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South Chatham Vacation Rentals

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Our top choices for South Chatham vacation rentals

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
9.8 out of 10, Exceptional, (106 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is CA $133
CA $715 total
includes taxes & fees
Oct 7 - Oct 8
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

2. Great for Families! Brewster Home 6 Mi to Beach

Great for Families! Brewster Home 6 Mi to Beach
Brewster
9.6 out of 10, Exceptional, (12 reviews)
"The kitchen was well stocked. The Beds were comfortable. "
United States
Stacey P.
The price is CA $145
CA $988 total
includes taxes & fees
Sep 20 - Sep 21
Great for Families! Brewster Home 6 Mi to Beach

3. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (145 reviews)
"We stay here every year! Love it!"
United States
Karel
The price is CA $299
CA $342 total
includes taxes & fees
Sep 24 - Sep 25
Brewster Green Resort

4. 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.
The price is CA $208
CA $716 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Large Home in Harwich with Patio near Wequassett Resort

5. 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 CA $201
CA $965 total
includes taxes & fees
Sep 20 - Sep 21
6 Mi to Beach: Home w/ Deck in Brewster!

6. Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
Harwich
10.0 out of 10, Exceptional, (9 reviews)
"Excellent location "
United States
Norman Y.
The price is CA $301
CA $943 total
includes taxes & fees
Sep 20 - Sep 21
Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

7. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (82 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 CA $441
CA $1,143 total
includes taxes & fees
Sep 20 - Sep 21
Family Cottage Close to Beach!!

8. Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (52 reviews)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is CA $193
CA $870 total
includes taxes & fees
Sep 22 - Sep 23
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

9. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (87 reviews)
"This is second time to stay here! We love the location and hospitality of the hosts! Great place!"
United States
Barbara P.
The price is CA $378
CA $860 total
includes taxes & fees
Oct 5 - Oct 6
Beautiful home near Jacknife Beach and bike trail

10. The Beachcomber Unit - #9

The Beachcomber Unit - #9
Harwich
10.0 out of 10, Exceptional, (21 reviews)
"We had an amazing time staying here, great location and it was very clean. "
United States
Mike B.
The price is CA $251
CA $415 total
includes taxes & fees
Sep 20 - Sep 21
The Beachcomber Unit - #9

11. Cape Cod Oceanside Condo across from beach!

Cape Cod Oceanside Condo across from beach!
Dennis
9.0 out of 10, Wonderful, (23 reviews)
"We had a wonderful stay! The place was very clean and fit 3 people comfortably. We loved having the beach right across the street. The check in process was very easy and the front desk staff was super nice! Would definitely stay here again!!"
United States
Lindsey Y.
The price is CA $140
CA $192 total
includes taxes & fees
Oct 7 - Oct 8
Cape Cod Oceanside Condo across from beach!

12. 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, (127 reviews)
"Amazing stay so close to town and CBI."
United States
Joanne B.
The price is CA $350
CA $810 total
includes taxes & fees
Oct 20 - Oct 21
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

13. Quiet getaway in a unique area of Cape Cod

Quiet getaway in a unique area of Cape Cod
Brewster
10.0 out of 10, Exceptional, (5 reviews)
"Perfect for a quiet getaway. Owner was in Constant contact. If I had a question replied very quickly. I highly recommend staying here."
United States
Anonymous traveller
The price is CA $350
CA $642 total
includes taxes & fees
Sep 20 - Sep 21
Quiet getaway in a unique area of Cape Cod

14. Seaside Getaway - Harwichport Beachhouse

Seaside Getaway - Harwichport Beachhouse
Harwich
9.0 out of 10, Wonderful, (16 reviews)
"Great stay! Clean and comfortable and close to town."
United States
Meredith R.
The price is CA $351
CA $733 total
includes taxes & fees
Sep 21 - Sep 22
Seaside Getaway - Harwichport Beachhouse

15. Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.2 out of 10, Wonderful, (27 reviews)
"Loved this property. "
United States
Carol S.
The price is CA $95
CA $609 total
includes taxes & fees
Oct 1 - Oct 2
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

16. Cape Calm: A Harwich Port Coastal Haven

Cape Calm: A Harwich Port Coastal Haven
Harwich
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place close to town and lots of beaches"
United States
Lee C.
The price is CA $368
CA $958 total
includes taxes & fees
Sep 21 - Sep 22
Cape Calm: A Harwich Port Coastal Haven

17. 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, (32 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is CA $333
CA $1,167 total
includes taxes & fees
Sep 28 - Sep 29
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

18. 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, (203 reviews)
"Great location and great host!! We’ll be back!!!"
United States
Patrick T.
The price is CA $161
CA $480 total
includes taxes & fees
Oct 12 - Oct 13
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

19. Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach

Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach
Chatham
9.8 out of 10, Exceptional, (8 reviews)
"Lock didn’t work"
United States
Claudine
The price is CA $502
CA $1,097 total
includes taxes & fees
Sep 22 - Sep 23
Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach

20. 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, (6 reviews)
The price is CA $559
CA $815 total
includes taxes & fees
Oct 9 - Oct 10
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
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

Find out more about South Chatham

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with South Chatham. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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 96 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.