Chatham Vacation Rentals

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Vacation Rentals in Chatham

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Chatham
9.6 out of 10, Exceptional, (29)
"Great visit! Clean property a bit tucked in the woods but overall close to everything and a great spot for the price!"
United States
Christian B.
The price is ¥14,575
¥52,464 total
includes taxes & fees
Dec 1 - Dec 2
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Chatham
9.6 out of 10, Exceptional, (99)
"We had a great time on the Cape and lucked out with beautiful weather too! We loved this house and were so grateful to be able to bring our dogs! Thank you"
United States
Judy M.
The price is ¥14,268
¥63,215 total
includes taxes & fees
Nov 17 - Nov 18
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Chatham
10.0 out of 10, Exceptional, (114)
"Great great great location. Super charming home. It worked perfectly for our family. Walk to shops and restaurants! I highly recommend. Host was lovely & easy to reach. We would’ve loved to utilize the properties outdoor space more. Other than that - it was terrific! Rent it now!"
United States
Rachel S.
The price is ¥27,616
¥75,328 total
includes taxes & fees
Nov 11 - Nov 12
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham

Chatham
8.6 out of 10, Excellent, (26)
"Lovely cottage and very clean. The Vacasa folks were very helpful. Highly recommend!"
United States
Kathy G.
The price is ¥30,684
¥80,769 total
includes taxes & fees
Nov 17 - Nov 18
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham

Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

4.0 star property
Chatham
10.0 out of 10, Exceptional, (21)
"We had a lovely time celebrating my wife’s 60th birthday at this beautiful Chatham property. The house fit four generations perfectly, with great spaces to gather, nearby beach access, and a fun swing set for the little ones. The Chatham Bars Inn, where we ate and played tennis, is in easy walking distance. Bill, the property manager, was very responsive. "
United States
Pierre V.
The price is ¥202,975
¥330,636 total
includes taxes & fees
Nov 11 - Nov 12
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!

4.0 star property
Chatham
10.0 out of 10, Exceptional, (18)
"Beautiful home right in the heart of town! Everything that Chatham has to offer is only steps away from this property. I would recommend this house to anyone looking to experience Chatham."
United States
Timothy P.
The price is ¥166,522
¥282,945 total
includes taxes & fees
Nov 11 - Nov 12
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!

Brewster Green Resort

3.5 star property
Brewster
9.4 out of 10, Exceptional, (119)
"The room was very clean and large. It was perfect for two people. The unit we stayed in was about .25 miles from clubhouse. So since it was cold, we didn't use the indoor pool. Staff was friendly. They have a game room where you can play table tennis and air hockey among other games. For the money, it was well worth staying there."
United States
Harry
The price is ¥21,325
¥24,406 total
includes taxes & fees
Nov 11 - Nov 12
Brewster Green Resort

Coastal Haven in West Dennis -15

2.0 star property
West Dennis
The price is ¥48,526
¥119,809 total
includes taxes & fees
Dec 5 - Dec 6
Coastal Haven in West Dennis -15

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

2.0 star property
West Brewster
10.0 out of 10, Exceptional, (24)
"We are long-time Cape renters and Iwould say this was one of the top 3 homes over 20 years!! Thoughtful layout, super clean, nice peaceful neighborhood.....just excellent! Thank you for our stay, Jenny."
United States
Lee H.
The price is ¥14,115
¥98,682 total
includes taxes & fees
Nov 18 - Nov 19
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

2.0 star property
Dennis
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveler
The price is ¥19,791
¥49,780 total
includes taxes & fees
Nov 11 - Nov 12
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

The Pet-Friendly Surf Shack Hideaway on the Cove

Eastham
10.0 out of 10, Exceptional, (21)
"Our family booked a spontaneous weekend in April, and we will sure be back! This beautiful spacious house was spotless when we arrived, and the arrival treats for our 2 legged and 4 legged boys was a thoughtful touch! Our family used the bikes and kayaks that were available, explored the coves and beaches with our dogs. It was the perfect place for our getaway!"
United States
Kristen S.
The price is ¥24,696
¥76,727 total
includes taxes & fees
Nov 11 - Nov 12
The Pet-Friendly Surf Shack Hideaway on the Cove

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Dennis
10.0 out of 10, Exceptional, (175)
"Perfect spot for a few days away with the kids. The house had everything we needed and was in a great location! Would definitely rent again. "
United States
Dana B.
The price is ¥13,670
¥47,956 total
includes taxes & fees
Nov 11 - Nov 12
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

West Brewster
9.6 out of 10, Exceptional, (50)
"The house was as described and very clean upon arrival. Loved the house! The location was very convenient. Will stay again in the future."
United States
Scott B.
The price is ¥20,251
¥79,476 total
includes taxes & fees
Nov 11 - Nov 12
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

National Seashore/Updated/Game Room~Blue Pearl

Eastham
10.0 out of 10, Exceptional, (8)
"Beautiful new house in a great location. Definitely would rent again"
United States
Timothy K.
The price is ¥23,855
¥75,590 total
includes taxes & fees
Nov 11 - Nov 12
National Seashore/Updated/Game Room~Blue Pearl

Seaside Getaway - Harwichport Beachhouse

Harwich
9.8 out of 10, Exceptional, (9)
"Great location great property"
United States
Glenn M.
The price is ¥26,097
¥63,582 total
includes taxes & fees
Nov 12 - Nov 13
Seaside Getaway - Harwichport Beachhouse

Pond House~Waterfront Oasis W/Jacuzzi Tub

Eastham
10.0 out of 10, Exceptional, (10)
"We loved the location. Beautiful views, excellent adventure with my family. Visiting Skull Island, Alleys Bowl, beaches and so many more fun activities we enjoyed. Communication with location was spectacular and the cleanliness of house was much appreciated."
United States
Martine F.
The price is ¥24,024
¥77,890 total
includes taxes & fees
Nov 11 - Nov 12
Pond House~Waterfront Oasis W/Jacuzzi Tub

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Wellfleet
10.0 out of 10, Exceptional, (74)
"Drew was one of the best landlords we’ve ever had on a vacation property. He was very responsive to the few questions that we had and asked proactively if there was anything that we needed throughout our week. The view from the porch was spectacular."
United States
David M.
The price is ¥21,402
¥66,461 total
includes taxes & fees
Nov 11 - Nov 12
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Secluded-Entire 2nd floor Suite with Private Bath

Barnstable
10.0 out of 10, Exceptional, (1)
"Great, very close to downtown hyannis. Charming and a nice owner. "
United States
sam s.
The price is ¥12,151
¥24,441 total
includes taxes & fees
Nov 15 - Nov 16
Secluded-Entire 2nd floor Suite with Private Bath

Lovely House 5 Min to Beach with Deck, Grill, Garage

Eastham
10.0 out of 10, Exceptional, (1)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is ¥22,860
¥74,753 total
includes taxes & fees
Nov 11 - Nov 12
Lovely House 5 Min to Beach with Deck, Grill, Garage

Water Access 5-bed 2-bath Retreat

2.0 star property
Hyannis
The price is ¥59,084
¥150,038 total
includes taxes & fees
Nov 17 - Nov 18
Water Access 5-bed 2-bath Retreat
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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Top Chatham Hotel Reviews

Find out more about Chatham

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:

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Look no further and take a look at our great range of rental properties in Chatham!

Frequently asked questions

Can I find a vacation rental in Chatham?

Yes, you can find vacation rentals in Chatham close to Chatham Railroad Museum, or you can select a more secluded option if you'd like a relaxing place to 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 vacation rentals that Chatham has to offer?

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!: This highly rated vacation home rental in Chatham is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation. Some other top choices in Chatham are Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches and Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK.

How many vacation rentals are there in Chatham?

With 287 Expedia vacation rentals, you're sure to find just the right place for your Chatham stay.

What can I see and do in Chatham?

Cultural attractions include Atwood House Museum and Gallery Antonia, 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 vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or longer in Chatham. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.