1. Sint Maarten
  2. Simpson Bay
  3. Winter Rental

Simpson Bay Winter Rentals & Holiday Homes

Discover winter rentals Simpson Bay - We found 174 exact matches

About Simpson Bay Winter Rental on PickleTrip

Planning on a winter vacation in Simpson Bay? Discover 174 places to stay in Simpson Bay, 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 Simpson Bay 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.

Simpson Bay winter accommodation starts at US $595, and the most popular properties in Simpson Bay 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 Simpson Bay, 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 Simpson Bay and unlock even more amazing deals.

Show more
Show less

Frequently Asked Questions About Simpson Bay Winter Rentals

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

The average cost for winter rentals in Simpson Bay is $595 per night. PickleTrip has a wide list of great winter places to stay near Simpson Bay 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 Simpson Bay that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Simpson Bay on PickleTrip

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Simpson Bay to find what works for you.
As of 2025, the data from PickleTrip shows that there are over 174 private swimming pools or indoor pools accommodations near Simpson Bay along with other great amenities.

About 174 holiday rentals in Simpson Bay 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 Simpson Bay for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Simpson Bay with all the best amenities for your next trip.