Chatham Holiday Rentals

Save an average of 15% on thousands of properties with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide

Find properties with these dates

Tonight
May 3 - May 4
Tomorrow
May 4 - May 5
This weekend
May 3 - May 5

Holiday Rentals in Chatham

Beach
Steps to the beach with an ocean view,
10.0 out of 10, Exceptional, (94)
"This condo is awesome for families or friends looking to get away. VERY clean and within walking distance to downtown. One of my favorite Cape rentals, can't wait to go back😊"
Steps to the beach with an ocean view,
Beach nearby, sun-loungers
Steps to the Ocean! Perfect Location!!!
10.0 out of 10, Exceptional, (166)
"Lovely cottage in a beautiful part of the world. Steps to the Ocean. Location provides easy access to the whole of Cape Cod and beyond. Stephen was an attentive host. We could not have asked for more."
Steps to the Ocean! Perfect Location!!!
Sun-loungers
Cozy beachfront cottage at Chases Ocean Grove
10.0 out of 10, Exceptional, (11)
"My friend and I had a wonderful time at your cottage. My friend had not visited the Cape in a long time so it was fun for both of us to go exploring. And it was great that the cottages were right on the beach so we did not have to drive anywhere to soak up the sunshine."
Cozy beachfront cottage at Chases Ocean Grove
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
TV, DVD player
Cape Cod Vacation Home Rental - Walk to Beach
10.0 out of 10, Exceptional, (6)
"Very good location. Close to beach, bike trail, and a great breakfast place called the Kitchen. The house was equipped and comfortable. I would imagine in the summertime if would be an ideal spot with the rail trail right there and close proximity to fun summer things. Really nice owners and great communication as needed."
Cape Cod Vacation Home Rental - Walk to Beach
Property grounds
Serene Waterview Renovated w/Kayaks Deck Firepit Dogs Welcome 5 Minutes to Ocean
10.0 out of 10, Exceptional, (20)
"Very clean and efficient cottage with nice view and deck overlooking the lake."
Serene Waterview Renovated w/Kayaks Deck Firepit Dogs Welcome 5 Minutes to Ocean
Interior
Cape Cod Oceanfront New Penthouse w Ocean View & Private Beach! capeoceanvista
10.0 out of 10, Exceptional, (49)
"This condo perfect for our quick winter getaway! Great views! Love the sound of the ocean! Would be great for entertaining too."
The price is HK$4,294
HK$6,983 total
includes taxes & fees
27 May - 28 May
Cape Cod Oceanfront New Penthouse w Ocean View & Private Beach! capeoceanvista
Beach/ocean view
Oceanfront Bliss: Experience the Best of Cape Cod
10.0 out of 10, Exceptional, (1)
"The house was great! Amazing views to wake up and watch the waves crash and the seals play."
Oceanfront Bliss: Experience the Best of Cape Cod
Beach nearby
Lovely Cape Cottage 2 bedroom with private beach and central air.
9.8 out of 10, Exceptional, (37)
"We had a wonderful time."
Lovely Cape Cottage 2 bedroom with private beach and central air.
Smart TV
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
9.8 out of 10, Exceptional, (123)
"Lovely house. Very clean and has everything you need. Location is awesome. Great side street off main road. Communication with host was easy and quick. Will be back."
The price is HK$469
HK$2,146 total
includes taxes & fees
14 May - 15 May
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Beach nearby, sun-loungers, beach towels
New House,2 Masters,Steps to Beach, Main Street, Ferry, Central AC, WiFi, Linens
9.8 out of 10, Exceptional, (123)
"Clean, well located, between beach and downtown. Responsive and friendly host."
New House,2 Masters,Steps to Beach, Main Street, Ferry, Central AC, WiFi, Linens
Beach
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
9.8 out of 10, Exceptional, (85)
"My husband and I needed a place to take our pup to enjoy the Cape. The tiny house was just what we needed, as it was perfectly located near so many places we wanted to go too, and also had everything we needed in such a small and affordable place. The place is super small and the mattress is not the most comfortable, but if you are like us and just need a place to rest your head a couple days so you can go out and check out the Cape all day this is the place for you! So worth it and will be...
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Property grounds
Cape Cod Oceanfront New Condo with Ocean View & Private Beach! capeoceanvista
9.8 out of 10, Exceptional, (74)
"Clean, comfortable, well appointed. Gorgeous ocean view and nice beach. Would definitely return."
Cape Cod Oceanfront New Condo with Ocean View & Private Beach! capeoceanvista
Beach nearby, sun-loungers, beach towels
Walk to DennisPort Beaches 4 min.Bars and restaurants 2min walk.Perfect Location
9.8 out of 10, Exceptional, (18)
"Great place for a short weekend stay! Host was wonderful and accommodating to our check-in/check-out needs and very responsive. Was greeted by sweet treats and a bottle of wine right in the door. Good distance from things to do! Weren’t able to enjoy the beach due to weather unfortunately but it was easy to get to walking or driving. Would recommend!"
The price is HK$2,336
HK$4,069 total
includes taxes & fees
5 May - 6 May
Walk to DennisPort Beaches 4 min.Bars and restaurants 2min walk.Perfect Location
Interior
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! capeoceanvista
9.6 out of 10, Exceptional, (109)
"Beautiful condo that overlooks the ocean and only steps away from the beach. Fireplace and hot tub were great for the chilly April nights. Balcony on the master bedroom overlooks the beach and was the perfect place for my morning yoga sessions. Host was very helpful and available to answer questions/concerns. We will definitely be staying here again."
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! capeoceanvista
TV, books
Oceanfront home with private beach, large deck, & washer/dryer - dog-friendly
9.6 out of 10, Exceptional, (5)
"Thank you for a great stay! Beautiful house and location. We had a great time!"
The price is HK$7,056
HK$13,623 total
includes taxes & fees
4 May - 5 May
Oceanfront home with private beach, large deck, & washer/dryer - dog-friendly
View from property
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista
9.6 out of 10, Exceptional, (95)
"We had a great family weekend. The house was perfect for our needs."
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista
Indoor pool, seasonal outdoor pool
The Cove at Yarmouth by VRI Americas
3.5 star property
9.2 out of 10, Wonderful, (273)
"I like how it has indoor pool and access inside so you dont have to go outside in winter to find pool"
The price is HK$909
HK$1,638 total
includes taxes & fees
14 May - 15 May
The Cove at Yarmouth by VRI Americas
BBQ/picnic Area
Holly Tree Resort by VRI Americas
3.0 star property
9.2 out of 10, Wonderful, (299)
"Great place to stay."
Holly Tree Resort by VRI Americas
Interior
Oceanfront Cape Cod Vacation Rental: Beach Access!
9.2 out of 10, Wonderful, (43)
"The house was perfect for dogs. The beach and new steps to the beach were very nice. Lovely view. The house and property need some TLC. Lawn chairs were rusted and one plastic one was cracked, chipping paint, broken window blinds, toys and debris scattered in yard and caught on bushes. The outdoor torches on ground are all broken and non-working. I know it is early in the season and I picked up as much as I could reach. It was chilly and it took awhile to heat up, as some of the rooms are space...
Oceanfront Cape Cod Vacation Rental: Beach Access!
Beach nearby, sun-loungers
THE BOAT HOUSE LOFT ~ THE CAPE'S BEST VALUE IN A RELAXING WATERFRONT VACATION!
9.2 out of 10, Wonderful, (85)
"This is a true get a way for 2. Larry was informative and hospitable. What a view!"
THE BOAT HOUSE LOFT ~ THE CAPE'S BEST VALUE IN A RELAXING WATERFRONT VACATION!
Don't see what you're looking for?
See all available properties in Chatham
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.

Other types of properties in Chatham you may be interested in

Seasonal outdoor pool
Chatham Bars Inn
5.0 star property
9.2 out of 10, Wonderful, (686)
"Long term homeowner in proximity to CBI and first time guest. Beautiful location and grounds, but stay fell short given established reputation and the cost of accommodations, Room smelled quit musty. Decor suggested a collection of castoff furnishings from perhaps past renovations. Bathroom needed updating! Nespresso machine was very dirty and dispensed old coffee grounds. Night guard container, obviously from a previous guest, found on floor near bed. Honestly, I have never posted such a...
The price is HK$2,956
HK$3,552 total
includes taxes & fees
6 May - 7 May
Chatham Bars Inn
Beach nearby
Chatham Wayside Inn
3.5 star property
9.2 out of 10, Wonderful, (368)
"awesome"
The price is HK$1,711
HK$2,271 total
includes taxes & fees
5 May - 6 May
Chatham Wayside Inn
Beach nearby
Chatham Seafarer Inn
3.5 star property
9.0 out of 10, Wonderful, (259)
"Would love to stay here again!"
The price is HK$1,339
HK$1,532 total
includes taxes & fees
5 May - 6 May
Chatham Seafarer Inn
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.

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.

How many holiday rentals are there in Chatham?

With 307 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 Cape Cod Beaches 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.

Recent reviews of Chatham properties
Expedia verified reviews

The Villages at Ocean Edge

The Villages at Ocean Edge

5/5 Excellent
"It was peaceful Exactly what I needed"
A verified traveller stayed at The Villages at Ocean Edge
Posted 2 days ago
The Villages at Ocean Edge