Holiday rentals near The Bookstore
We found 1,038 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:24 Oct - 31 Oct
Image gallery for Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10
1010 out of 10 rating
Exceptional
(6 reviews)
Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge, MA
8% off
Price is NZ$16,076
NZ$16,076
NZ$2,297 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 NZ$16,555
NZ$16,555
NZ$2,365 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 NZ$7,284
NZ$7,284
NZ$1,041 per night
includes taxes & fees
Image gallery for Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.89.8 out of 10 rating
Exceptional
(29 reviews)
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale, MA
12% off
Price is NZ$3,952
NZ$3,952
NZ$565 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 NZ$3,923
NZ$3,923
NZ$560 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 NZ$4,890
NZ$4,890
NZ$699 per night
includes taxes & fees
Image gallery for Waterfront oasis in heart of Berkshires
1010 out of 10 rating
Exceptional
(17 reviews)
Waterfront oasis in heart of Berkshires
Sandisfield, MA
8% off
Price is NZ$7,580
NZ$7,580
NZ$1,083 per night
includes taxes & fees
Image gallery for Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
South Egremont, MA
8% off
Price is NZ$5,722
NZ$5,722
NZ$817 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 NZ$8,899
NZ$8,899
NZ$1,271 per night
includes taxes & fees
Image gallery for Private home on a Beautiful lake. Large deck for entertaining
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Private home on a Beautiful lake. Large deck for entertaining
Canaan, NY
8% off
Price is NZ$5,407
NZ$5,407
NZ$772 per night
includes taxes & fees
Image gallery for Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
West Stockbridge, MA
8% off
Price is NZ$4,708
NZ$4,708
NZ$673 per night
includes taxes & fees
Image gallery for Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!
1010 out of 10 rating
Exceptional
(66 reviews)
Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!
West Stockbridge, MA
12% off
Price is NZ$3,625
NZ$3,625
NZ$518 per night
includes taxes & fees
Image gallery for Beautiful Timber Frame Home in the Berkshires /Available for Long Term
1010 out of 10 rating
Exceptional
(19 reviews)
Beautiful Timber Frame Home in the Berkshires /Available for Long Term
Washington, MA
16% off
Price is NZ$5,772
NZ$5,772
NZ$825 per night
includes taxes & fees
Image gallery for Secluded Mountaintop Retreat in the Heart of the Berkshires
8.68.6 out of 10 rating
Excellent
(12 reviews)
Secluded Mountaintop Retreat in the Heart of the Berkshires
West Stockbridge, MA
12% off
Price is NZ$4,606
NZ$4,606
NZ$658 per night
includes taxes & fees
Image gallery for Artist's Camp on Lake Mahkeenac
9.69.6 out of 10 rating
Exceptional
(19 reviews)
Artist's Camp on Lake Mahkeenac
Stockbridge, MA
7% off
Price is NZ$3,370
NZ$3,370
NZ$481 per night
includes taxes & fees
Image gallery for Family Fun in The Berkshires at Beautiful Hygge House
1010 out of 10 rating
Exceptional
(10 reviews)
Family Fun in The Berkshires at Beautiful Hygge House
Richmond, MA
8% off
Price is NZ$5,971
NZ$5,971
NZ$853 per night
includes taxes & fees
Image gallery for Hudson River Valley/Berkshires Rural Retreat
9.89.8 out of 10 rating
Exceptional
(36 reviews)
Hudson River Valley/Berkshires Rural Retreat
Canaan, NY
20% off
Price is NZ$2,271
NZ$2,271
NZ$324 per night
includes taxes & fees
Image gallery for Vacation in a Berkshire Farmhouse
9.89.8 out of 10 rating
Exceptional
(92 reviews)
Vacation in a Berkshire Farmhouse
West Stockbridge, MA
11% off
Price is NZ$4,215
NZ$4,215
NZ$602 per night
includes taxes & fees
Image gallery for Twin Maple Farm: Charming Modern Farmhouse
1010 out of 10 rating
Exceptional
(42 reviews)
Twin Maple Farm: Charming Modern Farmhouse
Great Barrington, MA
7% off
Price is NZ$5,729
NZ$5,729
NZ$818 per night
includes taxes & fees
Image gallery for The Meadows House @ Otis Ridge w/ 7-person hot tub
9.89.8 out of 10 rating
Exceptional
(34 reviews)
The Meadows House @ Otis Ridge w/ 7-person hot tub
Otis, MA
8% off
Price is NZ$3,460
NZ$3,460
NZ$494 per night
includes taxes & fees
Image gallery for Perfect Holiday Retreat, Completely Renovated, Central Location
9.89.8 out of 10 rating
Exceptional
(35 reviews)
Perfect Holiday Retreat, Completely Renovated, Central Location
Lee, MA
8% off
Price is NZ$5,516
NZ$5,516
NZ$788 per night
includes taxes & fees
Image gallery for Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.
9.49.4 out of 10 rating
Exceptional
(55 reviews)
Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.
New Ashford, MA
16% off
Price is NZ$2,943
NZ$2,943
NZ$420 per night
includes taxes & fees
Image gallery for Amazing 2-bedroom apartment sunny and quiet in Great Barrington
9.49.4 out of 10 rating
Exceptional
(26 reviews)
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Great Barrington, MA
12% off
Price is NZ$1,930
NZ$1,930
NZ$276 per night
includes taxes & fees
Image gallery for Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
9.69.6 out of 10 rating
Exceptional
(36 reviews)
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
Cummington, MA
17% off
Price is NZ$3,423
NZ$3,423
NZ$489 per night
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
162 reviews(162 reviews)
Villa with Access to Amazing Amenities!
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
127 reviews(127 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)
Cozy Cottage on the Lake
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sleeps 10 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
42 reviews(42 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