Chatham Holiday Rentals

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Check prices for these dates

Tonight
24 Nov - 25 Nov
Tomorrow
25 Nov - 26 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Holiday Rentals in Chatham

Outdoor dining
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

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!
Terrace/patio
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

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
Beach nearby, sun-loungers
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

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

Chatham
10.0 out of 10, Exceptional, (115)
"Comfortable and terrific location"
United States
Barry L.
The price is HK$1,401
HK$3,822 total
includes taxes & fees
30 Nov - 1 Dec
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Microwave, oven, stovetop, dishwasher
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

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

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 HK$693
HK$3,169 total
includes taxes & fees
30 Nov - 1 Dec
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Dining
See the World Cup AND Enjoy a Chatham Vacation June 2026

See the World Cup AND Enjoy a Chatham Vacation June 2026

Chatham
10.0 out of 10, Exceptional, (100)
"Great stay. House is in a great location and is well maintained. Bonnie was super helpful. "
United States
Will M.
See the World Cup AND Enjoy a Chatham Vacation June 2026
Front of property
Holly Tree Resort

Holly Tree Resort

3.0 star property
West Yarmouth
9.0 out of 10, Wonderful, (368)
"We had a great stay!"
United States
Shelly
Holly Tree Resort
BBQ/picnic Area
Edgewater Beach Resort, a VRI resort

Edgewater Beach Resort, a VRI resort

3.5 star property
Dennis Port
8.8 out of 10, Excellent, (291)
"Room was clean and the staff was great"
United States
Linda
Edgewater Beach Resort, a VRI resort
Indoor pool, outdoor pool
Brewster Green Resort

Brewster Green Resort

3.5 star property
Brewster
9.4 out of 10, Exceptional, (119)
"Super clean and a really large space! "
United States
Linda
Brewster Green Resort
Terrace/patio
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!

Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!

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!
Sun deck
Riverview Resort

Riverview Resort

3.0 star property
Bass River
9.2 out of 10, Wonderful, (169)
"The room was big and very clean. The hotel is quaint and quiet. It does not have an elevator which could be an issue for some but we made it work. Overall a great place to stay. Very comfortable and inviting and we loved the amenities."
United States
Kathleen
Riverview Resort
Aerial view
The Cove at Yarmouth by VRI Americas

The Cove at Yarmouth by VRI Americas

3.5 star property
West Yarmouth
9.2 out of 10, Wonderful, (327)
"First time staying here and i was impressed"
United States
Wayne
The Cove at Yarmouth by VRI Americas
Beach nearby, sun-loungers
Steps to the Ocean! Perfect Location!!!

Steps to the Ocean! Perfect Location!!!

Barnstable
10.0 out of 10, Exceptional, (234)
"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!!!
Fridge, microwave, oven, stovetop
Lovely Dog Friendly Beach Home Close to Everything. Jan-April monthly discounts

Lovely Dog Friendly Beach Home Close to Everything. Jan-April monthly discounts

Eastham
10.0 out of 10, Exceptional, (222)
"Always a great place to stay!!!!"
United States
Christine J.
Lovely Dog Friendly Beach Home Close to Everything. Jan-April monthly discounts
On the beach, sun-loungers
beachfront cottage at Chases Ocean Grove

beachfront cottage at Chases Ocean Grove

Dennis Port
9.6 out of 10, Exceptional, (33)
"Such a cool place! Just a few feet from the beach, we began and ended each day in the sand. The location is also great for traveling to all the cape cod hot spots. The cottage is really sweet and cozy— we hope to be back! "
United States
trisha d.
beachfront cottage at Chases Ocean Grove
Beach nearby
The Cove At Yarmouth

The Cove At Yarmouth

3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (243)
"Great place to stay. Clean, friendly and accommodating!"
United States
Mike
The price is HK$899
HK$1,029 total
includes taxes & fees
25 Nov - 26 Nov
The Cove At Yarmouth
Fridge, microwave, oven, stovetop
Charming Cape Escape: Steps to the Beach, Large Deck, 2 Bikes & Outdoor Shower!

Charming Cape Escape: Steps to the Beach, Large Deck, 2 Bikes & Outdoor Shower!

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!
Exterior
OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR

OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR

Bass River
10.0 out of 10, Exceptional, (110)
"Great family time! Beautiful location right on the beach. "
United States
David A.
OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR
Fridge, microwave, oven, stovetop
Walk To Beach - Comfortable 2BR Cottage

Walk To Beach - Comfortable 2BR Cottage

Dennis Port
9.6 out of 10, Exceptional, (35)
"Perfect house, everything you need. Close to beach and restaurants. Very clean and beds were comfortable "
United States
Dan K.
Walk To Beach - Comfortable 2BR Cottage
Pool
Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach

Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach

Orleans
10.0 out of 10, Exceptional, (73)
"Great spot"
United States
Eugene P.
Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach
On the beach
Waterfront Cottage Steps to Private Beach! (2052)

Waterfront Cottage Steps to Private Beach! (2052)

Wellfleet
9.2 out of 10, Wonderful, (51)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Right on the beach, close to the pier and restaurants, quiet and relaxing."
United States
Jonathan G.
Waterfront Cottage Steps to Private Beach! (2052)
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

Hyannis Travel Inn

Hyannis Travel Inn

10/10 Excellent
"Nice staff Clean room Comfortable bed Convenient location "
Teria 3-night trip
Posted 4 days ago
Hyannis Travel Inn

Find out more about Chatham

Search for holiday rentals in Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in Chatham using one of the methods below:

  • View our selection of featured holiday rentals in Chatham
  • Use the map to find apartments and other holiday homes in the Chatham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chatham while they last

Look no further and take a look at our great range of rental properties in Chatham!

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 275 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.