Search results; Over 1,000 places in Hillsdale

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Guest favorite
Cabin in Hillsdale
Secluded Mountain Getaway with Swimming Pond.
8 guests4 bedrooms4 beds3 baths
Jun 8 – 13
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Jun 8 – 13
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R27,805 ZAR for 5 nights
for 5 nights

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Top guest favorite
Apartment in Hillsdale
Serene Suite by Catamount, Hudson, Tanglewood
1 queen bed
Jun 1 – 6
R15,079 ZAR for 5 nights
for 5 nights
4.99 out of 5 average rating, 205 reviews
Top guest favorite
Room in Hillsdale
Stay with KellyThe non-profit sector,
Historic Victorian - Berkshires, Hudson, Catamount
Jun 8 – 13
R12,298 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 316 reviews
Guest favorite
Apartment in Hillsdale
The Reynolds Room at the Historic Hillsdale House
1 queen bed
Jun 1 – 6
R10,802 ZAR for 5 nights
for 5 nights
4.82 out of 5 average rating, 71 reviews
Superhost
Home in Hillsdale
Fenced yard, playroom & the Berkshires - $0 fees
5 beds
Jun 7 – 12
R23,059 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 144 reviews
Top guest favorite
Farm stay in Chatham
Charming Cabin Studio Amid the Hudson Valley
Free cancellation
Jun 14 – 19
R18,489 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 52 reviews
Home in Spencertown
Goodbye city, hello woods!
4 beds
Jun 7 – 12
R31,896 ZAR for 5 nights
for 5 nights
New place to stay
Guest favorite
Apartment in Great Barrington
Kitchenette|King Bed|Couch
Free cancellation
Jun 9 – 14
R11,400 ZAR for 5 nights
for 5 nights
4.88 out of 5 average rating, 104 reviews
Top guest favorite
Home in Copake
Modern Rustic Getaway | Quiet | Wifi |Parking
3 beds
Jun 7 – 12
R28,241 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 35 reviews
Top guest favorite
Home in Hillsdale
Private unit in shared 1830 Farmhouse
2 beds
Jun 1 – 6
R23,848 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 15 reviews
Guest favorite
Home in Hillsdale
Sun-drenched cottage surrounded by farmland.
3 beds
Jun 9 – 14
R31,548 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 82 reviews
Home in Hillsdale
Camp Hideaway | S’mores, Lake Days & Starry Nights
Free cancellation
Jun 5 – 10
R27,270 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Guesthouse in Hillsdale
Hudson Valley and The Berkshires Cottage
1 queen bed
Jun 1 – 6
R14,137 ZAR for 5 nights
for 5 nights
4.77 out of 5 average rating, 35 reviews
Guest favorite
Apartment in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
Free cancellation
Jun 10 – 15
R12,277 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 75 reviews
Top guest favorite
Guesthouse in Great Barrington
Sweet Victorian in Housatonic
Free cancellation
Jun 8 – 13
R18,715 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 120 reviews
Top guest favorite
Apartment in Great Barrington
Private En Suite in Beautiful Victorian
Free cancellation
Sep 7 – 12
R11,229 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 368 reviews
Guest favorite
Home in Hillsdale
Hillsdale 7BR | Pool | Hot tub | Game Rm | Firepit
9 beds
Jun 11 – 16
R82,153 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 20 reviews
Top guest favorite
Cottage in Hillsdale
Underhill Cottage
3 beds
Jun 1 – 6
R34,649 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 49 reviews
Guest favorite
Apartment in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio|Berkshires
1 bed
Jun 1 – 6
R8,342 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 93 reviews