Boston Summer Rentals, Cottages & Cabins

Book a Place to Stay in Boston for Your Summer Getaway

About Boston Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Boston are perfect for your next summer getaway. We offer a wide range of properties to choose from, including homes with top-notch pickleball courts or nearby facilities, private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, and more. Whether you're traveling with family, friends, or a group, we have a rental that will suit your needs.

Enjoy the perfect summer vacation in Boston with PickleTrip™. Our summer rental homes are designed to provide you with maximum comfort and relaxation. Choose from a variety of properties, including condos, resorts, villas, bungalows, cozy cabins, RVs, and cottages. Stay and play pickleball when you travel with PickleTrip™.

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Frequently Asked Questions About Boston Luxury Rentals

There are a lot of options in Boston. If you plan on staying in the Boston area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Boston:

In 2025, PickleTrip offers 241 summer rentals in or around Boston. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Boston is $128. Check the full list of summer accommodations in Boston.
There are 241 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with PickleTrip.

Yes, here are some popular summer holiday rentals in Boston that have a private or indoor pool:

Check all holiday rentals with a pool in Boston on PickleTrip.

Yes, We have 241 summer rental homes in Boston and types of place to stay in Boston include:

  • Vacation Homes: 241 available for rent
  • Villas: 241 Rentals available for rent
  • Holiday Apartments: 241 Rentals available for rent
  • Hotels with Suites: 241 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Boston. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Boston.