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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Chatham vacation homes

TV, fireplace, books

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
Exterior

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 AED 883
AED 2,078 total
includes taxes & fees
2 May - 3 May
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Interior

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

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 AED 796
AED 2,202 total
includes taxes & fees
30 Apr - 1 May
Gray Whale - 3 bedrm/2 bath/gameroom
Smart TV, fireplace, books

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 AED 1,194
AED 2,884 total
includes taxes & fees
1 May - 2 May
Classic Cape House Walking Distance to the Beach - Many recent upgrades
Outdoor dining

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 AED 485
AED 2,155 total
includes taxes & fees
30 Apr - 1 May
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Exterior

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 AED 1,157
AED 3,002 total
includes taxes & fees
30 Apr - 1 May
Family Cottage Close to Beach!!
Smart TV

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 AED 704
AED 2,416 total
includes taxes & fees
3 May - 4 May
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
Smart TV, fireplace, books

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 AED 674
AED 2,126 total
includes taxes & fees
6 May - 7 May
Modern Beach & Pond Getaway; Heart of Cape Cod
Smart TV, fireplace

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 AED 1,188
AED 2,562 total
includes taxes & fees
30 Apr - 1 May
Coastal Haven in West Dennis
Smart TV, fireplace

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 AED 591
AED 1,892 total
includes taxes & fees
30 Apr - 1 May
The Pet-Friendly Surf Shack Hideaway on the Cove
Pool

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 AED 547
AED 1,880 total
includes taxes & fees
4 May - 5 May
Cozy Large Home in Harwich with Patio near Wequassett Resort
Outdoor dining

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 AED 571
AED 1,890 total
includes taxes & fees
4 May - 5 May
Sleeps 2-8/Soaking Tub/FirePit~Burrows
Property grounds

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 AED 533
AED 1,471 total
includes taxes & fees
30 Apr - 1 May
Charming 3 bed room with magnificent views & large deck
Beach nearby

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 AED 584
AED 1,940 total
includes taxes & fees
3 May - 4 May
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Outdoor dining

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 AED 1,370
AED 2,892 total
includes taxes & fees
1 May - 2 May
40 - 4BR Lakeview - Lakeside retreat near GJK View
Interior

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 AED 684
AED 2,065 total
includes taxes & fees
28 May - 29 May
New! Island Pines-A Dog Friendly Boutique Oasis
Outdoor dining

Driftmoor~Dog Frndly 3bd/2 bth~Luxe

Driftmoor~Dog Frndly 3bd/2 bth~Luxe
Eastham
The price is AED 680
AED 2,035 total
includes taxes & fees
3 May - 4 May
Driftmoor~Dog Frndly 3bd/2 bth~Luxe
Interior

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
Dennis
The price is AED 658
AED 1,924 total
includes taxes & fees
30 Apr - 1 May
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
On the beach

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 AED 668
AED 1,895 total
includes taxes & fees
30 Apr - 1 May
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chatham Hotel Reviews

Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Check in was simple and the view was excellent. The staff was accommodating and friendly. Good say, would recommend."
Isaac 1-night trip
Posted 13 hours ago
Cape Sands Inn

Explore a world of travel with Expedia