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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Chatham vacation homes

TV, fireplace

1. 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
9.8 out of 10, 106, (106 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is AED 349
AED 1,865 total
includes taxes & fees
7 Oct - 8 Oct
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Exterior

2. 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, 127, (127 reviews)
"Amazing stay so close to town and CBI."
United States
Joanne B.
The price is AED 1,095
AED 2,346 total
includes taxes & fees
7 Oct - 8 Oct
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Sun loungers, beach towels

3. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, 87, (87 reviews)
"This is second time to stay here! We love the location and hospitality of the hosts! Great place!"
United States
Barbara P.
The price is AED 992
AED 2,257 total
includes taxes & fees
5 Oct - 6 Oct
Beautiful home near Jacknife Beach and bike trail
Exterior

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

Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Chatham
10.0 out of 10, 22, (22 reviews)
"House was wonderful with plenty of room. Great outdoor spaces with a deck and patio. Very convenient location. Host responsive to our needs. Would definitely stay again. "
United States
Sally S.
The price is AED 3,841
AED 5,023 total
includes taxes & fees
12 Oct - 13 Oct
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Outdoor dining

5. Great for Families! Brewster Home 6 Mi to Beach

Great for Families! Brewster Home 6 Mi to Beach
Brewster
9.6 out of 10, 12, (12 reviews)
"The kitchen was well stocked. The Beds were comfortable. "
United States
Stacey P.
The price is AED 382
AED 2,573 total
includes taxes & fees
20 Sep - 21 Sep
Great for Families! Brewster Home 6 Mi to Beach
Pool

6. 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, 14, (14 reviews)
"Great host. Convenient location for a visit to Chatham."
United States
Bill F.
The price is AED 526
AED 1,827 total
includes taxes & fees
16 Sep - 17 Sep
Cozy Large Home in Harwich with Patio near Wequassett Resort
Exterior

7. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, 82, (82 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
16 Sep - 17 Sep
Family Cottage Close to Beach!!
Outdoor dining

8. Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
Harwich
10.0 out of 10, 9, (9 reviews)
"Excellent location "
United States
Norman Y.
The price is AED 826
AED 2,518 total
includes taxes & fees
16 Sep - 17 Sep
Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
TV, offices

9. 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, 52, (52 reviews)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is AED 650
AED 2,447 total
includes taxes & fees
22 Sep - 23 Sep
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
TV, books

10. New! Chatham Cottage- 1 Mile to Downtown & Beaches

New! Chatham Cottage- 1 Mile to Downtown & Beaches
Chatham
9.8 out of 10, 11, (11 reviews)
"Close to tpwn beach very clean great for us and pups sweet lplace"
United States
Deanna M.
The price is AED 1,450
AED 2,846 total
includes taxes & fees
3 Oct - 4 Oct
New! Chatham Cottage- 1 Mile to Downtown & Beaches
Sun loungers, beach towels

11. The Brewster Pearl

The Brewster Pearl
Brewster
10.0 out of 10, 2, (2 reviews)
"The home is so beautiful and the decor is like out of a magazine. Immaculately clean, our standards are high, being hosts ourselves. Every amenity thoughtfully provided. The furnishings, bedding, towels are of premium quality and top brand. Our host was incredible, responsive, kind and helpful. This home is perfectly located to many beaches , excellent restaurants and coffee shops. Brewster is a special place. I can understand why the owner chose it. Our family was immensely blessed to have the...
United States
PAULA
The price is AED 882
AED 2,573 total
includes taxes & fees
14 Oct - 15 Oct
The Brewster Pearl
Outdoor dining

12. 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, 203, (203 reviews)
"Great location and great host!! We’ll be back!!!"
United States
Patrick T.
The price is AED 422
AED 1,270 total
includes taxes & fees
12 Oct - 13 Oct
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Smart TV, books

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

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
West Brewster
10.0 out of 10, 32, (32 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is AED 996
AED 3,225 total
includes taxes & fees
16 Sep - 17 Sep
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Outdoor dining

14. Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
Dennis Port
4.0 out of 10, 1, (1 review)
"Excellent vacation in a great spot but the property needs some care."
United States
Art E.
The price is AED 312
AED 1,676 total
includes taxes & fees
16 Sep - 17 Sep
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
TV, DVD player, offices

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

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.2 out of 10, 27, (27 reviews)
"Loved this property. "
United States
Carol S.
The price is AED 250
AED 1,577 total
includes taxes & fees
5 Oct - 6 Oct
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Beach nearby

16. Seaside Getaway - Harwichport Beachhouse

Seaside Getaway - Harwichport Beachhouse
Harwich
9.2 out of 10, 15, (15 reviews)
"Great stay! Clean and comfortable and close to town."
United States
Meredith R.
The price is AED 922
AED 1,913 total
includes taxes & fees
21 Sep - 22 Sep
Seaside Getaway - Harwichport Beachhouse
Smart TV

17. 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, 4, (4 reviews)
"Our family enjoyed the downstairs activities, especially nice for the kids to play and adults upstairs. All the bedrooms/baths clean and very nice. Loved our stay. "
United States
Donna R.
The price is AED 708
AED 2,441 total
includes taxes & fees
5 Oct - 6 Oct
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
Exterior

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

Lovely House 5 Min to Beach with Deck, Grill, Garage
Eastham
10.0 out of 10, 4, (4 reviews)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is AED 584
AED 1,843 total
includes taxes & fees
30 Sep - 1 Oct
Lovely House 5 Min to Beach with Deck, Grill, Garage
Beach nearby, sun loungers, beach towels

19. Walk to Beach, Pet-Friendly, Ping Pong & Fire Pit

Walk to Beach, Pet-Friendly, Ping Pong & Fire Pit
Dennis
10.0 out of 10, 15, (15 reviews)
"We had a great stay! Beds were super comfy! House was great. So close to the beach and my dogs had a great time!"
United States
Lynne
The price is AED 833
AED 2,484 total
includes taxes & fees
17 Sep - 18 Sep
Walk to Beach, Pet-Friendly, Ping Pong & Fire Pit
Smart TV, fireplace

20. The Pet-Friendly Surf Shack Hideaway on the Cove

The Pet-Friendly Surf Shack Hideaway on the Cove
Eastham
10.0 out of 10, 27, (27 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 640
AED 1,892 total
includes taxes & fees
5 Oct - 6 Oct
The Pet-Friendly Surf Shack Hideaway on the Cove
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

Hyannis Harbor Hotel

Hyannis Harbor Hotel

10/10 Excellent
"X"
stephanie 1-night trip
Posted 1 hour ago
Hyannis Harbor Hotel