South Dennis holiday lettings

We found 1,363 holiday rentals — enter your dates for availability

Select from 84 homes, 11 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.

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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)
  • Cape Cod Baseball & Bumper Boats (4.3 mi / 6.9 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)
  • 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)
  • Bayview Beach (3.8 mi / 6.1 km)
  • Mayflower Beach (3.9 mi / 6.3 km)
  • Grays Beach (4.3 mi / 6.9 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 considering a holiday rental in South Dennis, Massachusetts, the area around Bass River is an excellent choice. This picturesque neighbourhood offers a charming mix of coastal beauty and local amenities. Visitors can enjoy the scenic Bass River, superb for kayaking and paddleboarding, or take leisurely strolls along the river's edge.

Another appealing aspect of South Dennis is its proximity to the beautiful beaches of Cape Cod, such as West Dennis Beach, which is just a short drive away. This family-friendly beach is renowned for its soft sands and gentle waves, making it an ideal spot for a relaxing day by the sea.

In terms of holiday rentals, South Dennis features a variety of properties, ranging from quaint cottages to spacious family homes, allowing for diverse accommodation options to suit different preferences.
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, travellers should explore the area surrounding the scenic beaches along Cape Cod. The neighbourhood near South Village Beach is particularly appealing, offering a selection of charming holiday rentals that provide easy access to soft sands and refreshing waters. Many of these properties come equipped with amenities such as outdoor patios, barbecue grills, and fully equipped kitchens, which are superb for families looking to enjoy the coastal lifestyle.

Additionally, the nearby location of Bass River offers more options, where you can find beachfront homes with private decks and views of the river, ideal for watching the sunset. These rentals often include amenities like kayaks or paddleboards for guests to use, enhancing the experience of being close to the water.

In South Dennis, visitors can also explore local shops and restaurants, adding to the convenience of their stay. The area is well-positioned for exploring Cape Cod's natural beauty, with nearby walking trails and parks, making it a great choice for those seeking both relaxation and outdoor activities.
What is the most popular type of holiday rental accomodation in South Dennis?
In South Dennis, holiday houses are the most popular type of holiday rental, with around 356 available throughout the area. These properties are often situated in tranquil neighbourhoods, providing a spacious and comfortable environment ideal for families or groups. Most holiday houses come equipped with full kitchens, multiple bedrooms, and outdoor spaces such as decks or gardens, great for enjoying the pleasant Massachusetts weather. Additionally, there are approximately 36 cottages, which offer a charming and rustic experience, typically featuring cozy interiors and often located near scenic spots like beaches or nature reserves.
Are there any family house rentals in South Dennis?
In South Dennis, Massachusetts, there are numerous family-friendly house rentals available, with around 71 options to choose from. This charming locale is a wonderful choice for families, offering spacious homes in close proximity to both the beautiful beaches of Cape Cod and various local attractions. Many properties feature amenities such as full kitchens, allowing for easy meal preparation, as well as outdoor spaces where children can play and families can gather.

Visitors to South Dennis can enjoy nearby points of interest including the scenic Cape Cod Rail Trail, great for cycling and walking, and the lovely beaches at Dennis Port, ideal for a day of sun and sand. Additionally, families might appreciate the convenience of outdoor showers and barbeque grills that many rentals offer, making for a relaxed stay.
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 and hot tubs, with around 10 options to choose from. This charming area on Cape Cod is known for its picturesque landscapes, making it a delightful destination for travellers seeking relaxation.

Rentals with pools often include spacious outdoor areas for sunbathing and entertaining, as well as amenities such as fully equipped kitchens and comfortable living spaces. Many properties may also offer hot tubs, superb for unwinding after a day of exploring the nearby beaches or local attractions.

The neighbourhood is close to various recreational opportunities, including beautiful parks and nature trails, enhancing the appeal of these accommodations.
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, providing a variety of options for travellers looking to enjoy a getaway with their furry companions. Many of these properties come equipped with amenities such as spacious backyards, outdoor seating areas, and fully equipped kitchens, making them ideal for families or groups.

The area is conveniently located near several pet-friendly points of interest, including local parks and beaches where pets are welcome. For instance, the nearby Bass River Beach offers a beautiful setting for walks, and the surrounding areas have trails suited for leisurely strolls with pets. Additionally, some holiday rentals may include features like dog beds and bowls to ensure a comfortable stay for your pets.
Are there any remote work holiday rentals in South Dennis?
In South Dennis, Massachusetts, there is a substantial selection of remote work holiday rentals, with around 392 options available. This charming town, situated on Cape Cod, offers a peaceful environment that is conducive to productivity. Many of these properties come equipped with essential amenities such as free Wi-Fi, ensuring that guests can stay connected while enjoying their getaway.

Travellers can expect a variety of accommodations, including cottages and homes with dedicated workspaces, comfortable seating, and quiet surroundings ideal for remote work. Additionally, properties often feature fully equipped kitchens, allowing for convenient meal preparation during longer stays.

The area is also known for its beautiful beaches, scenic nature trails, and proximity to attractions such as the Cape Cod Rail Trail, great for unwinding after a day of work. 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 rental amenities include kitchens, which allow guests to prepare their own meals, and outdoor spaces like decks or patios for enjoying the pleasant surroundings. Many rentals also feature coffee and tea makers, superb for those who appreciate a morning brew. Onsite parking is commonly available, providing convenience for travellers with vehicles.
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 peak season from June to August, with July being the most popular month. This vibrant period attracts families and beach enthusiasts eager to enjoy the beautiful Cape Cod coastline, where the warm temperatures, typically ranging from 20 to 30 degrees Celsius, create great conditions for outdoor activities and relaxation by the sea.

In addition to sun-soaked days at the beach, visitors can take advantage of the numerous local events and festivals that occur during the summer, providing a rich cultural experience. With families flocking to the area, the atmosphere is lively, making it an ideal time for social gatherings and enjoying the community spirit.

For those looking for a more budget-friendly option, consider visiting in October. This month offers a quieter experience with beautiful autumn scenery, as the foliage begins to change, creating picturesque landscapes great for leisurely walks or scenic drives. Plus, the mild weather can still allow for enjoyable outdoor activities, making it a great time to explore the charming local shops and restaurants without the summer crowds.
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.
What are the top attractions in South Dennis?
In South Dennis, visitors can enjoy a variety of attractions that highlight the charm of Cape Cod. One of the main draws is the picturesque Cape Cod Rail Trail, superb for cycling and walking, which offers scenic views of the region's natural beauty. The nearby Dennis Pond is an excellent spot for swimming and fishing, providing a peaceful retreat for families and nature lovers alike.

The area is also close to the historic Dennis Village, where travellers can explore quaint shops and enjoy local dining options. For those interested in history, the Cape Cod Museum of Natural History in nearby Brewster offers fascinating exhibits and nature trails that allow for a deeper understanding of the local ecology.

Additionally, visitors can easily reach the beautiful beaches of Cape Cod, such as Mayflower Beach, known for its soft sands and stunning sunsets, making it a superb destination for beachgoers looking to relax.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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