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Our top choices for Chatham vacation homes

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

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

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

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

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

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

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 694
AED 1,477 total
includes taxes & fees
21 May - 22 May
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

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

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

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 551
AED 1,497 total
includes taxes & fees
4 May - 5 May
Charming 3 bed room with magnificent views & large deck

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 644
AED 1,989 total
includes taxes & fees
3 May - 4 May
The Alpine/Walk to Beach for 2 or more!

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

Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
Eastham
9.6 out of 10, Exceptional, (4 reviews)
"The home was clean, cool and comfortable. Booking was easy and effortless! Can’t wait to go back!"
United States
Kim S.
The price is AED 571
AED 1,898 total
includes taxes & fees
3 May - 4 May
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

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

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

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

Ebb Tide~3b/2b and dog friendly for 2-10

Ebb Tide~3b/2b and dog friendly for 2-10
Wellfleet
8.0 out of 10, Very Good, (2 reviews)
"Great stay. Kind extra touches of hospitality appreciated!"
United States
Ross M.
The price is AED 680
AED 2,064 total
includes taxes & fees
7 May - 8 May
Ebb Tide~3b/2b and dog friendly for 2-10

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!!

Waterfront~Dog Friendly~ Lieutenant's Lodge

Waterfront~Dog Friendly~ Lieutenant's Lodge
Wellfleet
10.0 out of 10, Exceptional, (11 reviews)
"Great home for a relaxing weekend"
United States
Mike B.
The price is AED 1,524
AED 3,233 total
includes taxes & fees
12 May - 13 May
Waterfront~Dog Friendly~ Lieutenant's Lodge

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.
The price is AED 559
AED 1,830 total
includes taxes & fees
4 May - 5 May
National Seashore/Updated/Game Room~Blue Pearl
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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