Chatham Holiday Rentals

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Holiday Rentals in Chatham

Beach nearby, sun-loungers
Steps to the Ocean! Perfect Location!!!
10.0 out of 10, Exceptional, (168)
"Wonderful stay at this cottage. Very clean and comfortable! Beds comfortable. Location!! Steps away from beach. Will definitely stay at this cottage again."
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
Beach
Steps to the beach with an ocean view,
10.0 out of 10, Exceptional, (96)
"Tom Loved your perfect cottage !!!"
Steps to the beach with an ocean view,
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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
TV, DVD player
Cape Cod Vacation Home Rental - Walk to Beach
10.0 out of 10, Exceptional, (7)
"We loved being able to walk to cafes, restaurants and the bookstore and the proximity of the bike path meant that we didn't need our car much at all. We rode bikes to lunch spots, the beach, and to the pickleball courts. The house was tidy and had everything we needed."
Cape Cod Vacation Home Rental - Walk to Beach
Fridge, microwave, oven, stovetop
Lakefront retreat w/ deck, dock, sandy beach, 4 watercraft, <6 mins to 2 beaches
10.0 out of 10, Exceptional, (4)
"Beautiful place to stay, newly renovated, enjoyed being in Orleans. My young adult daughter enjoyed it, too. We made popovers in the kitchen to bring to a relative's house - kitchen even had muffin pans, so we were good to go."
The price is AU$866
includes taxes & fees
21 May - 22 May
Lakefront retreat w/ deck, dock, sandy beach, 4 watercraft, <6 mins to 2 beaches
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
Interior
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks
9.8 out of 10, Exceptional, (151)
"Lovely cottage right on the beach!"
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks
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 nearby
Lovely Cape Cottage 2 bedroom with private beach and central air.
9.8 out of 10, Exceptional, (38)
"The location was excellent, close to beaches and amenities. Property was clean and tidy, and host was easy to contact. Would visit again."
Lovely Cape Cottage 2 bedroom with private beach and central air.
Beach
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
9.8 out of 10, Exceptional, (86)
"The host was very helpful and friendly and got right back to me on questions. The space was small but very clean and had everything I needed as a single guest with one dog. The bed was quite comfortable too. As a woman traveling alone, my only issues were with the isolation of the area in the off-season (there were coyotes outside at night), and I would have liked to have had a more secure bolt lock and less see-through blinds."
The price is AU$425
includes taxes & fees
6 June - 7 June
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Smart TV
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
9.8 out of 10, Exceptional, (124)
"Exactly what we were looking for"
The price is AU$415
includes taxes & fees
21 May - 22 May
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
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 AU$783
includes taxes & fees
21 May - 22 May
Walk to DennisPort Beaches 4 min.Bars and restaurants 2min walk.Perfect Location
Property grounds
Cape Cod Oceanfront New Condo with Ocean View & Private Beach! capeoceanvista
9.8 out of 10, Exceptional, (75)
"The condo is as described and has lots of light. Plenty of space for two couples or a small family. The weather was variable while we were there so we used both the gas fireplace and the deck that faces the ocean! The location is close to great restaurants and our dog enjoyed walking the neighborhood and down to the ocean. Would highly recommend!"
The price is AU$985
includes taxes & fees
21 May - 22 May
Cape Cod Oceanfront New Condo with Ocean View & Private Beach! capeoceanvista
Beach
New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach
9.6 out of 10, Exceptional, (53)
"My husband and I had a weekend getaway and the space was great! Great location, clean, spacious. We had a wonderful time!"
New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach
Interior
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! capeoceanvista
9.6 out of 10, Exceptional, (110)
"It was a perfect place, the balcony by was in the right position to watch sunrise and sunsets. Condo was very clean and comfortable."
The price is AU$1,025
includes taxes & fees
4 June - 5 June
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 AU$3,280
includes taxes & fees
23 May - 24 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
Property grounds
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
9.4 out of 10, Exceptional, (25)
"A Retreat for Three Ladies. The house was spotless, it was beautiful, it was exactly what we needed! Comfortable Beds, HOT HOT (welcoming) Water, and a serene back yard.... we didn't' want to leave."
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
BBQ/picnic area
Holly Tree Resort by VRI Americas
3.0 star property
9.2 out of 10, Wonderful, (300)
"Great place to stay."
Holly Tree Resort by VRI Americas
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.

Chatham Holiday Home Travel Info

Number of holiday homes
352
Popular accommodation
Chatham private holiday homes
Known landmarks
Skaket Beach, Nickerson State Park and Bank Street Beach
International airports
Boston, MA (BOS-Logan Intl.) and Nantucket, MA (ACK-Nantucket Memorial)

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, (689)
"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 AU$725
includes taxes & fees
22 May - 23 May
Chatham Bars Inn
Beach nearby
Chatham Wayside Inn
3.5 star property
9.2 out of 10, Wonderful, (372)
"Very clean, nice restaurant, bar, walking on Main Street"
The price is AU$434
includes taxes & fees
21 May - 22 May
Chatham Wayside Inn
Beach nearby
Chatham Seafarer Inn
3.5 star property
9.0 out of 10, Wonderful, (260)
"The staff was very friendly and helpful. The room was comfortable. You could tell that the building was an older one but the room has been well taken care of and clean. The bathroom looks to have been renovated recently. Overall, I would stay again solo or as a couple. "
The price is AU$293
includes taxes & fees
21 May - 22 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.

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 favourite 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 depend 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 AU$223 per night. Entering your travel dates in the search wizard might find you 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?

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill: This holiday home rental outside of Chatham is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Chatham?

With 306 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.

Recent reviews of Chatham properties
Expedia verified reviews

Hyannis Travel Inn

Hyannis Travel Inn

5/5 Excellent
"We really enjoyed our time here! Staff was very welcoming and friendly, rooms were clean and quiet, and the pool and breakfast areas were nice. The hotel was in walking distance of many restaurants and shops, and it was an easy drive to several beaches and parks. We unfortunately had to leave early because my husband was sick and the staff was very kind and considerate about our situation. We definitely plan to come back! "
A verified traveller stayed at Hyannis Travel Inn
Posted 1 day ago
Hyannis Travel Inn