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 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 C$ 787.

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.

Chatham Vacation Rentals from C$ 431/night

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Best Chatham vacation rentals

Riviera Sunset

Chatham, MA, United States

8.4Very good(12)

C$ 415+

Check availability

Perfect couples escape. Close to beaches, great biking & walking & pet friendly.

Chatham, MA, United States

Free Wi-Fi

Pet friendly

C$ 952+

Check availability

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Chatham, MA, United States

C$ 443+

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Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham

Chatham, MA, United States

7.7Good(14)

C$ 469+

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New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach

Chatham, MA, United States

C$ 393+

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Lucky Number Seven

Chatham, MA, United States

9.4Wonderful(45)

Pet friendly

C$ 778+

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$\'Chatham Up\' - Come Stay, Relax, Have Fun! - Chatham - Restaurant$

\'Chatham Up\' - Come Stay, Relax, Have Fun!

Chatham, MA, United States

Pet friendly

C$ 573+

Check availability

Delightful Cottage for Two

Chatham, MA, United States

Free Wi-Fi

C$ 385+

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Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Chatham, MA, United States

C$ 793+

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Corner Cottage

Chatham, MA, United States

8.4Very good(7)

C$ 627+

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Updated Beach House Deck Outdoor Shower!

Chatham, MA, United States

9.4Wonderful(9)

Parking

Free Wi-Fi

Pet friendly

C$ 627+

Check availability

Seashell Wishes-Salty Kisses

Chatham, MA, United States

8.9Very good(13)

Pet friendly

C$ 507+

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Lovely Home Near Bike Path Dog Welcome!

Chatham, MA, United States

8.3Very good(6)

Parking

Free Wi-Fi

Pet friendly

C$ 523+

Check availability

Sea House

Chatham, MA, United States

8.5Very good(9)

C$ 382+

Check availability

A Chatham Pearl on Oyster River

Chatham, MA, United States

Pet friendly

Chatham, MA, United States

C$ 1,588+

Check availability

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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 C$ 473. In comparison, April is the most expensive month, with prices at C$ 3,547.

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 C$ 476. The highest prices are found on Friday, with average rates at C$ 2,535.

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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Low season	January
High season	January

Cheapest month to stay with an average 0% drop in price.

Most expensive month to stay with an average 0% rise in price.

Pet friendly is the most popular vacation rental property amenity in Chatham
Vacation rentals in Chatham are around 27% 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 Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham (10.0, 24 reviews), Excellent Chatham Cottage (10.0, 20), and Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches (9.9, 35), based on ratings and reviews from real travelers.
Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Chatham for 7 days.

See more tips

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 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 C$ 787. 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.