Vacation rentals near Otis Ridge
We found 697 vacation rentals — enter your dates for availability
Discover a selection of private vacation rentals near Otis Ridge that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation rentals have the amenities you need and want for your stay, which might include a garden and pool. You'll be sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.
Vacation rentals with weekly discounts - Otis Ridge
Showing deals for:Nov 21 - Nov 28
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
10% off
Price is CA $1,492
CA $1,492
CA $12,784 total
CA $12,784 total
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
10% off
Price is CA $1,343
CA $1,343
CA $11,730 total
CA $11,730 total
includes taxes & fees
Image gallery for Charming Cabin On Scenic Road
1010 out of 10 rating
Exceptional
(5 reviews)
Charming Cabin On Scenic Road
Great Barrington, MA
34% off
Price is CA $9,183
CA $9,183
CA $74,913 total
CA $74,913 total
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, MA
20% off
Price is CA $442
CA $442
CA $4,462 total
CA $4,462 total
includes taxes & fees
Image gallery for Beautiful retreat in a lake community to the enjoy the summer season.
1010 out of 10 rating
Exceptional
(41 reviews)
Beautiful retreat in a lake community to the enjoy the summer season.
Granville, MA
10% off
Price is CA $286
CA $286
CA $2,315 total
CA $2,315 total
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
10% off
Price is CA $653
CA $653
CA $5,956 total
CA $5,956 total
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
10% off
Price is CA $367
CA $367
CA $3,384 total
CA $3,384 total
includes taxes & fees
Image gallery for Perfect Nature Haven In Great Barrington
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Perfect Nature Haven In Great Barrington
Great Barrington, MA
5% off
Price is CA $530
CA $530
CA $5,427 total
CA $5,427 total
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
10% off
Price is CA $721
CA $721
CA $6,113 total
CA $6,113 total
includes taxes & fees
Image gallery for Stunning Renovated Victorian
1010 out of 10 rating
Exceptional
(54 reviews)
Stunning Renovated Victorian
Great Barrington, MA
15% off
Price is CA $1,431
CA $1,431
CA $12,687 total
CA $12,687 total
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
10% off
Price is CA $1,848
CA $1,848
CA $16,079 total
CA $16,079 total
includes taxes & fees
Image gallery for 5 Minutes from Catamount Ski Area
9.09.0 out of 10 rating
Wonderful
(21 reviews)
5 Minutes from Catamount Ski Area
Great Barrington, MA
10% off
Price is CA $285
CA $285
CA $2,638 total
CA $2,638 total
includes taxes & fees
Image gallery for Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
1010 out of 10 rating
Exceptional
(6 reviews)
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Monterey, MA
10% off
Price is CA $435
CA $435
CA $3,865 total
CA $3,865 total
includes taxes & fees
Image gallery for Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hinsdale, MA
10% off
Price is CA $211
CA $211
CA $1,874 total
CA $1,874 total
includes taxes & fees
Image gallery for Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Lee, MA
13% off
Price is CA $691
CA $691
CA $6,875 total
CA $6,875 total
includes taxes & fees
Image gallery for The Hideaway: Berkshire Home - Village of Egremont
9.69.6 out of 10 rating
Exceptional
(25 reviews)
The Hideaway: Berkshire Home - Village of Egremont
Great Barrington, MA
20% off
Price is CA $315
CA $315
CA $2,902 total
CA $2,902 total
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
10% off
Price is CA $1,182
CA $1,182
CA $10,323 total
CA $10,323 total
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
10% off
Price is CA $373
CA $373
CA $3,438 total
CA $3,438 total
includes taxes & fees
Image gallery for Romantic Berkshires Cottage - Stunning Views, Pool
1010 out of 10 rating
Exceptional
(51 reviews)
Romantic Berkshires Cottage - Stunning Views, Pool
Great Barrington, MA
5% off
Price is CA $295
CA $295
CA $2,694 total
CA $2,694 total
includes taxes & fees
Image gallery for Pristine Home In Becket Woods
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Pristine Home In Becket Woods
Becket, MA
20% off
Price is CA $283
CA $283
CA $3,104 total
CA $3,104 total
includes taxes & fees
Image gallery for Beachwood Cottage
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Beachwood Cottage
West Stockbridge, MA
10% off
Price is CA $367
CA $367
CA $3,384 total
CA $3,384 total
includes taxes & fees
Image gallery for NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
1010 out of 10 rating
Exceptional
(37 reviews)
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Great Barrington, MA
10% off
Price is CA $651
CA $651
CA $6,195 total
CA $6,195 total
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
20% off
Price is CA $883
CA $883
CA $7,901 total
CA $7,901 total
includes taxes & fees
Image gallery for Designer Berkshire Cottage
1010 out of 10 rating
Exceptional
(13 reviews)
Designer Berkshire Cottage
Richmond, MA
5% off
Price is CA $511
CA $511
CA $4,631 total
CA $4,631 total
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Otis Ridge
Charming 3-bedroom Modern cottage with lakeside views
Sleeps 12 · 3 bedrooms · 2 bathrooms
Cozy Cabin in the Berkshires
Sleeps 8 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Cozy Cottage on the Lake
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
Walk to Town/Lake – Spring ’25 Renovation!
Sleeps 10 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Top rated rentals - Otis Ridge
Wonderful olace
1010 out of 10
Exceptionalexceptional
235 reviews(235 reviews)
It is exactly as pictured
Murray M.
Stayed Jul 2024
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, yards and more
More for lessMore space, more privacy, more amenities — more value