The Vineyard Winter Rentals & Holiday Homes

Discover winter rentals The Vineyard - We found 4978 exact matches

About The Vineyard Winter Rental on SunSkiResorts

Planning a winter vacation in The Vineyard? Discover 4978 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in The Vineyard, FL 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 The Vineyard start at US $381. The most popular properties in The Vineyard 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 The Vineyard, 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 The Vineyard and unlock incredible deals.

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Frequently Asked Questions About The Vineyard Winter Rentals

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

The average cost for winter rentals in The Vineyard is $381 per night. SunSki has a wide list of great winter places to stay near The Vineyard 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 The Vineyard that allow you to bring your pet or dog:

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

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in The Vineyard to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 4978 private swimming pools or indoor pools accommodations near The Vineyard along with other great amenities.

About 4978 holiday rentals in The Vineyard 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 The Vineyard for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near The Vineyard with all the best amenities for your next trip.