A boat on a calm river, a large house with a red roof, and dense greenery in the background.

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Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

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
9.6 out of 10, Exceptional, (105 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is AED 577
AED 2,190 total
includes taxes & fees
29 Sep - 30 Sep
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, Exceptional, (127 reviews)
"Our stay was wonderful!"
United States
Corinne J.
The price is AED 1,146
AED 2,451 total
includes taxes & fees
4 Oct - 5 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, Exceptional, (86 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 1,435
AED 2,836 total
includes taxes & fees
9 Sep - 10 Sep
Beautiful home near Jacknife Beach and bike trail
Dining

4. Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard

Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard
Chatham
10.0 out of 10, Exceptional, (108 reviews)
"Great stay. House is in a great location and is well maintained. Bonnie was super helpful. "
United States
Will M.
The price is AED 1,735
AED 2,272 total
includes taxes & fees
10 Sep - 11 Sep
Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard
Exterior

5. 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, Exceptional, (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 5,293
AED 6,919 total
includes taxes & fees
4 Oct - 5 Oct
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Outdoor dining

6. 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, (11 reviews)
"The kitchen was well stocked. The Beds were comfortable. "
United States
Stacey P.
The price is AED 382
AED 2,590 total
includes taxes & fees
20 Sep - 21 Sep
Great for Families! Brewster Home 6 Mi to Beach
Pool

7. 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, (14 reviews)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is AED 547
AED 1,867 total
includes taxes & fees
28 Sep - 29 Sep
Cozy Large Home in Harwich with Patio near Wequassett Resort
TV, offices

8. 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 610
AED 2,405 total
includes taxes & fees
8 Sep - 9 Sep
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Terrace/patio

9. New! 4BR Fire Pit, Ping Pong, Movie Room

New! 4BR Fire Pit, Ping Pong, Movie Room
Harwich
10.0 out of 10, Exceptional, (2 reviews)
"Very responsive and friendly host. "
United States
Matt M.
New! 4BR Fire Pit, Ping Pong, Movie Room
Exterior

10. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (81 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
8 Sep - 9 Sep
Family Cottage Close to Beach!!
Exterior

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

New! Chatham Cottage- 1 Mile to Downtown & Beaches
Chatham
9.8 out of 10, Exceptional, (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 2,972 total
includes taxes & fees
3 Oct - 4 Oct
New! Chatham Cottage- 1 Mile to Downtown & Beaches
Sun loungers, beach towels

12. The Brewster Pearl

The Brewster Pearl
Brewster
10.0 out of 10, Exceptional, (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 1,028
AED 2,665 total
includes taxes & fees
30 Sep - 1 Oct
The Brewster Pearl
Outdoor dining

13. 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, (201 reviews)
"Great location and great host!! We’ll be back!!!"
United States
Patrick T.
The price is AED 459
AED 1,324 total
includes taxes & fees
27 Sep - 28 Sep
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Outdoor dining

14. 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, Exceptional, (8 reviews)
"Excellent location "
United States
Norman Y.
The price is AED 1,175
AED 2,980 total
includes taxes & fees
8 Sep - 9 Sep
Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
Property grounds

15. Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!

Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!
Chatham
10.0 out of 10, Exceptional, (33 reviews)
"The location of the house is great. We loved the view of the water we got to enjoy every day. Plus it’s just a short drive from Main Street in South Chatham, the Nantucket ferry on Harwich, and sunsets on Skaket beach or Rock Harbor. We enjoyed the fire pit and boating on the lake too. Perfect spot for a family."
United States
Anonymous traveler
The price is AED 2,498
AED 4,452 total
includes taxes & fees
12 Sep - 13 Sep
Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!
Beach nearby, sun loungers, beach umbrellas, beach towels

16. Beach Chic Chatham 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC

Beach Chic Chatham 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC
Chatham
10.0 out of 10, Exceptional, (88 reviews)
"Very communicative and helpful host. Be prepared to bring your own linens or rent them. Enjoyed our stay"
United States
Amanda B.
The price is AED 2,924
AED 4,927 total
includes taxes & fees
7 Sep - 8 Sep
Beach Chic Chatham 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC
TV, DVD player, offices

17. 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, (26 reviews)
"Loved this property. "
United States
Carol S.
The price is AED 283
AED 1,629 total
includes taxes & fees
1 Oct - 2 Oct
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
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, Exceptional, (3 reviews)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is AED 584
AED 1,834 total
includes taxes & fees
28 Sep - 29 Sep
Lovely House 5 Min to Beach with Deck, Grill, Garage
Smart TV, books

19. 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, Exceptional, (32 reviews)
"This house was a perfect place for us to stay during our trip exploring Cape Cod. It was centrally located to the various places we drove to and the proximity to the Cape Cod Rail Trail was great. The house is spacious and beautiful! It was clean and on a quiet street."
United States
Reba W.
The price is AED 1,098
AED 3,359 total
includes taxes & fees
28 Sep - 29 Sep
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
4 bedrooms, iron/ironing board, WiFi, bed sheets

20. Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays

Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
Harwich
9.8 out of 10, Exceptional, (6 reviews)
The price is AED 1,837
AED 2,615 total
includes taxes & fees
20 Sep - 21 Sep
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
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

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

10/10 Excellent
"breakfast was delicious .. however there was a very special young lady that was cleaning the tables and wiping them down... She went over and beyond to help but she and another one were waiting tables too .. terribly under staffed that morning. Other than that observation, the stay was wonderful. Thanks"
Juan 1-night trip
Posted less than an hour ago
Margaritaville Resort Cape Cod