Stockbridge Vacation Rentals

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Vacation Rentals in Stockbridge

Lobby
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (2065)
"Nice room clean and friendly staff"
$112 nightly
The price is $125
Oct 30 - Oct 31
Total with taxes and fees
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (981)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
$146 nightly
The price is $164
Oct 19 - Oct 20
Total with taxes and fees
Jiminy Peak Mountain Resort
Restaurant
Huttopia Berkshires
Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (5)
"Perfect place for a relaxing getaway! We loved everything! "
$98 nightly
The price is $109
Oct 16 - Oct 17
Total with taxes and fees
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow
The Ponds at Foxhollow
3.0 star property
8.6 out of 10, Excellent, (131)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
The Ponds at Foxhollow
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.
Amore Estate - beautiful room with many places to explore and relax in.
9.2 out of 10, Wonderful, (31)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
Amore Estate - beautiful room with many places to explore and relax in.
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi
Spacious 5-bedroom house in charming Lee with WiFi
$685 nightly
The price is $765
Oct 21 - Oct 22
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
Exterior
Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
10.0 out of 10, Exceptional, (14)
"Amazing Inn. Cozy and everything we needed. "
$969 nightly
The price is $1,047
Nov 7 - Nov 8
Total with taxes and fees
Hancock Village Inn at Jiminy Peak
Interior
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (224)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake
Outdoor banquet area
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
9.6 out of 10, Exceptional, (93)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISO
8.8 out of 10, Excellent, (6)
"Kind and responsive host."
$478 nightly
The price is $485
Oct 15 - Oct 16
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO
Interior
Charming 3-bedroom Cabin for nature lovers
Charming 3-bedroom Cabin for nature lovers
8.0 out of 10, Very Good, (1)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
$264 nightly
The price is $293
Oct 15 - Oct 16
Total with taxes and fees
Charming 3-bedroom Cabin for nature lovers
Property grounds
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.8 out of 10, Exceptional, (19)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Property grounds
The Lakeshore House
The Lakeshore House
10.0 out of 10, Exceptional, (1)
"Excellent stay!"
$716 nightly
The price is $802
Oct 15 - Oct 16
Total with taxes and fees
The Lakeshore House
Dining
Guesthouse Cabin vacation rentals in Berkshire County
Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
$640 nightly
The price is $715
Oct 26 - Oct 27
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Interior
Private Island - Largest Fresh Water Reservoir in Mass
Private Island - Largest Fresh Water Reservoir in Mass
8.8 out of 10, Excellent, (8)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass
Outdoor dining
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
9.8 out of 10, Exceptional, (149)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Property grounds
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
9.8 out of 10, Exceptional, (89)
"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
Fridge, microwave, oven, stovetop
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
2.0 star property
10.0 out of 10, Exceptional, (12)
"We came out to see James Taylor on the 4th. Kathy and Kit were terrific hosts. Friendly, accommodating and their home was very comfortable and clean. We would definitely rent from them again. Thank you! "
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (226)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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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Top Stockbridge Hotel Reviews

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Good"
jifang 1-night trip
Posted 2 days ago
Best Western Plus Berkshire Hills Inn & Suites

Find out more about Stockbridge

Everything you need to know about Stockbridge vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stockbridge vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stockbridge vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Stockbridge vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stockbridge. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Stockbridge in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $109 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Stockbridge rentals

At Expedia, we put the best Stockbridge vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Stockbridge rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stockbridge vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stockbridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Stockbridge?

Yes, we offer vacation rentals in Stockbridge close to Berkshire Botanical Garden, or you can select a more secluded option if you want a relaxing stay. Our travelers say Stockbridge has a good selection of bars. Make sure you have time to check out the gardens and museums during your trip.

What are some of the best vacation rentals in Stockbridge?

Spacious 5-bedroom house in charming Lee with WiFi: This vacation home rental outside of Stockbridge offers a fireplace, a barbecue grill, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a dishwasher and a microwave can make your vacation run smoothly.

How many vacation rentals will I find in Stockbridge?

Choose from 31 Expedia vacation rentals in Stockbridge for a memorable vacation.

What’s there to see and do in Stockbridge?

Enjoy the outdoors at Naumkeag Museum and Berkshire Botanical Garden, or simply take in cultural attractions like Norman Rockwell Museum and Frelinghuysen Morris House and Studio. National Shrine of the Divine Mercy and Housatonic River are other places to visit while you're in town.

What’s a vacation rental in Stockbridge like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Stockbridge. Vacation rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family trips.