Pleasant Point holiday lettings

We found 89 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.
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in Pleasant Point?
Prices for holiday 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 holiday 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.
Are there any Pleasant Point holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 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.
Can I find long-stay holiday rentals in Pleasant Point?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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.
How early should I book a Pleasant Point holiday rental?
Book your Pleasant Point 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 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.
Can I change or cancel my Pleasant Point home rental booking on Vrbo?
To find Pleasant Point 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 Pleasant Point 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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