Chatham Vacation Rentals

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Tonight
Nov 10 - Nov 11
Tomorrow
Nov 11 - Nov 12
This weekend
Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation 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)
"The house and property was simply amazing and such a perfect spot for our company team retreat of 12"
United States
Jennifer S.
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, (71)
"Beautiful house great views of the river. Peaceful weekend away"
United States
Anthony G.
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, (114)
"Great great great location. Super charming home. It worked perfectly for our family. Walk to shops and restaurants! I highly recommend. Host was lovely & easy to reach. We would’ve loved to utilize the properties outdoor space more. Other than that - it was terrific! Rent it now!"
United States
Rachel S.
The price is ￥27,616
￥75,328 total
includes taxes & fees
Nov 11 - Nov 12
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, (99)
"We had a great time on the Cape and lucked out with beautiful weather too! We loved this house and were so grateful to be able to bring our dogs! Thank you"
United States
Judy M.
The price is ￥14,268
￥63,215 total
includes taxes & fees
Nov 17 - Nov 18
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, (363)
"Yearly trip that makes it all worth it with our stay at the Holly Tree!"
United States
Angel
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, (290)
"All around a great place to stay!"
United States
Samantha
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)
"The room was very clean and large. It was perfect for two people. The unit we stayed in was about .25 miles from clubhouse. So since it was cold, we didn't use the indoor pool. Staff was friendly. They have a game room where you can play table tennis and air hockey among other games. For the money, it was well worth staying there."
United States
Harry
The price is ￥21,325
￥24,406 total
includes taxes & fees
Nov 11 - Nov 12
Brewster Green Resort
Sundeck
Riverview Resort

Riverview Resort

3.0 star property
Bass River
9.2 out of 10, Wonderful, (168)
"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, (324)
"First time staying here and i was impressed"
United States
Wayne
The Cove at Yarmouth by VRI Americas
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)
"From the moment we arrived we were overtaken by the stunning views and private location. The accommodations and amenities went far beyond our high expectations. David is the ultimate host. He truly assisted us with all aspects of our stay. From changing our dates, to restaurant recommendations his guidance is genuine and compassionate. Thank you David, we appreciate all that you have done for us, and until the next time, may your visits to the Cape give you sunny days, and warm water!"
United States
Don H.
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!
Beach nearby, sun loungers
Steps to the Ocean! Perfect Location!!!

Steps to the Ocean! Perfect Location!!!

Barnstable
10.0 out of 10, Exceptional, (230)
"Perfect for a couple and two kids"
United States
Shelly R.
Steps to the Ocean! Perfect Location!!!
On the beach, sun loungers, beach towels
Steps to a private beach in a classic Cape cottage. Pet-friendly!

Steps to a private beach in a classic Cape cottage. Pet-friendly!

Dennis
8.8 out of 10, Excellent, (27)
"I love tiny living and this was the perfect tiny cottage gettaway! Beach is just a short walk, the cottage community is adorable and the hosts were timely with their communication! Will definitely book again! "
United States
Tjona S.
Steps to a private beach in a classic Cape cottage. Pet-friendly!
Fridge, microwave, stovetop, dishwasher
Quaint condo near private beach access with fireplace - close to dining

Quaint condo near private beach access with fireplace - close to dining

Dennis Port
9.0 out of 10, Wonderful, (61)
"Loved our stay in Dennis. The condo was so nice and so clean.. I would certainly consider next summer to revisit. "
United States
Rosemarie P.
The price is ￥9,819
￥44,552 total
includes taxes & fees
Nov 17 - Nov 18
Quaint condo near private beach access with fireplace - close to dining
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)
"This was the perfect spot for our family get away. Plenty of room for myself, my husband, and son. The home was clean and a stones throw from the beach where you could sit out and hear the waves as you have your morning coffee. Will definitely be booking with them again next summer!"
United States
Domenique W.
beachfront cottage at Chases Ocean Grove
Terrace/patio
Charming Waterview Victorian w/Cottages near beach, harbor & town

Charming Waterview Victorian w/Cottages near beach, harbor & town

Wellfleet
9.8 out of 10, Exceptional, (53)
"The Moors was the perfect place for our family of 17 & 2 additional babysitters. We were celebrating a 4th July birthday, a 45th wedding anniversary, and the many summer memories of our grown children spent working as Truro & Wellfleet camp counselors, BJ’s & Beachcomber waitresses, and Wellfleet pond & ocean lifeguards. The owner was fantastic and quickly responded to all forms of communications and requests. The location was ideal for viewing the 4th July Wellfleet Parade, and every local...
United States
Kevin T.
Charming Waterview Victorian w/Cottages near beach, harbor & town
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)
"Fantastic location, right on the beach and convenient to restaurants and shops."
United States
Timothy M.
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)
"My friend and I spent 3 nights here while we explored this area of Cape Cod and Martha’s Vineyard. Clean and had what we needed!"
United States
Jill B.
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, sun loungers, beach towels
Steps to the beach with an ocean view,

Steps to the beach with an ocean view,

Barnstable
10.0 out of 10, Exceptional, (139)
"Great stay."
United States
Richard D.
Steps to the beach with an ocean view,
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

Chatham Bars Inn

Chatham Bars Inn

10/10 Excellent
"Great accommodation and staff."
Michael 2-night trip
Posted 2 days ago
Chatham Bars 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
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Look no further and take a look at our great range of rental properties in Chatham!

Frequently asked questions

Can I find a vacation rental in Chatham?

Yes, you can find vacation rentals in Chatham close to Chatham Railroad Museum, or you can select a more secluded option if you'd like a relaxing place to 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 vacation rentals that Chatham has to offer?

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!: This highly rated vacation home rental in Chatham is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation. Some other top choices in Chatham are Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches and Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK.

How many vacation rentals are there in Chatham?

With 287 Expedia vacation rentals, you're sure 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 vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or longer in Chatham. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.