Stockbridge Vacation Rentals

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Check prices for these dates

Next weekend
Jul 11 - Jul 13
In two weeks
Jul 18 - Jul 20
In one month
Aug 1 - Aug 3
In two months
Aug 29 - Aug 31

Browse Select Stockbridge Vacation Homes

Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is CA $148
CA $196 total
includes taxes & fees
Aug 3 - Aug 4
Deluxe Queen Room with 2 Queen Beds
Imagine Being Lakeside This Summer! Book Now!
Interior

Imagine Being Lakeside This Summer! Book Now!

10.0 out of 10, Exceptional, (16)
"Had a great trip. House was perfect for our group. Comfy beds, great fireplace and nice location near lots of local attractions."
Imagine Being Lakeside This Summer! Book Now!
Large Barn styled vacation home that fits groups with space to spare.
Miscellaneous

Large Barn styled vacation home that fits groups with space to spare.

10.0 out of 10, Exceptional, (64)
"Was an amazing place "
Large Barn styled vacation home that fits groups with space to spare.
4 Mi to Great Barrington: Berkshires Retreat!
Fridge, microwave, stovetop, dishwasher

4 Mi to Great Barrington: Berkshires Retreat!

10.0 out of 10, Exceptional, (1)
"Cozy little place with great space for dogs. The owner was responsive and ensured we had a lovely stay. "
4 Mi to Great Barrington: Berkshires Retreat!
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Property grounds

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

10.0 out of 10, Exceptional, (52)
"Great spot on the lake. Super quiet and relaxing."
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Stay Lakeside This Summer!
Exterior

Stay Lakeside This Summer!

9.8 out of 10, Exceptional, (73)
"Great location near town and on a pretty lake. Owners easy to deal with and very responsive. Our family had a great trip to the Berkshires!"
Stay Lakeside This Summer!
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Exterior

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (57)
"We had a wonderful time and loved the house! We will definitely be back!"
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Rustic 3bd Lake Front Country Cottage
Smart TV, fireplace, stereo

Rustic 3bd Lake Front Country Cottage

9.6 out of 10, Exceptional, (4)
"Enjoy our hikes and lake front view as well as kayaking around lake. Pretty area."
Rustic 3bd Lake Front Country Cottage
Spectacular views and close to Great Barrington.
Smart TV, fireplace

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Garfield Townhouse in the Berkshires on Main St
Fridge, microwave, oven, stovetop

Garfield Townhouse in the Berkshires on Main St

10.0 out of 10, Exceptional, (12)
"Great location and comfortable."
Garfield Townhouse in the Berkshires on Main St
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Property grounds

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (7)
"Delightful property, worked well for our needs"
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (44)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Berkshire Lake at the Pillow, and EV!
Fridge, microwave, oven, stovetop

Berkshire Lake at the Pillow, and EV!

9.4 out of 10, Exceptional, (15)
"Had a lovely time at this lake house. The lake access was a plus and the house was well stocked with water accessories and food items. Otis is a short distance from Lee and Lenox providing easy Berkshire access. Having a garage to park the car in was also nice. The only downside is the relatively poor condition of the driveway / shared road the house is on. The neighborhood is made up of single lane dirt roads that have suffered from some wet weather. All in all would definitely recommend."
Berkshire Lake at the Pillow, and EV!
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Terrace/patio

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (12)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
1840's Whaling Captain's Farm Estate, 6-10 guests
Interior

1840's Whaling Captain's Farm Estate, 6-10 guests

10.0 out of 10, Exceptional, (3)
"Such a beautiful home and property. We had a great time exploring during the day and spending time together at night. Sunsets over the pond are particularly lovely and the screened in porch and sitting around a fire in the chiminea outside are the perfect spots for a cocktail. We look forward to our next visit!"
1840's Whaling Captain's Farm Estate, 6-10 guests
Home w/ Fire Pit, Near Downtown Hudson + Skiing!
Terrace/patio

Home w/ Fire Pit, Near Downtown Hudson + Skiing!

2.0 star property
10.0 out of 10, Exceptional, (6)
"This spacious and beautiful home provided the perfect setting for a family gathering! The host was extremely attentive and went out of her way to check that we had everything we needed. We’d definitely stay here again and recommend this house to our friends! "
Home w/ Fire Pit, Near Downtown Hudson + Skiing!
Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.
Smart TV, fireplace, video games, DVD player

Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.

10.0 out of 10, Exceptional, (2)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
The price is CA $388
CA $630 total
includes taxes & fees
Jul 16 - Jul 17
Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Aerial view

Sun Filled Lenox Retreat - Minutes to Tanglewood!

2.0 out of 10, (1)
"The management company told me there was an issue with the house the morning of my stay."
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.
Exterior

Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.

10.0 out of 10, Exceptional, (21)
"We stayed here for skiing over a holiday weekend. The place was *very* clean and Tara was very responsive to helping with the only issue we had (which was weather related and not related to the house). The house is well outfitted and they also left a few basics for us in the kitchen which was a nice touch."
Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.
Great Barrington Lakeside Getaway w/ Kayak & Grill
Microwave, stovetop, dishwasher, toaster

Great Barrington Lakeside Getaway w/ Kayak & Grill

8.6 out of 10, Excellent, (9)
"The house was clean, comfortable, and had everything we needed. One of our best VRBO rentals to date! Will definitely stay here again."
Great Barrington Lakeside Getaway w/ Kayak & Grill
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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