South Dennis holiday lettings

We found 1,372 holiday rentals — enter your dates for availability

Select from 107 homes, 13 cottages and other holiday rentals in South Dennis to find one that's perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and a washer and dryer. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - South Dennis

Showing deals for:9 Jan - 16 Jan

Image gallery for ⭐️FABULOUS-WATERFRONT⭐️3bdrm 2bth. Kayaks & Firepit⭐️

Waterfront on Follins Bay. Sit back on this beautiful stone patio and enjoy!
10 out of 10, Exceptional, (94 reviews)
Exceptional
(94 reviews)

⭐️FABULOUS-WATERFRONT⭐️3bdrm 2bth. Kayaks & Firepit⭐️

Yarmouth Port, MA

11% off
Price is £2,217
for 7 nights, 1 cottage
£317 per night
includes taxes & fees
⭐️FABULOUS-WATERFRONT⭐️3bdrm 2bth. Kayaks & Firepit⭐️

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Find out more about South Dennis

Find out more about South Dennis

Book a holiday rental for your South Dennis getaway

Learn about the unique charm of South Dennis with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around South Dennis

Are you searching for attractions to visit while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes South Dennis a fun place to get away to. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Cape Cod Lavender Farm (4.1 mi / 6.5 km)
  • Ocean Edge Golf Club (6 mi / 9.6 km)
  • Cape Cod Inflatable Park (6.2 mi / 10 km)
  • Cape Codder Water Park (8.7 mi / 14 km)
  • Eden Hand Arts (2 mi / 3.2 km)
  • The Club at Yarmouthport (3 mi / 4.9 km)

Exploring the natural landscape of South Dennis

Whether you're an active traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in South Dennis. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Cape Cod Rail Trail (1.8 mi / 3 km)
  • Corporation Beach (2.8 mi / 4.5 km)
  • Paine's Creek Beach (3.7 mi / 5.9 km)
  • Mayflower Beach (3.9 mi / 6.3 km)
  • Grays Beach (4.3 mi / 6.9 km)
  • Swan Pond River (4.5 mi / 7.2 km)

Transport options to and around South Dennis

Fly into Hyannis, MA (HYA-Barnstable Municipal), the closest airport, located 7.7 mi (12.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Provincetown, MA (PVC-Provincetown Municipal), which is 25.1 mi (40.3 km) away.

Frequently asked questions

What is the best area to stay in South Dennis when booking a holiday rental?
When looking to book a holiday rental in South Dennis, Massachusetts, a wonderful area to consider is the vicinity of Bass River. This charming neighbourhood is not only picturesque but also offers easy access to some of the region's most delightful attractions. One of the highlights is the Bass River itself, where you can enjoy various water activities such as kayaking and paddleboarding. The nearby Smuggler's Beach is superb for a relaxing day by the sea, providing a lovely spot for sunbathing and swimming.

In terms of rental properties, Bass River has a range of options, with numerous charming cottages and homes available, suiting different group sizes and budgets. This area is particularly appealing for those looking for a balance of tranquillity and convenience, as it is close to local shops and restaurants, ensuring that everything you need is within easy reach.
How much does it cost to rent a holiday home in South Dennis?
Prices for holiday rentals in South Dennis vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in South Dennis to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for South Dennis holiday house rentals?
You can find great discounts on house rentals in South Dennis on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in South Dennis?
For renting a beach house in South Dennis, Massachusetts, the area around the northern shores of Bass River is particularly appealing. This stretch offers a range of holiday rentals that provide easy access to sandy beaches and calm waters, superb for families and groups looking to enjoy a seaside getaway. Many properties in this neighbourhood come equipped with desirable amenities such as outdoor decks, BBQ grills, and spacious living areas, creating an ideal environment for relaxation and entertaining.

The nearby West Dennis Beach is another fantastic option, known for its picturesque views and gentle surf. Here, travellers can find charming cottages and larger homes that often feature amenities like private yards, outdoor showers, and beach gear provided for guest convenience. The proximity to local shops and restaurants adds to the appeal, allowing visitors to enjoy fresh seafood and other local fare without straying far from their accommodations.
What is the most popular type of holiday rental accomodation in South Dennis?
In South Dennis, holiday houses are the most popular type of rental, with around 99 available throughout the area. These properties are typically situated in charming neighbourhoods and offer a cozy feel, making them ideal for families or groups. Most holiday houses feature multiple bedrooms, fully equipped kitchens, spacious living areas, and often outdoor spaces such as decks or patios for relaxing after a day at the beach or exploring local attractions. Additionally, there are about 11 cottages available, which provide a cozier, more rustic option, often located in quieter spots with lovely views. While apartments are less common, several can still be found, offering similar amenities.
Are there any family house rentals in South Dennis?
In South Dennis, Massachusetts, there are numerous family-friendly house rentals available—about 82 options throughout the area. This charming locale, situated near the beautiful Cape Cod coastline, is ideal for families looking to enjoy a seaside getaway. Many of these homes feature spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely.
Can I rent a holiday home with a pool or hot tub in South Dennis?
In South Dennis, there are several holiday homes available for rent that feature pools or hot tubs. This charming Cape Cod town offers a delightful mix of coastal charm and relaxation. Many properties come equipped with private swimming pools, outdoor hot tubs, and spacious decks, ideal for enjoying the pleasant summer weather.
Can I find long-stay holiday rentals in South Dennis?
A long-stay holiday rental in South Dennis is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in South Dennis?
In South Dennis, there are numerous pet-friendly house rentals available, with around 36 options to choose from. This charming coastal town offers a variety of accommodations, ranging from cosy cottages to spacious family homes, many of which come equipped with amenities such as outdoor patios, fully stocked kitchens, and laundry facilities. These features make them ideal for families or groups looking to enjoy a relaxing getaway with their furry companions.
Are there any remote work holiday rentals in South Dennis?
In South Dennis, there are plenty of options for remote work holiday rentals, with around 108 properties available. This charming area on Cape Cod offers a peaceful setting for those looking to combine work and leisure. Many rentals come equipped with essential amenities such as Wi-Fi, dedicated workspaces including desks and ergonomic chairs, and additional features like a laptop-friendly workspace and even a computer monitor in some cases. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any South Dennis holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in South Dennis with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in South Dennis?
In South Dennis, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also feature patios, which provide a lovely outdoor space for relaxing or dining al fresco. Refrigerators are standard in the rentals, along with microwaves and stovetops, ensuring that guests have all the necessary conveniences for a comfortable stay.
When is the best time to visit South Dennis for a holiday rental?
The best time to visit South Dennis for a holiday rental is during the summer months, specifically from June to August. This peak season draws families and beach enthusiasts eager to soak up the sun along Cape Cod's beautiful shores. With warm temperatures averaging around 26°C, it's great for enjoying outdoor activities such as sailing, fishing, and exploring the charming local shops.

July is particularly popular, bustling with holidaymakers who flock to the area for its vibrant atmosphere and variety of events. You'll find plenty of opportunities for relaxation on the sandy beaches or taking leisurely strolls through picturesque towns, all while benefitting from the lively summer spirit.

If you're looking for a more budget-friendly option, consider visiting in October. This month offers a quieter experience, allowing you to enjoy the stunning autumn foliage that blankets the region in vibrant colours. With fewer crowds, it's a wonderful time for scenic walks and enjoying local cuisine at a more relaxed pace.
How early should I book a South Dennis holiday rental?
Book your South Dennis holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my South Dennis home rental booking on Vrbo?
To find South Dennis holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the South Dennis holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

More holiday ideas

More holiday ideas