Search Stockbridge Cottage Rentals from CA $289

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Check prices for these dates

Next weekend
Mar 7 - Mar 9
In two weeks
Mar 14 - Mar 16
In one month
Mar 28 - Mar 30
In two months
Apr 25 - Apr 27

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!
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Fridge, microwave, stovetop, dishwasher

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was exactly as advertised and was in a safe and private location. The hosts perfectly accommodated our stay and we cannot be more thankful to them for a fully-functional house that was suitable for the adults and children. It was truly a pleasure to stay at this home."
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
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
Cozy Berkshire cottage with fireplace.
Fridge, microwave, oven, stovetop

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (23)
"Very good! Enjoyed every moment once we got the thermostat set to the right temp for us. Clean and cozy!"
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!
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 $289
CA $592 total
includes taxes & fees
Mar 3 - Mar 4
The Blue Elm - A Historic Berkshire Cottage
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, (107)
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"
Charming historic cottage on scenic road to Mt. Greylock
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Interior

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.2 out of 10, Wonderful, (11)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Family-Friendly Richmond Cottage w/ Private Yard
Property grounds

Family-Friendly Richmond Cottage w/ Private Yard

2.0 star property
10.0 out of 10, Exceptional, (4)
"Comfortable. Homey. Very well stocked, especially the kitchen. Plenty of room and light. Thank you for our visit. "
Family-Friendly Richmond Cottage w/ Private Yard
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Fridge, microwave, stovetop, dishwasher

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Lake Views & Dock Access - Pittsfield Cottage!
Outdoor dining

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (1)
"This house was more than we could ask for it’s right on the water and has everything you could possibly forget handy! A all around, great place to enjoy nature and spend time with family and friends. Super straightforward didn’t need to ask the host any questions Will be booking here again! "
Lake Views & Dock Access - Pittsfield 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
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
Plan your Berkshires by the lake
Exterior

Plan your Berkshires by the lake

Plan your Berkshires by the lake
Fun Getaway Lakehouse in the Hudson Valley
Terrace/patio

Fun Getaway Lakehouse in the Hudson Valley

10.0 out of 10, Exceptional, (15)
"Can't say enough about this place. It looked like it was just recently built or renovated, and was very very clean. The place was warm, inviting, and very comfortable for my family of 5. Leticia is amazing, very very responsive and understanding. If you are staying in the area (the lake, skiing, etc.) I would highly recommend this place. We will definitely look to book this place again the next time we go skiing at Catamount."
Fun Getaway Lakehouse in the Hudson Valley
Cozy Hudson Valley Lake Cottage :CATAMOUNT SKI/SNOW BOARD
Interior

Cozy Hudson Valley Lake Cottage :CATAMOUNT SKI/SNOW BOARD

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 :CATAMOUNT SKI/SNOW BOARD
Perfect Vacation Get Away - Historical New Marlborough
Property grounds

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"Beautiful wrap-around porch. Views were wonderful. Had to use the pullout sofa, because the stairs to the loft was basically a stepladder and for us seniors, was a no go. It does need a microwave. We gave it a four star overall, but for a younger couple would be a five."
Perfect Vacation Get Away - Historical New Marlborough
Picturesque Cottage with Sunroom on Ashmere Lake!
Interior

Picturesque Cottage with Sunroom on Ashmere Lake!

9.4 out of 10, Exceptional, (21)
"Everything was just like it was listed. We had trouble with the t.v. but other than that it was great. "
Picturesque Cottage with Sunroom on Ashmere Lake!
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!
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

A Grand property in Historic Stockbridge
Fridge, microwave, oven, stovetop

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (96)
"We had an amazing time. We had several out of town guests who stayed at the home and then a birthday party with local guests in the ballroom. The ballroom is absolutely stunning. The chef enjoyed the kitchen. There was plenty of parking and a beautiful setting. I would stay again. "
A Grand property in Historic 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, (1777)
"Great stay as always! Highly recommend."
The price is CA $141
CA $169 total
includes taxes & fees
Mar 2 - Mar 3
Vacation Village in the Berkshires
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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 $289 and CA $289 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 87 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.