- British Virgin Islands
- Tortola
- Road Town
- Winter Rental
Road Town Winter Rentals & Holiday Homes
Discover winter rentals Road Town - We found 47 exact matches
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- View
- Ocean View
- Designated Smoking Area
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- Ocean View
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- Designated Smoking Area
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- Pet Friendly
Frequently Asked Questions About Road Town Winter Rental
What are the top rated Winter Rentals in Road Town?
There are a lot of options in Road Town. If you plan on staying in the Road Town area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Road Town:
- Breathtaking Ocean View 2 bedroom-2 bathroom.
- 49' Luxury Sailing Catamaran Sleeps 8 All inclusive with Captain & Private Chef
- Experience Utopia in the islands!
- 52 Feet 2020 Lagoon Catamaran (6 bedroom/6 Bath + single cabin with bath)
- New Yacht Charter Week Special 2018 BVI's
- Turquoise Turtle, fully inclusive crewed charter.nDiscover your treasure.
- Captained, or bareboat, yacht for island hopping and dining in the amazing BVI!n
- Sailing the Grenadines and Eastern Caribbean 2025/2026
- Amazing ocean views, newly renovated, large pool, AC all 4 bedrooms, sleeps 8
- Huge 80% off last minute discounts for April
How much does it cost to rent a place to stay near Road Town in the wintertime?
The average cost for winter rentals in Road Town is $2,086 per night. Vacationpirate has a wide list of great winter places to stay near Road Town that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Road Town that allow pets?
Yes, here are the top cottage/chalet rentals in Road Town that allow you to bring your pet or dog:
- AnaCapri Estate-Beautiful Caribbean Villa with pool and sea views
- Village Cay Hotel and Marina
- Maxi Cooper - The Cooper Bay Villas Tortola BVI
- Modern, private, serene
See all pet-friendly vacation rentals in Road Town on Vacationpirate
Do you have any winter rentals in Road Town that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Road Town to find what works for you.
Are there winter accommodations in Road Town that have indoor swimming pools?
As of 2026, the data from Vacationpirate shows that there are over 47 private swimming pools or indoor pools accommodations near Road Town along with other great amenities.
