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Our top choices for Chatham holiday homes

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, Exceptional, (106 reviews)
"Excellent location and stay at the lucky 7 cottage. The communication with the host was outstanding, best I’ve experienced. We’ll definitely be back for another time at this location."
United States
Mark K.
The price is £394
includes taxes & fees
12 Oct - 13 Oct
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

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, (128 reviews)
"Amazing stay so close to town and CBI."
United States
Joanne B.
The price is £432
includes taxes & fees
4 Oct - 5 Oct
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

3. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (90 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 £462
includes taxes & fees
29 Sept - 30 Sept
Beautiful home near Jacknife Beach and bike trail

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, Exceptional, (23 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 £1,189
includes taxes & fees
25 Oct - 26 Oct
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

5. 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)
"Great host. Convenient location for a visit to Chatham."
United States
Bill F.
The price is £343
includes taxes & fees
29 Sept - 30 Sept
Cozy Large Home in Harwich with Patio near Wequassett Resort

6. Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
Harwich
10.0 out of 10, Exceptional, (10 reviews)
"Excellent location "
United States
Norman Y.
The price is £519
includes taxes & fees
29 Sept - 30 Sept
Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

7. 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, (35 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is £668
includes taxes & fees
2 Oct - 3 Oct
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

8. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (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 £610
includes taxes & fees
29 Sept - 30 Sept
Family Cottage Close to Beach!!

9. 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 review)
"Excellent vacation in a great spot but the property needs some care."
United States
Art E.
The price is £355
includes taxes & fees
1 Oct - 2 Oct
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

10. 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 £500
includes taxes & fees
27 Oct - 28 Oct
The Brewster Pearl

11. 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, (205 reviews)
"Great location and great host!! We’ll be back!!!"
United States
Patrick T.
The price is £246
includes taxes & fees
14 Oct - 15 Oct
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

12. 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, Wonderful, (27 reviews)
"Property is convenient to beaches and restaurants."
United States
Laurie and Rick A.
The price is £329
includes taxes & fees
5 Oct - 6 Oct
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

13. Cape Cod Cottage Near Beaches & Bike Trail

Cape Cod Cottage Near Beaches & Bike Trail
Harwich
9.4 out of 10, Exceptional, (3 reviews)
"We absolutely LOVED this home. We have stayed in condo style prior each year, and we loved the space, inside and outside, of this quintessential Cape Cod home and neighborhood. It has been updated with appliances and home decor which made it comfortable for all. It is a pet friendly home, as we had a dog with us- and we didn’t walk in to anything different than a non pet friendly home. I will request to rent this home again and again and recommend it highly. The owners were very communicative...
United States
Holly c.
The price is £832
includes taxes & fees
29 Sept - 30 Sept
Cape Cod Cottage Near Beaches & Bike Trail

14. 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 £397
includes taxes & fees
4 Oct - 5 Oct
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays

15. Beach Walks, Books & Bay Sunsets

Beach Walks, Books & Bay Sunsets
Brewster
10.0 out of 10, Exceptional, (1 review)
"The property was very clean, lots of little excellent touches, and amazing views. We truly enjoyed the pathway to the private beach. I wished we could have stayed longer. We will definitely be booking again."
United States
Sandra G.
The price is £437
includes taxes & fees
30 Sept - 1 Oct
Beach Walks, Books & Bay Sunsets

16. 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 £402
includes taxes & fees
29 Sept - 30 Sept
10 min walk to Beach - Home with Amazing View & Huge Deck

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, Exceptional, (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 £497
includes taxes & fees
29 Sept - 30 Sept
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

18. 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, (28 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 £389
includes taxes & fees
5 Oct - 6 Oct
The Pet-Friendly Surf Shack Hideaway on the Cove

19. Lovely 3-bedroom house in Dennis perfect for a relaxing getaway

Lovely 3-bedroom house in Dennis perfect for a relaxing getaway
Dennis
The price is £403
includes taxes & fees
29 Sept - 30 Sept
Lovely 3-bedroom house in Dennis perfect for a relaxing getaway

20. Cape Cod's "Beach Rose"

Cape Cod's "Beach Rose"
Dennis
10.0 out of 10, Exceptional, (32 reviews)
"Beautiful home very easy check in and out host was great will definitely be staying their again in the future"
United States
Rachael M.
The price is £177
includes taxes & fees
5 Oct - 6 Oct
Cape Cod's "Beach Rose"
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

Find out more about Chatham

Chatham Holiday Homes information

Number of reviews
704
Accommodation
2541 Holiday Homes
Lowest Price
£177
Highest Price
£1,189