Chatham vacation rentals

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Best Chatham vacation rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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$209 - $887$887 - $1,565$1,565 - $2,243$2,243 - $2,920$2,920+ per night

Property Types

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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
10Wonderful(12)
Free Wi-Fi
Pet friendly
$548+
Check availability
Lucky Number Seven - Chatham
Lucky Number Seven
Chatham, MA
9.5Wonderful(60)
Pet friendly
$490+
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B By the Sea - Chatham - Living room
B By the Sea
Chatham, MA
8.3Very good(21)
$494+
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
9.2Wonderful(22)
$332+
Check availability
Riviera Sunset - Chatham - Living room
Riviera Sunset
Chatham, MA
8.5Very good(17)
$533+
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Quaint 2 Bedroom Cottage Overlooking White Pond - Chatham - Balcony
Quaint 2 Bedroom Cottage Overlooking White Pond
Chatham, MA
9.2Wonderful(15)
$377+
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Delightful Cottage for Two - Chatham - Living room
Delightful Cottage for Two
Chatham, MA
8.9Very good(20)
Free Wi-Fi
$271+
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Seashell Wishes-Salty Kisses - Chatham - Balcony
Seashell Wishes-Salty Kisses
Chatham, MA
9.1Wonderful(17)
Pet friendly
$360+
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Lovely Home Near Bike Path Dog Welcome! - Chatham - Building
Lovely Home Near Bike Path Dog Welcome!
Chatham, MA
8.5Very good(7)
Parking
Free Wi-Fi
Pet friendly
$319+
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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
$894+
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Updated Beach House Deck Outdoor Shower! - Chatham - Living room
Updated Beach House Deck Outdoor Shower!
Chatham, MA
9.4Wonderful(14)
Parking
Free Wi-Fi
Pet friendly
$398+
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Corner Cottage - Chatham - Building
Corner Cottage
Chatham, MA
7.2Good(12)
$320+
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Sea House - Chatham
Sea House
Chatham, MA
8.9Very good(11)
$344+
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A Chatham Pearl on Oyster River - Chatham
A Chatham Pearl on Oyster River
Chatham, MA
7.6Good(13)
Pet friendly
$554+
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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
\'Chatham Up\' - Come Stay, Relax, Have Fun! - Chatham
\'Chatham Up\' - Come Stay, Relax, Have Fun!
Chatham, MA
6.8Okay(10)
Pet friendly
$414+
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 $397. The highest prices are found on Tuesday, with average rates at $902.

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

High season

Average price (weeknight)

Average price (weekend night)

February
April
$522
$622
Cheapest month to stay with an average 65% drop in price.
Most expensive month to stay with an average 160% 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 31% 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 Excellent Chatham Cottage (10.0, 24 reviews), Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches (9.9, 43), and New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach (9.6, 40), 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 Sunday. In contrast, the most expensive is Tuesday.
  • 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.
  • 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 $5,344.

  • 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 $22,901.

  • 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 this weekend?

    In the last 72 hours, users have found Chatham vacation rentals for this weekend for as low as $477 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

Not what you’re looking for? Find thousands of other hotels, flight deals, car rentals and package deals with KAYAK.