Holiday rentals near Stockbridge Bowl
We found 443 holiday rentals — enter your dates for availability
Choose the perfect holiday rental within easy reach of Stockbridge Bowl. Holiday rentals provide the best amenities for your family, friends or furry companion, such as Wi-Fi and a pool. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Stockbridge Bowl
Showing deals for:31 Oct - 7 Nov
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 NZ$14,830
NZ$14,830
NZ$2,119 per night
includes taxes & fees
Image gallery for Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
1010 out of 10 rating
Exceptional
(26 reviews)
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Great Barrington, MA
8% off
Price is NZ$9,983
NZ$9,983
NZ$1,426 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
17% off
Price is NZ$13,457
NZ$13,457
NZ$1,922 per night
includes taxes & fees
Image gallery for 1500 sqft private entrance with beautiful views of the Berkshire Mountains
1010 out of 10 rating
Exceptional
(44 reviews)
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Lee, MA
8% off
Price is NZ$4,217
NZ$4,217
NZ$602 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 NZ$7,456
NZ$7,456
NZ$1,065 per night
includes taxes & fees
Image gallery for Stonebridge Cabin: Modern Amenities, Enjoy Nature!
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Stonebridge Cabin: Modern Amenities, Enjoy Nature!
Lee, Massachusetts
15% off
Price is NZ$4,540
NZ$4,540
NZ$649 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$7,560
NZ$7,560
NZ$1,080 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 NZ$13,372
NZ$13,372
NZ$1,910 per night
includes taxes & fees
Image gallery for Best of the Berkshires & Hudson Valley
1010 out of 10 rating
Exceptional
(12 reviews)
Best of the Berkshires & Hudson Valley
Canaan, NY
8% off
Price is NZ$6,340
NZ$6,340
NZ$906 per night
includes taxes & fees
Image gallery for Completely Renovated Historic Home in the Heart of the Berkshires
1010 out of 10 rating
Exceptional
(13 reviews)
Completely Renovated Historic Home in the Heart of the Berkshires
South Lee, MA
8% off
Price is NZ$4,153
NZ$4,153
NZ$593 per night
includes taxes & fees
Image gallery for Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
1010 out of 10 rating
Exceptional
(126 reviews)
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
West Stockbridge, MA
8% off
Price is NZ$5,361
NZ$5,361
NZ$766 per night
includes taxes & fees
Image gallery for Amore Estate - beautiful room with many places to explore and relax in.
9.09.0 out of 10 rating
Wonderful
(25 reviews)
Amore Estate - beautiful room with many places to explore and relax in.
Lenox, MA
8% off
Price is NZ$12,929
NZ$12,929
NZ$1,847 per night
includes taxes & fees
Image gallery for Modern Victorian Walk to Main Street
1010 out of 10 rating
Exceptional
(25 reviews)
Modern Victorian Walk to Main Street
Great Barrington, MA
15% off
Price is NZ$5,900
NZ$5,900
NZ$843 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
14% off
Price is NZ$4,731
NZ$4,731
NZ$676 per night
includes taxes & fees
Image gallery for Imagine Being Lakeside This Summer! Book Now!
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Imagine Being Lakeside This Summer! Book Now!
Lenox, Massachusetts
15% off
Price is NZ$5,826
NZ$5,826
NZ$832 per night
includes taxes & fees
Image gallery for Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath
9.69.6 out of 10 rating
Exceptional
(28 reviews)
Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath
Canaan, NY
13% off
Price is NZ$3,671
NZ$3,671
NZ$524 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$3,695
NZ$3,695
NZ$528 per night
includes taxes & fees
Image gallery for The Maple House - Modern Retreat Near Town
1010 out of 10 rating
Exceptional
(9 reviews)
The Maple House - Modern Retreat Near Town
Lenox, MA
8% off
Price is NZ$6,366
NZ$6,366
NZ$909 per night
includes taxes & fees
Image gallery for West Stockbridge Sanctuary by Evergreen Home
9.89.8 out of 10 rating
Exceptional
(16 reviews)
West Stockbridge Sanctuary by Evergreen Home
West Stockbridge, MA
11% off
Price is NZ$6,779
NZ$6,779
NZ$968 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$5,512
NZ$5,512
NZ$787 per night
includes taxes & fees
Image gallery for Beautiful Berkshire Farm House on 160+ Acres
1010 out of 10 rating
Exceptional
(43 reviews)
Beautiful Berkshire Farm House on 160+ Acres
Great Barrington, MA
7% off
Price is NZ$12,911
NZ$12,911
NZ$1,844 per night
includes taxes & fees
Image gallery for Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!
Austerlitz, NY
9% off
Price is NZ$11,567
NZ$11,567
NZ$1,652 per night
includes taxes & fees
Image gallery for * Private Berkshire Escape* Monthly Pricing Avail
9.89.8 out of 10 rating
Exceptional
(16 reviews)
* Private Berkshire Escape* Monthly Pricing Avail
Lee, MA
8% off
Price is NZ$8,854
NZ$8,854
NZ$1,265 per night
includes taxes & fees
Image gallery for Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
Housatonic, Massachusetts
6% off
Price is NZ$5,854
NZ$5,854
NZ$836 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 - Stockbridge Bowl
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Sleeps 8 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
126 reviews(126 reviews)
Luxurious, Family Friendly, Nature Retreat at Meadows Edge!
Sleeps 10 · 4 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 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)
Berkshires Home Makeover ~ Immaculate Lakefront Getaway ~ Dreamy Sunsets!
Sleeps 8 · 4 bedrooms · 6 bathrooms
9.89.8 out of 10
Exceptionalexceptional
38 reviews(38 reviews)
Private home on a Beautiful lake. Large deck for entertaining
Sleeps 8 · 5 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Imagine Being Lakeside This Summer! Book Now!
Sleeps 10 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
18 reviews(18 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