Discover winter rentals Middleburg - We found 16 exact matches
About Middleburg Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Middleburg, FL 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 Middleburg. 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 Middleburg and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Middleburg Winter Rentals
What are the top rated Winter Rentals in Middleburg?
There are a lot of options in Middleburg. If you plan on staying in the Middleburg area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Middleburg:
- ★Modern Green Cove Springs 7Beds Fence Beach45min★
- Amazing Home on Black Creek |Watersports Fun |Hot Tub |Firepit |BBQ |Boat Parking|Close to Boat Ramp
- Pool Home Retreat · Tesla EV Charger · Firepit · RV/Boat Access Near Ramp
- Rare 30 Acres Along Black Creek |Country Retreat |Escape the City |Covered Balcony |Firepit & BBQ
- Private Loft at a Working Show Barn ~ Pets Welcome!
- Beautiful Lake getaway with pool, upgraded, pet friendly with lots of extras!
- Fabulous Home on the Black Creek, firepit, water access, great views, outdoor bar, pool table, darts
- Creek House Hideaway W/NEW HOT TUB
- Country Ranch Retreat
- Lakeside, Water View, Kayak, BBQ Grill, Fire Pit
How much does it cost to rent a place to stay near Middleburg in the wintertime?
The average cost for winter rentals in Middleburg is $295 per night. Vacation Cottage has a wide list of great winter places to stay near Middleburg that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Middleburg that allow pets?
Yes, here are the top cottage/chalet rentals in Middleburg that allow you to bring your pet or dog:
- Rare 30 Acres Along Black Creek |Country Retreat |Escape the City |Covered Balcony |Firepit & BBQ
- Country Ranch Retreat
- Private Loft at a Working Show Barn ~ Pets Welcome!
- Lakeside, Water View, Kayak, BBQ Grill, Fire Pit
See all pet-friendly vacation rentals in Middleburg on Vacation Cottage
Do you have any winter rentals in Middleburg that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Middleburg to find what works for you.
Are there winter accommodations in Middleburg that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 16 private swimming pools or indoor pools accommodations near Middleburg along with other great amenities.
Do any winter holiday rentals in Middleburg have hot tubs?
About 16 holiday rentals in Middleburg boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Middleburg?
Yes, there are many luxury places to stay in Middleburg for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Middleburg with all the best amenities for your next trip.
