South Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for South Chatham vacation rentals

Front of property
Holly Tree Resort

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
Beach nearby
The Cove at Yarmouth by Westgate Resorts

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 ￥20,091
￥22,993 total
includes taxes & fees
Jan 25 - Jan 26, 2026
The Cove at Yarmouth by Westgate Resorts
Fridge, microwave, stovetop, dishwasher
Quaint condo near private beach access with fireplace - close to dining

Condo in Dennis Port

Quaint condo near private beach access with fireplace - close to dining
9.0 out of 10, Wonderful, (62)
"Clean, beautiful, great location "
United States
Jennifer B.
The price is ￥11,086
￥50,792 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Quaint condo near private beach access with fireplace - close to dining
Outdoor dining
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Vacation Home in Dennis

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
9.8 out of 10, Exceptional, (178)
"Great location, clean property!"
United States
Lisa B.
The price is ￥13,912
￥48,806 total
includes taxes & fees
Dec 28 - Dec 29
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Outdoor dining
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Vacation Home in Wellfleet

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
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 ￥21,754
￥67,374 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Exterior detail
The Nantucket Room Unit - #2

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 ￥19,518
￥35,035 total
includes taxes & fees
Dec 28 - Dec 29
The Nantucket Room Unit - #2
Fridge, microwave, oven, stovetop
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Cottage in Chatham

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
9.6 out of 10, Exceptional, (30)
"CutePrivateGreat outdoor showe "
United States
Stephanie D.
The price is ￥14,209
￥51,920 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
Beach nearby
Charming House by the Beach with Patio, Grill, FirePit

Vacation Home in Bass River

Charming House by the Beach with Patio, Grill, FirePit
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 ￥20,116
￥79,955 total
includes taxes & fees
Dec 28 - Dec 29
Charming House by the Beach with Patio, Grill, FirePit
Interior
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Vacation Home in Eastham

Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
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 ￥24,419
￥78,992 total
includes taxes & fees
Dec 29 - Dec 30
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
Beach
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Vacation Home in Dennis

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
2.0 star property
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveler
The price is ￥20,142
￥50,663 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Sundeck
Riverview Resort

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 ￥32,786
￥37,523 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Riverview Resort
Marina
Lovely House 5 Min to Beach with Deck, Grill, Garage

Vacation Home in Eastham

Lovely House 5 Min to Beach with Deck, Grill, Garage
10.0 out of 10, Exceptional, (1)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is ￥21,703
￥72,570 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Lovely House 5 Min to Beach with Deck, Grill, Garage
Exterior
Cozy Large Home in Harwich with Patio near Wequassett Resort

Vacation Home in Harwich

Cozy Large Home in Harwich with Patio near Wequassett Resort
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 ￥24,171
￥80,129 total
includes taxes & fees
Dec 27 - Dec 28
Cozy Large Home in Harwich with Patio near Wequassett Resort
Outdoor dining
The Alpine/Walk to Beach for 2 or more!

Vacation Home in Eastham

The Alpine/Walk to Beach for 2 or more!
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 ￥26,979
￥81,207 total
includes taxes & fees
Jan 8 - Jan 9, 2026
The Alpine/Walk to Beach for 2 or more!
Pool
Stylish 2nd floor Ocean Edge condo

Apartment in Brewster

Stylish 2nd floor Ocean Edge condo
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 ￥27,757
￥66,750 total
includes taxes & fees
Dec 29 - Dec 30
Stylish 2nd floor Ocean Edge condo
Interior
Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach

Cottage in Dennis

Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach
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
Microwave, oven, stovetop, dishwasher
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Vacation Home in Chatham

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
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 ￥17,933
￥68,771 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Smart TV, offices
New! Island Pines-A Dog Friendly Boutique Oasis

Vacation Home in Wellfleet

New! Island Pines-A Dog Friendly Boutique Oasis
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 ￥29,370
￥85,373 total
includes taxes & fees
Jan 7 - Jan 8, 2026
New! Island Pines-A Dog Friendly Boutique Oasis
Beach nearby, sun loungers
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Vacation Home in Chatham

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
10.0 out of 10, Exceptional, (116)
"Comfortable and terrific location"
United States
Barry L.
The price is ￥28,069
￥75,493 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Fridge, microwave, oven, stovetop
Sand Bar-Dog Friendly on Cooks Brook Beach

Vacation Home in Eastham

Sand Bar-Dog Friendly on Cooks Brook Beach
10.0 out of 10, Exceptional, (23)
"Lovely time!"
United States
Joan W.
The price is ￥27,014
￥74,521 total
includes taxes & fees
Jan 5 - Jan 6, 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.
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Top South Chatham Hotel Reviews

Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"Charming, cozy , clean! "
Erica 1-night trip
Posted 5 days ago
Chatham Wayside Inn

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:

  • View our selection of featured holiday rentals in South Chatham
  • Use the map to find apartments and other holiday homes in the South Chatham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in South Chatham while they last

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

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?

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!: This vacation home rental near South Chatham is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in South Chatham?

Choose from 92 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.