Winter Rentals in Bermuda

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

• Charming Private Cottage by the Beach
• Modern Beach House @ Tobacco Bay + Twizzy Charger
• New cottage with water views
• CHARMING THREE BEDROOM COTTAGE AT MARLEY BEACH, WARICK
• “Cavello Bay” Charming Spacious 2-Bedroom Family Getaway with ocean views.
• Natalia Pool Cottage - This is great for a weekend getaway !
• Extraordinary Bermuda retreat w/large cave, panoramic pool and viewing deck.
• Pembroke Villa - Business and Vacation Home
• Unique Bermuda retreat with large cave & panoramic pool nestled into hillside
• Entire Property: Luxury 3-Bedroom, Private Pool near Beaches in Paget Bermuda

The average cost for winter rentals in Bermuda is $744 per night. Smartours has a wide list of great winter places to stay near Bermuda 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 Bermuda that allow you to bring your pet or dog:

• Pool House Studio In A Garden Setting + EV chargers
• Frognal Apartment
• The Oxford House
• Private and Dreamy.Balcony, Wine, Sunset, Upstairs with its own entrance!

See all pet-friendly vacation rentals in Bermuda on Smartours

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Bermuda to find what works for you.

As of 2026, the data from Smartours shows that there are over 180 private swimming pools or indoor pools accommodations near Bermuda along with other great amenities.