Chatham vacation rentals

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Booking Insights
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Best Chatham vacation rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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$184 - $682$682 - $1,180$1,180 - $1,678$1,678 - $2,176$2,176+ per night

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Most recommended vacation rentals in Chatham

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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+
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Riviera Sunset - Chatham - Living room
Riviera Sunset
Chatham, MA
8.6Very good(19)
$377+
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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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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)
$351+
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
$388+
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B By the Sea - Chatham - Living room
B By the Sea
Chatham, MA
8.3Very good(21)
$544+
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Chatham Village: Large, Newly-Renovated 1 Bedroom Apartment in Antique Home - Chatham - Beach
Chatham Village: Large, Newly-Renovated 1 Bedroom Apartment in Antique Home
Chatham, MA
9.6Wonderful(12)
Free Wi-Fi
$323+
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Delightful Cottage for Two - Chatham - Beach
Delightful Cottage for Two
Chatham, MA
8.9Very good(20)
Free Wi-Fi
$269+
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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
$891+
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Seashell Wishes-Salty Kisses - Chatham - Balcony
Seashell Wishes-Salty Kisses
Chatham, MA
9.1Wonderful(17)
Pet friendly
$279+
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Quaint 2 Bedroom Cottage Overlooking White Pond - Chatham - Balcony
Quaint 2 Bedroom Cottage Overlooking White Pond
Chatham, MA
9.2Wonderful(16)
$387+
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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
$418+
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Beautiful home overlooking Emery Pond - Chatham - Kitchen
Beautiful home overlooking Emery Pond
Chatham, MA
10Wonderful(3)
$810+
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New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach - Chatham - Living room
New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach
Chatham, MA
9.6Wonderful(40)
$302+
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Sea House - Chatham
Sea House
Chatham, MA
8.9Very good(11)
$375+
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A Chatham Pearl on Oyster River - Chatham
A Chatham Pearl on Oyster River
Chatham, MA
7.6Good(13)
Pet friendly
$372+
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 $648.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

November
April
$525
$618
Cheapest month to stay with an average 56% drop in price.
Most expensive month to stay with an average 169% 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 80% 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, 26 reviews), Fully Updated Home w Great Outdoor Space (9.6, 23), 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 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.

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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