Holiday rentals near Ashley House
We found 772 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:3 Oct - 10 Oct
Image gallery for Berkshires Summer Chalet w/ Pool + Private Hiking Trails
1010 out of 10 rating
Exceptional
(6 reviews)
Berkshires Summer Chalet w/ Pool + Private Hiking Trails
Great Barrington, MA
16% off
Price is AU$8,349
AU$8,349
AU$1,193 per night
includes taxes & fees
Image gallery for Charming Columbia County Farm House
9.69.6 out of 10 rating
Exceptional
(24 reviews)
Charming Columbia County Farm House
Hillsdale, NY
8% off
Price is AU$2,763
AU$2,763
AU$395 per night
includes taxes & fees
Image gallery for 1500 sqft private entrance with beautiful views of the Berkshire Mountains
1010 out of 10 rating
Exceptional
(41 reviews)
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Lee, MA
8% off
Price is AU$3,778
AU$3,778
AU$540 per night
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 AU$6,728
AU$6,728
AU$961 per night
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 AU$13,942
AU$13,942
AU$1,992 per night
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 AU$4,637
AU$4,637
AU$662 per night
includes taxes & fees
Image gallery for Beautiful retreat in a lake community to the enjoy the summer season.
1010 out of 10 rating
Exceptional
(39 reviews)
Beautiful retreat in a lake community to the enjoy the summer season.
Granville, MA
9% off
Price is AU$2,545
AU$2,545
AU$364 per night
includes taxes & fees
Image gallery for Luxurious Mountain Retreat - Private 40-Acre Family Haven
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Luxurious Mountain Retreat - Private 40-Acre Family Haven
New Marlborough, MA
16% off
Price is AU$8,702
AU$8,702
AU$1,243 per night
includes taxes & fees
Image gallery for Mountain View Getaway
1010 out of 10 rating
Exceptional
(54 reviews)
Mountain View Getaway
West Cornwall, CT
8% off
Price is AU$3,385
AU$3,385
AU$484 per night
includes taxes & fees
Image gallery for Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
1010 out of 10 rating
Exceptional
(10 reviews)
Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
Lee, MA
8% off
Price is AU$6,701
AU$6,701
AU$957 per night
includes taxes & fees
Image gallery for Hudson Valley private 70's-style cabin on five acres, five minutes to town!
1010 out of 10 rating
Exceptional
(5 reviews)
Hudson Valley private 70's-style cabin on five acres, five minutes to town!
Millerton, NY
15% off
Price is AU$1,555
AU$1,555
AU$222 per night
includes taxes & fees
Image gallery for Imagine Being Lakeside This Summer! Book Now!
1010 out of 10 rating
Exceptional
(16 reviews)
Imagine Being Lakeside This Summer! Book Now!
Lenox, Massachusetts
15% off
Price is AU$6,463
AU$6,463
AU$923 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$8,332
AU$8,332
AU$1,190 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$5,880
AU$5,880
AU$840 per night
includes taxes & fees
Image gallery for Superb Views -- Sunsets, Mountains, Valley
1010 out of 10 rating
Exceptional
(16 reviews)
Superb Views -- Sunsets, Mountains, Valley
Copake Falls, NY
16% off
Price is AU$3,537
AU$3,537
AU$505 per night
includes taxes & fees
Image gallery for COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.69.6 out of 10 rating
Exceptional
(27 reviews)
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Craryville, NY
8% off
Price is AU$2,057
AU$2,057
AU$294 per night
includes taxes & fees
Image gallery for NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
1010 out of 10 rating
Exceptional
(35 reviews)
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Great Barrington, MA
8% off
Price is AU$6,424
AU$6,424
AU$918 per night
includes taxes & fees
Image gallery for Peacock Garden Cottage, A Unique Upstate Find
1010 out of 10 rating
Exceptional
(12 reviews)
Peacock Garden Cottage, A Unique Upstate Find
Pine Plains, NY
8% off
Price is AU$3,038
AU$3,038
AU$434 per night
includes taxes & fees
Image gallery for Beautiful House In The Woods, Huge Yard, Hot Tub
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Beautiful House In The Woods, Huge Yard, Hot Tub
Great Barrington, Massachusetts
16% off
Price is AU$7,680
AU$7,680
AU$1,097 per night
includes taxes & fees
Image gallery for Lakefront 4-Season Stunning Home and Guest House W/Tennis Court & Full Gym
9.89.8 out of 10 rating
Exceptional
(94 reviews)
Lakefront 4-Season Stunning Home and Guest House W/Tennis Court & Full Gym
Copake, NY
8% off
Price is AU$9,885
AU$9,885
AU$1,412 per night
includes taxes & fees
Image gallery for Log style home 4 miles to Catamount with fitness room
1010 out of 10 rating
Exceptional
(14 reviews)
Log style home 4 miles to Catamount with fitness room
Great Barrington, MA
6% off
Price is AU$5,248
AU$5,248
AU$750 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$11,811
AU$11,811
AU$1,687 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
(13 reviews)
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
South Egremont, MA
8% off
Price is AU$5,251
AU$5,251
AU$750 per night
includes taxes & fees
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$8,101
AU$8,101
AU$1,157 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Ashley House
Showing deals for: 29 Sept - 2 Oct
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
162 reviews(162 reviews)
The current price is AU$1,137
AU$1,137
for 3 nights, 1 chalet
AU$379 per night
includes taxes & fees
Villa with Access to Amazing Amenities!
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
126 reviews(126 reviews)
The current price is AU$1,003
AU$1,003
for 3 nights, 1 villa
AU$334 per night
includes taxes & fees
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
Sleeps 20 · 6 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
232 reviews(232 reviews)
The current price is AU$5,204
AU$5,204
for 3 nights, 1 home
AU$1,735 per night
includes taxes & fees
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Sleeps 10 · 4 bedrooms · 2 bathrooms
7.27.2 out of 10
Goodgood
44 reviews(44 reviews)
The current price is AU$1,765
AU$1,765
for 3 nights, 1 home
AU$588 per night
includes taxes & fees
Cozy Cottage on the Lake
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
The current price is AU$1,425
AU$1,425
for 3 nights, 1 cottage
AU$475 per night
includes taxes & fees
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
Sleeps 6 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
The current price is AU$1,096
AU$1,096
for 3 nights, 1 cabin
AU$365 per night
includes taxes & fees
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