1. USA
  2. Massachusetts
  3. Oak Bluffs
  4. Winter Rental

Oak Bluffs Winter Rentals & Holiday Homes

Discover winter rentals Oak Bluffs - We found 344 exact matches

About Oak Bluffs Winter Rental on SunSkiResorts

Planning a winter vacation in Oak Bluffs? Discover 344 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Oak Bluffs, MA perfect for your seasonal escape. Our listings include private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments. SunSki's winter vacation homes feature top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Winter accommodations in Oak Bluffs start at US $884. The most popular properties in Oak Bluffs include cabins, bungalows, and rental homes. Planning a snowboarding adventure? Explore our snowboard-friendly ski resorts, chalets, and cabins available for short-term or long-term stays. Whether it's a weekend getaway, monthly retreat, or an extended stay, SunSki ensures a memorable winter trip.

To book your winter vacation homes in Oak Bluffs, visit SunSki's filter option, enter your travel dates, narrow down your preferences, and choose from our extensive list of rentals hassle-free. Explore our interactive map to uncover all accommodations in or around Oak Bluffs and unlock incredible deals.

Show more
Show less

Frequently Asked Questions About Oak Bluffs Winter Rentals

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

The average cost for winter rentals in Oak Bluffs is $884 per night. SunSki has a wide list of great winter places to stay near Oak Bluffs that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Oak Bluffs that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Oak Bluffs on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Oak Bluffs to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 344 private swimming pools or indoor pools accommodations near Oak Bluffs along with other great amenities.

About 344 holiday rentals in Oak Bluffs boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Oak Bluffs for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Oak Bluffs with all the best amenities for your next trip.