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

Chatham Vacation Rentals

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Our top choices for Chatham vacation 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
9.6 out of 10, Exceptional, (109 reviews)
"Clean, well-appointed, quaint, pet-friendly home centrally located in a great area for driving to Harding's Beach and downtown Chatham."
United States
Jennifer B.
The price is CA $180
CA $740 total
includes taxes & fees
Dec 14 - Dec 15
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)
"Our stay was wonderful!"
United States
Corinne J.
The price is CA $321
CA $791 total
includes taxes & fees
Nov 16 - Nov 17
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, (94 reviews)
"Beautiful, clean home with very responsive and kind hosts!"
United States
Claire D.
The price is CA $385
CA $833 total
includes taxes & fees
Nov 16 - Nov 17
Beautiful home near Jacknife Beach and bike trail

4. Private Heated Pool • 5BR/3BA • Near Beaches and Nickerson Park

Private Heated Pool • 5BR/3BA • Near Beaches and Nickerson Park
Brewster
9.8 out of 10, Exceptional, (62 reviews)
"Very nice property in a good location for our family and our interests. The pool was great to relax in during the afternoons after active mornings out."
United States
Jack N.
The price is CA $107
CA $980 total
includes taxes & fees
Nov 25 - Nov 26
Private Heated Pool • 5BR/3BA • Near Beaches and Nickerson Park

5. Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard

Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard
Harwich
10.0 out of 10, Exceptional, (12 reviews)
"Excellent location "
United States
Norman Y.
The price is CA $242
CA $833 total
includes taxes & fees
Nov 16 - Nov 17
Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard

6. The Brewster Pearl

The Brewster Pearl
Brewster
10.0 out of 10, Exceptional, (3 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 CA $285
CA $846 total
includes taxes & fees
Nov 30 - Dec 1
The Brewster Pearl

7. 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, (8 reviews)
"We loved staying at this beautiful house in Harwich. The property was clean, cozy and felt just like home. There was a fenced in back yard which was perfect for our dog and kids. Very private and close to shops, restaurants and the beach. We look forward to visiting again in the future!"
United States
Nicole M.
The price is CA $353
CA $518 total
includes taxes & fees
Nov 19 - Nov 20
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays

8. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (83 reviews)
"Great place and location"
United States
Jennifer S.
The price is CA $449
CA $1,107 total
includes taxes & fees
Nov 14 - Nov 15
Family Cottage Close to Beach!!

9. 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, (38 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is CA $255
CA $979 total
includes taxes & fees
Nov 15 - Nov 16
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

10. 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 CA $154
CA $657 total
includes taxes & fees
Nov 14 - Nov 15
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

11. 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, (31 reviews)
"It was a beautiful house and well stocked with all your needs. Also located in a great area."
United States
Nancy S.
The price is CA $225
CA $664 total
includes taxes & fees
Nov 16 - Nov 17
The Pet-Friendly Surf Shack Hideaway on the Cove

12. Seaside Getaway - Harwichport Beachhouse

Seaside Getaway - Harwichport Beachhouse
Harwich
9.2 out of 10, Wonderful, (19 reviews)
"Great stay! Clean and comfortable and close to town."
United States
Meredith R.
The price is CA $294
CA $631 total
includes taxes & fees
Nov 14 - Nov 15
Seaside Getaway - Harwichport Beachhouse

13. Beach Walks, Books & Bay Sunsets

Beach Walks, Books & Bay Sunsets
Brewster
10.0 out of 10, Exceptional, (3 reviews)
"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 CA $275
CA $785 total
includes taxes & fees
Nov 19 - Nov 20
Beach Walks, Books & Bay Sunsets

14. 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, (4 reviews)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is CA $204
CA $656 total
includes taxes & fees
Nov 15 - Nov 16
Lovely House 5 Min to Beach with Deck, Grill, Garage

15. 10 min walk to Beach - Home with Amazing View & Huge Deck

10 min walk to Beach - Home with Amazing View & Huge Deck
Eastham
10.0 out of 10, Exceptional, (1 review)
"My husband and I, plus daughter, son-in-law, and new baby, had a lovely stay at this property. It’s a beautiful, peaceful location, convenient to beaches, shops, and restaurants. We ate in a couple nights; the kitchen has everything you need to make a nice meal. The house is spacious and tastefully decorated. We will keep happy memories of staying here."
United States
Sabrina H.
The price is CA $255
CA $760 total
includes taxes & fees
Dec 2 - Dec 3
10 min walk to Beach - Home with Amazing View & Huge Deck

16. 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 CA $282
CA $866 total
includes taxes & fees
Nov 16 - Nov 17
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

17. Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge

Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
Orleans
9.8 out of 10, Exceptional, (18 reviews)
"Great house, so much room! We enjoyed our stay!!"
United States
Gina M.
The price is CA $2,565
CA $4,249 total
includes taxes & fees
Nov 16 - Nov 17
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge

18. Mazi's-A Waterfront/2 Bd/Dog Friendly Oasis for 4

Mazi's-A Waterfront/2 Bd/Dog Friendly Oasis for 4
Eastham
10.0 out of 10, Exceptional, (5 reviews)
"Just perfect all around!"
United States
Alexis N.
The price is CA $324
CA $677 total
includes taxes & fees
Nov 19 - Nov 20
Mazi's-A Waterfront/2 Bd/Dog Friendly Oasis for 4

19. Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
Dennis
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Spacious house."
United States
Diana S.
The price is CA $214
CA $669 total
includes taxes & fees
Nov 15 - Nov 16
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

20. Beach Bungalow: Steps to Beach, Luxury Family Fun

Beach Bungalow: Steps to Beach, Luxury Family Fun
Harwich
10.0 out of 10, Exceptional, (11 reviews)
"We had an excellent stay on the cape at this beautiful home that was walking distance to the beach. The location was perfect and neighborhood was exactly what we dreamed of for an offseason getaway."
United States
Christopher R.
The price is CA $315
CA $857 total
includes taxes & fees
Nov 22 - Nov 23
Beach Bungalow: Steps to Beach, Luxury Family Fun
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 Vacation Homes information

Number of reviews
633
Accommodation
2435 Vacation Homes
Lowest Price
CA $518
Highest Price
CA $4,249

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