A sign for the Town of Chatham Visitor Information Center with a directional arrow.

Search Vacation Homes in South Chatham

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 South 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
9.6 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 AED 408
AED 1,778 total
includes taxes & fees
19 Oct - 20 Oct
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 AED 621
AED 2,241 total
includes taxes & fees
19 Oct - 20 Oct
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, (93 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 resort with a large pool, sun loungers, and a pier extending into the water.

4. 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 514
AED 1,827 total
includes taxes & fees
27 Oct - 28 Oct
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.

5. 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 AED 1,157
AED 3,002 total
includes taxes & fees
19 Oct - 20 Oct
Family Cottage Close to Beach!!
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 AED 826
AED 2,026 total
includes taxes & fees
2 Nov - 3 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.

7. 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 AED 1,322
AED 1,934 total
includes taxes & fees
21 Oct - 22 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.

8. 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 AED 757
AED 1,699 total
includes taxes & fees
19 Oct - 20 Oct
Seaside Getaway - Harwichport Beachhouse
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.

9. 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 price is AED 661
AED 1,927 total
includes taxes & fees
19 Oct - 20 Oct
The Genoa | Your Perfect Dennis Port Beach Escape
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 593
AED 2,697 total
includes taxes & fees
20 Oct - 21 Oct
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 AED 790
AED 2,476 total
includes taxes & fees
22 Oct - 23 Oct
The Brewster Pearl
A wooden deck with outdoor furniture, a covered seating area, and a view of neighboring houses.

12. 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 368
AED 1,605 total
includes taxes & fees
19 Oct - 20 Oct
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
A modern kitchen with white cabinets, a wooden ceiling, and a herringbone-patterned floor.

13. 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 AED 881
AED 2,345 total
includes taxes & fees
2 Nov - 3 Nov
Beach Bungalow: Steps to Beach, Luxury Family Fun
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.

14. 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 584
AED 1,830 total
includes taxes & fees
2 Nov - 3 Nov
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
A modern two-story building with large windows and a flat roof.

15. 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 2,481 total
includes taxes & fees
19 Oct - 20 Oct
Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!
A house with a well-maintained garden, a white picket fence, and a garage door.

16. 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 AED 826
AED 2,136 total
includes taxes & fees
25 Oct - 26 Oct
Dennisport! Walk to 3 Public Beaches! Charming 4-bedroom 3 bath House with AC
A two-story house with a covered porch and a stone staircase leading to the entrance.

17. 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 4,803
AED 6,279 total
includes taxes & fees
22 Oct - 23 Oct
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
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 AED 992
AED 2,619 total
includes taxes & fees
19 Oct - 20 Oct
Lovely 3-bedroom house in Dennis perfect for a relaxing getaway
A sandy beach path leading to the ocean with a clear sky.

19. 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 AED 889
AED 2,350 total
includes taxes & fees
19 Oct - 20 Oct
Beach Walks, Books & Bay Sunsets
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 AED 686
AED 1,996 total
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Chatham Hotel Reviews

Hyannis Plaza Hotel

Hyannis Plaza Hotel

10/10 Excellent
"Relaxing"
Karen 1-night trip
Posted 12 hours ago
Hyannis Plaza Hotel