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
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sep - 20 Sep

Our top choices for Chatham vacation homes

TV, fireplace

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.
The price is AED 382
AED 1,915 total
includes taxes & fees
28 May - 29 May
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, (121 reviews)
"Clean, quiet, and great location."
United States
Tyler B.
The price is AED 959
AED 2,211 total
includes taxes & fees
2 Jun - 3 Jun
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.
The price is AED 3,405
AED 6,012 total
includes taxes & fees
31 May - 1 Jun
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!
Iron/ironing board, WiFi, bed sheets

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 2,242 total
includes taxes & fees
28 May - 29 May
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Outdoor dining

Great for Families! Brewster Home 6 Mi to Beach

Great for Families! Brewster Home 6 Mi to Beach
Brewster
10.0 out of 10, Exceptional, (6 reviews)
"The kitchen was well stocked. The Beds were comfortable. "
United States
Stacey P.
The price is AED 382
AED 2,564 total
includes taxes & fees
29 May - 30 May
Great for Families! Brewster Home 6 Mi to Beach
Beach nearby

The Alpine/Walk to Beach for 2 or more!

The Alpine/Walk to Beach for 2 or more!
Eastham
9.2 out of 10, Wonderful, (11 reviews)
"The location was awesome, the house was clean and spacious, and overall it was terrific! I would highly recommend."
United States
Jennifer G.
The price is AED 837
AED 2,269 total
includes taxes & fees
2 Jun - 3 Jun
The Alpine/Walk to Beach for 2 or more!
Outdoor dining

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

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Dennis
10.0 out of 10, Exceptional, (191 reviews)
"Good location, pet friendly and clean"
United States
Megan R.
The price is AED 413
AED 1,263 total
includes taxes & fees
1 Jun - 2 Jun
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
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 579
AED 1,911 total
includes taxes & fees
28 May - 29 May
Sleeps 2-8/Soaking Tub/FirePit~Burrows
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 583
AED 1,866 total
includes taxes & fees
28 May - 29 May
The Pet-Friendly Surf Shack Hideaway on the Cove
Dining

National Seashore/Updated/Game Room~Blue Pearl

National Seashore/Updated/Game Room~Blue Pearl
Eastham
10.0 out of 10, Exceptional, (9 reviews)
"The house was exactly as advertised and location was great. Host was very easy to communicate with and responded quickly when contacted. I have nothing but positives for our stay. Looking forward to staying here again."
United States
Susan N.
National Seashore/Updated/Game Room~Blue Pearl
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
29 May - 30 May
Gray Whale - 3 bedrm/2 bath/gameroom
Iron/ironing board, WiFi, bed sheets

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.0 out of 10, Wonderful, (24 reviews)
"Loved this property. "
United States
Carol S.
The price is AED 386
AED 1,788 total
includes taxes & fees
28 May - 29 May
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Smart TV

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

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Dennis
9.0 out of 10, Wonderful, (4 reviews)
"We enjoyed this Cape Cottage, centrally located in mid-cape. Clean with comfortable beds and host is very helpful. We will be back!"
United States
Linda P.
The price is AED 680
AED 1,465 total
includes taxes & fees
2 Jun - 3 Jun
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Beach nearby

Walk to Beach: Chatham Gem w/ Ocean-View Sunroom!

Walk to Beach: Chatham Gem w/ Ocean-View Sunroom!
Chatham
9.2 out of 10, Wonderful, (15 reviews)
"Very close to the beach, great little neighborhood in a quiet part of Chatham"
United States
Alex R.
The price is AED 1,087
AED 3,232 total
includes taxes & fees
3 Jun - 4 Jun
Walk to Beach: Chatham Gem w/ Ocean-View Sunroom!
Dining

NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH

NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH
Dennis
10.0 out of 10, Exceptional, (11 reviews)
"Wonderful place! Thank you so much! "
United States
Jess W.
The price is AED 760
AED 2,165 total
includes taxes & fees
1 Jun - 2 Jun
NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH
Smart TV

New! Sandy Point-Private beach/Dog Friendly

New! Sandy Point-Private beach/Dog Friendly
Eastham
10.0 out of 10, Exceptional, (1 review)
"The little touches included with this listing are what makes the difference between returning to a “house we rented” and returning to a “home away from home”. Thoughtful items like nightlights, labeled light switches (so easy but so useful), and motion sensing lights on the outdoor deck stairs for when you were out later than expected and forgot to leave the outside lights on. The kitchen is well stocked with pots, pans, and all manner of cooking gear. WiFi was super fast all throughout the...
United States
Matthew and Kym P.
The price is AED 917
AED 2,521 total
includes taxes & fees
1 Jun - 2 Jun
New! Sandy Point-Private beach/Dog Friendly
Terrace/patio

10 min walk to Beach - Home with Amazing View & Huge Deck

10 min walk to Beach - Home with Amazing View & Huge Deck
Eastham
The price is AED 823
AED 2,216 total
includes taxes & fees
28 May - 29 May
10 min walk to Beach - Home with Amazing View & Huge Deck
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
28 May - 29 May
Family Cottage Close to Beach!!
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
8.8 out of 10, Excellent, (9 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 551
AED 1,903 total
includes taxes & fees
2 Jun - 3 Jun
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Outdoor dining

Driftmoor~Dog Frndly 3bd/2 bth~Luxe

Driftmoor~Dog Frndly 3bd/2 bth~Luxe
Eastham
10.0 out of 10, Exceptional, (1 review)
"We stayed here two nights while exploring cape cod on a family vacation. The house was beautiful, clean, beds were comfortable and it was pet friendly. The cookies and dog bones were a nice surprise when we arrived. Arrival and departure Instructions were clear and communication with Tara was excellent. Tara provided a lot of information about the area. The neighborhood was nice and quiet and getting in and out was easy. I would definitely stay here again. Thanks Tara! "
United States
Diane G.
The price is AED 1,174
AED 2,694 total
includes taxes & fees
28 May - 29 May
Driftmoor~Dog Frndly 3bd/2 bth~Luxe
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

Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"The Inn was in a brilliant location on Main St. Lots of parking. The room was spacious. We used the gym and the pool as well."
Sam 3-night trip
Posted 1 hour ago
Chatham Wayside Inn

Explore a world of travel with Expedia