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
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 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, (104 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is AED 1,095
AED 2,975 total
includes taxes & fees
9 Sep - 10 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.
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, (84 reviews)
"This is second time to stay here! We love the location and hospitality of the hosts! Great place!"
United States
Barbara P.
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, (106 reviews)
"Great stay. House is in a great location and is well maintained. Bonnie was super helpful. "
United States
Will M.
Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard
Property grounds

5. Spacious 4BR house in perfect Chatham with AC

Spacious 4BR house in perfect Chatham with AC
Chatham
Spacious 4BR house in perfect Chatham with AC
Exterior

6. 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, (21 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 4,797
AED 6,192 total
includes taxes & fees
21 Sep - 22 Sep
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
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, (13 reviews)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is AED 657
AED 2,018 total
includes taxes & fees
7 Sep - 8 Sep
Cozy Large Home in Harwich with Patio near Wequassett Resort
Terrace/patio

8. 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.
The price is AED 1,357
AED 3,528 total
includes taxes & fees
3 Sep - 4 Sep
New! 4BR Fire Pit, Ping Pong, Movie Room
Exterior

9. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (80 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
6 Sep - 7 Sep
Family Cottage Close to Beach!!
TV, offices

10. 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 786
AED 2,673 total
includes taxes & fees
22 Sep - 23 Sep
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Outdoor dining

11. 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 1,102
AED 2,884 total
includes taxes & fees
8 Sep - 9 Sep
Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
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 Brewster Pearl
TV, DVD player, offices

13. 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 386
AED 1,788 total
includes taxes & fees
16 Sep - 17 Sep
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Beach nearby

14. Beach Walks, Books & Bay Sunsets

Beach Walks, Books & Bay Sunsets
Brewster
Beach Walks, Books & Bay Sunsets
Beach nearby

15. Seaside Getaway - Harwichport Beachhouse

Seaside Getaway - Harwichport Beachhouse
Harwich
9.2 out of 10, Wonderful, (15 reviews)
"Great stay! Clean and comfortable and close to town."
United States
Meredith R.
The price is AED 988
AED 2,014 total
includes taxes & fees
21 Sep - 22 Sep
Seaside Getaway - Harwichport Beachhouse
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)
"Loved our stay. The location is a perfect central point for exploring Cape Cod. Plenty of amenities in the home, bikes, beach supplies. Well equipped home and John was so helpful the entire stay. "
United States
Ed N.
The price is AED 2,924
AED 4,893 total
includes taxes & fees
7 Sep - 8 Sep
Beach Chic Chatham 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC
Smart TV, books

17. 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 1,113
AED 3,376 total
includes taxes & fees
22 Sep - 23 Sep
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
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 621
AED 1,904 total
includes taxes & fees
21 Sep - 22 Sep
Lovely House 5 Min to Beach with Deck, Grill, Garage
Property grounds

19. 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)
"Lots of room for families to gather, easy remote check in."
United States
Michelle S.
The price is AED 2,938
AED 5,028 total
includes taxes & fees
12 Sep - 13 Sep
Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!
Property grounds

20. Secluded, Walk to Rail Trail, Dog-Friendly, Fire Pit

Secluded, Walk to Rail Trail, Dog-Friendly, Fire Pit
Harwich
10.0 out of 10, Exceptional, (11 reviews)
"Very comfortable and clean home in Harwich. We had prompt and excellent communication with the host."
United States
Amber J.
The price is AED 2,678
AED 5,393 total
includes taxes & fees
26 Aug - 27 Aug
Secluded, Walk to Rail Trail, Dog-Friendly, Fire Pit
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

Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"The resort was beautiful, we'll kept and clean. Staff was very friendly and helpful. Had a great stay, would definitely come again."
Amilcar 2-night trip
Posted less than an hour ago
Bayside Resort Hotel