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South Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for South Chatham vacation rentals

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)
"Clean, well-appointed, quaint, pet-friendly home centrally located in a great area for driving to Harding's Beach and downtown Chatham."
United States
Jennifer B.
$470 nightly
The price is $538
Nov 9 - Nov 10
Total with taxes and fees
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.
$486 nightly
The price is $556
Nov 9 - Nov 10
Total with taxes and fees
Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard
A deck with outdoor furniture including a sofa, chairs, and a table.

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.
$511 nightly
The price is $585
Nov 8 - Nov 9
Total with taxes and fees
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)
"From check-in to check-out, our experience was excellent. There were minor issues with the house, that didn’t affect our stay. It’s a quiet neighborhood, and we all slept well. The Internet was fast enough for my son’s gaming laptop (spent indoors on a rainy day). There are two outdoor grills available. I used the charcoal grill, as I prefer the flavoring from the burner charcoal. In the yard, you’ll see a wide assortment of birds. Everyday we had a visit by rabbits and chipmunks. Nearby,...
United States
Gil G.
$679 nightly
The price is $777
Nov 7 - Nov 8
Total with taxes and fees
Family Cottage Close to Beach!!
A bedroom with a bed, a desk, a chair, a TV, and a window.

5. 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.
$304 nightly
The price is $347
Nov 9 - Nov 10
Total with taxes and fees
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
A living room with a white cabinet, striped armchair, and a wicker chair.

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)
"Our stay was wonderful!"
United States
Corinne J.
$475 nightly
The price is $544
Nov 9 - Nov 10
Total with taxes and fees
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
A residential backyard with a white fence, outdoor seating, and a house in the background.

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.
$369 nightly
The price is $422
Nov 9 - Nov 10
Total with taxes and fees
Seaside Getaway - Harwichport Beachhouse
A living room with a fireplace, sofas, a coffee table, and a television.

8. 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, (210 reviews)
"Great location and perfect home for overnight stay!"
United States
Betsy D.
$258 nightly
The price is $295
Nov 8 - Nov 9
Total with taxes and fees
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
A large outdoor swimming pool surrounded by lounge chairs and umbrellas, with a clear sky above.

9. Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
Brewster
10.0 out of 10, Exceptional, (54 reviews)
"Great stay!"
United States
Rebecca R.
$274 nightly
The price is $314
Nov 8 - Nov 9
Total with taxes and fees
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
A pool area with lounge chairs and flags.

10. The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts
3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (273 reviews)
"The property is an older timeshare and dated."
United States
Kim
$107 nightly
The price is $122
Nov 9 - Nov 10
Total with taxes and fees
The Cove at Yarmouth by Westgate Resorts
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.

11. 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.
$641 nightly
The price is $733
Nov 8 - Nov 9
Total with taxes and fees
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
A living room with a fireplace, a sofa, a coffee table, and a television.

12. 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
$518 nightly
The price is $593
Nov 10 - Nov 11
Total with taxes and fees
The Brewster Pearl
A dining area with a wooden table, chairs, and a chandelier. There is a rug on the floor and a painting on the wall.

13. Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC

Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC
Harwich
9.0 out of 10, Wonderful, (6 reviews)
"would stay here again"
United States
david r.
$485 nightly
The price is $555
Nov 9 - Nov 10
Total with taxes and fees
Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC
A wooden deck with outdoor furniture, a covered seating area, and a view of neighboring houses.

14. 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.
$426 nightly
The price is $487
Nov 7 - Nov 8
Total with taxes and fees
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.

15. 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.
$500 nightly
The price is $573
Nov 10 - Nov 11
Total with taxes and fees
Beach Bungalow: Steps to Beach, Luxury Family Fun
A dining area with a table set for two, a chair, and a plant with pink flowers.

16. 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.
$474 nightly
The price is $543
Nov 9 - Nov 10
Total with taxes and fees
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.

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.
$442 nightly
The price is $489
Nov 30 - Dec 1
Total with taxes and fees
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
A room with a wooden dining table, four chairs, a flat-screen TV mounted on the wall, and a view through an open door to a dining area.

18. Cape Cod Beach Cottage, only 5 minute walk to Glendon beach & local restaurants

Cape Cod Beach Cottage, only 5 minute walk to Glendon beach & local restaurants
Dennis
9.6 out of 10, Exceptional, (92 reviews)
"We had a great stay! We loved how close it was to the beach and that we could bring our dog. We also really appreciated the outdoor shower and extra room with tv for space."
United States
Holleigh B.
$461 nightly
The price is $527
Nov 19 - Nov 20
Total with taxes and fees
Cape Cod Beach Cottage, only 5 minute walk to Glendon beach & local restaurants
A two-story house with a covered porch and a stone staircase leading to the entrance.

19. 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, (25 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.
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
A modern kitchen with white cabinets, a central island, and a dining area with a table set for four.

20. Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge

Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
Orleans
9.8 out of 10, Exceptional, (18 reviews)
"Great house, so much room! We enjoyed our stay!!"
United States
Gina M.
$2,605 nightly
The price is $2,981
Nov 8 - Nov 9
Total with taxes and fees
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
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

Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"Had a blast! Thank you"
April 1-night trip
Posted 5 hours ago
Bayside Resort Hotel

Find out more about South Chatham

Everything you need to know about South Chatham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Chatham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Chatham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Chatham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Chatham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Chatham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $122 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Chatham rentals

At Expedia, we put the best South Chatham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top South Chatham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Chatham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Chatham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in South Chatham?

Yes, we have vacation rentals close to well known attractions in South Chatham, or you can go with a more remote option if you'd like a relaxing place to stay. Nature enthusiasts will enjoy the beaches in South Chatham. Make sure you have time to check out the seafood restaurants and forests during your trip.

What are some of the best vacation rentals in South Chatham?

Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!: This vacation home rental near South Chatham is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade game room.

How many vacation rentals will I find in South Chatham?

Choose from 95 Expedia vacation rentals in South Chatham for a memorable vacation.

What can I see and do in South Chatham?

Cape Cod Beaches and Forest Beach are a couple of lovely local spots to get outside and enjoy nature. Cockle Cove Beach and Chatham Chamber of Commerce are a couple of places you'll find in the larger area.

What are vacation rentals like in South Chatham?

Vacation rentals are private properties where you can stay for several days or longer in South Chatham. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for family trips.