South Dennis Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for South Dennis vacation rentals

Private beach nearby, beach bar
The Club at New Seabury

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.
The Club at New Seabury
3 bedrooms, desk
Coastal Haven in West Dennis -15

Vacation Home in West Dennis

Coastal Haven in West Dennis -15
2.0 star property
The price is P19,437
P47,120 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Coastal Haven in West Dennis -15
Beach nearby
The Cove at Yarmouth by Westgate Resorts

Aparthotel in West Yarmouth

The Cove at Yarmouth by Westgate Resorts
3.0 star property
9.2 out of 10, Wonderful, (244)
"The staff are amazing! Love the amenities - the pool, recreation center, activities for the kids such as windchime arts and crafts. The arcade is always a hit. The Loft makes it so easy to not have to stress about a place to go to for dinner. The Cove is a great place for everyone! "
United States
Lauren
The price is P7,569
P8,662 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Cove at Yarmouth by Westgate Resorts
Shared kitchen
Sal's Place

Vacation Home in Hyannis

Sal's Place
2.0 star property
The price is P16,449
P25,876 total
includes taxes & fees
Dec 30 - Dec 31
Sal's Place
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Dennis Hotel Reviews

Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"After initial hiccup with the room which was taken care off - room was beautiful as well as the Inn. Best location on Main Street in Chatham. "
Emma 1-night trip
Posted 6 days ago
Chatham Wayside Inn

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:

  • View our selection of featured holiday rentals in South Dennis
  • Use the map to find apartments and other holiday homes in the South Dennis neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in South Dennis while they last

Look no further and take a look at our great range of rental properties in South Dennis!

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.

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.