What are the top rated Winter Rentals in Smith Island?

There are a lot of options in Smith Island. If you plan on staying in the Smith Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Smith Island: The Relax-Inn Deal Island with Kayaks and Canoe Entire 4-bedroom 2-bath Cabin with AC, Recreational rooms, WiFi in Crisfield, MD Crisfield Cabin by Homelystay Chesapeake Waterfront with Private Dock in Crisfield, Maryland Walk to Main Street: Family-Friendly Crisfield Gem Home of the Terrapin King Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island Walk to Main St Condo with Pool Access in Crisfield Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart Walk to Main St: Condo w/Pool Access in Crisfield

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

The average cost for winter rentals in Smith Island is $284 per night. Cabinns.com has a wide list of great winter places to stay near Smith Island that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

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

Yes, here are the top cottage/chalet rentals in Smith Island that allow you to bring your pet or dog: Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart Walk to Main St Condo with Pool Access in Crisfield Chesapeake Waterfront with Private Dock in Crisfield, Maryland Walk to Main Street Family-Friendly Crisfield Gem See all pet-friendly vacation rentals in Smith Island on Cabinns.com

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

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

Are there winter accommodations in Smith Island that have indoor swimming pools?

As of 2025, the data from Cabinns.com shows that there are over 30 private swimming pools or indoor pools accommodations near Smith Island along with other great amenities.

Do any winter holiday rentals in Smith Island have hot tubs?

About 30 holiday rentals in Smith Island boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include: Smith Island Rentals with hot tub

Are there luxury winter rentals in Smith Island?

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