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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Chatham vacation 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
9.8 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 1,852 total
includes taxes & fees
13 Oct - 14 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 AED 826
AED 2,035 total
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, (91 reviews)
"Beautiful, clean home with very responsive and kind hosts!"
United States
Claire D.
The price is AED 992
AED 2,257 total
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.
The price is AED 3,649
AED 4,774 total
includes taxes & fees
2 Nov - 3 Nov
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 AED 463
AED 1,761 total
includes taxes & fees
7 Oct - 8 Oct
Cozy Large Home in Harwich with Patio near Wequassett Resort
An outdoor patio with Adirondack chairs, a fire pit, and string lights.

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, (11 reviews)
"Excellent location "
United States
Norman Y.
The price is AED 771
AED 2,451 total
includes taxes & fees
6 Oct - 7 Oct
Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
A wooden-paneled room with a sofa, chairs, a table, a fireplace, and a clock.

7. 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 1,577 total
includes taxes & fees
7 Oct - 8 Oct
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
An outdoor dining area with white chairs and umbrellas, overlooking the ocean.

8. 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 AED 314
AED 1,124 total
includes taxes & fees
14 Oct - 15 Oct
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
A beach with footprints, a large rock, and a clear sky.

9. 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 918
AED 2,627 total
includes taxes & fees
2 Nov - 3 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.

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, (37 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is AED 618
AED 2,730 total
includes taxes & fees
6 Oct - 7 Oct
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
A wooden deck with outdoor furniture, a covered seating area, and a view of neighboring houses.

11. 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 1,689 total
includes taxes & fees
6 Oct - 7 Oct
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
A cozy living room with a sectional sofa, a fireplace, and wooden walls.

12. Family-Friendly Home! Walk to Sea Street Beach

Family-Friendly Home! Walk to Sea Street Beach
Dennis Port
6.4 out of 10, (5 reviews)
"Location was great! Cozy house. Easy to get in touch with host. Bathroom could use update. "
United States
Devin L.
The price is AED 224
AED 1,206 total
includes taxes & fees
11 Oct - 12 Oct
Family-Friendly Home! Walk to Sea Street Beach
A living room with a grey sofa, striped rug, and a lamp.

13. 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, (29 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 AED 603
AED 1,893 total
includes taxes & fees
3 Nov - 4 Nov
The Pet-Friendly Surf Shack Hideaway on the Cove
A two-story house with a front porch, a chimney, and a well-maintained lawn.

14. 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
6 Oct - 7 Oct
Family Cottage Close to Beach!!
A bedroom with a bed, a desk, a chair, a TV, and a window.

15. 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)
The price is AED 1,322
AED 1,934 total
includes taxes & fees
12 Oct - 13 Oct
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
A row of white buildings with storefronts, including a visible sign for 'Chatham' and a 'Chatham' sign above a window.

16. 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 AED 493
AED 1,729 total
includes taxes & fees
8 Oct - 9 Oct
Lovely House 5 Min to Beach with Deck, Grill, Garage
A beach with a wooden walkway leading to the shore, a rocky breakwater, and a clear sky at sunset.

17. Seaside Getaway - Harwichport Beachhouse

Seaside Getaway - Harwichport Beachhouse
Harwich
9.2 out of 10, Wonderful, (17 reviews)
"Great stay! Clean and comfortable and close to town."
United States
Meredith R.
The price is AED 889
AED 1,871 total
includes taxes & fees
6 Oct - 7 Oct
Seaside Getaway - Harwichport Beachhouse
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
10 min walk to Beach - Home with Amazing View & Huge Deck
A modern two-story building with large windows and a flat roof.

19. 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 AED 610
AED 2,464 total
includes taxes & fees
6 Oct - 7 Oct
Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!
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.

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

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
Dennis
The price is AED 592
AED 1,839 total
includes taxes & fees
6 Oct - 7 Oct
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
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
"Loved my stay here. Outdoor pool was open great hours, considering it was late in the season. Indoor pool and hot tub were clean, also with great hours. Breakfast had a much larger selection than usual continental breakfast menu. Loved the onsite bar, and the outdoor firepit area right on the edge of the saltmarsh. Rooms were clean, with a comfortable bed. Staff were very helpful and kind. I'm looking forward to staying again sometime soon!"
Laura 2-night trip
Posted 12 hours ago
Bayside Resort Hotel