Search and Rent Stockbridge Condos

Compare 44 Condo Rentals in Stockbridge with updated reviews, rates, and availability.

Fridge, microwave, oven, stovetop
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
10.0 out of 10, Exceptional, (21)
"I cannot say enough good things about this condo and the host! Colin was so easily reachable and even last minute we were able to add another night onto our stay. We had 2 little ones and 4 adults and we were so comfortable with all the space. Every amenity you think you may need was there, we didn’t find ourselves saying “Oh I wish there was…” one time! It was the perfect location for us while our group was there meeting in that building. The balcony views were phenomenal and if our group comes...
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Exterior
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
9.4 out of 10, Exceptional, (12)
"Justine was a great host, and was quick to respond to all my texts. The condo was clean equipped with the basic amenities. He provided us with a drip coffee machine, but you could also get complimentary Keurig coffee every morning from the lobby. The only small inconvenience to our stay was that there was no heat in the living room, and although there is a vent from the bedroom into the living room, it didn't seem to circulate the warm air from the bedroom into the living room. The front desk...
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Exterior
Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.
10.0 out of 10, Exceptional, (6)
"The property was as advertised. Clean and comfortable. And right on the mountain - ski-in/ski-out. Perfect for families."
Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.
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Exterior
Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.
9.8 out of 10, Exceptional, (9)
"The unit was clean and was accurately described on the listing. Check in was easy. This was our second time here and will return again."
Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.
Exterior
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
10.0 out of 10, Exceptional, (5)
"We love Bentley Brook! We will come back next year!"
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Beach
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
10.0 out of 10, Exceptional, (33)
"We loved our stay at this beautiful condo. Clean and perfectly suited at the base of Jiminy Peak. Host was responsive and provided excellent detailed instructions."
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Exterior
UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, (8)
"Very comfortable and convenient space. It easily accommodated me and my two teenaged children. The proximity to the ski lifts at Jiminy Peak is a great feature."
UNIQUE - 1BR Country Condo @ Jiminy Peak
Exterior
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
2 bedrooms, iron/ironing board, WiFi, bed sheets
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.
4.0 out of 10, (1)
"Listing is inaccurate. Clearly said 2 bedrooms in ad., but it is only 1."
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.
Snow and ski sports
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
9.6 out of 10, Exceptional, (7)
"Everything was perfect for a ski weekend"
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Property grounds
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
9.6 out of 10, Exceptional, (5)
"Perfect stay at Jiminy Peak. Unit had everything I needed."
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Exterior
Ski In & Ski Out - Deluxe 1 Bedroom Condo
10.0 out of 10, Exceptional, (6)
"We love Jiminy Peak and having a week at a ski-in, ski-out unit was fantastic. We skied back for lunch and skied back out for the afternoon; skied in for a quick dinner and the boys skied back out for night skiing. Terrific location! Kitchen was clean and serviceable (no oven but two burners, sink, dishwasher, microwave, and toaster) and beds were good. Everything was easy... check in, check out, so smooth. A great time was had by all!!!!"
Ski In & Ski Out - Deluxe 1 Bedroom Condo
Snow and ski sports
Outside Adventure-Skiing, Hiking, and Relaxation
10.0 out of 10, Exceptional, (1)
"Weather didn't help but the rental and the location were exceptional!"
Outside Adventure-Skiing, Hiking, and Relaxation
Fridge, microwave, oven, stovetop
Ski on ski off 1 Br loft condo in the village center with private gated parking
10.0 out of 10, Exceptional, (13)
"My friends and I were looking for a close escape from Albany, NY. When we entered the condo we immediately felt a sense of ease and once the wood burning fire was started we were in heaven. The condo is in the perfect location within the JP Village. We were able to walk to the Country Store, Bars and Restaurants. What was PERFECT was the close proximity to the lifts; right out the door. We could ski on, ski off and take breaks without dealing with the crowds in the food halls. The condo itself...
Ski on ski off 1 Br loft condo in the village center with private gated parking
Exterior
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
10.0 out of 10, Exceptional, (1)
"We very much enjoyed our stay. The place was very comfortable and very clean. The location worked out perfect and the parking was very convenient."
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Exterior
Wyndham Bentley Brook! 2 Bd. dlx. in Hancock
10.0 out of 10, Exceptional, (1)
"great stay as always!"
Wyndham Bentley Brook! 2 Bd. dlx. in Hancock
Exterior
Ski Jiminy Peak Xmas wk Thurs-Sun 3 nites; Ski In/Ski Out @Wyndham Bentley Brook
Ski Jiminy Peak Xmas wk Thurs-Sun 3 nites; Ski In/Ski Out @Wyndham Bentley Brook
Exterior
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
10.0 out of 10, Exceptional, (9)
"Love the ski in and out of this property. Family enjoyed staying here, highly recommended."
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Exterior
Perfect for Winter Skiing!!
Perfect for Winter Skiing!!
Snow and ski sports
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
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See all available properties in Stockbridge
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

Interior
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (11)
"We have a lovely stay, house is super clean and has all you need to relax and enjoy the space. I loved the fact we could take our small dog with us to make it a lovely family’s vacation. The house is central to everything and all towns in the Berkshires which we appreciated so much. We will return and would recommend to other highly also."
Stockbridge Home, Come Experience The Berkshires!
Outdoor dining
Find your Sanctuary at The Rectory at Stockbridge
10.0 out of 10, Exceptional, (2)
"I stayed here with seven girlfriends, all aged 25-30, for a weekend, and we found it incredibly homey and nice. As a Catholic, it was lovely staying at the rectory, visiting the beautiful altar in the backyard, and knowing that any proceeds from our stay were going to a good cause. All the rooms have saint names, and there is a lot of thoughtful charm throughout. Samantha was very helpful and great at communicating through the entire process. Highly recommend this stay in the heart of...
The price is CNY4,270
CNY7,203 total
includes taxes & fees
24 May - 25 May
Find your Sanctuary at The Rectory at Stockbridge
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.

Stockbridge Condo Rentals information

Number of reviews
138
Accommodation
44 Condo Rentals
Lowest Price
Highest Price

Frequently asked questions

How much do condos in Stockbridge cost?
Condos in Stockbridge range from to per night. These properties offer plenty of room for the entire family at a price you can afford. 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.
Why book your condo in Stockbridge with Expedia?
Expedia makes it a breeze to find your dream condo in Stockbridge. After someplace luxurious? Make the most of our filters to search for properties that have a 5-star rating. If you’re sticking to a budget, choose how much you’d like to spend and then browse our fabulous options. We’ll help you find the perfect fit whatever your trip looks like.
How can I find cheap condos in Stockbridge?
With Expedia’s user-friendly filter tool, locating cheap condos in Stockbridge is a piece of cake. To find accommodations that are very pocket friendly, narrow down your search by star rating, budget and amenities.
What is there to do in Stockbridge near my condo?
Stockbridge has enough experiences and sights to entertain you for weeks (or months!), beginning with Ski Butternut. Norman Rockwell Museum, Bousquet Ski Area and Shakespeare and Company are other terrific attractions. If you’re lingering longer, October Mountain State Forest and Mahaiwe Performing Arts Center will add the finishing touches to your itinerary.

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