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Chatham vacation rentals

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Booking Insights
Recommended by KAYAK

Best Chatham vacation rentals

These are the best prices for Oct 8 - 9.
Secluded Chatham Cottage Near Hardings Beach - Chatham - Beach
Secluded Chatham Cottage Near Hardings Beach
Chatham, MA
9.9Wonderful(35)
Cottage
$466+
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Cape Escape Chatham 5 Star Beach Chic 5 Min Walk to Beach-Newly Renovated Private Retreat AC - Chatham - Patio
Cape Escape Chatham 5 Star Beach Chic 5 Min Walk to Beach-Newly Renovated Private Retreat AC
Chatham, MA
9.8Wonderful(26)
House
$568+
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~ 4 Mi to Dtwn: Chatham Home w/ Fire Pit - Chatham - Living room
~ 4 Mi to Dtwn: Chatham Home w/ Fire Pit
Chatham, MA
9.0Wonderful(15)
House
$409+
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Nautical Comfort near Rail Trail - Chatham - Living room
Nautical Comfort near Rail Trail
Chatham, MA
House
$1,221+
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Walk To Beach South Chatham Home - Chatham - Living room
Walk To Beach South Chatham Home
Chatham, MA
Cottage
$463+
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Lucky Number Seven - Chatham - Patio
Lucky Number Seven
Chatham, MA
9.6Wonderful(68)
House
$496+
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Convenient to all amenities and beaches in Chatham - Chatham - Pool
Convenient to all amenities and beaches in Chatham
Chatham, MA
9.9Wonderful(108)
Cottage
$291+
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Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches - Chatham - Beach
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Chatham, MA
9.9Wonderful(57)
House
$523+
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Full Renovation Amazing Spot with Views - Chatham - Beach
Full Renovation Amazing Spot with Views
Chatham, MA
9.7Wonderful(43)
Condo
$419+
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Chatham Village - Adorable Studio Apartment in Antique Home - Chatham - Bedroom
Chatham Village - Adorable Studio Apartment in Antique Home
Chatham, MA
9.9Wonderful(29)
Apartment
$262+
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Chatham Village: Lovely 1-Bedroom Apartment in Antique Home - Chatham - Balcony
Chatham Village: Lovely 1-Bedroom Apartment in Antique Home
Chatham, MA
9.7Wonderful(45)
Apartment
$300+
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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(16)
House
$399+
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Quaint Two Bedroom Lakeside Cottage #18 with Screened-in Porch in Chatham - Chatham - Kitchen
Quaint Two Bedroom Lakeside Cottage #18 with Screened-in Porch in Chatham
Chatham, MA
9.7Wonderful(20)
Cottage
$431+
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Cape Cod Chatham Water View Retreat - Chatham - Living room
Cape Cod Chatham Water View Retreat
Chatham, MA
9.8Wonderful(53)
Apartment
$292+
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Fully Updated Home w Great Outdoor Space - Chatham - Outdoors view
Fully Updated Home w Great Outdoor Space
Chatham, MA
9.5Wonderful(27)
House
$296+
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Walk to Beach: Chatham Gem w/ Ocean-View Sunroom! - Chatham
Walk to Beach: Chatham Gem w/ Ocean-View Sunroom!
Chatham, MA
9.4Wonderful(8)
House
$638+
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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?

Friday offers the lowest rates in Chatham, with an average nightly price of $396. The highest prices are found on Saturday, with average rates at $887.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

December
June
$583
$676
Cheapest month to stay with an average 56% drop in price.
Most expensive month to stay with an average 34% 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 29% 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 Secluded Chatham Cottage Near Hardings Beach (9.9, 35 reviews), Convenient to all amenities and beaches in Chatham (9.9, 108), and Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches (9.9, 57), 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 December and November.
  • The cheapest night for renting a vacation home in Chatham is Friday. In contrast, the most expensive is Saturday.
  • 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

  • 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 $3,785.

  • 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 $16,220.

  • 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, cabins, condos, cottages and houses.

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

    There are a number of dog and pet-friendly Chatham vacation rentals, with around 16% 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 $1,491. 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.

More options for your stay in Chatham

Complete your trip to Chatham

Flights to Chatham
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