Search Holiday Rentals in Chatham

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Top Holiday Rentals in Chatham

Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants

10.0 out of 10, Exceptional, (94)
"Loved our stay. Property is very clean and in a quiet neighborhood close to town and beaches. Host Bonnie was great. Would definitely rent again."
Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants

Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

8.6 out of 10, Excellent, (14)
"This rental home set the stage for an enjoyable getaway. It was well stocked with what we needed for a few days away (dish soap, toiletries, sponge, towels, bedding, etc.), and the pictures are accurate to the setup of the home. It is located in a beautiful location near a private beach and marina which were the highlight of our stay. The area was quiet and allowed for quality family time."
The price is £730
includes taxes & fees
31 Aug - 1 Sept
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

9.6 out of 10, Exceptional, (96)
"Stayed here for a weekend with my fiance and our dog and it was perfect. Short 5 minute drive from downtown and all the great restaurants and shopping. Very dog friendly with fenced in backyard. "
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Holly Tree Resort

3.0 star property
9.0 out of 10, Wonderful, (347)
"Very nice place to stay "
Holly Tree Resort

The Cove at Yarmouth by VRI Americas

3.5 star property
9.2 out of 10, Wonderful, (308)
"All and all the property was decent. Not really located by any rea"
The Cove at Yarmouth by VRI Americas

Brewster Green Resort

3.5 star property
9.4 out of 10, Exceptional, (105)
"Nice and clean"
The price is £346
includes taxes & fees
7 Aug - 8 Aug
Brewster Green Resort

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (281)
"All around a great place to stay!"
The price is £305
includes taxes & fees
1 Sept - 2 Sept
Edgewater Beach Resort, a VRI resort

Riverview Resort

3.0 star property
9.2 out of 10, Wonderful, (161)
"The property was very nice very clean beautiful area a lot of parking very nice when you walk in front desk was sweet Only thing they need a new play ground for the kids kinda old but other then that beautiful "
The price is £244
includes taxes & fees
23 Aug - 24 Aug
Riverview Resort

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (124)
"We had a wonderful time staying in Hyannis off season (April vacation for CT, but not for MA)! The host provided us with everything we needed and the location can't be beat! It's in a very walkable area, close to Main Street and the beach! We would love to come back again in the warmer weather! "
Steps to the beach with an ocean view,

Ocean Breeze Motel - Standard Double

9.8 out of 10, Exceptional, (48)
"Clean, comfortable hotel with good sized room and great shower. Good coffee and breakfast included with many options. Joanna, the owner was very helpful with suggestions in the area- biking, beach, sunsets, sea food restaurants. Had a great stay! "
The price is £204
includes taxes & fees
1 Sept - 2 Sept
Ocean Breeze Motel - Standard Double

Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! capeoceanvista

9.6 out of 10, Exceptional, (133)
"Spent a week at this nice condo in mid-January. Cozy and warm, right on the beach. The Cape in mid-winter is very quiet but that is what we had wanted. Our 15 year old Shih-Tzu was comfortable and happy. Nice relaxing week on this terrific property."
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! capeoceanvista

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

10.0 out of 10, Exceptional, (159)
"Place was adorable perfect for what we needed. Perfect location, centralized for all your needs and wants"
The price is £289
includes taxes & fees
14 Aug - 15 Aug
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (217)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!

Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista

9.6 out of 10, Exceptional, (111)
"Absolutely gorgeous location with amazing views and lots of privacy in the winter. Will stay again!"
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista

Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks

9.8 out of 10, Exceptional, (174)
"Very happy with our stay"
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks

Deluxe 2 Queens Size Beds Hotel Room in Yarmouth, 2 miles from Hyannis Main St.

9.0 out of 10, Wonderful, (2)
"Very nice and clean. Would definitely stay here again "
The price is £453
includes taxes & fees
4 Aug - 5 Aug
Deluxe 2 Queens Size Beds Hotel Room in Yarmouth, 2 miles from Hyannis Main St.

Steps to private Beach, Golf Course, AC, tandem Kayak for Guests

9.6 out of 10, Exceptional, (23)
"Enjoyed our stay: clean, modern and great location."
Steps to private Beach, Golf Course, AC, tandem Kayak for Guests

"Awesome Vacation while staying at "HomeAway" from Home"

8.4 out of 10, Very good, (77)
"Great spot for a beach getaway!"
The price is £174
includes taxes & fees
1 Sept - 2 Sept
"Awesome Vacation while staying at "HomeAway" from Home"

Mermaid Cottage! beautiful propety!

10.0 out of 10, Exceptional, (102)
"Great property and location!"
Mermaid Cottage! beautiful propety!

Walk To Beach - Comfortable 2BR Cottage

9.8 out of 10, Exceptional, (32)
"We had a wonderful stay. Convenient location, clean and updated. Would stay here again!"
Walk To Beach - Comfortable 2BR Cottage
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chatham Hotel Reviews

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?

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill: This holiday home rental outside of Chatham offers a balcony, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Chatham?

With 297 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 Atwood House Museum and Gallery Antonia, whereas Chatham Lighthouse Beach and Ridgevale Beach are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Fish Pier and Chatham Lighthouse 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.