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Holiday Homes in South Chatham

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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
9.6 out of 10, Exceptional, (108 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 AU$759
includes taxes & fees
1 Dec - 2 Dec
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
An outdoor patio with Adirondack chairs, a fire pit, and string lights.

2. 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 AU$846
includes taxes & fees
1 Nov - 2 Nov
Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard
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, (94 reviews)
"Beautiful, clean home with very responsive and kind hosts!"
United States
Claire D.
The price is AU$848
includes taxes & fees
1 Nov - 2 Nov
Beautiful home near Jacknife Beach and bike trail
A two-story house with a front porch, a chimney, and a well-maintained lawn.

4. 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 AU$1,125
includes taxes & fees
1 Nov - 2 Nov
Family Cottage Close to Beach!!
A lighthouse with a cylindrical tower and a white building with a red roof.

5. 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 AU$766
includes taxes & fees
9 Nov - 10 Nov
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
A bedroom with a bed, a desk, a chair, a TV, and a window.

6. 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 AU$526
includes taxes & fees
1 Nov - 2 Nov
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.

7. 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 AU$643
includes taxes & fees
2 Nov - 3 Nov
Seaside Getaway - Harwichport Beachhouse
A wooden deck with outdoor furniture, a covered seating area, and a view of neighboring houses.

8. 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 AU$683
includes taxes & fees
14 Nov - 15 Nov
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
An outdoor dining area with white chairs and umbrellas, overlooking the ocean.

9. 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, (209 reviews)
"Great location and perfect home for overnight stay!"
United States
Betsy D.
The price is AU$419
includes taxes & fees
7 Nov - 8 Nov
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
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, (38 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is AU$1,081
includes taxes & fees
2 Nov - 3 Nov
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
A beach with footprints, a large rock, and a clear sky.

11. 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 AU$932
includes taxes & fees
1 Nov - 2 Nov
The Brewster Pearl
A house with a well-maintained garden, a white picket fence, and a garage door.

12. Dennisport! Walk to 3 Public Beaches! Charming 4-bedroom 3 bath House with AC

Dennisport! Walk to 3 Public Beaches! Charming 4-bedroom 3 bath House with AC
Dennis
10.0 out of 10, Exceptional, (4 reviews)
"Very lovely home. Comfortable plenty of room for my family and very clean. The location was fantastic. Host was great to deal with."
United States
Christine H.
The price is AU$807
includes taxes & fees
3 Nov - 4 Nov
Dennisport! Walk to 3 Public Beaches! Charming 4-bedroom 3 bath House with AC
A living room with a brick fireplace, a blue sectional sofa, a white coffee table, and a large window with blinds.

13. 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.
Coastal Haven in West Dennis
A modern kitchen with white cabinets, a wooden ceiling, and a herringbone-patterned floor.

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

Beach Bungalow: Steps to Beach, Luxury Family Fun
Harwich
10.0 out of 10, Exceptional, (10 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 AU$851
includes taxes & fees
10 Nov - 11 Nov
Beach Bungalow: Steps to Beach, Luxury Family Fun
A sandy beach path leading to the ocean with a clear sky.

15. 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 AU$763
includes taxes & fees
1 Dec - 2 Dec
Beach Walks, Books & Bay Sunsets
A two-story house with a covered porch and a stone staircase leading to the entrance.

16. 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, (24 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 AU$2,038
includes taxes & fees
4 Nov - 5 Nov
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
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
10.0 out of 10, Exceptional, (1 review)
"Great location. Spacious house."
United States
Diana S.
The price is AU$675
includes taxes & fees
2 Nov - 3 Nov
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
A spacious living area with a sofa, chairs, a fireplace, and a kitchen in the background.

18. 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$1,109
includes taxes & fees
5 Nov - 6 Nov
Lovely 3-bedroom house in Dennis perfect for a relaxing getaway
A single-story house with a front porch, a small deck, and a garden area with various plants.

19. Relaxing Cape Cod Cottage Getaway

Relaxing Cape Cod Cottage Getaway
Dennis
10.0 out of 10, Exceptional, (1 review)
"Clean and comfortable- Exactly what we needed for our trip to the Cape; we would definitely recommend!"
United States
Heathyr S.
The price is AU$779
includes taxes & fees
1 Nov - 2 Nov
Relaxing Cape Cod Cottage Getaway
A wooden deck with a fire pit, outdoor seating, and a pool area at dusk.

20. 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, (61 reviews)
"Great place to stay with your family "
United States
Mary H.
Private Heated Pool • 5BR/3BA • Near Beaches and Nickerson Park
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

Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"It was awesome"
David 2-night trip
Posted less than an hour ago
Uncommoner Hotel by Reverie Boutique Collection

Find out more about South Chatham

South Chatham Holiday Homes information

Number of reviews
784
Accommodation
2526 Holiday Homes
Lowest Price
AU$419
Highest Price
AU$2,038