Holiday rentals near Lenox Library
We found 1,005 holiday rentals — enter your dates for availability
Find the perfect holiday home that's close to Lenox Library. Holiday rentals offer the best amenities for your family, friends or furry companion, such as cable TV and a washer and dryer. What you'll find is a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Lenox Library
Showing deals for:15 May - 22 May
Image gallery for Best of the Berkshires & Hudson Valley
1010 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Best of the Berkshires & Hudson Valley
Canaan
8% off
Price is AU$5,598
AU$5,598
for 7 nights, 1 home
AU$800 per night
includes taxes & fees
Image gallery for Lake Front Home in Heart of the Berkshires Near Jiminy Peak
1010 out of 10, Exceptional, (64 reviews)
Exceptional
(64 reviews)
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Pittsfield
8% off
Price is AU$6,897
AU$6,897
for 7 nights, 1 home
AU$985 per night
includes taxes & fees
Image gallery for Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.89.8 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hinsdale
8% off
Price is AU$1,958
AU$1,958
for 7 nights, 1 home
AU$280 per night
includes taxes & fees
Image gallery for Serene rustic cabin in the Berkshires!
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Serene rustic cabin in the Berkshires!
West Stockbridge
15% off
Price is AU$3,088
AU$3,088
for 7 nights, 1 cabin
AU$441 per night
includes taxes & fees
Image gallery for The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
1010 out of 10, Exceptional, (245 reviews)
Exceptional
(245 reviews)
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
Lee
8% off
Price is AU$10,849
AU$10,849
for 7 nights, 1 home
AU$1,550 per night
includes taxes & fees
Image gallery for Beautiful Home in AMAZING Berkshire Location
1010 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)
Beautiful Home in AMAZING Berkshire Location
Lee
8% off
Price is AU$6,008
AU$6,008
for 7 nights, 1 home
AU$858 per night
includes taxes & fees
Image gallery for Waterfront Cottage 10 Min From Great Barrington
1010 out of 10, Exceptional, (100 reviews)
Exceptional
(100 reviews)
Waterfront Cottage 10 Min From Great Barrington
New Marlborough
8% off
Price is AU$3,504
AU$3,504
for 7 nights, 1 cottage
AU$501 per night
includes taxes & fees
Image gallery for Beautiful Estate: Pool, Pond, Gym, Trails, Library, Arcade, Barn, Theatre & Gift
9.69.6 out of 10, Exceptional, (94 reviews)
Exceptional
(94 reviews)
Beautiful Estate: Pool, Pond, Gym, Trails, Library, Arcade, Barn, Theatre & Gift
Old Chatham
8% off
Price is AU$17,099
AU$17,099
for 7 nights, 1 home
AU$2,443 per night
includes taxes & fees
Image gallery for Canary Lodge - Berkshires Mountaintop Retreat - 8 Guests
8.68.6 out of 10, Excellent, (12 reviews)
Excellent
(12 reviews)
Canary Lodge - Berkshires Mountaintop Retreat - 8 Guests
West Stockbridge
8% off
Price is AU$5,447
AU$5,447
for 7 nights, 1 home
AU$778 per night
includes taxes & fees
Image gallery for Vacation in a Berkshire Farmhouse
9.89.8 out of 10, Exceptional, (98 reviews)
Exceptional
(98 reviews)
Vacation in a Berkshire Farmhouse
West Stockbridge
8% off
Price is AU$3,677
AU$3,677
for 7 nights, 1 room
AU$525 per night
includes taxes & fees
Image gallery for NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
1010 out of 10, Exceptional, (46 reviews)
Exceptional
(46 reviews)
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Great Barrington
7% off
Price is AU$6,066
AU$6,066
for 7 nights, 1 home
AU$867 per night
includes taxes & fees
Image gallery for Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
1010 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Sheffield
8% off
Price is AU$6,134
AU$6,134
for 7 nights, 1 home
AU$876 per night
includes taxes & fees
Image gallery for Spectacular setting on your own private lake close to it all!
1010 out of 10, Exceptional, (84 reviews)
Exceptional
(84 reviews)
Spectacular setting on your own private lake close to it all!
Lee
8% off
Price is AU$6,479
AU$6,479
for 7 nights, 1 home
AU$926 per night
includes taxes & fees
Image gallery for Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
1010 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Great Barrington
8% off
Price is AU$5,671
AU$5,671
for 7 nights, 1 home
AU$810 per night
includes taxes & fees
Image gallery for Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
1010 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Hancock
12% off
Price is AU$7,864
AU$7,864
for 7 nights, 1 home
AU$1,123 per night
includes taxes & fees
Image gallery for Twin Maple Farm: Charming Modern Farmhouse
1010 out of 10, Exceptional, (47 reviews)
Exceptional
(47 reviews)
Twin Maple Farm: Charming Modern Farmhouse
Great Barrington
7% off
Price is AU$3,701
AU$3,701
for 7 nights, 1 home
AU$529 per night
includes taxes & fees
Image gallery for Butternut Lux Ski Chalet on Lake with Hot Tub & Sauna Near Great Barrington
9.89.8 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Butternut Lux Ski Chalet on Lake with Hot Tub & Sauna Near Great Barrington
Monterey
5% off
Price is AU$8,515
AU$8,515
for 7 nights, 1 home
AU$1,216 per night
includes taxes & fees
Image gallery for Family Fun in The Berkshires at Beautiful Hygge House
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Family Fun in The Berkshires at Beautiful Hygge House
Pittsfield
8% off
Price is AU$5,180
AU$5,180
for 7 nights, 1 home
AU$740 per night
includes taxes & fees
Image gallery for New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Richmond
17% off
Price is AU$3,564
AU$3,564
for 7 nights, 1 apartment
AU$509 per night
includes taxes & fees
Image gallery for Beautiful Timber Frame Home in the Berkshires /Available for Long Term
1010 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)
Beautiful Timber Frame Home in the Berkshires /Available for Long Term
Washington
16% off
Price is AU$4,929
AU$4,929
for 7 nights, 1 home
AU$704 per night
includes taxes & fees
Image gallery for Secluded Family Home in Serene Stockbridge Woods
1010 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)
Secluded Family Home in Serene Stockbridge Woods
Stockbridge
8% off
Price is AU$5,351
AU$5,351
for 7 nights, 1 home
AU$764 per night
includes taxes & fees
Image gallery for Renovated Colonial on the River! Fantastic Views
1010 out of 10, Exceptional, (44 reviews)
Exceptional
(44 reviews)
Renovated Colonial on the River! Fantastic Views
Stockbridge
8% off
Price is AU$3,559
AU$3,559
for 7 nights, 1 home
AU$508 per night
includes taxes & fees
Image gallery for Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
1010 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
Sheffield
12% off
Price is AU$3,577
AU$3,577
for 7 nights, 1 home
AU$511 per night
includes taxes & fees
Image gallery for Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
West Stockbridge
12% off
Price is AU$4,446
AU$4,446
for 7 nights, 1 home
AU$635 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Lenox Library
Great Barrington, Cabin Sleeps 14, Walk To Town
Sleeps 14 · 3 bedrooms · 2+ bathrooms
9.69.6 out of 10
Exceptional
exceptional
47 reviews
(47 reviews)
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
6 bedrooms · 5 bathrooms
1010 out of 10
Exceptional
exceptional
245 reviews
(245 reviews)
The Ponds at Foxhollow
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellent
excellent
141 reviews
(141 reviews)
The Kemble- Built by a US Secretary of State in Lenox
Sleeps 35 · 13 bedrooms · 13+ bathrooms
1010 out of 10
Exceptional
exceptional
19 reviews
(19 reviews)
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Sleeps 15 · 7 bedrooms · 6+ bathrooms
1010 out of 10
Exceptional
exceptional
31 reviews
(31 reviews)
Family Ski Getaway in the Berkshires
Sleeps 8 · 3 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderful
wonderful
9 reviews
(9 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