Chatham Holiday Rentals

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Holiday Rentals in Chatham

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!!!
Steps to the beach with an ocean view,
10.0 out of 10, Exceptional, (96)
"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,
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
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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
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
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 NZ$951
per night
13 May - 14 May
Lakefront retreat w/ deck, dock, sandy beach, 4 watercraft, <6 mins to 2 beaches
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
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks
9.8 out of 10, Exceptional, (149)
"We enjoyed our 4 night stay in early September. The weather was hot and muggy, so we were grateful for the air conditioning. The cottage is tiny but it had everything we needed to cook meals. We found the murphy bed to be very comfortable and easy to open and close."
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks
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
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 NZ$455
per night
12 May - 13 May
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
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.
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."
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
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 NZ$1,031
per night
17 May - 18 May
Cape Cod Oceanfront New Condo with Ocean View & Private Beach! capeoceanvista
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 NZ$857
per night
12 May - 13 May
Walk to DennisPort Beaches 4 min.Bars and restaurants 2min walk.Perfect Location
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
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."
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! capeoceanvista
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 NZ$3,642
per night
23 May - 24 May
Oceanfront home with private beach, large deck, & washer/dryer - dog-friendly
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
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
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 NZ$248
per night
29 May - 30 May
The Cove at Yarmouth by VRI Americas
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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

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 NZ$744
per night
12 May - 13 May
Chatham Bars Inn
Chatham Wayside Inn
3.5 star property
9.2 out of 10, Wonderful, (368)
"awesome"
The price is NZ$481
per night
12 May - 13 May
Chatham Wayside Inn
Chatham Seafarer Inn
3.5 star property
9.0 out of 10, Wonderful, (259)
"Would love to stay here again!"
The price is NZ$325
per night
12 May - 13 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chatham holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chatham. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chatham. Seeing all the best attractions is bound to make you fall in love with Chatham. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chatham short-term rentals, that won’t be hard to do.

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 309 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.

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