South Dennis Holiday Rentals

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Holiday Rentals in South Dennis

Dennis Family Retreat: Private Pool, Sauna & Beach Fun!

The price is NZ$11,089
includes taxes & fees
13 July - 14 July
Dennis Family Retreat: Private Pool, Sauna & Beach Fun!

Near Mayflower! Pool & Hottub! Dogs OK! Slps 10!

2.0 star property
10.0 out of 10, Exceptional, (3)
"The house was very clean and spacious. Our group of ten had plenty of room to spread out. The home had great amenities to keep everyone happy. Our hosts were also responsive. We recommend! "
The price is NZ$3,820
includes taxes & fees
2 Aug - 3 Aug
Near Mayflower! Pool & Hottub! Dogs OK! Slps 10!

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

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"
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ

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

9.8 out of 10, Exceptional, (9)
"Our family had a wonderful time and truly enjoyed the home. The family voted and this is our favorite home out of the past 4 yrs of renting in the Cape! Beautiful, clean, and great location tucked in a quiet neighborhood but close to it all."
NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH

3 Mi to Beach: Historic Farmhouse on Cape Cod!

3 Mi to Beach: Historic Farmhouse on Cape Cod!

Newly renovated home near beaches with fire pit, AC, electric vehicle charging

10.0 out of 10, Exceptional, (2)
"Nina’s place was the perfect spot for our quick family beach getaway! From the moment we arrived, our little one felt right at home. The space is beautifully designed with a calm, beachy feel and so thoughtfully laid out—especially for families with young kids.Everything we needed for a smooth and relaxing stay was already there: a cozy floor bed, a nightlight, and a sound machine made bedtime easy, and kid-friendly plates, trays, and utensils were all set up at just the right height. The...
Newly renovated home near beaches with fire pit, AC, electric vehicle charging

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, (44)
"Our family had a great experience. We would highly recommend this property"
The price is NZ$1,456
includes taxes & fees
15 July - 16 July
Chatham 3 Bedroom/2 Bath Retreat

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

9.6 out of 10, Exceptional, (95)
"Great location"
The price is NZ$1,026
includes taxes & fees
9 July - 10 July
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quiet South Chatham 2-Bedroom House, Close To Beaches

9.4 out of 10, Exceptional, (3)
"We had a great stay. The location was perfect for visiting family, beach, and downtown Chatham. The house was spotless. We wouldn't hesitate to stay again!"
The price is NZ$1,163
includes taxes & fees
18 July - 19 July
Quiet South Chatham 2-Bedroom House, Close To Beaches

Jaws Nest~Dog Friendly~Oceanside Beauty

The price is NZ$1,500
includes taxes & fees
21 July - 22 July
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 NZ$2,559
includes taxes & fees
14 July - 15 July
Beachside Bliss: Modern Comfort Steps from Scenic Trails, Sleeps 10!

National Seashore/Updated/Game Room~Blue Pearl

10.0 out of 10, Exceptional, (7)
"This house is like brand new and so clean. Well stocked with basics like glasses, dishes, pots and pans. The owner is very responsive and helpful!!"
The price is NZ$1,289
includes taxes & fees
30 July - 31 July
National Seashore/Updated/Game Room~Blue Pearl

Newly Renovated Guest House For 10 Near The Beach!

10.0 out of 10, Exceptional, (4)
"Space was great for our family/friends gathering Location perfect for events we were attending on the Cape"
The price is NZ$2,035
includes taxes & fees
8 July - 9 July
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, (13)
"Property was clean and as described in the listing, owner was communicative and easy to check in"
The price is NZ$5,142
includes taxes & fees
8 July - 9 July
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 NZ$1,764
includes taxes & fees
7 Aug - 8 Aug
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 NZ$1,243
includes taxes & fees
24 July - 25 July
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 NZ$2,910
includes taxes & fees
15 July - 16 July
Eastham is Cape Cod’s best kept secret!

Gray Whale - 3 bedrm/2 bath/gameroom

The price is NZ$1,461
includes taxes & fees
8 July - 9 July
Gray Whale - 3 bedrm/2 bath/gameroom
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?

Cape Cod Getaway – 3BR Sandwich Home, Walk to Beach, AC & WiFi: This holiday home rental outside of South Dennis offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals will I find in South Dennis?

Choose from 112 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.