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Holiday Homes in South Chatham

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for South 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
9.8 out of 10, 106, (106 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is AU$695
includes taxes & fees
7 Oct - 8 Oct
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
A resort with a large pool, sun loungers, and a pier extending into the water.

2. 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, 14, (14 reviews)
"Great host. Convenient location for a visit to Chatham."
United States
Bill F.
The price is AU$682
includes taxes & fees
16 Sept - 17 Sept
Cozy Large Home in Harwich with Patio near Wequassett Resort
A two-story house with a front porch, a chimney, and a well-maintained lawn.

3. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, 82, (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 AU$1,111
includes taxes & fees
16 Sept - 17 Sept
Family Cottage Close to Beach!!
An outdoor patio with Adirondack chairs, a fire pit, and string lights.

4. Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
Harwich
10.0 out of 10, 9, (9 reviews)
"Excellent location "
United States
Norman Y.
The price is AU$960
includes taxes & fees
16 Sept - 17 Sept
Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
A covered deck with a grill, outdoor furniture, and a view of trees.

5. Great for Families! Brewster Home 6 Mi to Beach

Great for Families! Brewster Home 6 Mi to Beach
Brewster
9.6 out of 10, 12, (12 reviews)
"The kitchen was well stocked. The Beds were comfortable. "
United States
Stacey P.
The price is AU$985
includes taxes & fees
20 Sept - 21 Sept
Great for Families! Brewster Home 6 Mi to Beach
A sandy beach with a grassy path leading to the water.

6. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, 87, (87 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 AU$848
includes taxes & fees
5 Oct - 6 Oct
Beautiful home near Jacknife Beach and bike trail
A living room with a fireplace, sofas, a TV, and a bookshelf.

7. Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, 52, (52 reviews)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is AU$928
includes taxes & fees
22 Sept - 23 Sept
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
A beach with a wooden walkway leading to the shore, a rocky breakwater, and a clear sky at sunset.

8. Seaside Getaway - Harwichport Beachhouse

Seaside Getaway - Harwichport Beachhouse
Harwich
9.2 out of 10, 15, (15 reviews)
"Great stay! Clean and comfortable and close to town."
United States
Meredith R.
The price is AU$732
includes taxes & fees
21 Sept - 22 Sept
Seaside Getaway - Harwichport Beachhouse
A lighthouse with a cylindrical tower and a white building with a red roof.

9. 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, 127, (127 reviews)
"Amazing stay so close to town and CBI."
United States
Joanne B.
The price is AU$887
includes taxes & fees
7 Oct - 8 Oct
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
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, 32, (32 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is AU$1,200
includes taxes & fees
16 Sept - 17 Sept
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, (1 review)
"Excellent vacation in a great spot but the property needs some care."
United States
Art E.
The price is AU$627
includes taxes & fees
16 Sept - 17 Sept
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
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, 6, (6 reviews)
The price is AU$802
includes taxes & fees
4 Oct - 5 Oct
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
An outdoor dining area with white chairs and umbrellas, overlooking the ocean.

13. 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, 203, (203 reviews)
"Great location and great host!! We’ll be back!!!"
United States
Patrick T.
The price is AU$479
includes taxes & fees
12 Oct - 13 Oct
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
A wooden-paneled room with a sofa, chairs, a table, a fireplace, and a clock.

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, 27, (27 reviews)
"Loved this property. "
United States
Carol S.
The price is AU$591
includes taxes & fees
5 Oct - 6 Oct
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
A spacious living room with a sofa, a patterned armchair, a wooden chest, and a lamp.

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

New! Chatham Cottage- 1 Mile to Downtown & Beaches
Chatham
9.8 out of 10, 11, (11 reviews)
"Close to tpwn beach very clean great for us and pups sweet lplace"
United States
Deanna M.
The price is AU$1,102
includes taxes & fees
3 Oct - 4 Oct
New! Chatham Cottage- 1 Mile to Downtown & Beaches
A beach with footprints, a large rock, and a clear sky.

16. The Brewster Pearl

The Brewster Pearl
Brewster
10.0 out of 10, 2, (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 AU$958
includes taxes & fees
14 Oct - 15 Oct
The Brewster Pearl
A modern kitchen with wooden cabinets, a central island, and orange bar stools.

17. NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH

NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH
Dennis
9.6 out of 10, 13, (13 reviews)
"Wonderful place! Thank you so much! "
United States
Jess W.
The price is AU$857
includes taxes & fees
28 Sept - 29 Sept
NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH
An aerial view of a coastal hotel with multiple buildings, a beach, and a clear blue sea.

18. Walk to Beach, Pet-Friendly, Ping Pong & Fire Pit

Walk to Beach, Pet-Friendly, Ping Pong & Fire Pit
Dennis
10.0 out of 10, 15, (15 reviews)
"We had a great stay! Beds were super comfy! House was great. So close to the beach and my dogs had a great time!"
United States
Lynne
The price is AU$980
includes taxes & fees
17 Sept - 18 Sept
Walk to Beach, Pet-Friendly, Ping Pong & Fire Pit
A spacious living area with a sofa, chairs, a fireplace, and a kitchen in the background.

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 AU$740
includes taxes & fees
28 Sept - 29 Sept
Lovely 3-bedroom house in Dennis perfect for a relaxing getaway
A house with a wooden deck, a brick chimney, and a porch with wicker furniture.

20. Charming Dennis Port Retreat Near the Beach

Charming Dennis Port Retreat Near the Beach
Dennis Port
7.6 out of 10, 4, (4 reviews)
Charming Dennis Port Retreat Near the Beach
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 South Chatham Hotel Reviews

Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Always a pleasure to stay there. The staff is nice and accommodating, the property is very clean and the parking is great"
Nedenia 1-night trip
Posted 1 hour ago
Cape Sands Inn

Find out more about South Chatham

South Chatham Holiday Homes information

Number of reviews
708
Accommodation
2581 Holiday Homes
Lowest Price
AU$479
Highest Price
AU$1,200