1. USA
  2. Maryland
  3. Shady Side
  4. Winter Rental

Shady Side Winter Rentals & Golf course

Discover winter rentals Shady Side - We found 35 exact matches

About Shady Side Winter Rental on StayAndPlay

StayAndPlay offers a diverse selection of golf retreats and elevated accommodations in Shady Side, MD, perfect for your winter golf escape or seasonal retreat. Our listings include golf villas, golf cabins, luxurious golf resorts, charming golf cottage, and other unique properties, ensuring you'll find the perfect golf getaway. These accommodations feature premium amenities such as Wi-Fi, heated outdoor hot tubs, private decks, fireplaces, and breathtaking views of golf courses or mountains, making for an unforgettable experience.

Whether you're looking to unwind in a peaceful golf course setting or enjoy winter golf adventures, StayAndPlay connects you with the finest golf retreats and elevated accommodations. From snow-dusted fairways to tranquil mountain escapes, our collection ensures your winter golf getaway is truly magical.

StayAndPlay offers incredible deals for travelers seeking elevated golf accommodations in Shady Side. Choose from a variety of winter golf vacation rentals with ease. Use our interactive map to explore all golf villas and other golf retreats in and around Shady Side.

Show more
Show less

Frequently Asked Questions About Shady Side Winter Rentals

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

The average cost for winter rentals in Shady Side is $588 per night. StayAndPlay.com has a wide list of great winter places to stay near Shady Side 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 Shady Side that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Shady Side on StayAndPlay

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Shady Side to find what works for you.
As of 2025, the data from StayAndPlay shows that there are over 35 private swimming pools or indoor pools accommodations near Shady Side along with other great amenities.

About 35 holiday rentals in Shady Side 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 Shady Side for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Shady Side with all the best amenities for your next trip.