Holiday rentals near Housatonic River Walk
We found 954 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:14 Nov - 21 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 AU$6,230
AU$6,230
AU$890 per night
includes taxes & fees
Image gallery for Peaceful, Post and Beam Loft, Sleeps 9
1010 out of 10 rating
Exceptional
(20 reviews)
Peaceful, Post and Beam Loft, Sleeps 9
Great Barrington, MA
14% off
Price is AU$2,405
AU$2,405
AU$344 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 AU$3,239
AU$3,239
AU$463 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 AU$13,169
AU$13,169
AU$1,881 per night
includes taxes & fees
Image gallery for Lakeside 3-BR Berkshires Residence
1010 out of 10 rating
Exceptional
(5 reviews)
Lakeside 3-BR Berkshires Residence
Becket, MA
7% off
Price is AU$3,574
AU$3,574
AU$511 per night
includes taxes & fees
Image gallery for Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
Sandisfield, MA
8% off
Price is AU$2,454
AU$2,454
AU$351 per night
includes taxes & fees
Image gallery for Chalet in the Berkshires, Wellness, Hike, Sauna, Gas Fireplace, EV charger & Home Office
1010 out of 10 rating
Exceptional
(5 reviews)
Chalet in the Berkshires, Wellness, Hike, Sauna, Gas Fireplace, EV charger & Home Office
Otis, MA
12% off
Price is AU$6,378
AU$6,378
AU$911 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
(45 reviews)
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Lee, MA
8% off
Price is AU$3,809
AU$3,809
AU$544 per night
includes taxes & fees
Image gallery for Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
1010 out of 10 rating
Exceptional
(25 reviews)
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Ghent, NY
10% off
Price is AU$9,943
AU$9,943
AU$1,420 per night
includes taxes & fees
Image gallery for Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
1010 out of 10 rating
Exceptional
(27 reviews)
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Great Barrington, MA
8% off
Price is AU$8,962
AU$8,962
AU$1,280 per night
includes taxes & fees
Image gallery for General Williams Estate House Lenox/Stockbridge
9.89.8 out of 10 rating
Exceptional
(110 reviews)
General Williams Estate House Lenox/Stockbridge
Stockbridge, MA
8% off
Price is AU$14,331
AU$14,331
AU$2,047 per night
includes taxes & fees
Image gallery for Romantic and Secluded Berkshire's Gem
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Romantic and Secluded Berkshire's Gem
New Marlborough, MA
8% off
Price is AU$7,541
AU$7,541
AU$1,077 per night
includes taxes & fees
Image gallery for Cozy Red Cottage on Robinson Pond nestled between the Berkshires and Catskills.
1010 out of 10 rating
Exceptional
(5 reviews)
Cozy Red Cottage on Robinson Pond nestled between the Berkshires and Catskills.
Copake, NY
15% off
Price is AU$3,201
AU$3,201
AU$457 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 AU$6,783
AU$6,783
AU$969 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 AU$6,755
AU$6,755
AU$965 per night
includes taxes & fees
Image gallery for Peaceful Retreat Compound 10 Minutes to Great Barrington!
1010 out of 10 rating
Exceptional
(28 reviews)
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Great Barrington, MA
8% off
Price is AU$12,053
AU$12,053
AU$1,722 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 AU$6,886
AU$6,886
AU$984 per night
includes taxes & fees
Image gallery for Charming Columbia County Farm House
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Charming Columbia County Farm House
Hillsdale, NY
7% off
Price is AU$2,599
AU$2,599
AU$371 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 AU$6,580
AU$6,580
AU$940 per night
includes taxes & fees
Image gallery for Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
1010 out of 10 rating
Exceptional
(128 reviews)
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
West Stockbridge, MA
8% off
Price is AU$4,842
AU$4,842
AU$692 per night
includes taxes & fees
Image gallery for Stunning Renovated Victorian
1010 out of 10 rating
Exceptional
(54 reviews)
Stunning Renovated Victorian
Great Barrington, MA
16% off
Price is AU$11,266
AU$11,266
AU$1,609 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 AU$5,975
AU$5,975
AU$854 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
(26 reviews)
Amore Estate - beautiful room with many places to explore and relax in.
Lenox, MA
8% off
Price is AU$11,458
AU$11,458
AU$1,637 per night
includes taxes & fees
Image gallery for Beachwood Cottage
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Beachwood Cottage
West Stockbridge, MA
8% off
Price is AU$3,751
AU$3,751
AU$536 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
9.49.4 out of 10
Exceptionalexceptional
81 reviews(81 reviews)
Perfect Nature Haven In Great Barrington
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.29.2 out of 10
Wonderfulwonderful
5 reviews(5 reviews)
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Becket Home w/ 3-Season Porch: Walk to Lake Access
Sleeps 7 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Lakeside Estate: 2 Homes For Family Gatherings
Sleeps 18 · 8 bedrooms · 5 bathrooms
Stay Lakeside This Summer!
Sleeps 6 · 3 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
75 reviews(75 reviews)
Top rated rentals - Housatonic River Walk
Lakeside in the Berkshires
1010 out of 10
Exceptionalexceptional
61 reviews(61 reviews)
Comfortable cottage with helpful host 5 minute walk from centre of town
1010 out of 10
Exceptionalexceptional
15 reviews(15 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