South Chatham Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Our top choices for South Chatham holiday rentals

Aparthotel in West Yarmouth

Holly Tree Resort
3.0 star property
9.0 out of 10, Wonderful, (385)
"Best place in massachusetts "
United States
Michael
Holly Tree Resort

Aparthotel in West Yarmouth

The Cove at Yarmouth by Westgate Resorts
3.0 star property
9.2 out of 10, Wonderful, (243)
"Great place to stay. Clean, friendly and accommodating!"
United States
Mike
The price is NZ$253
includes taxes & fees
4 Jan - 5 Jan 2026
The Cove at Yarmouth by Westgate Resorts
9.0 out of 10, Wonderful, (62)
"Clean, beautiful, great location "
United States
Jennifer B.
The price is NZ$555
includes taxes & fees
4 Jan - 5 Jan 2026
Quaint condo near private beach access with fireplace - close to dining
9.8 out of 10, Exceptional, (178)
"Great location, clean property!"
United States
Lisa B.
The price is NZ$535
includes taxes & fees
28 Dec - 29 Dec
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
10.0 out of 10, Exceptional, (75)
"Beautiful views in a quiet and private location. Cottage had everything we needed and nicely appointed."
United States
Janice H.
The price is NZ$746
includes taxes & fees
5 Jan - 6 Jan 2026
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Condo in Harwich port

The Nantucket Room Unit - #2
9.8 out of 10, Exceptional, (49)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is NZ$384
includes taxes & fees
28 Dec - 29 Dec
The Nantucket Room Unit - #2
9.6 out of 10, Exceptional, (30)
"CutePrivateGreat outdoor showe "
United States
Stephanie D.
The price is NZ$569
includes taxes & fees
4 Jan - 5 Jan 2026
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
9.8 out of 10, Exceptional, (7)
"Great location, walk to beach. Close to restaurants and pirate's cove mini golf. Beds were comfy. In-house laundry was convenient. Great outdoor shower. "
United States
Amanda W.
The price is NZ$878
includes taxes & fees
28 Dec - 29 Dec
Charming House by the Beach with Patio, Grill, FirePit
9.6 out of 10, Exceptional, (4)
"The home was clean, cool and comfortable. Booking was easy and effortless! Can’t wait to go back!"
United States
Kim S.
The price is NZ$869
includes taxes & fees
28 Dec - 29 Dec
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
2.0 star property
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
The price is NZ$556
includes taxes & fees
5 Jan - 6 Jan 2026
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Aparthotel in Bass River

Riverview Resort
3.0 star property
9.2 out of 10, Wonderful, (173)
"The staff was very helpful and upgraded us to a room with a view. The amenities were perfect. We definitely would go back there."
United States
John
The price is NZ$408
includes taxes & fees
2 Jan - 3 Jan 2026
Riverview Resort
10.0 out of 10, Exceptional, (1)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is NZ$796
includes taxes & fees
4 Jan - 5 Jan 2026
Lovely House 5 Min to Beach with Deck, Grill, Garage
9.8 out of 10, Exceptional, (11)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is NZ$880
includes taxes & fees
27 Dec - 28 Dec
Cozy Large Home in Harwich with Patio near Wequassett Resort
9.2 out of 10, Wonderful, (11)
"The location was awesome, the house was clean and spacious, and overall it was terrific! I would highly recommend."
United States
Jennifer G.
The price is NZ$904
includes taxes & fees
1 Jan - 2 Jan 2026
The Alpine/Walk to Beach for 2 or more!
9.8 out of 10, Exceptional, (9)
"Great property. It looks like it was recently renovated and done really well. Convenient to the beaches and restaurants, and golf. We love Brewster. "
United States
Garret J.
The price is NZ$733
includes taxes & fees
29 Dec - 30 Dec
Stylish 2nd floor Ocean Edge condo
9.6 out of 10, Exceptional, (177)
"Fenced in yard was perfect and close walk to both beach and restaurants."
United States
Mike Kayla B.
Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach
9.6 out of 10, Exceptional, (102)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is NZ$761
includes taxes & fees
7 Jan - 8 Jan 2026
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
9.4 out of 10, Exceptional, (11)
"Loved the place. Very clean and updated. You have to time the tides because it is on an island, but that was fine for us. "
United States
Brian F.
The price is NZ$943
includes taxes & fees
5 Jan - 6 Jan 2026
New! Island Pines-A Dog Friendly Boutique Oasis
10.0 out of 10, Exceptional, (116)
"Comfortable and terrific location"
United States
Barry L.
The price is NZ$839
includes taxes & fees
5 Jan - 6 Jan 2026
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
10.0 out of 10, Exceptional, (23)
"Lovely time!"
United States
Joan W.
The price is NZ$817
includes taxes & fees
5 Jan - 6 Jan 2026
Sand Bar-Dog Friendly on Cooks Brook Beach
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.
Save an average of 15% on thousands of hotels when you're signed in

Top South Chatham Hotel Reviews

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, 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 NZ$370 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 92 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.