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

Holiday Homes in Chatham

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chatham holiday homes

A room with a blue sofa, wicker chairs, a round table, a wall-mounted lamp, and a glass door leading outside.

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, (107 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 €421
includes taxes & fees
18 Oct - 19 Oct
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
A lighthouse with a cylindrical tower and a white building with a red roof.

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 €498
includes taxes & fees
2 Nov - 3 Nov
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
A sandy beach with a grassy path leading to the water.

3. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (93 reviews)
"Beautiful, clean home with very responsive and kind hosts!"
United States
Claire D.
The price is €547
includes taxes & fees
1 Nov - 2 Nov
Beautiful home near Jacknife Beach and bike trail
A two-story house with a covered porch and a stone staircase leading to the entrance.

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.
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
A resort with a large pool, sun loungers, and a pier extending into the water.

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 €439
includes taxes & fees
27 Oct - 28 Oct
Cozy Large Home in Harwich with Patio near Wequassett Resort
An outdoor patio with Adirondack chairs, a fire pit, and string lights.

6. 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, (11 reviews)
"Excellent location "
United States
Norman Y.
The price is €565
includes taxes & fees
19 Oct - 20 Oct
Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard
A beach with footprints, a large rock, and a clear sky.

7. 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 €608
includes taxes & fees
1 Nov - 2 Nov
The Brewster Pearl
A spacious living room with a large sliding glass door leading to an outdoor patio, a ceiling fan, and a white sofa with patterned cushions.

8. 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, (37 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is €663
includes taxes & fees
19 Oct - 20 Oct
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
A two-story house with a front porch, a chimney, and a well-maintained lawn.

9. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (83 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 €724
includes taxes & fees
27 Oct - 28 Oct
Family Cottage Close to Beach!!
A wooden deck with outdoor furniture, a covered seating area, and a view of neighboring houses.

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 €399
includes taxes & fees
19 Oct - 20 Oct
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
A living room with a grey sofa, striped rug, and a lamp.

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, (30 reviews)
"We had such a wonderful time at the Surf Shack. The location was perfect. Within 15 minutes the best beaches, best dining, best shopping..everything. The house was incredibly clean with all the amenities needed to have a great family vacation. The host was incredibly quick to reply to any and all inquiries and was so pleasant to deal with. We couldn’t be any happier with our stay and will definitely stay there again if our travels return us to the Cape."
United States
Justin R.
The price is €460
includes taxes & fees
26 Oct - 27 Oct
The Pet-Friendly Surf Shack Hideaway on the Cove
A bedroom with a bed, a desk, a chair, a TV, and a window.

12. 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, (7 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 €466
includes taxes & fees
18 Oct - 19 Oct
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
A beach with a wooden walkway leading to the shore, a rocky breakwater, and a clear sky at sunset.

13. Seaside Getaway - Harwichport Beachhouse

Seaside Getaway - Harwichport Beachhouse
Harwich
9.0 out of 10, Wonderful, (18 reviews)
"Great stay! Clean and comfortable and close to town."
United States
Meredith R.
The price is €457
includes taxes & fees
27 Oct - 28 Oct
Seaside Getaway - Harwichport Beachhouse
A modern two-story building with large windows and a flat roof.

14. Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!

Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!
Dennis Port
9.8 out of 10, Exceptional, (17 reviews)
"The property was great and hope to be back in the future."
United States
Jason H.
The price is €587
includes taxes & fees
19 Oct - 20 Oct
Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!
A row of white buildings with storefronts, including a visible sign for 'Chatham' and a 'Chatham' sign above a window.

15. 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 €419
includes taxes & fees
19 Oct - 20 Oct
Lovely House 5 Min to Beach with Deck, Grill, Garage
A sandy beach path leading to the ocean with a clear sky.

16. 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 €578
includes taxes & fees
19 Oct - 20 Oct
Beach Walks, Books & Bay Sunsets
A room with a wooden piano, a round mirror, a white door leading to a balcony with a view of greenery, and a hanging light fixture.

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

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
Dennis
The price is €461
includes taxes & fees
2 Nov - 3 Nov
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
A spacious living area with wooden floors, a large dining table, and multiple windows offering a view of the beach.

18. 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 €548
includes taxes & fees
5 Nov - 6 Nov
10 min walk to Beach - Home with Amazing View & Huge Deck
Living room with plenty of seating and beautiful coastal design

19. 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 €575
includes taxes & fees
18 Oct - 19 Oct
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
A living room with a brick fireplace, a blue sectional sofa, a white coffee table, and a large window with blinds.

20. Coastal Haven in West Dennis

Coastal Haven in West Dennis
Dennis
10.0 out of 10, Exceptional, (5 reviews)
"This was a great place to stay and relax, just a short walk to the beach and quick drive to great restaurants and activities. Highly recommend!!"
United States
Melissa J.
The price is €490
includes taxes & fees
19 Oct - 20 Oct
Coastal Haven in West Dennis
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

Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

8/10 Good
"Sus desayunos muy buenos"
Maria 3-night trip
Posted 1 hour ago
Holiday Inn Express Hyannis Cape Cod by IHG

Find out more about Chatham

Chatham Holiday Homes information

Number of reviews
585
Accommodation
2524 Holiday Homes
Lowest Price
€399
Highest Price
€724