Search Stockbridge Cottage Rentals from CA $287

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Browse Select Stockbridge Cottages

Private Island - Largest Fresh Water Reservoir in Mass....
Outdoor dining

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....
East Otis Vacation Rental w/ Private Deck & BBQ!
Desk, internet, bed sheets

East Otis Vacation Rental w/ Private Deck & BBQ!

9.6 out of 10, Exceptional, (7)
"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"
East Otis Vacation Rental w/ Private Deck & BBQ!
Charming historic cottage on scenic road to Mt. Greylock
Outdoor dining

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (104)
"Great cottage, pretty much at the foot of Mount Greylock - very spacious and comfortable - in the country but close to many of the towns of the Berkshires - the hosts Cheryl and Rich were very kind and informative about the area -thank you Cheryl and Rich - I hope to return sometime -"
Charming historic cottage on scenic road to Mt. Greylock
Cozy Berkshire cottage with fireplace.
Fridge, microwave, oven, stovetop

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (22)
"We had a wonderful experience- house was clean and very comfy with all the amenities. Hosts went out of their way both before and during our stay to provide information and make sure all our needs were met! We enjoyed relaxing in the house and the location was also very close to many great Berkshires sights!! Highly recommend this listing! "
Cozy Berkshire cottage with fireplace.
Welcome to the Red Bridge Cottage!
Interior

Welcome to the Red Bridge Cottage!

10.0 out of 10, Exceptional, (1)
"Good experience. Love the front porch"
Welcome to the Red Bridge Cottage!
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Paper towels

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Private Lake Cottage on 3 acres w/350 sq. ft. deck
Perfect Vacation Get Away - Historical New Marlborough
Property grounds

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"It was a pleasure to find this gem of a cabin available for a night so we could attend a concert at Tanglewood, despite living out of state. The location was lovely, convenient and quiet; the cabin was impeccably appointed (thanks for the fresh flowers in every room and bottle of Riesling!) and very clean with every possible amenity; and the hosts were communicative, friendly and helpful. Overall, this was an idyllic mix of quaint/cute/unique and function/comfort/ease. I will absolutely seek out...
Perfect Vacation Get Away - Historical New Marlborough
The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (7)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is CA $287
CA $596 total
includes taxes & fees
Jan 2 - Jan 3, 2025
The Blue Elm - A Historic Berkshire Cottage
Quiet rustic cottage with shared lake access
Fridge, microwave, oven, stovetop

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (103)
"I am originally from Western Mass, and was looking for a quiet get away for my fiancé and I for my birthday weekend. This more than fit the bill, we had many romantic nights in front of the fire (big y or tractor supply good for indoor wood). The cabin was delightful, quaint. And it was so quiet this time of year with no one else around us, which was just what I was looking for. Our hosts were great, made everything very easy for check in and check out and were easily valve through the App....
Quiet rustic cottage with shared lake access
Fun Getaway Lakehouse in the Hudson Valley
Terrace/patio

Fun Getaway Lakehouse in the Hudson Valley

10.0 out of 10, Exceptional, (14)
"Beautiful clean property. A lovely location. Exceeded expectations."
Fun Getaway Lakehouse in the Hudson Valley
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Dining

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

10.0 out of 10, Exceptional, (3)
"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Interior

Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!

10.0 out of 10, Exceptional, (5)
"Very clean, cute house right on the lake. We enjoyed our time there. "
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Beachwood Cottage
Interior

Beachwood Cottage

10.0 out of 10, Exceptional, (3)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Spacious Historic Home in the Berkshires!
TV, fireplace, books

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Golf

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (37)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
A Charming Cottage - Secluded in Nature and Relaxing
Fridge, microwave, oven, stovetop

A Charming Cottage - Secluded in Nature and Relaxing

10.0 out of 10, Exceptional, (3)
"The rental was nice. It was convenient for viewing the fall foliage and just enjoying the countryside. "
A Charming Cottage - Secluded in Nature and Relaxing
Waterfalls and Trails at 'the Mills At Green Hole'
Miscellaneous

Waterfalls and Trails at 'the Mills At Green Hole'

3.0 star property
Waterfalls and Trails at 'the Mills At Green Hole'
Underhill Cottage
Interior

Underhill Cottage

Underhill Cottage
Cottage in the Clouds With Mountain Views
Miscellaneous

Cottage in the Clouds With Mountain Views

9.4 out of 10, Exceptional, (3)
"A nice place to relax. A bit toasty on warm days but otherwise enjoyed our stay."
Cottage in the Clouds With Mountain Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Stockbridge

Find your Sanctuary at The Rectory at Stockbridge
Dining

Find your Sanctuary at The Rectory at Stockbridge

10.0 out of 10, Exceptional, (8)
"We could not have been happier. The house was walking distance to all shops, restaurants and attractions of the town of Stockbridge. House was large enough to comfortably accommodate 9 adults. Thoroughly enjoyed "Christmas in Stockbridge"."
The price is CA $933
CA $1,539 total
includes taxes & fees
Dec 29 - Dec 30
Find your Sanctuary at The Rectory at Stockbridge
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is CA $269
CA $310 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is CA $271
CA $298 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Jiminy Peak Mountain Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do cottages in Stockbridge cost?
Rates for cottages in Stockbridge range between CA $287 and CA $287 per night. No matter your budget, you’re sure to find the ideal place to relax and reconnect with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Stockbridge?
Pack your suitcase and pick from 86 cottages in Stockbridge. Yearning for a place where you can dive into nature and forget the world? Expedia will help you find your ideal escape in a simple click or two.
Why book your cottage in Stockbridge with Expedia?
Booking a cottage in Stockbridge is as easy as clicking on your travel dates and choosing your ideal place for a getaway in the outdoors. From ritzy retreats to affordable properties and cottages that offer amenities like a kitchenette, Expedia has something for all traveler tastes. As for awesome deals? We’ve got your back!
How can I find cheap cottages in Stockbridge?
With Expedia’s user-friendly filter tool, getting your hands on cheap cottages in Stockbridge has never been simpler. To discover stays that’ll make your hip pocket happy, fine-tune your search results by amenities, budget and star rating.
What is there to do in Stockbridge near my cottage?
Whatever you’re into, Stockbridge has a whole lot to keep you on the hop. Norman Rockwell Museum, Berkshire Theatre Festival and Naumkeag Museum are on most travelers’ itineraries. You shouldn’t miss Mission House, Schantz Galleries and National Shrine of the Divine Mercy either. With Expedia’s Stockbridge hotel deals, you’ll be able to discover more fantastic attractions like these with the money you save.