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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
9.8 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 ￥14,958
￥79,934 total
includes taxes & fees
Oct 5 - Oct 6
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 ￥23,460
￥80,041 total
includes taxes & fees
Oct 21 - Oct 22
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, 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 ￥49,597
￥122,899 total
includes taxes & fees
Sep 24 - Sep 25
Family Cottage Close to Beach!!
An outdoor patio with Adirondack chairs, a fire pit, and string lights.

4. 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 ￥34,639
￥106,139 total
includes taxes & fees
Sep 27 - Sep 28
Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
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, (88 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 ￥42,512
￥96,048 total
includes taxes & fees
Sep 28 - Sep 29
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, (127 reviews)
"Amazing stay so close to town and CBI."
United States
Joanne B.
The price is ￥39,339
￥91,875 total
includes taxes & fees
Sep 29 - Sep 30
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, (6 reviews)
The price is ￥56,632
￥82,821 total
includes taxes & fees
Oct 4 - Oct 5
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
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.

8. 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, (33 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is ￥30,380
￥116,584 total
includes taxes & fees
Sep 24 - Sep 25
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.

9. 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 ￥13,383
￥72,391 total
includes taxes & fees
Sep 24 - Sep 25
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
A spacious living room with a sofa, a patterned armchair, a wooden chest, and a lamp.

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

New! Chatham Cottage- 1 Mile to Downtown & Beaches
Chatham
9.8 out of 10, Exceptional, (11 reviews)
"Close to tpwn beach very clean great for us and pups sweet lplace"
United States
Deanna M.
The price is ￥62,177
￥127,745 total
includes taxes & fees
Oct 3 - Oct 4
New! Chatham Cottage- 1 Mile to Downtown & Beaches
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
9.0 out of 10, Wonderful, (16 reviews)
"Great stay! Clean and comfortable and close to town."
United States
Meredith R.
The price is ￥42,370
￥85,796 total
includes taxes & fees
Oct 5 - Oct 6
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)
"Loved this property. "
United States
Carol S.
The price is ￥10,707
￥67,973 total
includes taxes & fees
Oct 1 - Oct 2
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, (204 reviews)
"Great location and great host!! We’ll be back!!!"
United States
Patrick T.
The price is ￥14,958
￥50,098 total
includes taxes & fees
Oct 14 - Oct 15
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 ￥151,939
￥278,987 total
includes taxes & fees
Oct 5 - Oct 6
Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen
A beach with footprints, a large rock, and a clear sky.

15. 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 ￥33,852
￥105,059 total
includes taxes & fees
Oct 22 - Oct 23
The Brewster Pearl
A living room with a brick fireplace, a blue sofa, a coffee table, and a large window with blinds.

16. Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15
2.0 star property
West Dennis
The price is ￥38,316
￥104,313 total
includes taxes & fees
Sep 24 - Sep 25
Coastal Haven in West Dennis -15
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, Exceptional, (13 reviews)
"Wonderful place! Thank you so much! "
United States
Jess W.
The price is ￥35,395
￥96,683 total
includes taxes & fees
Oct 1 - Oct 2
NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH
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 ￥21,237
￥83,360 total
includes taxes & fees
Oct 5 - Oct 6
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, (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 ￥30,482
￥90,751 total
includes taxes & fees
Oct 5 - Oct 6
Beach Walks, Books & Bay Sunsets
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 ￥28,158
￥82,932 total
includes taxes & fees
Oct 19 - Oct 20
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.
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

Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

10/10 Excellent
"I loved my stay; it was only for one night, but I was able to enjoy the pool and the wonderful breakfast the next morning—very varied and nutritious. We will definitely be back."
Silvia 1-night trip
Posted less than an hour ago
Holiday Inn Express Hyannis Cape Cod by IHG

Find out more about South Chatham

South Chatham Vacation Homes information

Number of reviews
633
Accommodation
2566 Vacation Homes
Lowest Price
￥50,098
Highest Price
￥278,987