South Dennis Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for South Dennis holiday rentals

Interior

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
Dennis
The price is HK$1,164
HK$3,825 total
includes taxes & fees
2 Mar - 3 Mar
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
Meeting facility

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (349 reviews)
"Everything was superb, accommodations, check in service, check out service!!"
United States
Dianna
The price is HK$1,279
HK$1,464 total
includes taxes & fees
16 Feb - 17 Feb
The Club at New Seabury
Indoor spa tub

Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (124 reviews)
"The front desk staff are So pleasant to deal with. Pool is huge and the kids loved the game room"
United States
PAUL
Brewster Green Resort
TV, fireplace, books

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
9.6 out of 10, Exceptional, (102 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is HK$695
HK$3,704 total
includes taxes & fees
10 Feb - 11 Feb
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Interior

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Sandwich
10.0 out of 10, Exceptional, (3 reviews)
"We really enjoyed our stay at this property. The view was amazing and had our own private beach to lounge at!"
United States
Sean H.
The price is HK$1,172
HK$3,005 total
includes taxes & fees
11 Feb - 12 Feb
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Interior

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (50 reviews)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is HK$774
HK$1,494 total
includes taxes & fees
10 Feb - 11 Feb
The Nantucket Room Unit - #2
Outdoor dining

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Wellfleet
10.0 out of 10, Exceptional, (79 reviews)
"Beautiful views in a quiet and private location. Cottage had everything we needed and nicely appointed."
United States
Janice H.
The price is HK$1,172
HK$3,505 total
includes taxes & fees
10 Feb - 11 Feb
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Outdoor dining

🦀Waterfront at The Velvet Crab~Amazing Sunsets

🦀Waterfront at The Velvet Crab~Amazing Sunsets
Eastham
9.8 out of 10, Exceptional, (23 reviews)
"Everything was great, we really enjoyed our stay!"
United States
Anna T.
The price is HK$1,189
HK$3,319 total
includes taxes & fees
10 Feb - 11 Feb
🦀Waterfront at The Velvet Crab~Amazing Sunsets
Outdoor dining

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, (50 reviews)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is HK$1,031
HK$4,601 total
includes taxes & fees
10 Feb - 11 Feb
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Smart TV, books

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, (25 reviews)
"Lovely house with nice location."
United States
amy d.
The price is HK$996
HK$5,370 total
includes taxes & fees
10 Feb - 11 Feb
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Exterior

Lovely House 5 Min to Beach with Deck, Grill, Garage

Lovely House 5 Min to Beach with Deck, Grill, Garage
Eastham
10.0 out of 10, Exceptional, (2 reviews)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is HK$1,164
HK$3,816 total
includes taxes & fees
10 Feb - 11 Feb
Lovely House 5 Min to Beach with Deck, Grill, Garage
On the beach

Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach
Eastham
10.0 out of 10, Exceptional, (25 reviews)
"The hosts were so thoughtful and the sunset view was incredible "
United States
Jill K.
The price is HK$1,403
HK$3,850 total
includes taxes & fees
10 Feb - 11 Feb
Sand Bar-Dog Friendly on Cooks Brook Beach
Outdoor dining

Sleeps 2-8/Soaking Tub/FirePit~Burrows

Sleeps 2-8/Soaking Tub/FirePit~Burrows
Eastham
10.0 out of 10, Exceptional, (7 reviews)
"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.
The price is HK$1,223
HK$3,976 total
includes taxes & fees
12 Feb - 13 Feb
Sleeps 2-8/Soaking Tub/FirePit~Burrows
Indoor pool, seasonal outdoor pool

The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts
3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (251 reviews)
"Was unaware that pool facilities were closed for 2 weeks of maintenance which was primary purpose of stay"
United States
Edward
The price is HK$812
HK$930 total
includes taxes & fees
10 Feb - 11 Feb
The Cove at Yarmouth by Westgate Resorts
Smart TV

Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
Eastham
10.0 out of 10, Exceptional, (2 reviews)
"The house was beautiful, tucked away, and clean. It was spacious for two families with room for more comfortably. "
United States
michele I.
The price is HK$1,497
HK$5,130 total
includes taxes & fees
10 Feb - 11 Feb
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
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, (42 reviews)
"Great place!"
United States
Michael P.
The price is HK$1,610
HK$2,854 total
includes taxes & fees
10 Feb - 11 Feb
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
Dining

National Seashore/Updated/Game Room~Blue Pearl

National Seashore/Updated/Game Room~Blue Pearl
Eastham
10.0 out of 10, Exceptional, (8 reviews)
"Best rental we have stayed in on Cape, and we go every year. Exceptionally clean, comfortable. I can not say enough about it. Great location as well. What stood out the most was the high quality linens, as well as comfortable mattresses. It is very well kept with attention to detail. The grill and appliances were also of a higher quality and made it a pleasure to cook. Will absolutely stay at Blue Pearl again. "
United States
Nicole V.
The price is HK$1,198
HK$3,839 total
includes taxes & fees
10 Feb - 11 Feb
National Seashore/Updated/Game Room~Blue Pearl
Property grounds

Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
Eastham
10.0 out of 10, Exceptional, (18 reviews)
"Just a great location, and a very comfortable place. We loved the porch bed and chair. We are looking forward to returning."
United States
David B.
The price is HK$1,412
HK$3,780 total
includes taxes & fees
5 Mar - 6 Mar
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
Property grounds

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Dennis
8.8 out of 10, Excellent, (3 reviews)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
The price is HK$1,008
HK$2,544 total
includes taxes & fees
10 Feb - 11 Feb
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Interior

Pond House~Waterfront Oasis W/Jacuzzi Tub

Pond House~Waterfront Oasis W/Jacuzzi Tub
Eastham
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful spot ! House was clean and well equipped. "
United States
Cynthia P.
The price is HK$1,223
HK$3,967 total
includes taxes & fees
10 Feb - 11 Feb
Pond House~Waterfront Oasis W/Jacuzzi Tub
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

Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

10/10 Excellent
"Location was perfect, the staff in particular at the the check in desk were beyond friendly and helpful. Would 110% recommend and stay here again."
Zach 1-night trip
Posted 7 days ago
Anchor In Distinctive Waterfront Lodging

Find out more about South Dennis

Search for holiday rentals in South Dennis on Expedia! You can easily find your home rentals, villas, holiday apartments in South Dennis 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 Dennis!

Frequently asked questions

Can I find holiday rentals in South Dennis?

Yes, there are holiday rentals close to the most popular sights in South Dennis, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that South Dennis has to offer?

Cape Cod Farmhouse 1800s Charm: This highly rated holiday home rental in South Dennis offers a garden, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in South Dennis?

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

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 wider area.

What’s a holiday rental in South Dennis like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in South Dennis. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of 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 option for families.