Dennis holiday lettings

We found 4,336 holiday rentals — enter your dates for availability
Select from 115 homes, 10 cottages and other holiday rentals in Dennis to find one that's perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a pool. What you'll find is a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Dennis

Showing deals for:9 Oct - 16 Oct

Image gallery for Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach

The private back yard is dominated by a dramatic 60 ft. oblong swimming pool
10 out of 10, Exceptional, (78 reviews)
Exceptional
(78 reviews)

Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach

Orleans

8% off
Price is £10,807
for 7 nights, 1 home
£1,544 per night
includes taxes & fees
Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach

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Why visit Dennis

  • Beautiful Beaches: Dennis boasts stunning beaches like West Dennis Beach, perfect for family fun and relaxation under the sun.
  • Scenic Lighthouses: Explore picturesque lighthouses that offer breathtaking views and a glimpse into the town's maritime history.
  • Outdoor Activities: Enjoy a range of outdoor pursuits including surfing, cycling along scenic trails, and tranquil walks along the coastline.
  • Rich Cultural Heritage: Discover historic houses and local museums that showcase Dennis's charming history and culture.
  • Charming Accommodation: Choose from cosy cottages, private vacation homes, and modern condos for a delightful stay in this coastal haven.

Popular types of accommodation in Dennis

Welcome to Dennis, Massachusetts, a charming coastal town brimming with natural beauty and delightful experiences. Known for its stunning beaches, picturesque lighthouses, and scenic bike trails, Dennis offers a perfect retreat for nature lovers and families alike. When it comes to accommodation, you can choose from an array of options, including houses, cosy cottages, and modern condos, ensuring a comfortable stay while you explore all that this enchanting destination has to offer.

  • Houses: The most sought-after choice for holidaymakers in Dennis, offering spacious and comfortable living spaces for families and groups.
  • Cottages: Charming and quaint, these cosy retreats provide a perfect blend of comfort and character, ideal for a relaxing getaway.
  • Condos: Modern and convenient, these stylish accommodations offer great amenities and are often situated in prime locations.
  • Apartments: A practical option for visitors, providing self-catering facilities in close proximity to local attractions.
  • Cabins: Rustic and inviting, these lodgings provide a unique experience surrounded by nature, perfect for a peaceful escape.**

Top attractions in and around Dennis

Dennis, Massachusetts, is a charming coastal town perfect for beach lovers and outdoor enthusiasts. Visitors can enjoy stunning beaches, explore scenic harbours, and delve into the town's rich history through its historic houses. With a blend of culture and natural beauty, Dennis offers a variety of activities that cater to families, couples, and solo travellers alike, ensuring a delightful experience for all who visit.

  • Mayflower Beach: Renowned for its stunning sandy shores, Mayflower Beach offers a tranquil escape with gentle waves and picturesque sunsets. Perfect for sunbathing, picnicking, and beachcombing, it’s an ideal spot for families and nature lovers alike.
  • Hyannis Harbor: While not in Dennis, Hyannis Harbour is a scenic gateway for boat excursions and ferry services. The vibrant atmosphere features beautiful views and opportunities for whale watching or simply enjoying the coastal charm.
  • Main Street Hyannis: A lively area filled with shops, eateries, and family-friendly attractions, it’s perfect for leisurely strolls, dining, and exploring local culture and history.

Things to do recommended for couples

Discover the charm of Dennis with a romantic beach stroll at Mayflower Beach, followed by a sunset picnic. Explore the quaint shops in Dennis Village and enjoy a candlelit dinner at a local seafood restaurant, creating unforgettable memories together amidst the stunning Cape Cod scenery.

Things to do recommended for families

Families visiting Dennis, Massachusetts can enjoy a delightful day at the Cape Cod Museum of Natural History, exploring its interactive exhibits. Additionally, they can relax on the sandy beaches or partake in a fun-filled whale-watching tour, creating wonderful memories together.

Things to do recommended for groups

Experience the thrill of the Adventure Park at Heritage Museums & Gardens, a zipline and ropes course located 26km from Dennis. Enjoy the outdoor vibes and challenge your group with exciting activities that foster teamwork and fun.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Dennis

When travelling with a group, family, pets, or planning for extended stays, it's essential to prioritise your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Dennis with a group: Think about how many bedrooms you'll require, along with additional features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options, and much more, on Vrbo.
  • Traveling to Dennis with young kids: Travelling with young children can be quite a task. It's essential to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can be beneficial.
  • Taking your pets with you to Dennis: For many, a family holiday wouldn’t be the same without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Dennis: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include preferences such as a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Dennis

Discover the charm of Dennis, Massachusetts, a delightful destination perfect for beach lovers and outdoor enthusiasts. Enjoy the sun-soaked shores of Dennis beaches, such as West Dennis Beach, ideal for family-friendly fun and relaxation. East Dennis offers picturesque scenery and a quaint atmosphere, while the town itself is rich in culture. Experience the thrill of surfing in Dennis or unwind with romantic excursions along its scenic coastline. This captivating town promises a memorable vacation filled with diverse vibes.

  • Cape Cod: Located a mere 8km from Dennis, Cape Cod is a picturesque destination famed for its stunning beaches and scenic landscapes. Visitors flock to this region for a quintessential outdoor experience, where activities abound from water parks to golf courses. The area boasts a variety of family-friendly beaches and charming local landmarks, making it an ideal spot for relaxation and exploration. With its captivating coastal charm, Cape Cod offers ample opportunities for adventure and leisure alike.
  • Hyannis: Approximately 11km away from Dennis, Hyannis is a vibrant city known for its lively atmosphere and beautiful seashores. This bustling hub attracts tourists seeking a blend of beach relaxation and cultural experiences, including theatres and music concerts. The local beaches provide a family-friendly environment, while the scenic views of the cape enhance the overall experience. Whether you’re soaking up the sun or enjoying a captivating show, Hyannis promises an enjoyable visit.
  • South Yarmouth: Conveniently situated just 6km from Dennis, South Yarmouth is a welcoming city that captures the essence of Cape Cod. It offers a perfect blend of natural beauty and recreational activities, including water parks and playgrounds, making it a great spot for families. The area is dotted with lovely beaches and scenic landscapes, inviting visitors to unwind and enjoy the outdoors. South Yarmouth's charm and accessibility make it a delightful addition to your travel itinerary.

Best time to go to Dennis

If you're planning a trip to Dennis, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January34.7°F (1.5°C)Light RainMostly SunnyAverageSlightly Low
February34.9°F (1.6°C)Light RainMostly CloudyAverageSlightly Low
March38.5°F (3.6°C)Light RainMostly SunnyAverageSlightly Low
April45.9°F (7.7°C)Light RainMostly SunnyAverageAverage
May54.1°F (12.3°C)Light RainMostly SunnyAverageAverage
June62.6°F (17.0°C)Light RainMostly SunnyHighSlightly High
July70.5°F (21.4°C)Light RainMostly SunnyHighSlightly High
August70.9°F (21.6°C)Light RainMostly SunnyHighSlightly High
September65.8°F (18.8°C)Light RainMostly SunnyAverageAverage
October57.7°F (14.3°C)Light RainMostly SunnyLowAverage
November48.2°F (9.0°C)Light RainMostly SunnyLowAverage
December40.8°F (4.9°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, extending your stay often results in substantial savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform for planning your journeys, allowing you to resume where you last left off or to view and organise your travel arrangements. You can find properties that you’ve saved or booked neatly organised under Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Explore the beachside setting in Dennis

Enjoy the culture and other features of Dennis. Travellers to this scenic city praise the seafood restaurants, beaches and fishing. Cape Cod Beaches and Cape Cod National Seashore are just a couple of the must-see attractions in the area. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Dennis

Do you want to find attractions to see while you're in town? Venture out of your holiday home and experience everything that makes Dennis a fun place to get away to. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Cape Cod Inflatable Park (6.2 mi / 10 km)
  • Cape Cod Lavender Farm (6.6 mi / 10.6 km)
  • Cape Cod Baseball & Bumper Boats (6.8 mi / 10.9 km)
  • Cape Codder Water Park (7.4 mi / 11.9 km)
  • Ocean Edge Golf Club (7.4 mi / 11.9 km)
  • The Club at Yarmouthport (1.7 mi / 2.8 km)

Exploring the natural landscape of Dennis

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Dennis is a great place to get outside. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Cape Cod Beaches (8.1 mi / 13 km)
  • Bayview Beach (1.3 mi / 2.1 km)
  • Corporation Beach (1.3 mi / 2.1 km)
  • Mayflower Beach (1.4 mi / 2.3 km)
  • Grays Beach (2.3 mi / 3.7 km)
  • Cape Cod Rail Trail (3.8 mi / 6.2 km)

Transport to and around Dennis

The nearest airport is in Hyannis, MA (HYA-Barnstable Municipal), located 6.7 mi (10.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Provincetown, MA (PVC-Provincetown Municipal), which is 23.6 mi (38 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Dennis?
Prices for holiday rentals in 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 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 Dennis holiday house rentals?
You can find great discounts on house rentals in 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 Dennis?
For renting a beach house in Dennis, you should explore the picturesque stretch along the Cape Cod coastline, particularly around Dennis Port and West Dennis. Dennis Port offers a variety of charming beach houses that provide easy access to sandy shores and quaint local shops. Many of these properties come equipped with amenities like outdoor decks, private gardens, and fully stocked kitchens, making them great for families or groups looking to enjoy a coastal retreat.

In West Dennis, you'll find lovely homes close to the beach, often featuring amenities such as outdoor showers, barbecues, and spacious living areas for relaxing after a day in the sun. The stunning West Dennis Beach is known for its gentle waves, ideal for swimming and family activities, while also being a great spot for sunset views.

Additionally, the area provides opportunities for recreational activities like kayaking and paddleboarding, with local rental shops nearby. Visitors can also explore the scenic Cape Cod Rail Trail for biking or walking, which runs through the area, adding to the charm and appeal of renting a beach house in Dennis.
What is the most popular type of holiday rental accomodation in Dennis?
In Dennis, holiday houses are the most prevalent type of holiday rental, with around 432 available throughout the area. These spacious properties are typically located in family-friendly neighbourhoods close to the beautiful beaches and scenic spots, making them ideal for summer getaways. Most holiday houses come equipped with full kitchens, multiple bedrooms, and outdoor spaces such as decks or gardens, providing ample room for families or groups to relax and enjoy their stay. Additionally, there are around 36 charming cottages and several condos and apartments, which offer a more compact living option while still featuring essential amenities like kitchen facilities and comfortable living areas.
Are there any family house rentals in Dennis?
In Dennis, Massachusetts, there are numerous family-friendly house rentals available, with around 93 options to choose from. This charming area is known for its beautiful beaches and family-friendly attractions. Many of these homes offer spacious living areas, well-equipped kitchens, and outdoor patios or decks, superb for barbecues and family gatherings.

Visitors will find themselves close to local highlights such as the Cape Cod Museum of Natural History, where kids can learn about the region's wildlife, and the scenic beaches of Dennis, ideal for swimming and sandcastle building. The nearby Dennis Village features quaint shops and restaurants, adding to the convenience of family outings.
Can I rent a holiday home with a pool or hot tub in Dennis?
In Dennis, Massachusetts, there are several holiday homes available for rent that feature pools or hot tubs, with around 16 options to choose from. This charming town, located on Cape Cod, offers a variety of neighbourhoods where these properties can be found, including the picturesque Dennis Port area, which is known for its beautiful beaches and family-friendly atmosphere, and the more tranquil East Dennis, which provides a serene setting for relaxation.

Travellers can expect a range of amenities in these rentals, including private swimming pools, hot tubs, and spacious outdoor decks great for entertaining or unwinding after a day of exploring. Many properties also come with fully equipped kitchens, allowing for convenient meal preparation, as well as comfortable living spaces and access to nearby beaches.
Can I find long-stay holiday rentals in Dennis?
A long-stay holiday rental in 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 Dennis?
In Dennis, Massachusetts, there are numerous pet-friendly house rentals available, with around 30 options to choose from. This charming coastal town offers a variety of holiday homes that typically come equipped with amenities such as fully stocked kitchens, outdoor patios, and spacious living areas, making them suitable for families and groups travelling with pets.

Many of these rentals are conveniently located near beautiful beaches, including the popular Sea Street Beach and Mayflower Beach, which are ideal for long walks with your furry companions. Additionally, the surrounding area features various pet-friendly parks and nature trails, allowing for enjoyable outdoor experiences. Dennis also boasts a welcoming community with pet-friendly dining options, enhancing the overall experience for travellers with pets.
Are there any remote work holiday rentals in Dennis?
In Dennis, Massachusetts, there is a substantial selection of remote work holiday rentals, with around 444 options available. This charming area, situated on Cape Cod, is great for those looking to combine work and leisure. Many properties offer essential amenities for remote workers, including high-speed Wi-Fi and dedicated office spaces, ensuring a comfortable working environment.

The town is known for its picturesque beaches, such as Mayflower Beach, where you can unwind after a day of work. Additionally, the local attractions like the Cape Cod Rail Trail provide opportunities for outdoor activities, great for a leisurely stroll or bike ride. Many rentals also feature outdoor spaces, such as patios or gardens, allowing guests to take their meetings outside when the weather permits. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Dennis holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in 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 Dennis?
In Dennis, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals, and outdoor spaces such as decks or patios, superb for enjoying the pleasant coastal weather. Many rentals also feature coffee and tea makers, providing a convenient way to enjoy a warm beverage at any time. Onsite parking is commonly available, making it easier for visitors to explore the beautiful beaches and nearby attractions in the area.
When is the best time to visit Dennis for a holiday rental?
The best time to visit Dennis for a holiday rental is during the peak season, which runs from June to August. This vibrant period draws families and beach enthusiasts eager to bask in the sun along the Cape Cod shoreline. With warm temperatures averaging between 20 to 30 degrees Celsius, visitors can enjoy a myriad of outdoor activities, from swimming and sunbathing to exploring the picturesque bike trails that weave through the region.

July stands out as the most popular month, bustling with holidaymakers taking advantage of the lively option, local festivals, and the stunning beaches. A visit at this time offers a fantastic opportunity to engage in beach games and enjoy fresh seafood at nearby waterfront restaurants.

If you're looking for a more tranquil experience, consider visiting in November. This month allows you to appreciate the serene beauty of Dennis during the off-peak season. You can stroll along the beach, enjoy the crisp autumn air, and take in the peaceful surroundings.
How early should I book a Dennis holiday rental?
Book your 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 Dennis?
In Dennis, Massachusetts, visitors can enjoy a variety of attractions that highlight the area's natural beauty and cultural heritage. One of the main draws is the Cape Cod Rail Trail, which offers scenic biking and walking paths through picturesque landscapes.

The area is also home to several beautiful beaches, such as Mayflower Beach and Chapin Beach, where families can relax, swim, and enjoy stunning sunsets over the Cape Cod Bay. For those interested in history, the Josiah Dennis Manse and Old West Schoolhouse provide insight into the region's past and are often open for tours.

Additionally, the Dennis Village offers charming shops, local restaurants, and art galleries, creating a delightful atmosphere for leisurely strolls. Nature enthusiasts may want to explore the nearby Scargo Tower, which provides panoramic views of the surrounding area, including the bay and the Cape's lush greenery.
Can I change or cancel my Dennis home rental booking on Vrbo?
To find 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 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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