Chatham Holiday Rentals

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Holiday Rentals in Chatham

View from property
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
8.0 out of 10, Very good, (51)
"It’s hard to find a place that a 16 year old boy, 13 year old girl and 7 year old boy ALL enjoy but this did it! The space is clean (except the couches could use being replaced) and the location is awesome. Kitchen is well equipped. There’s a grill on the deck too. Aside from the couches it’s really hard to think of something to complain about. The local support team was SUPER responsive! My son forgot his wallet when we checked out and they sent someone over to get it and then drove to...
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
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
BBQ/picnic area
Holly Tree Resort by VRI Americas
3.0 star property
9.2 out of 10, Wonderful, (301)
"Loved this property "
Holly Tree Resort by VRI Americas
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Children's play area - outdoor
Cape Winds Resort by VRI Americas
3.5 star property
8.8 out of 10, Excellent, (390)
"The facilities are old and there are things that do not work well"
The price is NZ$245
per night
28 May - 29 May
Cape Winds Resort by VRI Americas
Indoor pool, seasonal outdoor pool
The Cove at Yarmouth by VRI Americas
3.5 star property
9.2 out of 10, Wonderful, (274)
"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$263
per night
29 May - 30 May
The Cove at Yarmouth by VRI Americas
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 NZ$1,109
per night
4 Jun - 5 Jun
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! capeoceanvista
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!
Fridge, microwave, stovetop, dishwasher
Quaint condo near private beach access with fireplace - close to dining
9.0 out of 10, Wonderful, (39)
"It was the perfect location for our anniversary getaway! My wife and I would certainly stay here again!! Five stars!!!"
The price is NZ$699
per night
27 Jun - 28 Jun
Quaint condo near private beach access with fireplace - close to dining
Beach nearby, sun-loungers
Steps to the Ocean! Perfect Location!!!
10.0 out of 10, Exceptional, (169)
"We absolutely loved our stay at The Breakwaters. The cottage was exactly as advertised! It was super clean, comfortable and contained everything we needed for our delightful 4 night stay. The location was perfect, steps away from a very lovely, quiet beach and blocks away from downtown shops and restaurants. We also appreciated our host Steve, for his communications and his recommendations. We highly recommend The Breakwaters and Steve!"
Steps to the Ocean! Perfect Location!!!
2 bedrooms, Internet, bed sheets
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
9.0 out of 10, Wonderful, (33)
"All the things we needed: beach, comfortable place to sleep, eat and shower. Appreciated the extra beach chairs! Plenty of towels for showering. Plenty of movies and games if there’s a bad weather day - we were lucky to have none of those! We hope to return. Thanks for sharing your place!"
The price is NZ$685
per night
28 May - 29 May
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
Interior
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks
9.8 out of 10, Exceptional, (152)
"Perfect for two. Loved having the ocean at our doorstep. The Murphy bed was sturdy and comfortable. The small kitchen area was likely not suitable for gourmet cooking, but could serve well for basic vacation meals (We ate all our meals out. ). Overall, the cabin was clean and neat and cozy. The early May weather was cool but pleasant. Some of our time was spent (with jackets on) sitting on the deck drinking morning coffee while watching the ocean and the few people who walked by. We also did...
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks
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
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
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
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 NZ$3,855
per night
28 May - 29 May
Oceanfront home with private beach, large deck, & washer/dryer - dog-friendly
Beach
Steps to the beach with an ocean view,
10.0 out of 10, Exceptional, (97)
"A late April getaway was enhanced by staying in this lovely cottage. It was wonderful ‘coming home’ to after a busy day exploring Cape Cod. The cottage is cosy and clean with a well-equipped kitchen - exactly what we want in a vacation rental. Communication was timely and efficient from start to finish. Thank you, Tom!"
Steps to the beach with an ocean view,
Fridge, microwave, oven, stovetop
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach
8.6 out of 10, Excellent, (20)
"Everything we wanted and more! Located right up the road from the beach. Very cozy feel inside with a fenced in back yard and a fire place! If your looking for a more personal stay at the cape, this is the spot!!!"
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach
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.
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
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!
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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

Seasonal outdoor pool
Chatham Bars Inn
5.0 star property
9.2 out of 10, Wonderful, (693)
"This is a great hotel with super service "
The price is NZ$826
per night
9 Jun - 10 Jun
Chatham Bars Inn
Beach nearby
Chatham Wayside Inn
3.5 star property
9.2 out of 10, Wonderful, (377)
"Stayed at this convenient and lovely inn for two nights while attending a wedding nearby. Comfortable rooms, large bath with nice amenities, conveniently located in center of Chatham - close to many restaurants and stores. Free parking, while sometimes a bit chaotic, was a plus. Free continental breakfast was nice. "
The price is NZ$475
per night
28 May - 29 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 NZ$320
per night
28 May - 29 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.

What are some of the best holiday rentals that Chatham has to offer?

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach: This holiday home rental outside of Chatham is located near the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 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
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