Chatham Holiday Rentals

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Holiday Rentals in Chatham

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

8.0 out of 10, Very good, (64)
"Wonderful off season vacation home with a fabulous view of the river. Avoid going in the summer as there is no upstairs air conditioning .and all the glass"
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach

9.6 out of 10, Exceptional, (62)
"Stayed here for a friends wedding and loved the natural lit, well appointed apartment. The dedicated parking space was great, and close enough to walk to anything I needed over the duration of the stay. Very clean and well kept, would gladly stay again. "
New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (255)
"We loved our stay! The 1 bedroom was very clean fully equipped with everything we needed. All the extras like soap for dishes , dishwasher towels for the pool. Pool area very clean beautiful grounds. Friendly staff. "
Edgewater Beach Resort, a VRI resort

The Cove at Yarmouth by VRI Americas

3.5 star property
9.2 out of 10, Wonderful, (295)
"Nice place"
The price is AU$230
includes taxes & fees
2 Jan - 3 Jan 2025
The Cove at Yarmouth by VRI Americas

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (198)
"This cottage was perfect for me, my husband, and two adult daughters. It is exactly as advertised and the owner is very communicative and helpful recommending local restaurants, etc. We definitely would stay here again if we travel to the Cape. The beach is very close and we could see the water from the cottage. Great location! "
Steps to the Ocean! Perfect Location!!!

Holly Tree Resort by VRI Americas

3.0 star property
9.0 out of 10, Wonderful, (341)
"Our room was great - spacious, clean and comfortable. My only problem was that there wasn’t an elevator to the 2nd floor for my aging parents. "
Holly Tree Resort by VRI Americas

The Cove At Yarmouth

3.0 star property
9.2 out of 10, Wonderful, (218)
"This is my wife and my favorite spot to just come and relax in the off season and get some great hot chocolates from our favorite bakery in town. "
The price is AU$236
includes taxes & fees
2 Jan - 3 Jan 2025
The Cove At Yarmouth

Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! capeoceanvista

9.6 out of 10, Exceptional, (121)
"The furniture needs upgrading. Mattresses uncomfortable and the chairs are very uncomfortable. But the location and views are priceless. Sitting on the deck, listening to the ocean, watching the sun glisten off the water, sipping coffee….replenishes your soul ♥️"
The price is AU$689
includes taxes & fees
2 Jan - 3 Jan 2025
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! capeoceanvista

Oceanfront Cape Cod Gem w/ Balcony, Pets Welcome

9.2 out of 10, Wonderful, (57)
"We had a wounderful long weekend. "
Oceanfront Cape Cod Gem w/ Balcony, Pets Welcome

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

9.0 out of 10, Wonderful, (41)
"Small cabin, refrigerator went out before we realized and we lost food. Heater was red tagged, fortunately we did not need it on. Window air conditioner leaked terribly, stuffed a towel around the bottom to stop the gale force wind from coming in. The beach was at the bottom of a bluff we no access except to climb the fence next door!"
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

Cozy beachfront cottage at Chases Ocean Grove

9.8 out of 10, Exceptional, (24)
"Enjoyed coffee on the enclosed porch overlooking ocean. Great communication with owner. Bathroom nicely done. Very clean, cute, well setup for a cottage. "
Cozy beachfront cottage at Chases Ocean Grove

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

9.0 out of 10, Wonderful, (52)
"Our stay was good it was in the perfect area everything was close by. The condo was very clean and roomy. The heat was tricky in the beginning but overall great weekend away"
The price is AU$461
includes taxes & fees
1 Jan - 2 Jan 2025
Quaint condo near private beach access with fireplace - close to dining

Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks

9.8 out of 10, Exceptional, (166)
"Beautiful, well-equipped house right on the beach, convenient to Hyannis port and all the Cape has to offer. "
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

9.6 out of 10, Exceptional, (100)
"A very comfortable few days on the mid-Cape. Great location, great little cottage. Quiet, private, clean. I'd do it again!"
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Oceanfront home with private beach, large deck, & washer/dryer - dog-friendly

9.4 out of 10, Exceptional, (11)
"The property was fantastic, location magical and we hope to return… our big issue was that a good chunk of the house had been closed off, including the washer and dryer, and the room I was going to sleep in, really put a kink into the stay. Website listed those as available until off-season when it was going to be renovated."
Oceanfront home with private beach, large deck, & washer/dryer - dog-friendly

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (112)
"We came to visit Nantucket and Martha’s Vineyard and one of the best parts of our trip is this gem. It was the perfect size for 4 of us. Close to the beach and the seashell collecting was amazing. Lots of shops and restaurants close by. We had some questions and the owner was very responsive. We would stay here again!"
Steps to the beach with an ocean view,

Lovely Cape Cottage 2 bedroom with private beach and central air.

10.0 out of 10, Exceptional, (44)
"Such a cute and comfortable place. We enjoyed the neighborhood and the beach down the street. Owner was really responsive if we needed anything "
Lovely Cape Cottage 2 bedroom with private beach and central air.

New Coastal House, Steps to Keyes Beach, Main Street, Harbor; AC, Linens, Wi-Fi

9.8 out of 10, Exceptional, (145)
"We just returned from our Vrbo stay in Hyannis. The property is perfectly located for a morning beach walk or any walk for that matter. Clean, good size bedrooms and very well equipped. One flaw, the heating situation is way off ! Upstairs bedrooms were boiling as well as the 2 downstairs bedrooms and the kitchen, living/ dining area were cool. This made sleeping almost impossible for everyone. If the heating was not a problem I would have given this rental 5 stars. "
New Coastal House, Steps to Keyes Beach, Main Street, Harbor; AC, Linens, Wi-Fi

Serene Waterview Renovated w/Kayaks Deck Firepit Dogs Welcome 5 Minutes to Ocean

10.0 out of 10, Exceptional, (36)
"Enjoyed the quiet location which was not too far from Hyannis and other towns for easy travel to activities. Cottage was clean and comfortable with a nice touch of having a few basic staples available upon arrival. "
Serene Waterview Renovated w/Kayaks Deck Firepit Dogs Welcome 5 Minutes to Ocean

Grandma's Cottage: Olde Cape Cod at its best. Steps to the beach. Dog-friendly!

8.8 out of 10, Excellent, (18)
"Could use some updates and repairs but overall a nice cottage close to the ocean / beach, shopping and restaurants. Outdoor shower was great and nice hot water! Furniture in living space could be better. More comt seating and the table and chairs inside weren't needed and just took up space. Extra countertop would be good as it was hard to cook and the stove needs to be leveled. Some kind of high top bar with stools would have been great and a different arrangement with the living room...
Grandma's Cottage: Olde Cape Cod at its best. Steps to the beach. Dog-friendly!
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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Other types of properties in Chatham you may be interested in

Chatham Bars Inn

5.0 star property
9.2 out of 10, Wonderful, (739)
"Great service. Beautiful location and had the best room "
The price is AU$641
includes taxes & fees
22 Jan - 23 Jan 2025
Chatham Bars Inn

Chatham Wayside Inn

4.0 star property
9.2 out of 10, Wonderful, (457)
"Quaint, comfortable and very friendly. Also provided an EV charging station in the parking lot. This is really helpful to those of who travel by EV."
The price is AU$375
includes taxes & fees
1 Jan - 2 Jan 2025
Chatham Wayside Inn

Chatham Seafarer Inn

3.5 star property
9.0 out of 10, Wonderful, (285)
"I really liked my stay at the Seafarer! Such a cute spot and the people were super nice. I was in town visiting family, so my room was the perfect convenience with a cute little spot to sit outside my room and sip coffee in the morning and watch the world go by. The bed was comfortable, and it was a short distance to downtown Chatham where I could run to Chatham Light. Highly recommend. "
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.

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?

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK: This highly rated holiday home rental in Chatham is located on a river, and has a patio, a selection of games and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chatham?

With 288 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.