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Compare 80 Cottages in Stockbridge with updated reviews, rates, and availability.

Property grounds
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - Largest Fresh Water Reservoir in Mass....
Property grounds
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (94)
"I had a wonderful time. The lil stone house school is restored in a loving way! It feels homie and cosy and has a lot of stories to tell. The location is great for seeing museums or just go for a hike. Rich and Cheryl are on top with everything and very nice hosts!"
Charming historic cottage on scenic road to Mt. Greylock
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!
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Outdoor dining
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
9.0 out of 10, Wonderful, (32)
"Quaint cabin tucked away in the Berkshires. For those vacationing with a pet, be aware that on Labor Day weekend this neighborhood puts on a fireworks show right by this house. Also, there really is not any yard, just a small patio. Lots of great hiking in the area."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Fridge, microwave, oven, stovetop
Cottage in the Berkshires 10 min. to Great Barrington
Cottage in the Berkshires 10 min. to Great Barrington
Property grounds
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is $150
$270 total
includes taxes & fees
May 20 - May 21
Perfect Vacation Get Away - Historical New Marlborough
Exterior
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (2)
"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...
The price is $200
$413 total
includes taxes & fees
May 23 - May 24
The Blue Elm - A Historic Berkshire Cottage
Fridge, microwave, oven, stovetop
Quiet rustic cottage with shared lake access
10.0 out of 10, Exceptional, (94)
"A very nice stay. Communication with the host was great. We kept bothering her with questions and she responded quickly. The place is really beautiful. We lit a fire each night and played some of the provided games and watched Netflix. It's an easy drive to Great Barrington to get groceries at the Berkshire coop. We also took advantage of our surroundings and hikes on the AT a little each day. Next time we'll use the host's canoe to explore Lake Buel. The only minor complaint I would have is...
Quiet rustic cottage with shared lake access
Property grounds
Cozy Cottage in the Woods
10.0 out of 10, Exceptional, (1)
"I have nothing but great things to say about our stay! Our hosts were great and very welcoming. The property was beautiful and our cottage as well. We will most definitely be back! Thank you!"
Cozy Cottage in the Woods
Property grounds
Fun Getaway Lakehouse in the Hudson Valley
10.0 out of 10, Exceptional, (8)
"This was an excellent stay in a perfect location to explore both the Hudson Valley and the Berkshires. Host communicated seamlessly, and house is precisely as described. Very spacious and furnished in a neutral tones, minimalist style. Would recommend."
Fun Getaway Lakehouse in the Hudson Valley
Dining
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
10.0 out of 10, Exceptional, (2)
"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
Fridge, microwave, oven, stovetop
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (20)
"the property was very well maintain, the host put alot of very personal and special touches inside the house.i have stayed in alot of houses over the years, but this one the host made you feel right at home."
Cozy Berkshire cottage with fireplace.
Property grounds
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
10.0 out of 10, Exceptional, (2)
"The house is very cozy with a well appointed kitchen and a beautiful view of the lake. We would like to go back some day. The host is very responsive and kind."
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Property grounds
Beachwood Cottage
10.0 out of 10, Exceptional, (1)
"Second time staying at the property. Comfortable, low key cabin. Access to private beach a big plus. Near Lenox, Stockbridge and Tanglewood."
Beachwood Cottage
Fridge, microwave, oven, stovetop
Caretaker's Cottage: 20 minutes to Tanglewood
10.0 out of 10, Exceptional, (3)
"Excellent home, beautiful views, no issues."
Caretaker's Cottage: 20 minutes to Tanglewood
Interior
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3.5 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Interior
Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
Interior
Beautiful Berkshires Cottage on Lake Buel
10.0 out of 10, Exceptional, (1)
"I’ve been visiting the Berkshires for decades and never stayed at a place with such an amazing view of Lake Buel! Sunrise right from my bed. The house was stocked with everything that was needed for an amazing weekend. Wonderful place to stay!"
Beautiful Berkshires Cottage on Lake Buel
Interior
Waterfalls and Trails at 'the Mills At Green Hole'
3.5 star property
Waterfalls and Trails at 'the Mills At Green Hole'
Fridge, microwave, oven, stovetop
A Charming Cottage - Secluded in Nature and Relaxing
10.0 out of 10, Exceptional, (2)
"I’ve been dreaming of a NYC getaway for years and fell in love with this home!!! I love the cozy feeling of being in such magical woods with such a beautiful lake nearby. Having access to the teepee was so special and added even more character. The beds are soooo comfortable I can’t wait to go back!!!"
A Charming Cottage - Secluded in Nature and Relaxing
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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.

Other property types in Stockbridge

Stockbridge Cottages information

Number of reviews
291
Accommodation
80 Cottages
Lowest Price
$150
Highest Price
$200

Frequently asked questions

How much do cottages in Stockbridge cost?
Rates for cottages in Stockbridge range between $150 and $200 per night. No matter your budget, you’re sure to find an ideal place to immerse yourself in nature. This price was 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?
Pick from 80 cottages in Stockbridge. No matter if you’re traveling with the family or organizing a weekend escape with your pals, Expedia can help you find the perfect space to get in touch with nature.
Why book your cottage in Stockbridge with Expedia?
Booking a cottage in Stockbridge is as simple as working out your travel dates and picking your ideal place for outdoor recreation and relaxation. From ritzy retreats to inexpensive properties and cottages that have perks like free WiFi, Expedia has something for all styles. As for awesome deals? We’ve got you covered!
How can I find cheap cottages in Stockbridge?
A wonderful way to find cheap cottages in Stockbridge is with Expedia’s convenient filter tool. Narrow down your search by budget, amenities and star rating to secure awesome bargains in a few clicks.
What is there to do in Stockbridge near my cottage?
There are loads of awesome things to put on your itinerary in Stockbridge. Head for well-known attractions like Ski Butternut, Norman Rockwell Museum and Bousquet Ski Area. Shakespeare and Company, October Mountain State Forest and Mahaiwe Performing Arts Center are other must-do’s.

Recent reviews of Stockbridge hotels
Expedia verified reviews