Holiday Rentals in Hillsdale
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37 rentals in Hillsdale.
Secluded and Private Location in the Mountain Fall color galore & Skiing
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hudson Valley Escape
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
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Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautifully decorated & immaculate log chalet on 3 acres, winter views.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming, modernized 1810 Farmhouse perfectly located in Hillsdale, NY
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful, Unique Country House w/Large Deck
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Quiet Renovated Barn
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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It's All About the Mountain Views, Modern Farmhouse
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
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Ideal location for summer and winter activities with plenty of outdoor space.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Serene Hudson Valley Farmhouse
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Private Contemporary Country Chalet
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Two Rooms with En-Suite in Quiet Woodland
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Art Studio House in Private Mountaintop Nature Preserve
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Clean & Cozy Hillsdale Cabin, minutes to Catamount, Tanglewood
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Nature's Way Farmhouse on 24 acres -25 min to Hudson or Gt Barrington
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Beautifully decorated & immaculate log chalet
Cabin Holiday Rental
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Underhill Cottage
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming, modernized 1810 Farmhouse perfectly located in Hillsdale, NY
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming, Quiet, River Front
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Country Karma -Quiet Wooded Getaway
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Hillhouse Log Cabin
Cabin Holiday Rental
3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Secluded Country Getaway On 22 Magical Acres. Catamount ski resort 5 min away
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Farm House Getaway on 200 acre horse racing farm
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Hilltop: Spectacular vista, true luxury with pool.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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R&R in the treetops with lrg outdoor living space and all the comforts of home.
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Beautifully Restored, Secluded Farmhouse
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
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Serene Hillsdale Cottage Amped with Tech and Wifi
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hillsdale home with Stunning Views. Dog friendly!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Hudson & The Berkshires Upstate Hideaway
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Chef’s Kitchen, Organic Veggie Garden, Fast Wi-Fi
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Lg Beautiful Country Home in Scenic Upstate NY!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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5 bedroom house with a pool
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Silver Ridge: sweeping views in luxury chalet
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Views of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Private, spacious vacation home, deck, mountain views, minutes to Catamount
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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CHALET-STYLE STUNNER ON A COUNTRY ROAD
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Total Privacy! Tanglewood Retreat With Berkshire Views!
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Showing results 1-37 of 37
Frequently Asked Questions about Hillsdale
- Yes, here are some popular holiday rentals in Hillsdale that have a pool:
- Secluded and Private Location in the Mountain Fall color galore & Skiing
- Hudson Valley Escape
- Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
- Yes, here are some popular holiday rentals in Hillsdale that have internet access:
- Secluded and Private Location in the Mountain Fall color galore & Skiing
- Hudson Valley Escape
- Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
- The best pet friendly rentals in Hillsdale are:
- Secluded and Private Location in the Mountain Fall color galore & Skiing
- It's All About the Mountain Views, Modern Farmhouse
- Ideal location for summer and winter activities with plenty of outdoor space.
- Some of the most popular kid friendly rentals in Hillsdale are:
- Secluded and Private Location in the Mountain Fall color galore & Skiing
- Hudson Valley Escape
- Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
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