Pleasant Point vacation rentals

We found 84 vacation rentals — enter your dates for availability

Discover a selection of 12 homes and other vacation rentals in Pleasant Point that are perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include WiFi and a pool. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

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Find out more about Pleasant Point

Why visit Pleasant Point

  • Beautiful Beaches: Enjoy the stunning shores of Pleasant Point, perfect for sunbathing and swimming.
  • Outdoor Adventures: Explore nearby national parks and islands, ideal for hiking, biking, and nature walks.
  • Family-friendly Activities: Engage in a variety of activities suitable for all ages, ensuring fun for the whole family.
  • Charming Accommodations: Stay in cozy cottages or modern condos that cater to different preferences and budgets.
  • Local Culture: Immerse yourself in the warm, friendly atmosphere and experience the unique culture of Wellfleet.

Popular types of accommodation around Pleasant Point

Looking for the perfect getaway in Pleasant Point? You're in the right place. Our most popular vacation rentals include charming private homes, cozy cottages, and modern condos. Whether you’re seeking a waterfront cottage, a spacious bedroom cottage, or a pet-friendly option, we have a variety of accommodations to suit your needs. Enjoy your stay with transparency, savings, and peace of mind.

  • Houses: The top choice for visitors to Pleasant Point, offering spacious and comfortable accommodations perfect for families or groups.
  • Cottages: A charming option that provides a cozy atmosphere, ideal for a peaceful getaway near the beach.
  • Condos: These modern rentals offer convenient amenities and are a great choice for travelers seeking a home-like feel.
  • Apartments: Perfect for solo travelers or couples, these rentals provide a comfortable and affordable living space.
  • Cabins: A rustic option that brings you closer to nature, perfect for those looking to escape the hustle and bustle.**

Top attractions near Pleasant Point

Pleasant Point in Wellfleet, Massachusetts, offers a delightful vacation experience for families and outdoor enthusiasts alike. Visitors can explore beautiful beaches, national parks, and nearby islands, providing ample opportunities for cultural and outdoor activities. For a comfortable stay, consider pleasure point cottage rentals and gather vacation ideas to make the most of your trip. Whether you're looking for relaxation or adventure, Pleasant Point has something for everyone to enjoy.

  • Cape Cod Beaches: A stunning stretch of sandy shores located 5 miles from Pleasant Point, Cape Cod Beaches offers a quintessential beach experience with a relaxed atmosphere, perfect for sunbathing, swimming, and beachcombing.
  • Cape Cod National Seashore: Just 5 miles away, this national park showcases breathtaking scenery, diverse wildlife, and outdoor adventures like hiking, biking, and kayaking amid coastal landscapes.
  • Wellfleet Preservation Hall: Situated 2 miles from Pleasant Point, this historic building is a cultural hub hosting art exhibits, performances, and community events, reflecting the rich arts scene of Wellfleet.

Things to do recommended for couples

For a romantic getaway in Pleasant Point, consider a visit to Truro Vineyards for a delightful wine tasting just 9 miles away, or enjoy a fun round at Poit's Lighthouse Mini Golf, only 3 miles from your location. For ultimate relaxation, treat yourselves at The E Spa, 11 miles away.

Things to do recommended for families

Families can have a blast at the Orleans Bowling Center, an arcade and adventure zone just 9 miles from Pleasant Point. For more thrills, head to Bud's Go Karts, located 17 miles away, where the excitement of karting awaits.

Things to do recommended for groups

Your group can enjoy a captivating performance at the Wellfleet Harbor Actors Theater, hike the scenic Buttonbush Trail, or challenge yourselves on the beautiful Highland Golf Links. Each experience offers a unique blend of culture, adventure, and outdoor fun, perfect for making lasting memories together.

*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 traveling with friends, family, pets, or planning an extended stay, it's important to prioritize your preferences when searching. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Pleasant Point with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Pleasant Point with young kids: Traveling with little ones can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, consider how close you are to family-friendly attractions for a more enjoyable experience.
  • Taking your pets with you to Pleasant Point: For many, a family vacation feels incomplete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Pleasant Point: If you're in search of vacation rentals that offer 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 options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Pleasant Point

Pleasant Point offers a charming escape for families and outdoor enthusiasts alike. Nestled in Wellfleet, Massachusetts, this neighborhood boasts stunning scenery and a warm, friendly atmosphere. Explore nearby beaches, enjoy family-friendly activities, and immerse yourself in local culture. With budget-friendly excursions and perfect spots for relaxation, Pleasant Point is an ideal holiday destination that ensures memorable experiences for everyone. Discover the highlights of this inviting community and create lasting memories with your loved ones.

  • Wellfleet: Nestled on the Outer Cape, Wellfleet is renowned for its stunning outdoor experiences, scenic beauty, and beautiful beaches. As the host of Pleasant Point, this charming town offers a variety of attractions, including lush hiking trails and pristine golf courses. Visitors can enjoy the local beaches, perfect for family outings, or explore the iconic Cape Cod National Seashore. The town’s vibrant art scene, local galleries, and delicious seafood restaurants add to its allure, making it a must-visit destination.
  • South Wellfleet: Located just a mile from Pleasant Point, South Wellfleet is a quaint coastal community that provides a serene escape. Known for its stunning landscapes and outdoor adventures, visitors can access numerous hiking trails, explore the scenic beaches, and enjoy a round of golf. The area is particularly famous for its breathtaking sunsets and tranquil island views. South Wellfleet is a perfect spot for those looking to connect with nature while enjoying the laid-back atmosphere of Cape Cod.
  • Eastham: Situated 6 miles from Pleasant Point, Eastham is a picturesque town that captures the essence of Cape Cod living. Known for its scenic beauty and outdoor recreational opportunities, Eastham offers visitors access to beautiful beaches and hiking trails, ideal for exploration and relaxation. Golf enthusiasts can find excellent courses here, while families can enjoy the local beaches and the nearby Cape Cod National Seashore. The town also features charming shops and eateries, ensuring a delightful experience for all travelers.

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 months are August and August. Peak season runs in June, June to July, July to August and August, while off-peak times, like January, January to February, February to March and March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.4°F (1.9°C)Light RainMostly CloudyLowSlightly Low
January35.4°F (1.9°C)Light RainMostly CloudyLowSlightly Low
February35.4°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
March38.3°F (3.5°C)Light RainMostly CloudyLowSlightly Low
April44.8°F (7.1°C)Light RainMostly SunnyAverageAverage
April44.8°F (7.1°C)Light RainMostly SunnyAverageAverage
May52.5°F (11.4°C)Light RainMostly SunnyAverageAverage
May52.5°F (11.4°C)Light RainMostly SunnyAverageAverage
June61.0°F (16.1°C)Light RainMostly SunnyHighSlightly High
June61.0°F (16.1°C)Light RainMostly SunnyHighSlightly High
July68.9°F (20.5°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
August69.8°F (21.0°C)Light RainMostly SunnyHighSlightly High
September65.1°F (18.4°C)Light RainMostly SunnyAverageAverage
September65.1°F (18.4°C)Light RainMostly SunnyAverageAverage
October57.6°F (14.2°C)Light RainMostly SunnyAverageAverage
October57.6°F (14.2°C)Light RainMostly SunnyAverageAverage
November48.4°F (9.1°C)Light RainMostly SunnyAverageAverage
November48.4°F (9.1°C)Light RainMostly SunnyAverageAverage
December41.4°F (5.2°C)Light RainMostly CloudyAverageAverage
December41.4°F (5.2°C)Light RainMostly CloudyAverageAverage

Booking with Vrbo is a breeze

Are you eager to save on your upcoming travel adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that suits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit.

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. Being the organizer certainly has its perks. Become a part of our One Key rewards program to unlock special member discounts and accumulate OneKeyCash on qualifying stays. Sign up today and begin reaping the benefits.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new trips, pick up right where you left off, or manage and review your travel arrangements. You can easily find the properties you've saved and booked in the sections for Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Pleasant Point?
In Pleasant Point, vacation houses are the most popular type of rental, with about 13 available in the area. These houses typically offer spacious layouts, multiple bedrooms, and amenities such as fully equipped kitchens and outdoor areas for relaxation. Some of them may also provide charming features like porches or patios, great for enjoying the coastal ambiance. Additionally, there are several cottages in the vicinity, which offer a cozy, intimate atmosphere and often include kitchen facilities and comfortable living spaces, making them great options for couples or small families.
Are there any beach house rentals in Pleasant Point?
In Pleasant Point, Massachusetts, there are about 51 beach house vacation rentals available, primarily located near the scenic coastline and popular local attractions. These beach houses typically offer amenities such as spacious living areas, fully equipped kitchens, multiple bedrooms, and outdoor decks or patios where guests can enjoy the fresh sea breeze. Many properties are designed with families or groups in mind, featuring ample space for gatherings and relaxation after a day spent exploring the nearby beaches or enjoying water activities.
How much does it cost to rent a vacation home in Pleasant Point?
Prices for vacation rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Pleasant Point 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 Pleasant Point vacation house rentals?
You can find great discounts on house rentals in Pleasant Point 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.
What are popular rental amenities in Pleasant Point?
In Pleasant Point, popular vacation rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals. Many rentals also feature outdoor spaces like patios or decks, superb for enjoying the pleasant weather and scenic surroundings. Additionally, amenities such as coffee and tea makers provide a cozy touch for morning routines, while blenders can be great for making smoothies or cocktails.
Are there any family house rentals in Pleasant Point?
In Pleasant Point, Massachusetts, there are some family-friendly house rentals available, with around 11 options to choose from. This charming locale is great for families looking to enjoy a coastal getaway. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely.

Visitors will find themselves close to the picturesque shores of Pleasant Point Beach, ideal for sunbathing and swimming. Additionally, nearby attractions include local parks and nature trails that provide opportunities for hiking and exploring the natural beauty of the area.
Can I rent a vacation home with a pool or hot tub in Pleasant Point?
In Pleasant Point, Massachusetts, there are several vacation homes available for rent that feature pools and hot tubs, providing a relaxing retreat for travelers. The area offers a blend of coastal charm and serene surroundings, making it an appealing destination for those seeking a getaway. Many properties come equipped with amenities such as spacious outdoor areas, fully stocked kitchens for preparing meals, and comfortable living spaces superb for gatherings. Guests can also enjoy features like private hot tubs, which are ideal for unwinding after a day of exploration.
Are there any Pleasant Point vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Pleasant Point with parking available—perfect for families or travelers 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.
Are there pet-friendly vacation rentals in Pleasant Point?
In Pleasant Point, Massachusetts, travelers can indeed book several pet-friendly vacation rentals. This charming coastal area offers a variety of accommodations that cater to those traveling with pets. Many of the available rentals feature amenities such as spacious yards, easy beach access, and fully equipped kitchens, making it convenient for families or groups.

The nearby beaches provide ample opportunities for outdoor activities, where pets are often welcome to join in the fun. Additionally, the scenic landscapes and coastal trails in the vicinity are superb for leisurely walks with your furry friends.
Can I find long-stay vacation rentals in Pleasant Point?
A long-stay vacation rental in Pleasant Point is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Pleasant Point for a vacation rental?
The best time to visit Pleasant Point for a vacation rental is during the vibrant summer months of July to September. This period attracts families and beach enthusiasts who flock to the area to enjoy the sunny weather and the picturesque coastline. Expect temperatures to range from the mid-70s to mid-80s Fahrenheit, providing the superb backdrop for outdoor activities such as swimming, kayaking, and beachcombing.

July is particularly popular, as it marks the height of the tourist season. Visitors will find a lively atmosphere, with numerous local events, festivals, and opportunities for water sports. The warm evenings are superb for family gatherings on the beach or enjoying fresh seafood at nearby restaurants.

For those looking for a more budget-friendly option, November offers a unique charm with fewer crowds. While the weather cools down to the low 40s to mid-50s Fahrenheit, this serene time allows for quieter exploration of the area's natural beauty. You can enjoy scenic walks along the shoreline and experience the area's off-season tranquility.

Ultimately, your choice of when to visit Pleasant Point will depend on your preference for a bustling summer getaway or a peaceful fall retreat.
Are there any remote work vacation rentals in Pleasant Point?
In Pleasant Point, Massachusetts, there are several remote work-friendly vacation rentals available, with around 16 options to choose from. Travelers can expect properties equipped with essential amenities for remote work, including reliable Wi-Fi and dedicated desk spaces, allowing for a productive stay. Many of these rentals are situated in scenic locations, providing a peaceful environment conducive to both work and relaxation.

The area is known for its beautiful coastal views and proximity to local attractions, making it an ideal spot for balancing work and leisure. Visitors can explore nearby parks and beaches during their downtime, adding an element of outdoor enjoyment to their work trips. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Pleasant Point vacation rental?
Book your Pleasant Point vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Pleasant Point home rental booking on Vrbo?
To find Pleasant Point vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 Pleasant Point vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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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