South Dennis Holiday Rentals

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Holiday Rentals in South Dennis

Cozy Condo close to Sesuit

9.6 out of 10, Exceptional, (10)
"I loved cozy condo! Stayed here for 3 nights and it was the perfect stay. Everything was so clean and had everything you needed. I would totally stay again!!"
Cozy Condo close to Sesuit

Holly Tree Resort

3.0 star property
9.0 out of 10, Wonderful, (356)
"Nice rooms nice property great location"
Holly Tree Resort

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (286)
"All around a great place to stay!"
The price is NZ$441
includes taxes & fees
23 Oct - 24 Oct
Edgewater Beach Resort, a VRI resort

Brewster Green Resort

3.5 star property
9.4 out of 10, Exceptional, (113)
"Great centralized location for all of our travel destinations. Nantucket, Martha’s Vineyard, Hyannis, Chatham and Provincetown. Very clean and spacious accommodations. Highly recommend for families with small children. "
The price is NZ$391
includes taxes & fees
9 Oct - 10 Oct
Brewster Green Resort

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (336)
"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 "
The Club at New Seabury

Riverview Resort

3.0 star property
9.2 out of 10, Wonderful, (165)
"Everything was fine. "
The price is NZ$400
includes taxes & fees
22 Oct - 23 Oct
Riverview Resort

The Cove at Yarmouth by VRI Americas

3.5 star property
9.2 out of 10, Wonderful, (318)
"Clean, friendly staff and enjoyed the Loft Shack which is perfectly located adjacent to the outdoor pool. "
The Cove at Yarmouth by VRI Americas

Sea Mist Resort

3.0 star property
8.6 out of 10, Excellent, (137)
"Great resort with suites, very cosy with great amenities, close to excellent beach and shopping."
The price is NZ$476
includes taxes & fees
24 Oct - 25 Oct
Sea Mist Resort

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (132)
"Great stay."
Steps to the beach with an ocean view,

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (227)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!

*Oceanfront Beach Home*

10.0 out of 10, Exceptional, (82)
"Salt Eire was a lovely, cozy home. The beach views were phenomenal. The gas fireplace was perfect for a winter visit! The hosts supplied everything we could possibly need. It was a wonderful weekend getaway. "
*Oceanfront Beach Home*

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

10.0 out of 10, Exceptional, (38)
"Great place for a family get together "
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!

10.0 out of 10, Exceptional, (26)
"Heaven! Best spot on the end of cul de sac with stunning water views from all rooms, especially the outdoor deck. Clean, comfortable and nicely decorated. Great communication pre check-in and during stay. Did not want to leave! Look forward to future stay. "
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!

Cape Cod Bay Home w/ Deck + Private Beach Access

9.6 out of 10, Exceptional, (34)
"Stunning house! Beautifully appointed"
Cape Cod Bay Home w/ Deck + Private Beach Access

Steps to a private beach in a classic Cape cottage. Pet-friendly!

8.8 out of 10, Excellent, (26)
"Quaint, quiet on the off season, great outdoor shower with plenty of hot water! Perfect beach getaway! "
Steps to a private beach in a classic Cape cottage. Pet-friendly!

Cape Cod Estate: 2 Homes, Pool, Tennis Court, Game Barn and Bar, Sleeps 20

2.0 star property
10.0 out of 10, Exceptional, (9)
"This is such a wonderful property! Our group of 13 had plenty of space to hang out all together and also room to spread out. The owners are fantastic as well. We couldn't have asked for a better home away from home for our first trip to the Cape. Thank you!"
Cape Cod Estate: 2 Homes, Pool, Tennis Court, Game Barn and Bar, Sleeps 20

Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! [in Building A]

9.6 out of 10, Exceptional, (136)
"Great location by the beach. We loved staying here!"
The price is NZ$1,030
includes taxes & fees
13 Oct - 14 Oct
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! [in Building A]

THE BOAT HOUSE LOFT ~ CAPE COD'S MOST AFFORDABLE WATERFRONT ~ OFF SEASON RATES!

9.4 out of 10, Exceptional, (117)
"Exceptional location on Swan Lake. We enjoyed kayaking and biking every day. Our dog had a blast as well. Very gracious owner, gave us lots of good info."
THE BOAT HOUSE LOFT ~ CAPE COD'S MOST AFFORDABLE WATERFRONT ~ OFF SEASON RATES!

beachfront cottage at Chases Ocean Grove

9.6 out of 10, Exceptional, (33)
"Beautiful cottage within feet of the beach and can walk to almost anything you may need. Great communication with the owner. "
beachfront cottage at Chases Ocean Grove

Gorgeous Cottage steps from the beach

8.4 out of 10, Very good, (23)
"Location to town & beach was great. Cottage was listed accurate online. Communication with owner was welcoming. The cottage was a nice weekend get away."
Gorgeous Cottage steps from the 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 Dennis Hotel Reviews

Find out more about South Dennis

Find out more about South Dennis

Everything you need to know about South Dennis holiday rentals

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

South Dennis holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Dennis holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Dennis holiday rentals we have selected for you start as low as NZ$391 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Dennis rentals

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

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 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?

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

How many holiday rentals will I find in South Dennis?

Choose from 105 Expedia holiday rentals in South Dennis for a memorable holiday.

What can I see and do in South Dennis?

Explore the area and family-friendly sights such as Cape Cod Lavender Farm, or get out into nature at a spot like Cape Cod Rail Trail. 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.