Hillsdale holiday lettings
We found 565 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Hillsdale
Showing deals for:14 Nov - 21 Nov
Image gallery for Modern Glass House designed by renowned architect Thomas Phifer
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Modern Glass House designed by renowned architect Thomas Phifer
Hudson, NY
7% off
Price is £2,566
£2,566
£367 nightly
Includes taxes & fees
Image gallery for Navywood: Scandi | Peaceful | Red Hook/Rhinebeck
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Navywood: Scandi | Peaceful | Red Hook/Rhinebeck
Elizaville, NY
11% off
Price is £1,688
£1,688
£241 nightly
Includes taxes & fees
Image gallery for General Williams Estate House Lenox/Stockbridge
9.89.8 out of 10 rating
Exceptional
(110 reviews)
General Williams Estate House Lenox/Stockbridge
Stockbridge, MA
8% off
Price is £7,263
£7,263
£1,038 nightly
Includes taxes & fees
Image gallery for Cheerful 3-bedroom cottage with woodstove
1010 out of 10 rating
Exceptional
(39 reviews)
Cheerful 3-bedroom cottage with woodstove
Sheffield, MA
9% off
Price is £1,602
£1,602
£229 nightly
Includes taxes & fees
Image gallery for Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
1010 out of 10 rating
Exceptional
(6 reviews)
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge, MA
8% off
Price is £6,613
£6,613
£945 nightly
Includes taxes & fees
Image gallery for Waterfront Cottage 10 Min From Great Barrington
1010 out of 10 rating
Exceptional
(97 reviews)
Waterfront Cottage 10 Min From Great Barrington
Great Barrington, MA
8% off
Price is £2,318
£2,318
£331 nightly
Includes taxes & fees
Image gallery for Taghkanic Glass House
1010 out of 10 rating
Exceptional
(7 reviews)
Taghkanic Glass House
Hudson, NY
8% off
Price is £25,881
£25,881
£3,697 nightly
Includes taxes & fees
Image gallery for Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Great Barrington, MA
5% off
Price is £2,969
£2,969
£424 nightly
Includes taxes & fees
Image gallery for Modern home with Catskill views, guesthouse and heated pool near Chatham/Hudson
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Modern home with Catskill views, guesthouse and heated pool near Chatham/Hudson
Chatham, NY
8% off
Price is £7,682
£7,682
£1,097 nightly
Includes taxes & fees
Image gallery for Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
1010 out of 10 rating
Exceptional
(25 reviews)
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Ghent, NY
10% off
Price is £4,999
£4,999
£714 nightly
Includes taxes & fees
Image gallery for Charming Cabin On Scenic Road
1010 out of 10 rating
Exceptional
(5 reviews)
Charming Cabin On Scenic Road
Great Barrington, MA
30% off
Price is £41,393
£41,393
£5,913 nightly
Includes taxes & fees
Image gallery for Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
1010 out of 10 rating
Exceptional
(27 reviews)
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Great Barrington, MA
8% off
Price is £4,458
£4,458
£637 nightly
Includes taxes & fees
Image gallery for Beautiful Home in AMAZING Berkshire Location
1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful Home in AMAZING Berkshire Location
Lee, MA
8% off
Price is £3,383
£3,383
£483 nightly
Includes taxes & fees
Image gallery for Completely Renovated Historic Home in the Heart of the Berkshires
1010 out of 10 rating
Exceptional
(13 reviews)
Completely Renovated Historic Home in the Heart of the Berkshires
South Lee, MA
8% off
Price is £1,862
£1,862
£266 nightly
Includes taxes & fees
Image gallery for Charming Columbia County Farm House
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Charming Columbia County Farm House
Hillsdale, NY
7% off
Price is £1,288
£1,288
£184 nightly
Includes taxes & fees
Image gallery for Peaceful Retreat Compound 10 Minutes to Great Barrington!
1010 out of 10 rating
Exceptional
(28 reviews)
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Great Barrington, MA
7% off
Price is £6,149
£6,149
£878 nightly
Includes taxes & fees
Image gallery for Stunning Renovated Victorian
1010 out of 10 rating
Exceptional
(54 reviews)
Stunning Renovated Victorian
Great Barrington, MA
15% off
Price is £5,648
£5,648
£807 nightly
Includes taxes & fees
Image gallery for 5 Minutes from Catamount Ski Area
9.09.0 out of 10 rating
Wonderful
(21 reviews)
5 Minutes from Catamount Ski Area
Great Barrington, MA
8% off
Price is £1,449
£1,449
£207 nightly
Includes taxes & fees
Image gallery for Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
9.09.0 out of 10 rating
Wonderful
(40 reviews)
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Great Barrington, MA
10% off
Price is £1,165
£1,165
£166 nightly
Includes taxes & fees
Image gallery for Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
9.49.4 out of 10 rating
Exceptional
(13 reviews)
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Lee, MA
9% off
Price is £2,390
£2,390
£341 nightly
Includes taxes & fees
Image gallery for Fun Getaway Lakehouse in the Hudson Valley
1010 out of 10 rating
Exceptional
(15 reviews)
Fun Getaway Lakehouse in the Hudson Valley
Craryville, NY
11% off
Price is £2,694
£2,694
£385 nightly
Includes taxes & fees
Image gallery for Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
1010 out of 10 rating
Exceptional
(6 reviews)
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Monterey, MA
8% off
Price is £2,108
£2,108
£301 nightly
Includes taxes & fees
Image gallery for The Hideaway: Berkshire Home - Village of Egremont
9.69.6 out of 10 rating
Exceptional
(25 reviews)
The Hideaway: Berkshire Home - Village of Egremont
Great Barrington, MA
16% off
Price is £1,590
£1,590
£227 nightly
Includes taxes & fees
Image gallery for Beautifully Restored, Secluded Farmhouse
1010 out of 10 rating
Exceptional
(24 reviews)
Beautifully Restored, Secluded Farmhouse
Hillsdale, NY
7% off
Price is £3,059
£3,059
£437 nightly
Includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Hillsdale
magical cabin in the woods
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Beautifully decorated & immaculate log chalet on 3 acres, winter views.
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
132 reviews(132 reviews)
Lakefront home on Copake Lake - Close to Hudson, Great Barrington & Millerton.
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
95 reviews(95 reviews)
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Sleeps 8 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
★Private Pool★ Spacious Historic 1850s "Bell House" @ Hillsdale, NY Town Center
Sleeps 10 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Hudson valley and The Berkshires Cottage
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value