Discover winter rentals Cumberland - We found 2779 exact matches
About Cumberland Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Cumberland, MD 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 Cumberland. 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 Cumberland and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Cumberland Winter Rentals
What are the top rated Winter Rentals in Cumberland?
There are a lot of options in Cumberland. If you plan on staying in the Cumberland area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Cumberland:
- Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
- LAKEFRONT Cabin: Hot Tub, Kayaks, Private Dock & Gardens - OWLS NEST Deep Creek
- The Love Shack- The BEST Couples and Small Family Retreat at Deep Creek Lake!
- Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)
- Boulder Ridge Cabin -a private chalet in the woods
- Minutes from Deep Creek Lake, Located on 24-acre farm with private 1-acre lake
- Sunny Escape 2 - A new era for a familiar lake front home
- Peaceful Lakefront! Private deep water dock, evening sun, quiet dead end street!
- Beautiful Lakefront Home with Hot Tub Near Mountain and Attractions
- Level lakefront, family-friendly, hot tub, low fees, private dock
How much does it cost to rent a place to stay near Cumberland in the wintertime?
The average cost for winter rentals in Cumberland is $526 per night. Vacation Cottage has a wide list of great winter places to stay near Cumberland that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Cumberland that allow pets?
Yes, here are the top cottage/chalet rentals in Cumberland that allow you to bring your pet or dog:
- Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
- Lake Pointe Inn
- Blue Moon Rising
- LAKEFRONT Cabin: Hot Tub, Kayaks, Private Dock & Gardens - OWLS NEST Deep Creek
See all pet-friendly vacation rentals in Cumberland on Vacation Cottage
Do you have any winter rentals in Cumberland that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Cumberland to find what works for you.
Are there winter accommodations in Cumberland that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 2779 private swimming pools or indoor pools accommodations near Cumberland along with other great amenities.
Do any winter holiday rentals in Cumberland have hot tubs?
About 2779 holiday rentals in Cumberland boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Cumberland?
Yes, there are many luxury places to stay in Cumberland for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Cumberland with all the best amenities for your next trip.
