Holiday rentals near Ashley House
We found 746 holiday rentals — enter your dates for availability
Select the perfect holiday home that's near Ashley House. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as parking and a hot tub. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Ashley House
Showing deals for:15 Aug - 22 Aug
Image gallery for Modern, private, spacious vacation home, deck, mountain views, 5 mi to Catamount
1010 out of 10 rating
Exceptional
(10 reviews)
Modern, private, spacious vacation home, deck, mountain views, 5 mi to Catamount
Hillsdale, NY
8% off
Price is AU$8,313
AU$8,313
AU$1,188 per night
includes taxes & fees
Image gallery for Imagine Being Lakeside This Summer! Book Now!
1010 out of 10 rating
Exceptional
(15 reviews)
Imagine Being Lakeside This Summer! Book Now!
Lenox, Massachusetts
16% off
Price is AU$10,465
AU$10,465
AU$1,495 per night
includes taxes & fees
Image gallery for Views of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!
1010 out of 10 rating
Exceptional
(43 reviews)
Views of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!
Hillsdale, NY
8% off
Price is AU$12,229
AU$12,229
AU$1,747 per night
includes taxes & fees
Image gallery for Lovely cottage on quiet country road in Millerton, New York, on 23 acres.
1010 out of 10 rating
Exceptional
(10 reviews)
Lovely cottage on quiet country road in Millerton, New York, on 23 acres.
Millerton, NY
8% off
Price is AU$3,385
AU$3,385
AU$484 per night
includes taxes & fees
Image gallery for Two Rooms with En-Suite in Quiet Woodland
1010 out of 10 rating
Exceptional
(30 reviews)
Two Rooms with En-Suite in Quiet Woodland
Hillsdale, NY
8% off
Price is AU$2,786
AU$2,786
AU$398 per night
includes taxes & fees
Image gallery for Salisbury Cottage Retreat
1010 out of 10 rating
Exceptional
(9 reviews)
Salisbury Cottage Retreat
Salisbury, CT
16% off
Price is AU$2,870
AU$2,870
AU$410 per night
includes taxes & fees
Image gallery for Doodletown Cabin: Pond—Outdoor Dining—Games Barn!
9.69.6 out of 10 rating
Exceptional
(65 reviews)
Doodletown Cabin: Pond—Outdoor Dining—Games Barn!
Ancram, NY
12% off
Price is AU$7,136
AU$7,136
AU$1,019 per night
includes taxes & fees
Image gallery for Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'
9.49.4 out of 10 rating
Exceptional
(68 reviews)
Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'
Pine Plains, NY
8% off
Price is AU$2,928
AU$2,928
AU$418 per night
includes taxes & fees
Image gallery for Berkshire Lake at the Pillow, and EV!
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Berkshire Lake at the Pillow, and EV!
Lee, MA
8% off
Price is AU$4,824
AU$4,824
AU$689 per night
includes taxes & fees
Image gallery for Luxury Barn Retreat . Year-Round Scenic “Park Like”Paradise.
1010 out of 10 rating
Exceptional
(134 reviews)
Luxury Barn Retreat . Year-Round Scenic “Park Like”Paradise.
Craryville, NY
8% off
Price is AU$6,054
AU$6,054
AU$865 per night
includes taxes & fees
Image gallery for Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
1010 out of 10 rating
Exceptional
(11 reviews)
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
South Egremont, MA
8% off
Price is AU$4,791
AU$4,791
AU$684 per night
includes taxes & fees
Image gallery for Charming Cottage, New Marlborough Village Green in the Berkshires
1010 out of 10 rating
Exceptional
(62 reviews)
Charming Cottage, New Marlborough Village Green in the Berkshires
Great Barrington, MA
8% off
Price is AU$2,872
AU$2,872
AU$410 per night
includes taxes & fees
Image gallery for Cozy Cabin in the Berkshires
1010 out of 10 rating
Exceptional
(16 reviews)
Cozy Cabin in the Berkshires
Sandisfield, MA
12% off
Price is AU$2,924
AU$2,924
AU$418 per night
includes taxes & fees
Image gallery for Hudson valley and The Berkshires Cottage
1010 out of 10 rating
Exceptional
(5 reviews)
Hudson valley and The Berkshires Cottage
Hillsdale, NY
8% off
Price is AU$2,182
AU$2,182
AU$312 per night
includes taxes & fees
Image gallery for Taconic Hideaway – Fireplace, Fire Pit & Swimming
1010 out of 10 rating
Exceptional
(5 reviews)
Taconic Hideaway – Fireplace, Fire Pit & Swimming
Copake, NY
12% off
Price is AU$4,151
AU$4,151
AU$593 per night
includes taxes & fees
Image gallery for Serene Berkshires Home On 5+ Acres, Rustic & Chic
8.88.8 out of 10 rating
Excellent
(6 reviews)
Serene Berkshires Home On 5+ Acres, Rustic & Chic
Otis, Massachusetts
15% off
Price is AU$7,865
AU$7,865
AU$1,124 per night
includes taxes & fees
Image gallery for An acclaimed photographers country estate, arts community, near private schools!
9.49.4 out of 10 rating
Exceptional
(22 reviews)
An acclaimed photographers country estate, arts community, near private schools!
Sharon, CT
16% off
Price is AU$6,727
AU$6,727
AU$961 per night
includes taxes & fees
Image gallery for Perfect Vacation Get Away - Historical New Marlborough
9.49.4 out of 10 rating
Exceptional
(54 reviews)
Perfect Vacation Get Away - Historical New Marlborough
Great Barrington, MA
12% off
Price is AU$2,244
AU$2,244
AU$321 per night
includes taxes & fees
Image gallery for Chalet des Collines: 5 Mins to Catamount
9.89.8 out of 10 rating
Exceptional
(26 reviews)
Chalet des Collines: 5 Mins to Catamount
Great Barrington, Massachusetts
11% off
Price is AU$7,586
AU$7,586
AU$1,084 per night
includes taxes & fees
Image gallery for Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
Cornwall Bridge, CT
8% off
Price is AU$8,551
AU$8,551
AU$1,222 per night
includes taxes & fees
Image gallery for Guesthouse Cabin vacation rentals in Berkshire County
1010 out of 10 rating
Exceptional
(6 reviews)
Guesthouse Cabin vacation rentals in Berkshire County
Sheffield, MA
8% off
Price is AU$7,860
AU$7,860
AU$1,123 per night
includes taxes & fees
Image gallery for Beautifully Restored, Secluded Farmhouse
1010 out of 10 rating
Exceptional
(23 reviews)
Beautifully Restored, Secluded Farmhouse
Hillsdale, NY
7% off
Price is AU$6,124
AU$6,124
AU$875 per night
includes taxes & fees
Image gallery for Beautiful, Unique Country House w/Large Deck
9.89.8 out of 10 rating
Exceptional
(34 reviews)
Beautiful, Unique Country House w/Large Deck
Hillsdale, NY
8% off
Price is AU$2,518
AU$2,518
AU$360 per night
includes taxes & fees
Image gallery for Catamount, Zip Line, Private Setting, Book Now!
1010 out of 10 rating
Exceptional
(6 reviews)
Catamount, Zip Line, Private Setting, Book Now!
Great Barrington, Massachusetts
7% off
Price is AU$9,168
AU$9,168
AU$1,310 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Ashley House
East Otis, MA, Waterfront Summer Cottage, Big Pond,
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
Sleeps 5 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
157 reviews(157 reviews)
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sleeps 10 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
40 reviews(40 reviews)
East Otis, MA, Waterfront Summer Cottage, Big Pond,
Sleeps 5 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Cozy Cottage on the Lake
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
Sleeps 20 · 6 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
230 reviews(230 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, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value