Pleasant Point holiday rentals

We found 92 holiday rentals — enter your dates for availability

Discover a selection of 13 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

What is the most popular type of holiday home accommodation in Pleasant Point?
The most sought-after types of holiday homes in Pleasant Point are houses. Ready for more choices? Stayz has many options to match our guests' unique requirements, so you'll see holiday properties in all sizes, and for all budgets. The perfect home away from home is waiting for you — get yours today.
How much does it cost to rent a holiday home in Pleasant Point?
The average price for a holiday home in Pleasant Point is based on a number of factors, such as season, length of stay and property type. Whether you're looking for a sprawling villa with a pool or a comfy cabin that's perfect for two, just add your travel dates to see stays with unbeatable value.
How much does it cost to rent a beach house in Pleasant Point?
When you travel and the style and size of the property will determine the cost of your beachside holiday home. Enter your Pleasant Point travel dates to view your options on Stayz. Did someone just say "private pool"? Use our filters to choose the features and amenities you need.
Are there pet-friendly holiday homes in Pleasant Point?
With 11 properties that host four-legged guests, your happy hound can also come along on your Pleasant Point getaway. Use the filter tool to search our pet-friendly holiday homes and find your pawfect holiday home on Stayz.
What are popular home amenities in Pleasant Point?
A garden, a nearby river and a water view are rated the most popular home amenities in Pleasant Point. Whether you're planning to travel by yourself, with your other half or a group of family members, Stayz will help you find a holiday home that matches your tastes with all the features you'll enjoy.
Are there large group holiday homes in Pleasant Point?
With 10 Pleasant Point holiday properties that can accommodate a group of five or more people, you can bring a few extra family members or friends along. Whether you're planning a casual get-together or a special event, Stayz will help you book a comfy space for the occasion.
Are there holiday homes in Pleasant Point that welcome kids?
Bring the whole family together for fun-filled adventures in Pleasant Point at one of our 11 family-friendly properties. Many of these stays provide conveniences that are suitable for trips with the kids, including kitchens, extra bedrooms and entertainment units. Simply check the "Properties good for families" filter and choose your favourite.
What are the top attractions for families in Pleasant Point?
Keeping the kids happy during your holiday in Pleasant Point is a breeze with these exciting family-friendly attractions:

  • Indian Neck Beach
  • Mayo Beach
  • Ryder Beach

Can I find two-bedroom holiday homes in Pleasant Point?
Gather your nearest and dearest and experience complete comfort and privacy in one of the two two-bedroom holiday properties Pleasant Point has to offer.
Are there holiday homes with WiFi in Pleasant Point?
Whether you'd like to keep up with the latest headlines, look over emails or surf your social networks, there are two holiday homes with WiFi in Pleasant Point. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.
How can I find holiday homes with air conditioning in Pleasant Point?
You can choose from six Stayz holiday homes with air conditioning in Pleasant Point providing that cooling breeze and extra comfort level. Enter your chosen travel dates and then make use of our filters to locate properties with air conditioning.
How old do you have to be to rent a holiday home in Pleasant Point?
Age restrictions can vary across properties on Stayz, so be sure to check the rules of the holiday home in Pleasant Point you want to book. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Pleasant Point for?
The length of time you can book a holiday home in Pleasant Point is down to the property. Just enter your chosen dates to look at a list of options offering extended stays. With a range of features like washing machines and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find somewhere perfect to call your home away from home in Pleasant Point.