Holiday rentals near Otis Ridge
We found 670 holiday rentals — enter your dates for availability
Discover a selection of private holiday rentals within easy reach of Otis Ridge 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 spending time at your holiday home, which might include a fireplace and a washer and dryer. 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 - Otis Ridge
Showing deals for:26 Sept - 3 Oct
Image gallery for Berkshires Summer Chalet w/ Pool + Private Hiking Trails
1010 out of 10 rating
Exceptional
(6 reviews)
Berkshires Summer Chalet w/ Pool + Private Hiking Trails
Great Barrington, MA
15% off
Price is NZ$8,170
NZ$8,170
NZ$1,167 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 NZ$16,048
NZ$16,048
NZ$2,293 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
(41 reviews)
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Lee, MA
8% off
Price is NZ$4,176
NZ$4,176
NZ$597 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$7,573
NZ$7,573
NZ$1,082 per night
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
8% off
Price is NZ$5,111
NZ$5,111
NZ$730 per night
includes taxes & fees
Image gallery for Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hinsdale, MA
8% off
Price is NZ$2,277
NZ$2,277
NZ$325 per night
includes taxes & fees
Image gallery for Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
1010 out of 10 rating
Exceptional
(24 reviews)
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale, MA
12% off
Price is NZ$3,990
NZ$3,990
NZ$570 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
(23 reviews)
Amore Estate - beautiful room with many places to explore and relax in.
Lenox, MA
8% off
Price is NZ$12,942
NZ$12,942
NZ$1,849 per night
includes taxes & fees
Image gallery for Luxurious Mountain Retreat - Private 40-Acre Family Haven
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Luxurious Mountain Retreat - Private 40-Acre Family Haven
New Marlborough, MA
16% off
Price is NZ$9,689
NZ$9,689
NZ$1,384 per night
includes taxes & fees
Image gallery for Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
1010 out of 10 rating
Exceptional
(10 reviews)
Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
Lee, MA
8% off
Price is NZ$7,540
NZ$7,540
NZ$1,077 per night
includes taxes & fees
Image gallery for Imagine Being Lakeside This Summer! Book Now!
1010 out of 10 rating
Exceptional
(16 reviews)
Imagine Being Lakeside This Summer! Book Now!
Lenox, Massachusetts
15% off
Price is NZ$6,298
NZ$6,298
NZ$900 per night
includes taxes & fees
Image gallery for Catamount, Zip Line, Private Setting, Book Now!
1010 out of 10 rating
Exceptional
(6 reviews)
Catamount, Zip Line, Private Setting, Book Now!
Great Barrington, Massachusetts
7% off
Price is NZ$5,445
NZ$5,445
NZ$778 per night
includes taxes & fees
Image gallery for Beautiful retreat in a lake community to the enjoy the summer season.
1010 out of 10 rating
Exceptional
(39 reviews)
Beautiful retreat in a lake community to the enjoy the summer season.
Granville, MA
9% off
Price is NZ$2,810
NZ$2,810
NZ$401 per night
includes taxes & fees
Image gallery for NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
1010 out of 10 rating
Exceptional
(35 reviews)
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Great Barrington, MA
8% off
Price is NZ$7,057
NZ$7,057
NZ$1,008 per night
includes taxes & fees
Image gallery for Beautiful House In The Woods, Huge Yard, Hot Tub
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Beautiful House In The Woods, Huge Yard, Hot Tub
Great Barrington, Massachusetts
15% off
Price is NZ$7,438
NZ$7,438
NZ$1,063 per night
includes taxes & fees
Image gallery for Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
9.29.2 out of 10 rating
Wonderful
(11 reviews)
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Great Barrington, MA
8% off
Price is NZ$4,372
NZ$4,372
NZ$625 per night
includes taxes & fees
Image gallery for Cozy Berkshire cottage with fireplace.
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Cozy Berkshire cottage with fireplace.
Pittsfield, MA
8% off
Price is NZ$3,323
NZ$3,323
NZ$475 per night
includes taxes & fees
Image gallery for Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
1010 out of 10 rating
Exceptional
(12 reviews)
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
South Egremont, MA
8% off
Price is NZ$5,792
NZ$5,792
NZ$827 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
(18 reviews)
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
West Stockbridge, MA
13% off
Price is NZ$3,977
NZ$3,977
NZ$568 per night
includes taxes & fees
Image gallery for Log style home 4 miles to Catamount with fitness room
1010 out of 10 rating
Exceptional
(14 reviews)
Log style home 4 miles to Catamount with fitness room
Great Barrington, MA
5% off
Price is NZ$5,229
NZ$5,229
NZ$747 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$6,465
NZ$6,465
NZ$924 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$6,044
NZ$6,044
NZ$863 per night
includes taxes & fees
Image gallery for Charming Farmhouse - quiet, private & peaceful
9.69.6 out of 10 rating
Exceptional
(66 reviews)
Charming Farmhouse - quiet, private & peaceful
Worthington, MA
8% off
Price is NZ$2,664
NZ$2,664
NZ$381 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 NZ$8,388
NZ$8,388
NZ$1,198 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Otis Ridge
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sleeps 10 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
41 reviews(41 reviews)
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Sleeps 4 · 2 bedrooms · 1 bathroom
Charming 3-bedroom Modern cottage with lakeside views
Sleeps 12 · 3 bedrooms · 2 bathrooms
Berkshires Cabin 2 Mi to Appalachian Trail!
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Cozy Cottage on the Lake
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Walk to Town/Lake – Spring ’25 Renovation!
Sleeps 10 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
7 reviews(7 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