Holiday Rentals in Chatham

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Our top choices for Chatham holiday rentals

9.6 out of 10, Exceptional, (102 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is €410
includes taxes & fees
25 Feb - 26 Feb
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
The price is €585
includes taxes & fees
9 Mar - 10 Mar
Luxury Chatham Retreat. Walk to Main St & Beach
10.0 out of 10, Exceptional, (117 reviews)
"Clean, quiet, and great location."
United States
Tyler B.
The price is €419
includes taxes & fees
25 Feb - 26 Feb
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
10.0 out of 10, Exceptional, (25 reviews)
"Lovely house with nice location."
United States
amy d.
The price is €591
includes taxes & fees
25 Feb - 26 Feb
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
8.8 out of 10, Excellent, (3 reviews)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
The price is €292
includes taxes & fees
2 Mar - 3 Mar
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
9.8 out of 10, Exceptional, (23 reviews)
"Everything was great, we really enjoyed our stay!"
United States
Anna T.
The price is €361
includes taxes & fees
25 Feb - 26 Feb
🦀Waterfront at The Velvet Crab~Amazing Sunsets
10.0 out of 10, Exceptional, (2 reviews)
"The house was beautiful, tucked away, and clean. It was spacious for two families with room for more comfortably. "
United States
michele I.
The price is €557
includes taxes & fees
25 Feb - 26 Feb
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
9.6 out of 10, Exceptional, (50 reviews)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is €499
includes taxes & fees
25 Feb - 26 Feb
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
10.0 out of 10, Exceptional, (7 reviews)
"Overall, we had a really great stay. The home is in a quiet neighborhood & close to the beach. Everything was clean and as described in the listing. "
United States
Kallee M.
The price is €437
includes taxes & fees
25 Feb - 26 Feb
Sleeps 2-8/Soaking Tub/FirePit~Burrows
9.8 out of 10, Exceptional, (11 reviews)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is €431
includes taxes & fees
27 Feb - 28 Feb
Cozy Large Home in Harwich with Patio near Wequassett Resort

Holiday Home in Dennis

Coastal Haven in West Dennis
10.0 out of 10, Exceptional, (3 reviews)
"Overall the property was perfect. Great location, super clean and plenty of room for our family of 4. The only negative I can say is that the property is a duplex and that’s not mentioned in the listing. Overall great spot and would stay there again!"
United States
Edward R.
The price is €488
includes taxes & fees
2 Mar - 3 Mar
Coastal Haven in West Dennis
10.0 out of 10, Exceptional, (19 reviews)
"Just a great location, and a very comfortable place. We loved the porch bed and chair. We are looking forward to returning."
United States
David B.
The price is €416
includes taxes & fees
5 Mar - 6 Mar
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
10.0 out of 10, Exceptional, (12 reviews)
"Great location and very comfortable rental home. Everything you need is included and the house is well stocked and clean!"
United States
Dennis S.
The price is €455
includes taxes & fees
2 Mar - 3 Mar
Modern Beach & Pond Getaway; Heart of Cape Cod

Holiday Home in Harwichport

Family Cottage Close to Beach!!
9.8 out of 10, Exceptional, (75 reviews)
"Everything was exactly as described - they provided beach towels and chairs which we used - the property was perfect for our stay"
United States
John N.
The price is €698
includes taxes & fees
25 Feb - 26 Feb
Family Cottage Close to Beach!!
10.0 out of 10, Exceptional, (42 reviews)
"Great place!"
United States
Michael P.
The price is €317
includes taxes & fees
25 Feb - 26 Feb
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
10.0 out of 10, Exceptional, (79 reviews)
"Beautiful views in a quiet and private location. Cottage had everything we needed and nicely appointed."
United States
Janice H.
The price is €387
includes taxes & fees
25 Feb - 26 Feb
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
10.0 out of 10, Exceptional, (22 reviews)
"We loved the luxury bed linens, large kitchen & living area & the fact that it was pet friendly in a lovely neighborhood!"
United States
Jennifer G.
The price is €423
includes taxes & fees
25 Feb - 26 Feb
The Pet-Friendly Surf Shack Hideaway on the Cove
The price is €466
includes taxes & fees
5 Mar - 6 Mar
Driftmoor~Dog Frndly 3bd/2 bth~Luxe
9.4 out of 10, Exceptional, (11 reviews)
"Loved the place. Very clean and updated. You have to time the tides because it is on an island, but that was fine for us. "
United States
Brian F.
The price is €464
includes taxes & fees
26 Mar - 27 Mar
New! Island Pines-A Dog Friendly Boutique Oasis
10.0 out of 10, Exceptional, (6 reviews)
"Lovely property with attentive hosts "
United States
marian t.
The price is €1,039
includes taxes & fees
25 Feb - 26 Feb
Cape Cod Villa pond front vacation home, retreat, spa, venue, film location
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chatham Hotel Reviews

Find out more about Chatham

Everything you need to know about Chatham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chatham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chatham holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chatham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chatham. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chatham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chatham holiday rentals we have selected for you start as low as €125 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chatham rentals

At Expedia, we put the best Chatham holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chatham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chatham holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chatham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Chatham?

Yes, there are holiday rentals in Chatham close to Chatham Railroad Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the popular beaches and waterfront in Chatham. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best holiday rentals that Chatham has to offer?

5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet: This highly rated holiday home rental in Chatham is located in the city centre, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Another good choice for your trip to Chatham is Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!.

How many holiday rentals are there in Chatham?

With 277 Expedia holiday rentals, you're guaranteed to find just the right place for your Chatham stay.

What can I see and do in Chatham?

Cultural attractions include Gallery Antonia and Monomoy Theatre, whereas Chatham Lighthouse Beach and Ridgevale Beach are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Lighthouse and Cape Cod Beaches are other places worth a visit.

What are holiday rentals like in Chatham?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chatham. Holiday rentals offer extras such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.