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Top Holiday Rentals in South Dennis

July 7-19 still open as well two weeks open in August so book soon.

9.8 out of 10, Exceptional, (28)
"Host was very welcoming and helpful. The house is located on a quiet dead end road and cozy interior"
July 7-19 still open as well two weeks open in August so book soon.

3 Mi to Beach: Historic Farmhouse on Cape Cod!

The price is £546
includes taxes & fees
6 Jul - 7 Jul
3 Mi to Beach: Historic Farmhouse on Cape Cod!

NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH

9.8 out of 10, Exceptional, (9)
"We had a great vacation & experience at this rental house! It was clean, had everything we needed and is located in a quiet neighborhood with easy access to the highway."
The price is £520
includes taxes & fees
7 Jul - 8 Jul
NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH

Modern & Comfy Family Oasis ~ Games, Backyard, BBQ

8.0 out of 10, Very good, (3)
"Our family stayed here for a quick Cape get away at the end of summer. The host was responsive and kind. The property was in a great location with a kitchen that had everything we needed. Great spot"
The price is £379
includes taxes & fees
2 Jul - 3 Jul
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ

New Home in the heart of South Dennis

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great location - easy accesst o RT. 6 and various beaches. Host was very accommodating and easy to communicate with. Would definitely stay again."
New Home in the heart of South Dennis

Beachfront - Sauna - Screened Patio - 2 King Beds - Dogs Encouraged!

10.0 out of 10, Exceptional, (2)
"This is definitely one of our better stays and it really felt like a home away from home. Cozy, with a beautiful lakefront view and incredible amenities, I highly recommend staying here."
The price is £1,037
includes taxes & fees
25 Jul - 26 Jul
Beachfront - Sauna - Screened Patio - 2 King Beds - Dogs Encouraged!

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Chatham 3 Bedroom/2 Bath Retreat

9.0 out of 10, Wonderful, (43)
"Our family had a great experience. We would highly recommend this property"
The price is £678
includes taxes & fees
15 Jul - 16 Jul
Chatham 3 Bedroom/2 Bath Retreat

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

9.6 out of 10, Exceptional, (94)
"Great location"
The price is £602
includes taxes & fees
9 Jul - 10 Jul
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Jaws Nest~Dog Friendly~Oceanside Beauty

The price is £499
includes taxes & fees
7 Jul - 8 Jul
Jaws Nest~Dog Friendly~Oceanside Beauty

Beachside Bliss: Modern Comfort Steps from Scenic Trails, Sleeps 10!

9.0 out of 10, Wonderful, (2)
"Nice, clean property. We all slept comfortably and had a great, fun stay at a quiet location. The hosts were very informative, kind and communicative. We will definitely be staying here in the future. Thank you again for a pleasurable experience from beginning to end!"
The price is £1,015
includes taxes & fees
29 Jun - 30 Jun
Beachside Bliss: Modern Comfort Steps from Scenic Trails, Sleeps 10!

Newly Renovated Guest House For 10 Near The Beach!

10.0 out of 10, Exceptional, (3)
"Our stay in Harwich was exceptionally comfortable and convenient, ideal for a larger group or family. The multiple spacious bedrooms provided ample private space, complemented by the practical 2.5 baths. We particularly appreciated the expansive backyard, perfect for outdoor activities, and the generous parking—the driveway easily accommodated four cars, with extra space alongside for two more—making arrivals and departures stress-free. This property truly felt like a home away from home,...
The price is £814
includes taxes & fees
30 Jun - 1 Jul
Newly Renovated Guest House For 10 Near The Beach!

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

10.0 out of 10, Exceptional, (12)
"Property was clean and as described in the listing, owner was communicative and easy to check in"
The price is £2,336
includes taxes & fees
29 Jun - 30 Jun
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge

Cape Cod Sunscape.

10.0 out of 10, Exceptional, (15)
"The property was very nice and the host was very responsive. Would definitely stay there again."
The price is £752
includes taxes & fees
14 Jul - 15 Jul
Cape Cod Sunscape.

Pond House~Waterfront Oasis W/Jacuzzi Tub

10.0 out of 10, Exceptional, (6)
"We had a great stay at the Pond House. Everything was clean and functional. Beds were extremely comfortable! Nice spot for a two night stay."
The price is £448
includes taxes & fees
2 Jul - 3 Jul
Pond House~Waterfront Oasis W/Jacuzzi Tub

Eastham is Cape Cod’s best kept secret!

9.8 out of 10, Exceptional, (7)
"This house is beautifully decorated, especially the main floor. The screened-in porch was so relaxing. We all enjoyed the pool and the lovely patio area surrounding it. The beds were all uncomfortable. The sheets on one of the beds were very dirty upon arrival. "
The price is £1,314
includes taxes & fees
15 Jul - 16 Jul
Eastham is Cape Cod’s best kept secret!

Gray Whale - 3 bedrm/2 bath/gameroom

The price is £654
includes taxes & fees
29 Jun - 30 Jun
Gray Whale - 3 bedrm/2 bath/gameroom

Driftmoor~Dog Frndly 3bd/2 bth~Luxe

The price is £535
includes taxes & fees
29 Jun - 30 Jun
Driftmoor~Dog Frndly 3bd/2 bth~Luxe

New! Sandy Point-Private beach/Dog Friendly

The price is £580
includes taxes & fees
30 Jun - 1 Jul
New! Sandy Point-Private beach/Dog Friendly

Beachfront~Seaside Sea-duction-Dog Friendly

10.0 out of 10, Exceptional, (7)
"Quick winter getaway with another couple celebrating a birthday, also. Everything was perfect. The view was gorgeous.The house was adorable, even in the dead of winter.Can't even imagine how great it would be in the summertime."
The price is £1,256
includes taxes & fees
12 Jul - 13 Jul
Beachfront~Seaside Sea-duction-Dog Friendly
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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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?

Walk To Beach - Comfortable 2BR Cottage: This holiday home rental outside of South Dennis is located near the beach, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a private garden.

How many holiday rentals will I find in South Dennis?

Choose from 111 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 Cape Playhouse 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.