South Dennis Vacation Rentals

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Our top choices for South Dennis vacation rentals

$434 nightly
The price is $480
Jan 5 - Jan 6, 2026
Total with taxes and fees
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
8.8 out of 10, Excellent, (8)
"Five star because hosts were very responsive and truly went out of their way to make sure our stay was comfortable and enjoyable. Mid cape location is perfect for all the beaches we visit and biking we do. "
United States
Mark L.
$472 nightly
The price is $540
Jan 4 - Jan 5, 2026
Total with taxes and fees
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ

Condo resort in New Seabury

The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (341)
"Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again "
United States
Jose O.
$147 nightly
The price is $169
Dec 30 - Dec 31
Total with taxes and fees
The Club at New Seabury
9.6 out of 10, Exceptional, (30)
"CutePrivateGreat outdoor showe "
United States
Stephanie D.
$285 nightly
The price is $327
Jan 4 - Jan 5, 2026
Total with taxes and fees
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
2.0 star property
10.0 out of 10, Exceptional, (25)
"Lovely house with nice location."
United States
amy d.
$629 nightly
The price is $720
Jan 16 - Jan 17, 2026
Total with taxes and fees
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
9.8 out of 10, Exceptional, (23)
"Everything was great, we really enjoyed our stay!"
United States
Anna T.
$373 nightly
The price is $427
Dec 29 - Dec 30
Total with taxes and fees
🦀Waterfront at The Velvet Crab~Amazing Sunsets
9.8 out of 10, Exceptional, (11)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
$468 nightly
The price is $518
Jan 9 - Jan 10, 2026
Total with taxes and fees
Cozy Large Home in Harwich with Patio near Wequassett Resort
2.0 star property
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveler
$293 nightly
The price is $324
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
9.6 out of 10, Exceptional, (102)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
$365 nightly
The price is $418
Jan 4 - Jan 5, 2026
Total with taxes and fees
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
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.
$379 nightly
The price is $433
Jan 2 - Jan 3, 2026
Total with taxes and fees
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
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.
$441 nightly
The price is $505
Dec 29 - Dec 30
Total with taxes and fees
Sleeps 2-8/Soaking Tub/FirePit~Burrows
10.0 out of 10, Exceptional, (23)
"Lovely time!"
United States
Joan W.
$417 nightly
The price is $477
Jan 5 - Jan 6, 2026
Total with taxes and fees
Sand Bar-Dog Friendly on Cooks Brook Beach
9.6 out of 10, Exceptional, (50)
"House was perfect for our family reunion! "
United States
Gregg H.
$468 nightly
The price is $536
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
10.0 out of 10, Exceptional, (21)
"We loved the luxury bed linens, large kitchen & living area & the fact that it was pet friendly in a lovely neighborhood!"
United States
Jennifer G.
$437 nightly
The price is $500
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Pet-Friendly Surf Shack Hideaway on the Cove
9.8 out of 10, Exceptional, (178)
"Great location, clean property!"
United States
Lisa B.
$273 nightly
The price is $313
Dec 29 - Dec 30
Total with taxes and fees
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
10.0 out of 10, Exceptional, (1)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
$429 nightly
The price is $475
Jan 4 - Jan 5, 2026
Total with taxes and fees
Lovely House 5 Min to Beach with Deck, Grill, Garage
10.0 out of 10, Exceptional, (2)
"The house was beautiful, tucked away, and clean. It was spacious for two families with room for more comfortably. "
United States
michele I.
$569 nightly
The price is $651
Jan 4 - Jan 5, 2026
Total with taxes and fees
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
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.
$441 nightly
The price is $505
Dec 29 - Dec 30
Total with taxes and fees
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
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.
$461 nightly
The price is $528
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Alpine/Walk to Beach for 2 or more!
9.0 out of 10, Wonderful, (62)
"Clean, beautiful, great location "
United States
Jennifer B.
$279 nightly
The price is $319
Jan 4 - Jan 5, 2026
Total with taxes and fees
Quaint condo near private beach access with fireplace - close to dining
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 Dennis Hotel Reviews

Find out more about South Dennis

Everything you need to know about South Dennis vacation rentals

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

South Dennis vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Dennis. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Dennis in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $148 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Dennis rentals

At Expedia, we put the best South Dennis vacation 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 Dennis 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 Dennis vacation.

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 Dennis. 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

Can I find vacation rentals in South Dennis?

Yes, we have vacation rentals close to well known local attractions in South Dennis, or you can select a more secluded option if you're looking for relaxation.

What are some of the best vacation rentals in South Dennis?

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!: This vacation home rental outside of South Dennis 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 Dennis?

Choose from 86 Expedia vacation rentals in South Dennis for a memorable vacation.

What can I see and do in South Dennis?

Cape Cod Rail Trail and Cape Cod Beaches are a couple of lovely local spots to get outside and enjoy nature. Crowe's Pasture and Follins Pond are a couple of places you'll find in the larger area.

What’s a vacation rental in South Dennis like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in South Dennis. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for small groups.