Chatham Holiday Rentals

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Holiday Rentals in Chatham

Holiday Home in Chatham

10.0 out of 10, Exceptional, (39)
"Gorgeous well stocked home accommodated our large family in style!! Plenty of Beach & Pool towels, beach chairs, and kitchen appliances for all of our meals! Loved the house and Chatham! Walkable to beach, restaurants and shops. So Fun!"
United States
Kim K.
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Holiday Home in Chatham

10.0 out of 10, Exceptional, (115)
"Comfortable and terrific location"
United States
Barry L.
The price is NZ$854
includes taxes & fees
6 Dec - 7 Dec
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Holiday Home in Chatham

8.2 out of 10, Very good, (73)
"Great stay at this bright, airy, cozy cottage. We enjoyed coffee and happy hour on the deck overlooking the river and boats each day. Hated to leave!"
United States
Cathy S.
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Holiday Home in Chatham

9.6 out of 10, Exceptional, (101)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is NZ$717
includes taxes & fees
8 Dec - 9 Dec
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Holiday Home in Chatham

10.0 out of 10, Exceptional, (100)
"Great location to Chatham. Owner was very communicative with my several questions. The place was neat, clean, and had everything we could need. Highly recommend. Thank you!"
United States
Dana F.
See the World Cup AND Enjoy a Chatham Vacation June 2026

Aparthotel in West Yarmouth

3.0 star property
9.0 out of 10, Wonderful, (374)
"Best place in massachusetts "
United States
Michael
Holly Tree Resort

Aparthotel in Dennis Port

3.5 star property
8.8 out of 10, Excellent, (294)
"Room was clean and the staff was great"
United States
Linda
Edgewater Beach Resort, a VRI resort

Aparthotel in Brewster

3.5 star property
9.4 out of 10, Exceptional, (119)
"Super clean and a really large space! "
United States
Linda
The price is NZ$306
includes taxes & fees
6 Dec - 7 Dec
Brewster Green Resort

Aparthotel in Bass River

3.0 star property
9.2 out of 10, Wonderful, (171)
"Check in and check out flexibility- thank you!"
United States
Christine
Riverview Resort

Holiday Home in Eastham

10.0 out of 10, Exceptional, (27)
"Heaven! Best spot on the end of cul de sac with stunning water views from all rooms, especially the outdoor deck. Clean, comfortable and nicely decorated. Great communication pre check-in and during stay. Did not want to leave! Look forward to future stay. "
United States
Kristin
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!

Condo resort in West Yarmouth

3.5 star property
9.2 out of 10, Wonderful, (328)
"First time staying here and i was impressed"
United States
Wayne
The Cove at Yarmouth by VRI Americas

Holiday Home in Dennis

10.0 out of 10, Exceptional, (176)
"Excellent property, super clean and location is perfect! "
United States
Karen B.
The price is NZ$543
includes taxes & fees
6 Dec - 7 Dec
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Holiday Home in Eastham

10.0 out of 10, Exceptional, (224)
"Always a great place to stay!!!!"
United States
Christine J.
Lovely Dog Friendly Beach Home Close to Everything. Jan-April monthly discounts

Cottage in Barnstable

10.0 out of 10, Exceptional, (235)
"I absolutely loved my stay at this charming cottage in Hyannis! The place was cozy, spotless, and beautifully maintained. A perfect mix of comfort and Cape Cod charm. The location was great, close to the beach and local shops, yet quiet enough to relax and unwind."
United States
Maria
Steps to the Ocean! Perfect Location!!!

Holiday Home in West Hyannisport

10.0 out of 10, Exceptional, (112)
"The house was perfect for our family gathering. We did not lack for anything. The owners were very responsive. The view is fantastic and we enjoyed the beach. "
United States
Anthony F.
Ocean Views From Every Room, Beach 30 Seconds Away!

Cottage in Dennis Port

9.6 out of 10, Exceptional, (33)
"Great location and friendly beach neighborhood "
Canada
Jeremy H.
beachfront cottage at Chases Ocean Grove

Condo in Dennis

9.8 out of 10, Exceptional, (114)
"Nice location, right on the water. Owner was very accommodating. Plenty of rest and relaxation on the beach"
United States
Timothy C.
Cape Cod Oceanfront New Condo with Ocean View & Private Beach! [in Building B]

Holiday Home in Barnstable

10.0 out of 10, Exceptional, (151)
"Great house - extra clean and great location"
United States
Matt S.
New, dog-friendly 5-bed home. Steps to Keyes Beach, Main Street, and Harbor!

Holiday Home in West Hyannisport

10.0 out of 10, Exceptional, (92)
"Had an amazing stay—such an amazing location and beautiful property! Deborah was also extremely responsive the entire stay, quickly answering any questions that I had and giving great recommendations of good restaurants/things to do in the area!"
United States
Danyon H.
Unique oceanfront windmill with breathtaking views of Nantucket Sound.

Cottage in Dennis Port

10.0 out of 10, Exceptional, (108)
"Our stay was absolutely perfect! The cottage is so cute, the bed was super comfy, the location was ideal, the kitchen had everything we could possibly need.We loved our time at Beach Camp and hope to stay there again!"
United States
Melissa B.
Charming Cape Escape: Steps to the Beach, Large Deck, 2 Bikes & Outdoor Shower!
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, 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 NZ$306 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?

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!: This highly rated holiday home rental in Chatham is located in the city centre, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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 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.