Vineyard Haven Winter Rentals & Holiday Homes

Discover winter rentals Vineyard Haven - We found 210 exact matches

About Vineyard Haven Winter Rental on SunSkiResorts

Planning a winter vacation in Vineyard Haven? Discover 210 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Vineyard Haven, 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 Vineyard Haven start at US $945. The most popular properties in Vineyard Haven 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 Vineyard Haven, 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 Vineyard Haven and unlock incredible deals.

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Frequently Asked Questions About Vineyard Haven Winter Rentals

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

The average cost for winter rentals in Vineyard Haven is $945 per night. SunSki has a wide list of great winter places to stay near Vineyard Haven 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 Vineyard Haven that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Vineyard Haven on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Vineyard Haven to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 210 private swimming pools or indoor pools accommodations near Vineyard Haven along with other great amenities.

About 210 holiday rentals in Vineyard Haven 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 Vineyard Haven for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Vineyard Haven with all the best amenities for your next trip.