Photo by William Keller

Stockbridge Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Stockbridge vacation rentals

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (32 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
$575 nightly
The price is $642
Jan 19 - Jan 20
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7 reviews)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
$166 nightly
The price is $186
Jan 11 - Jan 12
Total with taxes and fees
Huttopia Berkshires

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
$320 nightly
The price is $361
Jan 12 - Jan 13
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (6 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
$320 nightly
The price is $361
Jan 12 - Jan 13
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,204 reviews)
"I great place to stay!!"
United Kingdom
Maricel
$126 nightly
The price is $141
Jan 11 - Jan 12
Total with taxes and fees
Vacation Village in the Berkshires

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$337 nightly
The price is $376
Jan 12 - Jan 13
Total with taxes and fees
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.6 out of 10, Exceptional, (10 reviews)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$353 nightly
The price is $395
Jan 12 - Jan 13
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Little Longbow Lakefront Chalet

Little Longbow Lakefront Chalet
Becket
9.8 out of 10, Exceptional, (21 reviews)
"Absolutely perfect quiet get away to relax and recharge will be back! "
United States
Dana V.
$456 nightly
The price is $509
Jan 16 - Jan 17
Total with taxes and fees
Little Longbow Lakefront Chalet

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (35 reviews)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
$376 nightly
The price is $420
Jan 11 - Jan 12
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
2.0 star property
Hancock
10.0 out of 10, Exceptional, (1 review)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
$246 nightly
The price is $275
Jan 11 - Jan 12
Total with taxes and fees
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
$224 nightly
The price is $250
Jan 26 - Jan 27
Total with taxes and fees
Home in Great Barrington

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
8.8 out of 10, Excellent, (20 reviews)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
$330 nightly
The price is $370
Jan 12 - Jan 13
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very Good, (988 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
$208 nightly
The price is $233
Jan 12 - Jan 13
Total with taxes and fees
Jiminy Peak Mountain Resort

Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (3 reviews)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
$234 nightly
The price is $249
Jan 11 - Jan 12
Total with taxes and fees
Berkshires Apartment at the Stephentown Hotel

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.4 out of 10, Exceptional, (3 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
$412 nightly
The price is $460
Jan 11 - Jan 12
Total with taxes and fees
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
2.0 star property
New Lebanon
10.0 out of 10, Exceptional, (1 review)
$1,619 nightly
The price is $1,640
Jan 12 - Jan 13
Total with taxes and fees
Berkshires farm, 30+ guests, 50 acres

Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers
Stephentown
7.0 out of 10, Good, (2 reviews)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
$259 nightly
The price is $287
Feb 9 - Feb 10
Total with taxes and fees
Charming 3-bedroom Cabin for nature lovers

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
$499 nightly
The price is $554
Jan 11 - Jan 12
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.6 out of 10, Exceptional, (24 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
$313 nightly
The price is $350
Jan 12 - Jan 13
Total with taxes and fees
Near Tanglewood: Historic Summer Retreat

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (8 reviews)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
$247 nightly
The price is $276
Jan 11 - Jan 12
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Stockbridge Hotel Reviews

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 $141 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.

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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This vacation home rental outside of Stockbridge offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

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 Mission House. National Shrine of the Divine Mercy and Stockbridge Bowl 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.