chatham vacation rentals

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Best Chatham vacation rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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$172 - $1,377$1,377 - $2,582$2,582 - $3,787$3,787 - $4,991$4,991+ per night

Property Types

ApartmentCondoCottageHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Chatham

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Lucky Number Seven - Chatham - Living room
Lucky Number Seven
Chatham, MA
9.5Wonderful(63)
Pet friendly
$411+
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Riviera Sunset - Chatham - Living room
Riviera Sunset
Chatham, MA
8.6Very good(19)
$379+
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Perfect couples escape. Close to beaches, great biking & walking & pet friendly. - Chatham - Bedroom
Perfect couples escape. Close to beaches, great biking & walking & pet friendly.
Chatham, MA
10Wonderful(14)
Free Wi-Fi
$458+
Check availability
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
9.3Wonderful(24)
$348+
Check availability
Lovely Home Near Bike Path Dog Welcome! - Chatham - Building
Lovely Home Near Bike Path Dog Welcome!
Chatham, MA
8.7Very good(8)
Parking
Free Wi-Fi
Pet friendly
$319+
Check availability
Chatham Village: Large, Newly-Renovated 1 Bedroom Apartment in Antique Home - Chatham - Living room
Chatham Village: Large, Newly-Renovated 1 Bedroom Apartment in Antique Home
Chatham, MA
9.6Wonderful(12)
Free Wi-Fi
$340+
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Charming Chatham House Walk to Downtown - Chatham - Beach
Charming Chatham House Walk to Downtown
Chatham, MA
10Wonderful(14)
Free Wi-Fi
$956+
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Updated Beach House Deck Outdoor Shower! - Chatham - Living room
Updated Beach House Deck Outdoor Shower!
Chatham, MA
9.5Wonderful(15)
Parking
Free Wi-Fi
Pet friendly
$306+
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Steps to Oyster Pond Private Dock! - Chatham - Kitchen
Steps to Oyster Pond Private Dock!
Chatham, MA
9.6Wonderful(11)
Parking
Free Wi-Fi
Pet friendly
$789+
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Beautiful home overlooking Emery Pond - Chatham - Kitchen
Beautiful home overlooking Emery Pond
Chatham, MA
10Wonderful(3)
$899+
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Seashell Wishes-Salty Kisses - Chatham - Balcony
Seashell Wishes-Salty Kisses
Chatham, MA
9.1Wonderful(17)
Pet friendly
$271+
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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
9.9Wonderful(45)
$494+
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Corner Cottage - Chatham - Building
Corner Cottage
Chatham, MA
7.2Good(12)
$325+
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Stay in a Chatham Windmill! Beautiful Water View, Steps to Beach & Main Street - Chatham - Kitchen
Stay in a Chatham Windmill! Beautiful Water View, Steps to Beach & Main Street
Chatham, MA
9.8Wonderful(13)
Free Wi-Fi
$361+
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Sea House - Chatham
Sea House
Chatham, MA
8.9Very good(11)
$371+
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A Chatham Pearl on Oyster River - Chatham
A Chatham Pearl on Oyster River
Chatham, MA
7.6Good(13)
Pet friendly
$363+
Check availability
Booking Insights

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.

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

Sunday offers the lowest rates in Chatham, with an average nightly price of $393. The highest prices are found on Friday, with average rates at $1,046.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

November
April
$525
$889
Cheapest month to stay with an average 60% drop in price.
Most expensive month to stay with an average 144% 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

  • Vacation rentals in Chatham are around 68% more expensive than hotels on average. Search here to compare prices for all accommodation types in Chatham.
  • The best vacation rental properties in Chatham are Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches (9.9, 45 reviews), Fully Updated Home w Great Outdoor Space (9.6, 23), and Beautiful home near Jacknife Beach and bike trail (9.6, 41), 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 November and May.
  • The cheapest night for renting a vacation home in Chatham is Sunday. 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 2 days.

FAQs when booking a vacation home in Chatham

  • 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 15% allowing you to bring your pet along with you.

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

    In the last 72 hours, users have found Chatham vacation rentals for tonight for as low as $370. Search here for similar prices

  • How much is a vacation rental in Chatham for this weekend?

    In the last 72 hours, users have found Chatham vacation rentals for this weekend for as low as $615 per night. Search here for similar prices

  • 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

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