Holiday rentals near The Bookstore
We found 1,027 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:7 Nov - 14 Nov
Image gallery for Berkshires Summer Chalet w/ Pool + Private Hiking Trails
1010 out of 10 rating
Exceptional
(7 reviews)
Berkshires Summer Chalet w/ Pool + Private Hiking Trails
Great Barrington, MA
16% off
Price is S$6,416
S$6,416
S$917 per night
includes taxes & fees
Image gallery for Chalet in the Berkshires, Wellness, Family, Lake, Kayaks, Sauna, EV charger & Home Office
1010 out of 10 rating
Exceptional
(5 reviews)
Chalet in the Berkshires, Wellness, Family, Lake, Kayaks, Sauna, EV charger & Home Office
Otis, MA
12% off
Price is S$6,163
S$6,163
S$880 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 S$3,945
S$3,945
S$564 per night
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 S$2,735
S$2,735
S$391 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
(13 reviews)
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Great Barrington, MA
6% off
Price is S$5,789
S$5,789
S$827 per night
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 S$11,688
S$11,688
S$1,670 per night
includes taxes & fees
Image gallery for Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
1010 out of 10 rating
Exceptional
(15 reviews)
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Sheffield, MA
8% off
Price is S$5,552
S$5,552
S$793 per night
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 S$13,324
S$13,324
S$1,903 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 S$5,721
S$5,721
S$817 per night
includes taxes & fees
Image gallery for Little Longbow Lakefront Chalet
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Little Longbow Lakefront Chalet
Becket, MA
8% off
Price is S$4,641
S$4,641
S$663 per night
includes taxes & fees
Image gallery for WINTER/SUMMER - ON 5 ACRES, PRIVATE LAKE GARFIELD DOCK, 5 MILES FROM BUTTERNUT
9.69.6 out of 10 rating
Exceptional
(17 reviews)
WINTER/SUMMER - ON 5 ACRES, PRIVATE LAKE GARFIELD DOCK, 5 MILES FROM BUTTERNUT
Monterey, MA
8% off
Price is S$5,357
S$5,357
S$765 per night
includes taxes & fees
Image gallery for Forget-Me-Not by AvantStay | Bold Lakefront Escape
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Forget-Me-Not by AvantStay | Bold Lakefront Escape
Monterey, Massachusetts
9% off
Price is S$9,011
S$9,011
S$1,287 per night
includes taxes & fees
Image gallery for Peaceful Retreat Compound 10 Minutes to Great Barrington!
1010 out of 10 rating
Exceptional
(26 reviews)
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Great Barrington, MA
7% off
Price is S$10,663
S$10,663
S$1,523 per night
includes taxes & fees
Image gallery for Private Berkshire Cabin on 27acres near Jiminy Peak.
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Private Berkshire Cabin on 27acres near Jiminy Peak.
Williamstown, MA
13% off
Price is S$3,048
S$3,048
S$435 per night
includes taxes & fees
Image gallery for Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
9.09.0 out of 10 rating
Wonderful
(39 reviews)
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Great Barrington, MA
10% off
Price is S$1,897
S$1,897
S$271 per night
includes taxes & fees
Image gallery for Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
1010 out of 10 rating
Exceptional
(13 reviews)
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
West Stockbridge, Massachusetts
16% off
Price is S$10,419
S$10,419
S$1,488 per night
includes taxes & fees
Image gallery for Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
1010 out of 10 rating
Exceptional
(11 reviews)
Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
Lee, MA
8% off
Price is S$5,697
S$5,697
S$814 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
14% off
Price is S$4,115
S$4,115
S$588 per night
includes taxes & fees
Image gallery for Walk to Town/Lake – Spring ’25 Renovation!
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Walk to Town/Lake – Spring ’25 Renovation!
Great Barrington, Massachusetts
15% off
Price is S$3,769
S$3,769
S$538 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 S$3,800
S$3,800
S$543 per night
includes taxes & fees
Image gallery for BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
9.69.6 out of 10 rating
Exceptional
(88 reviews)
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
Old Chatham, NY
8% off
Price is S$15,940
S$15,940
S$2,277 per night
includes taxes & fees
Image gallery for Pristine Home In Becket Woods
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Pristine Home In Becket Woods
Becket, Massachusetts
13% off
Price is S$2,707
S$2,707
S$387 per night
includes taxes & fees
Image gallery for Stunning Renovated Victorian
1010 out of 10 rating
Exceptional
(53 reviews)
Stunning Renovated Victorian
Great Barrington, MA
15% off
Price is S$9,955
S$9,955
S$1,422 per night
includes taxes & fees
Image gallery for Mountain Luxury Retreat-Amazing Views/Saltwater Pool/Family Friendly/Berkshires
1010 out of 10 rating
Exceptional
(46 reviews)
Mountain Luxury Retreat-Amazing Views/Saltwater Pool/Family Friendly/Berkshires
Copake Falls, NY
8% off
Price is S$10,449
S$10,449
S$1,493 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - The Bookstore
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
164 reviews(164 reviews)
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Sleeps 10 · 4 bedrooms · 2 bathrooms
7.27.2 out of 10
Goodgood
45 reviews(45 reviews)
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
Sleeps 20 · 6 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
235 reviews(235 reviews)
Villa with Access to Amazing Amenities!
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
127 reviews(127 reviews)
Private Island - Largest Fresh Water Reservoir in Mass....
Sleeps 6 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
7 reviews(7 reviews)
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sleeps 10 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
Top rated rentals - The Bookstore
Beautiful place, great location
1010 out of 10
Exceptionalexceptional
235 reviews(235 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