Vacation rentals near The Bookstore
We found 1,028 vacation rentals — enter your dates for availability
Discover a selection of private vacation rentals close to The Bookstore that are perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the amenities you expect for your stay, including WiFi and parking. You'll be able to choose a rental for everyone's needs, including places that are non-smoking or accessible.
Vacation rentals with weekly discounts - The Bookstore
Showing deals for:Nov 7 - Nov 14
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
20% off
Price is CA $739
CA $739
CA $6,876 total
CA $6,876 total
includes taxes & fees
Image gallery for Peaceful, Post and Beam Loft, Sleeps 9
1010 out of 10 rating
Exceptional
(19 reviews)
Peaceful, Post and Beam Loft, Sleeps 9
Great Barrington, Massachusetts
20% off
Price is CA $225
CA $225
CA $2,419 total
CA $2,419 total
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
15% off
Price is CA $745
CA $745
CA $6,607 total
CA $6,607 total
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
10% off
Price is CA $472
CA $472
CA $4,225 total
CA $4,225 total
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
12% off
Price is CA $310
CA $310
CA $2,917 total
CA $2,917 total
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
8% off
Price is CA $592
CA $592
CA $6,195 total
CA $6,195 total
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
10% off
Price is CA $651
CA $651
CA $5,942 total
CA $5,942 total
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
10% off
Price is CA $1,340
CA $1,340
CA $11,702 total
CA $11,702 total
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
10% off
Price is CA $1,551
CA $1,551
CA $13,449 total
CA $13,449 total
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
10% off
Price is CA $682
CA $682
CA $6,124 total
CA $6,124 total
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
10% off
Price is CA $558
CA $558
CA $5,014 total
CA $5,014 total
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
10% off
Price is CA $620
CA $620
CA $5,793 total
CA $5,793 total
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
15% off
Price is CA $381
CA $381
CA $3,250 total
CA $3,250 total
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
13% off
Price is CA $936
CA $936
CA $9,205 total
CA $9,205 total
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
15% off
Price is CA $191
CA $191
CA $2,020 total
CA $2,020 total
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
23% off
Price is CA $1,039
CA $1,039
CA $10,573 total
CA $10,573 total
includes taxes & fees
Image gallery for Treetop Hideaway in Tyringham
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Treetop Hideaway in Tyringham
Lee, Massachusetts
5% off
Price is CA $473
CA $473
CA $3,952 total
CA $3,952 total
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
10% off
Price is CA $720
CA $720
CA $6,098 total
CA $6,098 total
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
10% off
Price is CA $1,188
CA $1,188
CA $10,818 total
CA $10,818 total
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
20% off
Price is CA $393
CA $393
CA $4,037 total
CA $4,037 total
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
10% off
Price is CA $445
CA $445
CA $4,071 total
CA $4,071 total
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
20% off
Price is CA $412
CA $412
CA $4,409 total
CA $4,409 total
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
10% off
Price is CA $1,861
CA $1,861
CA $15,991 total
CA $15,991 total
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
20% off
Price is CA $257
CA $257
CA $2,889 total
CA $2,889 total
includes taxes & fees
Find spaces that suit your style
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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
Wonderful olace
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, yards and more
More for lessMore space, more privacy, more amenities — more value