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South Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (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.
$428 nightly
The price is $490
Oct 19 - Oct 20
Total with taxes and fees
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
A spacious living area with a large window, a wooden ceiling, a television, and a sofa.

2. Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Lovely spot on the water!"
United States
Elizabeth T.
$416 nightly
The price is $476
Oct 14 - Oct 15
Total with taxes and fees
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
A resort with a large pool, sun loungers, and a pier extending into the water.

3. 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.
$449 nightly
The price is $497
Oct 27 - Oct 28
Total with taxes and fees
Cozy Large Home in Harwich with Patio near Wequassett Resort
An outdoor patio with Adirondack chairs, a fire pit, and string lights.

4. 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.
$571 nightly
The price is $654
Oct 14 - Oct 15
Total with taxes and fees
Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard
A spacious living room with a large abstract painting, two chandeliers, and a coffee machine.

5. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (151 reviews)
"Very spacious rooms clean ,great location friendly staff,"
United States
Margaret
$244 nightly
The price is $279
Oct 22 - Oct 23
Total with taxes and fees
Brewster Green Resort
A sandy beach with a grassy path leading to the water.

6. 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.
$537 nightly
The price is $615
Nov 1 - Nov 2
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.

7. 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.
$714 nightly
The price is $817
Oct 14 - Oct 15
Total with taxes and fees
Family Cottage Close to Beach!!
A lighthouse with a cylindrical tower and a white building with a red roof.

8. 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.
$482 nightly
The price is $552
Nov 2 - Nov 3
Total with taxes and fees
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Bathroom

9. 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)
$457 nightly
The price is $523
Oct 18 - Oct 19
Total with taxes and fees
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.

10. 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.
$435 nightly
The price is $498
Oct 19 - Oct 20
Total with taxes and fees
Seaside Getaway - Harwichport Beachhouse
A pool area with lounge chairs and flags.

11. 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, (269 reviews)
"The property is an older timeshare and dated."
United States
Kim
$105 nightly
The price is $120
Nov 2 - Nov 3
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.

12. 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.
$648 nightly
The price is $741
Oct 14 - Oct 15
Total with taxes and fees
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
A beach with people, tents, and umbrellas.

13. 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, (52 reviews)
"We did a quick overnight The amenities were great and the condo was perfect !!!"
United States
Katie M.
$311 nightly
The price is $356
Nov 1 - Nov 2
Total with taxes and fees
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
An outdoor dining area with white chairs and umbrellas, overlooking the ocean.

14. 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, (208 reviews)
"Great location and great host!! We’ll be back!!!"
United States
Patrick T.
$268 nightly
The price is $306
Oct 14 - Oct 15
Total with taxes and fees
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
A dining area with a wooden table, chairs, and a chandelier. There is a rug on the floor and a painting on the wall.

15. 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.
$433 nightly
The price is $496
Oct 27 - Oct 28
Total with taxes and fees
Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC
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, (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
$589 nightly
The price is $674
Oct 28 - Oct 29
Total with taxes and fees
The Brewster Pearl
An outdoor seating area with wicker furniture and a fire pit, overlooking a calm lake and trees.

17. ★Waterfront & On Bike Path★Firepit ★Private beach★Bikes★Kayaks★Sm.Pet OK💥Sunsets

★Waterfront & On Bike Path★Firepit ★Private beach★Bikes★Kayaks★Sm.Pet OK💥Sunsets
West Brewster
10.0 out of 10, Exceptional, (31 reviews)
"The cottage is immaculate, has every amenity you would want and the host is very responsive. We absolutely loved our stay!"
United States
Katrina W.
★Waterfront & On Bike Path★Firepit ★Private beach★Bikes★Kayaks★Sm.Pet OK💥Sunsets
A modern two-story building with large windows and a flat roof.

18. 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.
$577 nightly
The price is $676
Oct 14 - Oct 15
Total with taxes and fees
Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!
A living room with a brick fireplace, a blue sectional sofa, a white coffee table, and a large window with blinds.

19. 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.
$507 nightly
The price is $543
Oct 14 - Oct 15
Total with taxes and fees
Coastal Haven in West Dennis
A modern kitchen with white cabinets, a wooden ceiling, and a herringbone-patterned floor.

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

Beach Bungalow: Steps to Beach, Luxury Family Fun
Harwich
10.0 out of 10, Exceptional, (9 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.
$525 nightly
The price is $600
Nov 1 - Nov 2
Total with taxes and fees
Beach Bungalow: Steps to Beach, Luxury Family Fun
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

Hyannis Travel Inn

Hyannis Travel Inn

8/10 Good
"Everything was good."
Wesley 2-night trip
Posted 8 hours ago
Hyannis Travel Inn

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 $120 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.