Marthas Vineyard Winter Rentals & Holiday Homes

Discover winter rentals Marthas Vineyard - We found 137 exact matches

About Marthas Vineyard Winter Rental on PickleTrip

Planning on a winter vacation in Marthas Vineyard? Discover 137 places to stay in Marthas Vineyard, for those traveling with their family, friends, in groups, or for a wedding retreat.

At PickleTrip™, we have a wide range of listings for accommodations in Marthas Vineyard, FL that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. PickleTrip™ winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Marthas Vineyard winter accommodation starts at US $237, and the most popular properties in Marthas Vineyard are cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, PickleTrip will make your winter trip memorable.

PickleTrip™ offers a great deal for travelers planning on renting a place in Marthas Vineyard, to enjoy these benefits and to book your winter vacation homes, go to PickleTrip™ filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around Marthas Vineyard and unlock even more amazing deals.

Show more
Show less

Frequently Asked Questions About Marthas Vineyard Winter Rentals

There are a lot of options in Marthas Vineyard. If you plan on staying in the Marthas 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 Marthas Vineyard:

The average cost for winter rentals in Marthas Vineyard is $237 per night. PickleTrip has a wide list of great winter places to stay near Marthas 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 Marthas Vineyard that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Marthas Vineyard on PickleTrip

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Marthas Vineyard to find what works for you.
As of 2025, the data from PickleTrip shows that there are over 137 private swimming pools or indoor pools accommodations near Marthas Vineyard along with other great amenities.

About 137 holiday rentals in Marthas 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 Marthas Vineyard for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Marthas Vineyard with all the best amenities for your next trip.