Bermuda Winter Rentals & Holiday Homes

Discover winter rentals Bermuda - We found 173 exact matches

From US $667 per night
|
9.5 (2 Reviews)
4 Bedrooms 9 Guests
From US $491 per night
|
9.4 (153 Reviews)
1 Bedroom 2 Guests
From US $400 per night
9.4 (15 Reviews)
2 Bedrooms 4 Guests
10.0 (120 Reviews)
1 Bedroom 2 Guests
From US $1,160 per night
|
9.0 (129 Reviews)
68 Bedrooms 13 Guests
From US $825 per night
|
8.9 (124 Reviews)
45 Bedrooms 6 Guests
From US $280 per night
|
8.9 (25 Reviews)
2 Bedrooms 6 Guests
From US $417 per night
|
8.9 (15 Reviews)
2 Bedrooms 4 Guests
From US $1,627 per night
|
8.8 (50 Reviews)
82 Bedrooms 28 Guests
10.0 (88 Reviews)
1 Bedroom 3 Guests
From US $1,200 per night
|
8.4 (102 Reviews)
188 Bedrooms 24 Guests
10.0 (87 Reviews)
2 Bedrooms 5 Guests
From US $1,534 per night
|
8.4 (75 Reviews)
68 Bedrooms 18 Guests
10.0 (86 Reviews)
1 Bedroom 2 Guests
From US $169 per night
|
7.7 (9 Reviews)
1 Bedroom 3 Guests
10.0 (76 Reviews)
1 Bedroom 2 Guests
From US $370 per night
10.0 (54 Reviews)
1 Bedroom 2 Guests
From US $97 per night
10.0 (48 Reviews)
1 Bedroom 2 Guests

About Bermuda Winter Rental on Vacation Cottage

At Vacation Cottage, we showcase a diverse array of accommodations in Bermuda perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, rent-by-owner homes, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.

Vacation Cottage presents luxury options for travelers seeking to rent a place in Bermuda. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within Bermuda and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.

Frequently Asked Questions About Bermuda Winter Rentals

How much does it cost to rent a place to stay near Bermuda in the wintertime?

The average cost for winter rentals in Bermuda is $764 per night. Vacation Cottage 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.

Are there any winter cottages/chalets in Bermuda that allow pets?

Yes, here are the top cottage/chalet rentals in Bermuda that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Bermuda on Vacation Cottage

Do you have any winter rentals in Bermuda that are suitable for families?

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.

Are there winter accommodations in Bermuda that have indoor swimming pools?

As of 2025, the data from Vacation Cottage shows that there are over 173 private swimming pools or indoor pools accommodations near Bermuda along with other great amenities.

Do any winter holiday rentals in Bermuda have hot tubs?

About 173 holiday rentals in Bermuda boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Are there luxury winter rentals in Bermuda?

Yes, there are many luxury places to stay in Bermuda for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Bermuda with all the best amenities for your next trip.