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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 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, 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 £394
includes taxes & fees
12 Oct - 13 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, Exceptional, (14 reviews)
"Great host. Convenient location for a visit to Chatham."
United States
Bill F.
The price is £343
includes taxes & fees
29 Sept - 30 Sept
Cozy Large Home in Harwich with Patio near Wequassett Resort
An outdoor patio with Adirondack chairs, a fire pit, and string lights.

3. 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, (10 reviews)
"Excellent location "
United States
Norman Y.
The price is £519
includes taxes & fees
29 Sept - 30 Sept
Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
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, (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 £610
includes taxes & fees
29 Sept - 30 Sept
Family Cottage Close to Beach!!
A sandy beach with a grassy path leading to the water.

5. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (90 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 £462
includes taxes & fees
29 Sept - 30 Sept
Beautiful home near Jacknife Beach and bike trail
A lighthouse with a cylindrical tower and a white building with a red roof.

6. 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 £432
includes taxes & fees
4 Oct - 5 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.

7. 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, (35 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is £668
includes taxes & fees
1 Oct - 2 Oct
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
A bedroom with a bed, a desk, a chair, a TV, and a window.

8. 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, (6 reviews)
The price is £397
includes taxes & fees
4 Oct - 5 Oct
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
A kitchen with white cabinetry, a granite countertop, an outdoor patio with a table and chairs, and a view of a house with a tree.

9. Cape Cod Cottage Near Beaches & Bike Trail

Cape Cod Cottage Near Beaches & Bike Trail
Harwich
9.4 out of 10, Exceptional, (3 reviews)
"We absolutely LOVED this home. We have stayed in condo style prior each year, and we loved the space, inside and outside, of this quintessential Cape Cod home and neighborhood. It has been updated with appliances and home decor which made it comfortable for all. It is a pet friendly home, as we had a dog with us- and we didn’t walk in to anything different than a non pet friendly home. I will request to rent this home again and again and recommend it highly. The owners were very communicative...
United States
Holly c.
The price is £832
includes taxes & fees
29 Sept - 30 Sept
Cape Cod Cottage Near Beaches & Bike Trail
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 £355
includes taxes & fees
1 Oct - 2 Oct
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
A beach with a wooden walkway leading to the shore, a rocky breakwater, and a clear sky at sunset.

11. 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 £421
includes taxes & fees
6 Oct - 7 Oct
Seaside Getaway - Harwichport Beachhouse
A wooden-paneled room with a sofa, chairs, a table, a fireplace, and a clock.

12. 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 £334
includes taxes & fees
5 Oct - 6 Oct
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
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, Exceptional, (205 reviews)
"Great location and great host!! We’ll be back!!!"
United States
Patrick T.
The price is £246
includes taxes & fees
14 Oct - 15 Oct
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
A modern outdoor pool area with a hot tub, lounge chairs, and a deck overlooking a residential property.

14. Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen

Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We had an awesome week! The entire family loved your beautiful house and couldn’t stop talking about that view! One of our BEST family vacations. Thanks for making it so special!!"
United States
julie g.
The price is £1,212
includes taxes & fees
5 Oct - 6 Oct
Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen
A modern kitchen with wooden cabinets, a central island, and orange bar stools.

15. 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, Exceptional, (13 reviews)
"Wonderful place! Thank you so much! "
United States
Jess W.
The price is £468
includes taxes & fees
29 Sept - 30 Sept
NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH
A beach with footprints, a large rock, and a clear sky.

16. 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 £500
includes taxes & fees
27 Oct - 28 Oct
The Brewster Pearl
A spacious living area with a sofa, chairs, a fireplace, and a kitchen in the background.

17. 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 £403
includes taxes & fees
29 Sept - 30 Sept
Lovely 3-bedroom house in Dennis perfect for a relaxing getaway
A wicker chair, a wicker table with a glass of water, a bottle of lemonade, a plate with watermelon slices, and a basket of bread rolls.

18. The Genoa | Your Perfect Dennis Port Beach Escape

The Genoa | Your Perfect Dennis Port Beach Escape
Dennis Port
10.0 out of 10, Exceptional, (5 reviews)
The Genoa | Your Perfect Dennis Port Beach Escape
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 £507
includes taxes & fees
29 Sept - 30 Sept
Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!
A sandy beach path leading to the ocean with a clear sky.

20. Beach Walks, Books & Bay Sunsets

Beach Walks, Books & Bay Sunsets
Brewster
10.0 out of 10, Exceptional, (1 review)
"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 £437
includes taxes & fees
30 Sept - 1 Oct
Beach Walks, Books & Bay Sunsets
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

Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

8/10 Good
"The king suite was a nice size and the bed was very comfortable. All of the suites are on the second floor with no elevator. The bathroom could use some updating. The plumbing worked but the toilet is low and the sink is quite small."
Heidi 1-night trip
Posted 6 hours ago
Holiday Hill Inn & Suites

Find out more about South Chatham

South Chatham Holiday Homes information

Number of reviews
676
Accommodation
2586 Holiday Homes
Lowest Price
£246
Highest Price
£1,212