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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 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, 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 AED 349
AED 1,865 total
includes taxes & fees
5 Oct - 6 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, Exceptional, (128 reviews)
"Amazing stay so close to town and CBI."
United States
Joanne B.
The price is AED 918
AED 2,143 total
includes taxes & fees
29 Sep - 30 Sep
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, (89 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 2,241 total
includes taxes & fees
28 Sep - 29 Sep
Beautiful home near Jacknife Beach and bike trail
Coffee/tea maker, fridge, microwave, oven

4. Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK

Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK
Chatham
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed the kitchen - cooked every meal all week. Great amount of space for a family gathering for spring break. "
United States
Kathy T.
Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK
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 6,826
AED 8,695 total
includes taxes & fees
8 Oct - 9 Oct
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
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, Exceptional, (14 reviews)
"Great host. Convenient location for a visit to Chatham."
United States
Bill F.
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
Exterior

7. 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.
New! Chatham Cottage- 1 Mile to Downtown & Beaches
Exterior

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 AED 1,157
AED 3,002 total
includes taxes & fees
27 Sep - 28 Sep
Family Cottage Close to Beach!!
Outdoor dining

9. 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 AED 845
AED 2,522 total
includes taxes & fees
27 Sep - 28 Sep
Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
Smart TV, books

10. 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, (34 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is AED 801
AED 2,968 total
includes taxes & fees
28 Sep - 29 Sep
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Outdoor dining

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, (204 reviews)
"Great location and great host!! We’ll be back!!!"
United States
Patrick T.
The price is AED 349
AED 1,169 total
includes taxes & fees
14 Oct - 15 Oct
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
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 845
AED 2,522 total
includes taxes & fees
22 Oct - 23 Oct
The Brewster Pearl
4 bedrooms, iron/ironing board, WiFi, bed sheets

13. 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 1,322
AED 1,934 total
includes taxes & fees
4 Oct - 5 Oct
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
TV, DVD player, offices

14. 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 AED 250
AED 1,586 total
includes taxes & fees
1 Oct - 2 Oct
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Outdoor dining

15. 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 AED 312
AED 1,676 total
includes taxes & fees
26 Sep - 27 Sep
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
Smart TV, fireplace

16. 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 AED 567
AED 1,860 total
includes taxes & fees
5 Oct - 6 Oct
The Pet-Friendly Surf Shack Hideaway on the Cove
A heated pool

17. Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen

Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We had an awesome week! The entire family loved your beautiful house and couldn’t stop talking about that view! One of our BEST family vacations. Thanks for making it so special!!"
United States
julie g.
Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen
Smart TV

18. 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 AED 708
AED 2,433 total
includes taxes & fees
28 Sep - 29 Sep
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
Beach nearby

19. 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 AED 714
AED 2,121 total
includes taxes & fees
30 Sep - 1 Oct
Beach Walks, Books & Bay Sunsets
Smart TV

20. 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 AED 496
AED 1,959 total
includes taxes & fees
28 Sep - 29 Sep
Lovely 3-bedroom house in Dennis perfect for a relaxing getaway
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

Freebird Motor Lodge by Reverie Boutique Collection

Freebird Motor Lodge by Reverie Boutique Collection

10/10 Excellent
"This has been our go to on Cape Cod for many, many years. Rooms are clean and well maintained, a/c is great, and doesn’t turn on and off like some places. The sink and mirror is outside the bathroom, so one person can get ready, while another showers. Each room has a mini fridge for food and drinks. Pool and hot tub are wonderful after a long day in the sun. Yummy drinks and flatbreads available at the bar truck. Located in a convenient spot, close to restaurants, shops, and mini golf. Beaches are a short drive away."
Becky 6-night trip
Posted 5 hours ago
Freebird Motor Lodge by Reverie Boutique Collection