Holiday Rentals in Hillsdale
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Bedrooms
Bathrooms
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Property type
Distinctive Features
Distance from
5 km
45 rentals in Hillsdale.
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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Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Quiet Renovated Barn
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Beautifully decorated & immaculate log chalet
Cabin Holiday Rental
3 bedrooms
2 bathrooms
Sleeps 6
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Charming, Quiet, River Front
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 13
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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
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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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Two Rooms with En-Suite in Quiet Woodland
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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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
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Beautiful, Unique Country House w/Large Deck
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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Quiet Guest House In The Green River Valley
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Farm House Getaway on 200 acre horse farm
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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Private Hillsdale Home With Views Of Catamount.
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Hillhouse Log Cabin
Cabin Holiday Rental
3 bedrooms
2 bathrooms
Sleeps 13
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NEW! Clean & Cozy Hillsdale Cabin, minutes to Catamount, Tanglewood
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
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Total Privacy! Tanglewood Retreat With Berkshire Views!
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 14
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Charming 1860s Farmhouse surrounded by 1000 acres of protected land
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Country Karma -Quiet Wooded Getaway
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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Hollywood Hills in the Berkshires
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 5
Match: Sleeps
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Secluded and Private Location Mountain Fall color & Ski by Berkshire Hudson Ny
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lg Beautiful Country Home in Scenic Upstate NY!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 11
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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
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Quiet Country road getaway
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
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Historic Hudson Valley Home in the Berkshire Foothills
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Historic Hillsdale House With Pool, Near Catamount Ski Area
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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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Art Studio House in Private Mountaintop Nature Preserve
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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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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Chef’s Kitchen, Organic Veggie Garden, Fast Wi-Fi
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
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Silver Ridge: sweeping views in luxury chalet
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 8
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Cozy Loft on a Country Road
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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Secluded Hudson Valley Compound
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautifully Restored, Secluded Farmhouse
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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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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Family-Friendly Stunner in Upstate New York
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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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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
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CHALET-STYLE STUNNER ON A COUNTRY ROAD
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Modern, private, spacious vacation home, deck, mountain views, near Catamount
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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4 bedroom house with a heated pool
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 6
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Hilltop: Spectacular vista, true luxury with pool.
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Underhill Cottage
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
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Private Contemporary Country Chalet
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hudson Valley Escape
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Hudson & The Berkshires Upstate Hideaway
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Showing results 1-45 of 45
Frequently Asked Questions about Hillsdale
- Yes, here are some popular holiday rentals in Hillsdale that have a pool:
- Beautifully decorated & immaculate log chalet
- Hillhouse Log Cabin
- Total Privacy! Tanglewood Retreat With Berkshire Views!
- Yes, here are some popular holiday rentals in Hillsdale that have internet access:
- Beautifully decorated & immaculate log chalet
- Hillhouse Log Cabin
- Total Privacy! Tanglewood Retreat With Berkshire Views!
- Some of the most popular kid friendly rentals in Hillsdale are:
- Beautifully decorated & immaculate log chalet
- Hillhouse Log Cabin
- Lg Beautiful Country Home in Scenic Upstate NY!