South Chatham Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for South Chatham holiday rentals

Smart TV, fireplace, books

Classic Cape House Walking Distance to the Beach - Many recent upgrades

Classic Cape House Walking Distance to the Beach - Many recent upgrades
Chatham
9.8 out of 10, Exceptional, (20 reviews)
"Mary was a wonderful host. The house was clean, close to beach and communication was wonderful! A great, relaxing stay!!"
United States
Kathleen T.
The price is HK$2,349
HK$5,942 total
includes taxes & fees
24 Apr - 25 Apr
Classic Cape House Walking Distance to the Beach - Many recent upgrades
Interior

1 Mi to Ferry: 'sea Street Cottage' in Hyannis

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
The price is HK$1,120
HK$2,844 total
includes taxes & fees
8 May - 9 May
1 Mi to Ferry: 'sea Street Cottage' in Hyannis
Outdoor dining

Cape Cod Villa pond front vacation home, retreat, spa, venue, film location

Cape Cod Villa pond front vacation home, retreat, spa, venue, film location
Harwich - Brewster Border
10.0 out of 10, Exceptional, (6 reviews)
"Lovely property with attentive hosts "
United States
marian t.
The price is HK$5,497
HK$10,029 total
includes taxes & fees
14 Apr - 15 Apr
Cape Cod Villa pond front vacation home, retreat, spa, venue, film location
Indoor spa tub

Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (128 reviews)
"Mike is the best. Very clean environment and family welcome"
United States
Catherine
The price is HK$1,793
HK$2,052 total
includes taxes & fees
14 Apr - 15 Apr
Brewster Green Resort
Lounge

Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is HK$3,132
HK$4,525 total
includes taxes & fees
14 Apr - 15 Apr
Sal's Place
Fridge, microwave, oven, stovetop

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
Barnstable
10.0 out of 10, Exceptional, (31 reviews)
"It was a great stay and clean home. Recommend people to stay here"
United States
Charbel T.
The price is HK$3,915
HK$7,663 total
includes taxes & fees
14 Apr - 15 Apr
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
Fridge, microwave, oven, stovetop

2021 CONSTRUCTION 3BR 3BA, close to Bike Trail & Beaches. Central AC Eastham

2021 CONSTRUCTION 3BR 3BA, close to Bike Trail & Beaches. Central AC Eastham
Eastham
10.0 out of 10, Exceptional, (44 reviews)
"Great place, very clean. Host was accessible and accommodating. "
United States
Christopher M.
The price is HK$3,172
HK$7,735 total
includes taxes & fees
26 Apr - 27 Apr
2021 CONSTRUCTION 3BR 3BA, close to Bike Trail & Beaches. Central AC Eastham
3 bedrooms, desk

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15
2.0 star property
West Dennis
The price is HK$2,458
HK$5,997 total
includes taxes & fees
25 Apr - 26 Apr
Coastal Haven in West Dennis -15
Smart TV, fireplace

Classic Cape Cod beach cottage

Classic Cape Cod beach cottage
Indian Neck Heights
9.8 out of 10, Exceptional, (40 reviews)
"We had a great time! Perfect location and all the amenities we needed. "
United States
Julianne K.
The price is HK$3,328
HK$6,856 total
includes taxes & fees
12 May - 13 May
Classic Cape Cod beach cottage
Beach nearby

Edgewood on Campground Beach/Steps to the Sand

Edgewood on Campground Beach/Steps to the Sand
Eastham
10.0 out of 10, Exceptional, (9 reviews)
"Cozy cottage right by the beach. Great area not for to restaurants and beaches. Would definitely stay again!"
United States
Melinda W.
The price is HK$1,543
HK$3,792 total
includes taxes & fees
19 Apr - 20 Apr
Edgewood on Campground Beach/Steps to the Sand
Dining

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

Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
Orleans
10.0 out of 10, Exceptional, (14 reviews)
"Property was clean and as described in the listing, owner was communicative and easy to check in"
United States
Darren Y.
The price is HK$14,096
HK$24,324 total
includes taxes & fees
14 Apr - 15 Apr
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
Front of property

6 Mi to Beach: Home w/ Deck in Brewster!

6 Mi to Beach: Home w/ Deck in Brewster!
3.0 star property
Brewster
The price is HK$908
HK$5,398 total
includes taxes & fees
24 Apr - 25 Apr
6 Mi to Beach: Home w/ Deck in Brewster!
Terrace/patio

Beachfront~Seaside Sea-duction-Dog Friendly

Beachfront~Seaside Sea-duction-Dog Friendly
Eastham
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful view of the water - the pictures don’t even do it justice. Great dog friendly property that is in a great neighborhood in Eastham. Spent a couple nights over the new year holiday for some quiet time and even in the off season it is a great property. Can’t imagine how magnificent it is in the summer! "
United States
Victoria T.
The price is HK$2,281
HK$5,550 total
includes taxes & fees
14 Apr - 15 Apr
Beachfront~Seaside Sea-duction-Dog Friendly
Interior

Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!

Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!
Dennis
9.6 out of 10, Exceptional, (121 reviews)
"We had a great time with the family on Cape Cod for Thanksgiving. The host was very accommodating even answering on the holiday when we locked ourselves out. The place is literally on the beach. We were able to enjoy sunrise and sunset this time of year. Perfectly placed mid cape to access wherever you want to go. Great rooms with sweeping views. Best spot on the cape"
United States
James S.
Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!
Exterior

Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (75 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 HK$2,467
HK$6,399 total
includes taxes & fees
14 Apr - 15 Apr
Family Cottage Close to Beach!!
4 bedrooms, desk, iron/ironing board, free WiFi

Private beach, hot tub, and dog friendly – The Keeper!

Private beach, hot tub, and dog friendly – The Keeper!
Brewster
9.8 out of 10, Exceptional, (17 reviews)
"The property is beautiful and in great location. The house is cozy and comfortable. We would stay there again!!!"
United States
Lori L.
The price is HK$3,001
HK$9,225 total
includes taxes & fees
16 Apr - 17 Apr
Private beach, hot tub, and dog friendly – The Keeper!
Beach nearby

🐚The Bay Cottage on Thumpertown Beach

🐚The Bay Cottage on Thumpertown Beach
Eastham
9.8 out of 10, Exceptional, (11 reviews)
"My group and I had another wonderful stay at the Bay Cottage! The space is sparkling clean when we arrived and the location cannot be beat. Tara is also very responsive and attentive which makes for an even better stay!"
United States
Sophia I.
The price is HK$1,158
HK$3,064 total
includes taxes & fees
15 Apr - 16 Apr
🐚The Bay Cottage on Thumpertown Beach
Beach nearby

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, (44 reviews)
"Great place!"
United States
Michael P.
The price is HK$1,755
HK$2,994 total
includes taxes & fees
14 Apr - 15 Apr
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
Interior

Summer 2026 Perfection!

Summer 2026 Perfection!
Barnstable
The price is HK$3,132
HK$4,069 total
includes taxes & fees
14 Apr - 15 Apr
Summer 2026 Perfection!
5 bedrooms

Water Access 5-bed 2-bath Retreat

Water Access 5-bed 2-bath Retreat
2.0 star property
Hyannis
Water Access 5-bed 2-bath Retreat
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

6/10 Okay
"The staff were very professional and welcoming. The room and property were clean. That is really the end of the good news. We stayed 2 nights off season, the cost 430.00+. The room clean but severely lacking. The showerhead, yuck, the tub filled with water when trying to take a shower, the towels, clean but paper thin, ditto bedding. Toilet backup day 1. The plugs next to the bed did not work had to charge phones on the floor with wall outlets. We did not complain, really what could staff do? These are management issues and should be addressed. There are so many options on the Cape, we were disappointed. Definitely not staff fault. "
Margaret 2-night trip
Posted 14 hours ago
Bayside Resort Hotel

Find out more about South Chatham

Search for holiday rentals in South Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in South Chatham using one of the methods below:

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Look no further and take a look at our great range of rental properties in South Chatham!

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?

Cape Cod's "Beach Rose": This holiday home rental outside of South Chatham has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals will I find in South Chatham?

Choose from 94 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. Chatham Chamber of Commerce and Cockle Cove Beach 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.