Chalkers Crossing Vineyard and Olive Grove Summer Rentals, Cottages & Cabins

Book a Place to Stay in Chalkers Crossing Vineyard and Olive Grove for Your Summer Getaway

About Chalkers Crossing Vineyard and Olive Grove Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Chalkers Crossing Vineyard and Olive Grove 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 Chalkers Crossing Vineyard and Olive Grove 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™.

Show more
Show less

Frequently Asked Questions About Chalkers Crossing Vineyard and Olive Grove Luxury Rentals

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

In 2025, PickleTrip offers 7 summer rentals in or around Chalkers Crossing Vineyard and Olive Grove. 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 Chalkers Crossing Vineyard and Olive Grove is $141. Check the full list of summer accommodations in Chalkers Crossing Vineyard and Olive Grove.
There are 7 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 Chalkers Crossing Vineyard and Olive Grove that have a private or indoor pool:

Check all holiday rentals with a pool in Chalkers Crossing Vineyard and Olive Grove on PickleTrip.

Yes, We have 7 summer rental homes in Chalkers Crossing Vineyard and Olive Grove and types of place to stay in Chalkers Crossing Vineyard and Olive Grove include:

  • Vacation Homes: 7 available for rent
  • Villas: 7 Rentals available for rent
  • Holiday Apartments: 7 Rentals available for rent
  • Hotels with Suites: 7 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Chalkers Crossing Vineyard and Olive Grove. 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 Chalkers Crossing Vineyard and Olive Grove.