Greensburg Winter Rentals & Holiday Homes

Discover winter rentals Greensburg - We found 19 exact matches

10.0 (3 Reviews)
2 Bedrooms 7 Guests
8.4 (189 Reviews)
9 Bedrooms 26 Guests
From US $773 per night
10.0 (18 Reviews)
7 Bedrooms 16 Guests
9.4 (3 Reviews)
3 Bedrooms 6 Guests
10.0 (15 Reviews)
2 Bedrooms 6 Guests
From US $205 per night
9.6 (30 Reviews)
3 Bedrooms 7 Guests
9.2 (15 Reviews)
2 Bedrooms 4 Guests
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9.2 (10 Reviews)
3 Bedrooms 6 Guests
From US $210 per night
9.8 (51 Reviews)
3 Bedrooms 8 Guests
9.6 (9 Reviews)
1 Bedroom 7 Guests
From US $187 per night
10.0 (1 Review)
1 Bedroom 6 Guests
8.6 (14 Reviews)
4 Bedrooms 12 Guests
10.0 (1 Review)
1 Bedroom 4 Guests
9.8 (29 Reviews)
3 Bedrooms 8 Guests

About Greensburg Winter Rental on Vacation Cottage

At Vacation Cottage, we showcase a diverse array of accommodations in Greensburg, KY 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 Greensburg. 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 Greensburg and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.

Frequently Asked Questions About Greensburg Winter Rentals

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

The average cost for winter rentals in Greensburg is $197 per night. Vacation Cottage has a wide list of great winter places to stay near Greensburg that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

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

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

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

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

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

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

As of 2026, the data from Vacation Cottage shows that there are over 19 private swimming pools or indoor pools accommodations near Greensburg along with other great amenities.

Do any winter holiday rentals in Greensburg have hot tubs?

About 19 holiday rentals in Greensburg boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Are there luxury winter rentals in Greensburg?

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