Holiday rentals near Housatonic River Walk
We found 928 holiday rentals — enter your dates for availability
Choose the perfect holiday home within easy reach of Housatonic River Walk. Holiday rentals offer the best amenities for your family, friends or furry companion, such as parking and a hot tub. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Housatonic River Walk
Showing deals for:26 Sept - 3 Oct
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$3,365
AU$3,365
AU$481 per night
includes taxes & fees
Image gallery for Newly renovated charming home , Brand new chefs kitchen very comfortable home .
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Newly renovated charming home , Brand new chefs kitchen very comfortable home .
Lakeville, CT
12% off
Price is AU$4,439
AU$4,439
AU$634 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$2,847
AU$2,847
AU$407 per night
includes taxes & fees
Image gallery for Wildlife Retreat in the Forest
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Wildlife Retreat in the Forest
Becket, MA
8% off
Price is AU$6,364
AU$6,364
AU$909 per night
includes taxes & fees
Image gallery for Tranquil 3-BR Waterfront Retreat
1010 out of 10 rating
Exceptional
(13 reviews)
Tranquil 3-BR Waterfront Retreat
Becket, MA
8% off
Price is AU$5,253
AU$5,253
AU$750 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$7,731
AU$7,731
AU$1,104 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$7,350
AU$7,350
AU$1,050 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
(160 reviews)
COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
Lee, MA
12% off
Price is AU$2,606
AU$2,606
AU$372 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$8,264
AU$8,264
AU$1,181 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$4,556
AU$4,556
AU$651 per night
includes taxes & fees
Image gallery for Custom Home In Scenic Wooded Area near small lake, Sleeps up to 16
1010 out of 10 rating
Exceptional
(112 reviews)
Custom Home In Scenic Wooded Area near small lake, Sleeps up to 16
Otis, MA
12% off
Price is AU$7,296
AU$7,296
AU$1,042 per night
includes taxes & fees
Image gallery for Cozy Log Cabin Retreat with Pool on 4 Acres
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Cozy Log Cabin Retreat with Pool on 4 Acres
Canaan, CT
7% off
Price is AU$3,799
AU$3,799
AU$543 per night
includes taxes & fees
Image gallery for Cozy Cabin in the Berkshires
1010 out of 10 rating
Exceptional
(16 reviews)
Cozy Cabin in the Berkshires
Sandisfield, MA
12% off
Price is AU$2,907
AU$2,907
AU$415 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$8,502
AU$8,502
AU$1,215 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$2,186
AU$2,186
AU$312 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$4,546
AU$4,546
AU$649 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$3,804
AU$3,804
AU$543 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$12,049
AU$12,049
AU$1,721 per night
includes taxes & fees
Image gallery for Stunning Lake Views & Privacy Only Mins. to Downtown Lenox, Stockbridge, Lee.
1010 out of 10 rating
Exceptional
(22 reviews)
Stunning Lake Views & Privacy Only Mins. to Downtown Lenox, Stockbridge, Lee.
Lee, MA
12% off
Price is AU$7,437
AU$7,437
AU$1,062 per night
includes taxes & fees
Image gallery for Salisbury Cottage Retreat
1010 out of 10 rating
Exceptional
(13 reviews)
Salisbury Cottage Retreat
Salisbury, CT
16% off
Price is AU$2,853
AU$2,853
AU$408 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$2,769
AU$2,769
AU$396 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$6,223
AU$6,223
AU$889 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$3,516
AU$3,516
AU$502 per night
includes taxes & fees
Image gallery for Near Hudson - Gorgeous Sunsets + Catskill Mountain Views
1010 out of 10 rating
Exceptional
(5 reviews)
Near Hudson - Gorgeous Sunsets + Catskill Mountain Views
Ancram, NY
8% off
Price is AU$4,002
AU$4,002
AU$572 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Housatonic River Walk
Summer Lake Cottage, private beach, Berkshire Hills, small village
Sleeps 18 · 5 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
78 reviews(78 reviews)
Becket Home w/ 3-Season Porch: Walk to Lake Access
Sleeps 7 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Lakeside Estate: 2 Homes For Family Gatherings
Sleeps 18 · 8 bedrooms · 5 bathrooms
1800s Carriage house in Berkshires / Hudson Valley
Sleeps 5 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
NEW RENO - Chalet-style farm loft near Tanglewood
Sleeps 5 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
NEW RENO - Historic Loft w/views of the Berkshires
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
4 reviews(4 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