Discover winter rentals Philipstown - We found 53 exact matches
About Philipstown Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Philipstown, NY 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 Philipstown. 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 Philipstown and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Philipstown Winter Rentals
What are the top rated Winter Rentals in Philipstown?
There are a lot of options in Philipstown. If you plan on staying in the Philipstown area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Philipstown:
- Bear Mountain House.
- Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town
- Cold Spring Mountain Retreat: Secluded Autumn Oasis
- Charming Cold Spring Village Home
- Luxury Garrison Retreat | Chef's Kitchen & Hot Tub
- Modern Luxurious Country Retreat w/Sauna + Hot tub 1hr from NYC
- Idyllic farmhouse retreat in lower Hudson Valley, hiking trails steps away!
- Hudson Valley's Nature Experience with Incredible Views!
- Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point!
- The Glabin Garrison Gem with Hot Tub and Fire Pit
How much does it cost to rent a place to stay near Philipstown in the wintertime?
The average cost for winter rentals in Philipstown is $778 per night. Vacation Cottage has a wide list of great winter places to stay near Philipstown that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Philipstown that allow pets?
Yes, here are the top cottage/chalet rentals in Philipstown that allow you to bring your pet or dog:
- Bear Mountain House.
- The Glabin Garrison Gem with Hot Tub and Fire Pit
- Garrison Home, 11 Mi to Bear Mountain!
- Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town
See all pet-friendly vacation rentals in Philipstown on Vacation Cottage
Do you have any winter rentals in Philipstown that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Philipstown to find what works for you.
Are there winter accommodations in Philipstown that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 53 private swimming pools or indoor pools accommodations near Philipstown along with other great amenities.
Do any winter holiday rentals in Philipstown have hot tubs?
About 53 holiday rentals in Philipstown boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Philipstown?
Yes, there are many luxury places to stay in Philipstown for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Philipstown with all the best amenities for your next trip.
