Holiday Rentals in South Chatham

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Holiday Rentals in South Chatham

Brewster Green Resort

3.5 star property
Brewster
9.4 out of 10, Exceptional, (119)
"The room was very clean and large. It was perfect for two people. The unit we stayed in was about .25 miles from clubhouse. So since it was cold, we didn't use the indoor pool. Staff was friendly. They have a game room where you can play table tennis and air hockey among other games. For the money, it was well worth staying there."
United States
Harry
The price is €256
includes taxes & fees
14 Nov - 15 Nov
Brewster Green Resort

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

2.0 star property
West Brewster
10.0 out of 10, Exceptional, (24)
"The house was very clean and comfortable. The outdoor patio is especially nice as well."
United States
Gina C.
The price is €569
includes taxes & fees
23 Nov - 24 Nov
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Dennis
10.0 out of 10, Exceptional, (175)
"Perfect spot for a few days away with the kids. The house had everything we needed and was in a great location! Would definitely rent again. "
United States
Dana B.
The price is €277
includes taxes & fees
22 Nov - 23 Nov
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Wellfleet
10.0 out of 10, Exceptional, (74)
"Drew was one of the best landlords we’ve ever had on a vacation property. He was very responsive to the few questions that we had and asked proactively if there was anything that we needed throughout our week. The view from the porch was spectacular."
United States
David M.
The price is €383
includes taxes & fees
18 Nov - 19 Nov
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Secluded-Entire 2nd floor Suite with Private Bath

Barnstable
10.0 out of 10, Exceptional, (1)
"Great, very close to downtown hyannis. Charming and a nice owner. "
United States
sam s.
The price is €141
includes taxes & fees
15 Nov - 16 Nov
Secluded-Entire 2nd floor Suite with Private Bath

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Chatham
9.6 out of 10, Exceptional, (99)
"We had a great time on the Cape and lucked out with beautiful weather too! We loved this house and were so grateful to be able to bring our dogs! Thank you"
United States
Judy M.
The price is €360
includes taxes & fees
17 Nov - 18 Nov
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Chatham
9.6 out of 10, Exceptional, (29)
"Great visit! Clean property a bit tucked in the woods but overall close to everything and a great spot for the price!"
United States
Christian B.
The price is €328
includes taxes & fees
13 Dec - 14 Dec
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Quaint condo near private beach access with fireplace - close to dining

Dennis Port
9.0 out of 10, Wonderful, (61)
"Loved our stay in Dennis. The condo was so nice and so clean.. I would certainly consider next summer to revisit. "
United States
Rosemarie P.
The price is €251
includes taxes & fees
17 Nov - 18 Nov
Quaint condo near private beach access with fireplace - close to dining

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

2.0 star property
Dennis
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
The price is €287
includes taxes & fees
17 Nov - 18 Nov
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

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

Brewster
10.0 out of 10, Exceptional, (40)
"Had a great stay here. Very clean. Very nice property. Well equipped for all our needs"
United States
Maureen D.
The price is €301
includes taxes & fees
16 Nov - 17 Nov
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

Eastham
10.0 out of 10, Exceptional, (18)
"Absolutely amazing!!! Very clean seems like you are walking in to your own home. Hot tub was superb the dock was amazing!!! Short drive to a couple great golf courses as well as beeches!!!"
United States
Wyatt S.
The price is €446
includes taxes & fees
16 Nov - 17 Nov
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

Sand Bar-Dog Friendly on Cooks Brook Beach

Eastham
10.0 out of 10, Exceptional, (23)
"The house is so close to the beach. We didn’t need to leave the front porch to see the sunset. There was enough room in the house for the 7 of us. We found the house well stocked with everything we needed to be comfortable. "
United States
Trish B.
The price is €446
includes taxes & fees
25 Nov - 26 Nov
Sand Bar-Dog Friendly on Cooks Brook Beach

Stylish 2nd floor Ocean Edge condo

Brewster
9.8 out of 10, Exceptional, (9)
"Comfortable and cozy condo"
United States
Elaine Z.
Stylish 2nd floor Ocean Edge condo

Lovely House 5 Min to Beach with Deck, Grill, Garage

Eastham
10.0 out of 10, Exceptional, (1)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is €431
includes taxes & fees
17 Nov - 18 Nov
Lovely House 5 Min to Beach with Deck, Grill, Garage

Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Eastham
9.6 out of 10, Exceptional, (4)
"Nice house in a quiet neighborhood and very close to Cooks Brook beach.Loved watching sunsets over Cape Cod bay.House was very clean when we arrived and well equipped with beach towels."
United States
Joel H.
The price is €447
includes taxes & fees
25 Nov - 26 Nov
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Pond House~Waterfront Oasis W/Jacuzzi Tub

Eastham
10.0 out of 10, Exceptional, (10)
"Beautiful spot ! House was clean and well equipped. "
United States
Cynthia P.
The price is €449
includes taxes & fees
25 Nov - 26 Nov
Pond House~Waterfront Oasis W/Jacuzzi Tub

National Seashore/Updated/Game Room~Blue Pearl

Eastham
10.0 out of 10, Exceptional, (8)
"Beautiful new house in a great location. Definitely would rent again"
United States
Timothy K.
The price is €435
includes taxes & fees
25 Nov - 26 Nov
National Seashore/Updated/Game Room~Blue Pearl

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Chatham
10.0 out of 10, Exceptional, (114)
"Great great great location. Super charming home. It worked perfectly for our family. Walk to shops and restaurants! I highly recommend. Host was lovely & easy to reach. We would’ve loved to utilize the properties outdoor space more. Other than that - it was terrific! Rent it now!"
United States
Rachel S.
The price is €434
includes taxes & fees
19 Nov - 20 Nov
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Sleeps 2-8/Soaking Tub/FirePit~Burrows

Eastham
10.0 out of 10, Exceptional, (7)
"Overall, we had a really great stay. The home is in a quiet neighborhood & close to the beach. Everything was clean and as described in the listing. "
United States
Kallee M.
The price is €450
includes taxes & fees
16 Nov - 17 Nov
Sleeps 2-8/Soaking Tub/FirePit~Burrows

Coastal Haven in West Dennis

2.0 star property
Dennis
10.0 out of 10, Exceptional, (3)
"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 €462
includes taxes & fees
16 Nov - 17 Nov
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.
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Find out more about South Chatham

Everything you need to know about South Chatham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Chatham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

South Chatham holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Chatham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Chatham holiday rentals we have selected for you start as low as €251 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Chatham rentals

At Expedia, we put the best South Chatham holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in South Chatham?

Yes, there are holiday rentals close to the most popular sights in South Chatham, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that South Chatham has to offer?

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!: This holiday home rental outside of South Chatham is located in the city centre, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in South Chatham?

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

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 wider area.

What are holiday rentals like in South Chatham?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in South Chatham. Holiday rentals feature extras like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for families.