Search Vacation Homes in Chatham

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chatham vacation homes

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

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham
9.6 out of 10, Exceptional, (102 reviews)
"We absolutely loved this house, very comfortable, well decorated and welcoming atmosphere. It was exactly what we needed for a weekend getaway. We will be back!"
United States
Margot C.
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

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

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Chatham
10.0 out of 10, Exceptional, (119 reviews)
"Clean, quiet, and great location."
United States
Tyler B.
The price is ¥38,345
¥90,274 total
includes taxes & fees
May 2 - May 3
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

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

Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!
Chatham
10.0 out of 10, Exceptional, (18 reviews)
"Downtown Chatham Gem was perfect for our girls getaway weekend. Parked the cars and walked everywhere. The house was clean, beautifully decorated, and had everything we needed. Loved everything about it and we will definitely be back. "
United States
Claire S.
The price is ¥166,854
¥285,836 total
includes taxes & fees
Apr 30 - May 1
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!

Gray Whale - 3 bedrm/2 bath/gameroom

Gray Whale - 3 bedrm/2 bath/gameroom
Eastham
10.0 out of 10, Exceptional, (3 reviews)
"very well appointed accommodations - great location - helpful amenities. would come back again!"
United States
Leonard
The price is ¥34,562
¥95,567 total
includes taxes & fees
Apr 30 - May 1
Gray Whale - 3 bedrm/2 bath/gameroom

Classic Cape House Walking Distance to the Beach - Many recent upgrades

Classic Cape House Walking Distance to the Beach - Many recent upgrades
Chatham
9.8 out of 10, Exceptional, (20 reviews)
"Mary was a wonderful host. The house was clean, close to beach and communication was wonderful! A great, relaxing stay!!"
United States
Kathleen T.
The price is ¥51,808
¥126,071 total
includes taxes & fees
May 6 - May 7
Classic Cape House Walking Distance to the Beach - Many recent upgrades

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

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (51 reviews)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is ¥21,063
¥93,604 total
includes taxes & fees
Apr 30 - May 1
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (75 reviews)
"Everything was exactly as described - they provided beach towels and chairs which we used - the property was perfect for our stay"
United States
John N.
The price is ¥50,214
¥130,267 total
includes taxes & fees
Apr 30 - May 1
Family Cottage Close to Beach!!

Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
Eastham
10.0 out of 10, Exceptional, (2 reviews)
"The house was beautiful, tucked away, and clean. It was spacious for two families with room for more comfortably. "
United States
michele I.
The price is ¥30,578
¥105,491 total
includes taxes & fees
May 5 - May 6
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Modern Beach & Pond Getaway; Heart of Cape Cod

Modern Beach & Pond Getaway; Heart of Cape Cod
South Yarmouth
10.0 out of 10, Exceptional, (15 reviews)
"Great location and very comfortable rental home. Everything you need is included and the house is well stocked and clean!"
United States
Dennis S.
The price is ¥29,297
¥91,973 total
includes taxes & fees
May 6 - May 7
Modern Beach & Pond Getaway; Heart of Cape Cod

Coastal Haven in West Dennis

Coastal Haven in West Dennis
Dennis
10.0 out of 10, Exceptional, (3 reviews)
"This was a great place to stay and relax, just a short walk to the beach and quick drive to great restaurants and activities. Highly recommend!!"
United States
Melissa J.
The price is ¥51,553
¥112,296 total
includes taxes & fees
May 6 - May 7
Coastal Haven in West Dennis

The Pet-Friendly Surf Shack Hideaway on the Cove

The Pet-Friendly Surf Shack Hideaway on the Cove
Eastham
10.0 out of 10, Exceptional, (23 reviews)
"Our host was very responsive and all the instructions were clear. The house was immaculate and a perfect spot of a winter getaway. Would stay again!"
United States
Anna P.
The price is ¥25,485
¥81,895 total
includes taxes & fees
Apr 30 - May 1
The Pet-Friendly Surf Shack Hideaway on the Cove

Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (11 reviews)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is ¥23,752
¥81,586 total
includes taxes & fees
May 6 - May 7
Cozy Large Home in Harwich with Patio near Wequassett Resort

Sleeps 2-8/Soaking Tub/FirePit~Burrows

Sleeps 2-8/Soaking Tub/FirePit~Burrows
Eastham
10.0 out of 10, Exceptional, (8 reviews)
"We went with a small group of friends and everything was amazing. The property is beautiful and well located. We had everything that we needed and the communication con the owner was good."
United States
Lourdes P.
The price is ¥24,787
¥83,102 total
includes taxes & fees
May 11 - May 12
Sleeps 2-8/Soaking Tub/FirePit~Burrows

Charming 3 bed room with magnificent views & large deck

Charming 3 bed room with magnificent views & large deck
Barnstable
8.0 out of 10, Very Good, (3 reviews)
"We had a great stay in Hyannis! The location is great for catching a ferry to Nantucket or the vineyard, and Main Street is within walking distance. The backyard is also very peaceful for a cup of coffee in the morning! "
United States
Meghan H.
The price is ¥23,114
¥63,856 total
includes taxes & fees
Apr 30 - May 1
Charming 3 bed room with magnificent views & large deck

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Barnstable
8.6 out of 10, Excellent, (8 reviews)
"This was an amazing property and our host was awesome and checked in to make sure everything was going well. Would definitely stay here again! Thank you! "
United States
Kim
The price is ¥25,372
¥84,272 total
includes taxes & fees
May 3 - May 4
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

40 - 4BR Lakeview - Lakeside retreat near GJK View

40 - 4BR Lakeview - Lakeside retreat near GJK View
South Yarmouth
7.6 out of 10, Good, (5 reviews)
"The house was immaculate. The property was picturesque. Neighborhood was stunning. We LOVED this home. "
United States
Mary R.
The price is ¥38,927
¥97,698 total
includes taxes & fees
Apr 30 - May 1
40 - 4BR Lakeview - Lakeside retreat near GJK View

New! Island Pines-A Dog Friendly Boutique Oasis

New! Island Pines-A Dog Friendly Boutique Oasis
Wellfleet
9.4 out of 10, Exceptional, (12 reviews)
"Loved the place. Very clean and updated. You have to time the tides because it is on an island, but that was fine for us. "
United States
Brian F.
The price is ¥29,704
¥89,698 total
includes taxes & fees
May 28 - May 29
New! Island Pines-A Dog Friendly Boutique Oasis

Driftmoor~Dog Frndly 3bd/2 bth~Luxe

Driftmoor~Dog Frndly 3bd/2 bth~Luxe
Eastham
The price is ¥29,500
¥89,044 total
includes taxes & fees
May 19 - May 20
Driftmoor~Dog Frndly 3bd/2 bth~Luxe

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
Dennis
The price is ¥28,550
¥83,510 total
includes taxes & fees
Apr 30 - May 1
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach
Eastham
10.0 out of 10, Exceptional, (27 reviews)
"The house is adorable. Great location. Would love to stay again!"
United States
Laura G.
The price is ¥29,005
¥82,325 total
includes taxes & fees
Apr 30 - May 1
Sand Bar-Dog Friendly on Cooks Brook Beach
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chatham Hotel Reviews

Find out more about Chatham

Chatham Vacation Homes information

Number of reviews
328
Accommodation
2394 Vacation Homes
Lowest Price
¥63,856
Highest Price
¥285,836

Explore a world of travel with Expedia