Pleasant Point holiday rentals

We found 90 holiday rentals — enter your dates for availability
Discover a selection of 12 homes and other holiday rentals in Pleasant Point that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, which might include Wi-Fi and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

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Why visit Pleasant Point

  • Beautiful Beaches: Pleasant Point boasts tranquil beaches perfect for sunbathing, swimming, and beachcombing.
  • Outdoor Activities: Explore the nearby national and state parks offering hiking, biking, and birdwatching opportunities.
  • Local Charm: Experience the warm, welcoming atmosphere of this coastal neighbourhood filled with local culture.
  • Family-Friendly Excursions: Enjoy a variety of activities suitable for families, ensuring fun for all ages.
  • Scenic Views: Revel in stunning coastal scenery, ideal for photography and leisurely strolls by the sea.

Popular types of accommodation around Pleasant Point

Pleasant Point in Wellfleet, Massachusetts offers an array of holiday rentals, including wellfleet cottages, wellfleet holiday homes, and cosy private holiday homes and condos. Visitors can enjoy local attractions and landmarks within this charming neighbourhood, ensuring a memorable seaside experience. Whether you're seeking a relaxing break or an adventurous coastal retreat, our selection of house rentals and pleasant point cottages caters to every traveller's needs.

  • Private Holiday Homes: The top choice for visitors, offering a cosy and secluded retreat to enjoy your stay in Pleasant Point.
  • Cottages: The second most favoured option, providing a charming, traditional escape in the area.
  • Condos: The third preferred style, offering modern comforts and convenience in Pleasant Point.
  • Apartments: The fourth popular choice, ideal for a relaxed, self-catering holiday experience.
  • Cabins: The fifth option, perfect for those seeking a rustic yet comfortable retreat.**

Top attractions near Pleasant Point

Pleasant Point in Wellfleet, Massachusetts, offers a delightful retreat for those seeking a beachside, outdoor, and scenic holiday. Visitors can enjoy tranquil beaches, explore national and state parks, and experience the charm of a local island atmosphere. Perfect for travellers looking to immerse themselves in nature and culture, this neighbourhood promises a refreshing blend of relaxation and adventure in a picturesque setting.

  • Cape Cod Beaches: Experience the quintessential beach vibes with soft sands and gentle waves, perfect for sunbathing, swimming, or leisurely strolls along the shore.
  • Cape Cod National Seashore: Embrace the great outdoors with stunning scenery, hiking trails, and opportunities for adventure, showcasing the natural beauty of the Cape.
  • Lieutenant Island: Explore this serene island offering idyllic beaches and outdoor activities, ideal for nature enthusiasts and those seeking a peaceful retreat.

Things to do recommended for couples

Seeking a romantic getaway in Pleasant Point? Enjoy sunset walks along the picturesque beaches, savour a candlelit dinner at a local seafood restaurant, or embark on a scenic boat ride to explore the tranquil waters of Wellfleet, creating cherished memories together.

Things to do recommended for families

Families can explore the stunning beaches of Wellfleet, such as Marconi Beach, or visit the Wellfleet Bay Wildlife Sanctuary to discover local wildlife. Don't miss the charming Wellfleet Drive-In Theatre for a nostalgic film experience under the stars.

Things to do recommended for groups

Groups visiting Pleasant Point can enjoy a delightful day at the nearby Cape Cod National Seashore, explore the charming town of Wellfleet with its local galleries and eateries, or partake in a whale-watching excursion to witness these magnificent creatures off the coast.

*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 around Pleasant Point

If you’re travelling with a group, as a family, bringing your pets along, or seeking longer stays, it’s important to filter according to your key priorities. Here are some helpful booking tips for your Stayz experience.

  • Traveling to Pleasant Point with a group: Consider how many bedrooms you will require, along with facilities such as a fully equipped kitchen or an outdoor area for group gatherings. Luckily, you can refine your search for all these features, and more, on Stayz.
  • Traveling to Pleasant Point with young kids: Traveling with young children can be challenging. You must ensure their comfort and safety, and provide age-appropriate amenities, such as a private swimming pool. It is also advisable to consider your proximity to family-friendly attractions.
  • Taking your pets with you to Pleasant Point: For many, a family holiday isn’t truly complete without their furry companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Pleasant Point: If you're after holiday lets offering special rates for stays of a month or more, you've come to the right spot. With the appropriate filter, you can effortlessly locate and save on monthly rentals. You might also want to include a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Pleasant Point

Discover the charm of Pleasant Point in Wellfleet, Massachusetts, where the beach, outdoor activities, and scenic views create an idyllic summer community. Enjoy family-friendly excursions and the warm, welcoming atmosphere of this coastal neighbourhood. Whether exploring the local community or simply relaxing by the sea, Pleasant Point offers a delightful, budget-friendly escape steeped in natural beauty and maritime allure.

  • Wellfleet: Wellfleet is a charming coastal town that serves as the gateway to Pleasant Point. Renowned for its stunning beaches and picturesque scenery, it offers an array of outdoor activities including golfing and theatre. Visitors can immerse themselves in the natural beauty of the Cape, with family-friendly beaches and scenic walking trails that showcase the area’s unique landscapes. The local golf courses provide a delightful experience for sport enthusiasts, while the vibrant arts scene adds a cultural touch to your holiday.
  • Eastham: Situated approximately 10km from Pleasant Point, Eastham is a delightful town known for its beautiful beaches and outdoor recreational opportunities. Travellers flock here to enjoy the scenic vistas, partake in various water sports, or simply relax on the sandy shores. The town also features shopping centres for those looking to indulge in a bit of retail therapy. Eastham’s proximity to the Cape Cod National Seashore means that visitors can easily explore the stunning coastal landscapes and enjoy family-friendly activities amidst nature.
  • Truro: Located around 10km from Pleasant Point, Truro is a picturesque town celebrated for its breathtaking beaches and outdoor experiences. It offers a perfect blend of relaxation and adventure, with opportunities for golfing and enjoying live theatre. Truro’s stunning coastline and family-friendly beaches are ideal for sunbathing, swimming, and beachcombing. Nature enthusiasts will appreciate the scenic trails and vistas that highlight the area’s natural beauty, making it a lovely spot for a day trip or a leisurely afternoon.

Best time to go to Pleasant Point

If you're planning a trip to Pleasant Point, 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 January to March tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.4°F (1.9°C)Light RainMostly CloudyLowSlightly Low
February35.4°F (1.9°C)Light RainMostly CloudyLowSlightly Low
March38.3°F (3.5°C)Light RainMostly CloudyLowSlightly Low
April44.8°F (7.1°C)Light RainMostly SunnyAverageAverage
May52.5°F (11.4°C)Light RainMostly SunnyAverageAverage
June61.0°F (16.1°C)Light RainMostly SunnyHighSlightly High
July68.9°F (20.5°C)Light RainMostly SunnyHighSlightly High
August69.8°F (21.0°C)Light RainMostly SunnyHighSlightly High
September65.1°F (18.4°C)Light RainMostly SunnyAverageAverage
October57.6°F (14.2°C)Light RainMostly SunnyAverageAverage
November48.4°F (9.1°C)Light RainMostly SunnyAverageAverage
December41.4°F (5.2°C)Light RainMostly CloudyAverageAverage

Booking with Stayz is simple

Looking to save on your upcoming break? Consider being flexible with your travel dates, as costs can fluctuate. Moreover, opting for a longer stay may offer significant savings. To discover the ideal Stayz property that fits your budget, simply apply our filters to search by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz's Trip Board provides a dedicated area for you to plan new journeys, manage your existing arrangements, or review your bookings. Your saved or booked properties are conveniently categorised into Potential, Upcoming, or Current Trips. To discover Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

When is the best time to visit Pleasant Point for a holiday rental?
The best time to visit Pleasant Point for a holiday rental is during the peak season from July to September. This vibrant period attracts many travellers eager to enjoy the stunning coastal scenery, with July being particularly popular. During these months, Pleasant Point comes alive with a variety of outdoor activities, from sunbathing on the picturesque beaches to exploring the scenic trails that wind through the area.In July, you can expect pleasantly warm temperatures, typically ranging from 15 to 28 degrees Celsius, making it an ideal time for beach outings and water sports. The lively option is enhanced by numerous local events, including summer markets and festivals, which provide a great opportunity to experience the community spirit and local culture.For those seeking a quieter experience, consider visiting in November. This month, while less crowded, offers a unique charm as the autumn colours begin to paint the landscape. You'll find that rental prices are generally lower during this time, allowing for a good balance of comfort and value while enjoying the tranquil beauty of Pleasant Point.
What are the top attractions in Pleasant Point, Massachusetts, United States of America?
In Pleasant Point, Massachusetts, visitors can enjoy a range of attractions that showcase the area's natural beauty and cultural heritage. The nearby Cape Cod National Seashore offers stunning coastal views, pristine beaches, and scenic walking trails, making it a superb spot for outdoor enthusiasts. The charming town of Wellfleet, just a short drive away, features art galleries, local shops, and the Wellfleet Bay Wildlife Sanctuary, where you can explore diverse ecosystems.Another highlight is the iconic Nauset Lighthouse, located in nearby Eastham, which provides a picturesque backdrop for photographs and a glimpse into the region's maritime history. Visitors can also indulge in fresh seafood at local eateries, particularly in the towns of Orleans and Chatham, where the coastal atmosphere adds to the dining experience.
Are all fees included in the Pleasant Point holiday homes prices shown on Stayz?
Stayz 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.
Are there any Pleasant Point holiday homes with parking?
Stayz offers a wide selection of holiday homes in Pleasant Point 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 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.
Are there any discounts for Pleasant Point holiday homes?
You can find great discounts on holiday homes in Pleasant Point on Stayz, 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.
Can I change or cancel my Pleasant Point holiday home booking on Stayz?
To find Pleasant Point holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pleasant Point?
A long-stay holiday home in Pleasant Point 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Pleasant Point holiday home?
Book your Pleasant Point holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pleasant Point?
Prices for holiday homes in Pleasant Point 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pleasant Point to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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