Holiday rentals near The Bookstore
We found 1,024 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals near The Bookstore that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the best amenities for hanging out with the people that matter most, which might include a garden and hot tub. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - The Bookstore
Showing deals for:12 Sept - 19 Sept
Image gallery for Converted Berkshire schoolhouse on a quiet river
1010 out of 10 rating
Exceptional
(32 reviews)
Converted Berkshire schoolhouse on a quiet river
Great Barrington, MA
8% off
Price is AU$3,347
AU$3,347
AU$478 per night
includes taxes & fees
Image gallery for Cozy Cottage on the Lake
9.49.4 out of 10 rating
Exceptional
(26 reviews)
Cozy Cottage on the Lake
Otis, MA
7% off
Price is AU$3,193
AU$3,193
AU$456 per night
includes taxes & fees
Image gallery for Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
1010 out of 10 rating
Exceptional
(63 reviews)
Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
Great Barrington, MA
8% off
Price is AU$7,689
AU$7,689
AU$1,098 per night
includes taxes & fees
Image gallery for Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Great Barrington, MA
6% off
Price is AU$7,398
AU$7,398
AU$1,057 per night
includes taxes & fees
Image gallery for COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
9.89.8 out of 10 rating
Exceptional
(159 reviews)
COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
Lee, MA
12% off
Price is AU$2,592
AU$2,592
AU$370 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$8,219
AU$8,219
AU$1,174 per night
includes taxes & fees
Image gallery for Gorgeous Sheffield Home in Heart of Berkshires
1010 out of 10 rating
Exceptional
(50 reviews)
Gorgeous Sheffield Home in Heart of Berkshires
Sheffield, MA
8% off
Price is AU$8,456
AU$8,456
AU$1,208 per night
includes taxes & fees
Image gallery for Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
9.89.8 out of 10 rating
Exceptional
(57 reviews)
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
Hinsdale, MA
8% off
Price is AU$2,702
AU$2,702
AU$386 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$4,532
AU$4,532
AU$647 per night
includes taxes & fees
Image gallery for Summertime at Left Bank Lodge
1010 out of 10 rating
Exceptional
(6 reviews)
Summertime at Left Bank Lodge
Hancock, MA
8% off
Price is AU$9,586
AU$9,586
AU$1,369 per night
includes taxes & fees
Image gallery for Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
1010 out of 10 rating
Exceptional
(19 reviews)
Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
Hancock, MA
8% off
Price is AU$7,356
AU$7,356
AU$1,051 per night
includes taxes & fees
Image gallery for Stay at Beaver Lodge!
1010 out of 10 rating
Exceptional
(29 reviews)
Stay at Beaver Lodge!
Monterey, MA
8% off
Price is AU$2,174
AU$2,174
AU$311 per night
includes taxes & fees
Image gallery for The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
1010 out of 10 rating
Exceptional
(20 reviews)
The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
Chatham, NY
8% off
Price is AU$4,521
AU$4,521
AU$646 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$11,983
AU$11,983
AU$1,712 per night
includes taxes & fees
Image gallery for Ashintully Cottage in spectacular setting
1010 out of 10 rating
Exceptional
(33 reviews)
Ashintully Cottage in spectacular setting
Lee, MA
17% off
Price is AU$3,784
AU$3,784
AU$541 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$14,146
AU$14,146
AU$2,021 per night
includes taxes & fees
Image gallery for Secluded Family Home in Serene Stockbridge Woods
1010 out of 10 rating
Exceptional
(21 reviews)
Secluded Family Home in Serene Stockbridge Woods
South Lee, MA
8% off
Price is AU$6,189
AU$6,189
AU$884 per night
includes taxes & fees
Image gallery for Mountain Luxury Retreat-Amazing Views/Saltwater Pool/Family Friendly/Berkshires
1010 out of 10 rating
Exceptional
(44 reviews)
Mountain Luxury Retreat-Amazing Views/Saltwater Pool/Family Friendly/Berkshires
Copake Falls, NY
8% off
Price is AU$11,896
AU$11,896
AU$1,699 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$2,754
AU$2,754
AU$393 per night
includes taxes & fees
Image gallery for Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
9.69.6 out of 10 rating
Exceptional
(97 reviews)
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
Richmond, MA
8% off
Price is AU$3,497
AU$3,497
AU$500 per night
includes taxes & fees
Image gallery for Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
1010 out of 10 rating
Exceptional
(120 reviews)
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Hillsdale, NY
16% off
Price is AU$3,498
AU$3,498
AU$500 per night
includes taxes & fees
Image gallery for Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
9.89.8 out of 10 rating
Exceptional
(54 reviews)
Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
Middlefield, MA
12% off
Price is AU$5,181
AU$5,181
AU$740 per night
includes taxes & fees
Image gallery for Classic Stockbridge Cottage
1010 out of 10 rating
Exceptional
(14 reviews)
Classic Stockbridge Cottage
Stockbridge, Massachusetts
14% off
Price is AU$4,355
AU$4,355
AU$622 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
15% off
Price is AU$5,732
AU$5,732
AU$819 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - The Bookstore
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
159 reviews(159 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
26 reviews(26 reviews)
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
Sleeps 20 · 6 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
231 reviews(231 reviews)
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)
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