Stockbridge Vacation Rentals from $121: Search Short-Term Rentals

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Our top choices for Stockbridge vacation rentals

A two-story house with a front porch, surrounded by a garden with various plants and rocks.

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

Stockbridge

Anonymous traveler

$766 nightly

Sep 28 - Sep 29

Total with taxes and fees

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Pittsfield

Robert

$109 nightly

Oct 1 - Oct 2

Total with taxes and fees

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

3. Vacation Village in the Berkshires

Williamstown

Jacob

$122 nightly

Sep 27 - Sep 28

Total with taxes and fees

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

4. Cozy 1-bedroom studio in serene Great Barrington with AC

Great Barrington

$125 nightly

Oct 11 - Oct 12

Total with taxes and fees

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

5. Riverside Retreat in the Berkshires

Great Barrington

Kelly B.

$284 nightly

Sep 27 - Sep 28

Total with taxes and fees

A sandy beach with a lake and forest in the background.

6. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Great Barrington

$294 nightly

Oct 1 - Oct 2

Total with taxes and fees

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

7. Home in Great Barrington

Great Barrington

HEATHER G.

$300 nightly

Oct 25 - Oct 26

Total with taxes and fees

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

8. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Varun M.

$205 nightly

Sep 27 - Sep 28

Total with taxes and fees

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

9. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

$312 nightly

Oct 11 - Oct 12

Total with taxes and fees

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

10. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

William C B.

$289 nightly

Oct 5 - Oct 6

Total with taxes and fees

A snow-covered outdoor area with a fire pit, tables, and chairs.

11. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock

Maura D.

$199 nightly

Sep 28 - Sep 29

Total with taxes and fees

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

12. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

$335 nightly

Sep 28 - Sep 29

Total with taxes and fees

A garden area with potted plants, a wooden fence, and outdoor furniture.

13. Cozy Camper tucked into the woods

Sandisfield

"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...

hannah w.

$180 nightly

Sep 28 - Sep 29

Total with taxes and fees

A bedroom with a bed, a dresser, a television, and a painting on the wall.

14. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

Hancock

Matthew B.

$199 nightly

Sep 28 - Sep 29

Total with taxes and fees

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

15. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

$552 nightly

Sep 28 - Sep 29

Total with taxes and fees

A hot tub with a string of lights above it, set against a dark night sky.

16. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

$352 nightly

Sep 29 - Sep 30

Total with taxes and fees

A spacious living room with a dining area, a kitchen, and a large window.

17. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

$226 nightly

Sep 28 - Sep 29

Total with taxes and fees

A covered outdoor seating area with two chairs and a view of a grassy landscape.

18. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Lenox

$285 nightly

Sep 27 - Sep 28

Total with taxes and fees

A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

19. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Hancock

Tom C.

$194 nightly

Sep 28 - Sep 29

Total with taxes and fees

A camping setup with a metal chair and a table by a river in a forest.

20. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

Jess S.

$293 nightly

Sep 27 - Sep 28

Total with taxes and fees

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Top Stockbridge Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"Great location to Tanglewood, 11 min ride. Clean room, comfy beds, great shower. Loved the pool and hot tub. Breakfast was just okay. We went down 20 minutes before breakfast was to be closed and not much there to be had. I had to ask for a bagel and no waffles."

Berkshire Mountain Lodge

8/10 Good

"One of the most important aspects of a good hotel is the smell of it when I first walk in the door. This lodge smelled clean and was clean. The second important thing is the customer service. This place was just okay. Polite but not very friendly. The third important aspect is the plumbing and that was just okay too. Workable enough so we didn’t have to ask for another room but the little soaps were tiny and the toilet was in okay condition. A little hard to flush sometimes. They act like it’s someplace special but it really isn’t. It was a good stay but nothing special. Location was convenient to everything - restaurants and stores."

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 $121 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.

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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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental outside Stockbridge is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease 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 garden and a selection of games.

How many vacation rentals will I find in Stockbridge?

Choose from 35 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 Berkshire Theatre Festival. 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.

Stockbridge Vacation Rentals

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Check prices for these dates

Our top choices for Stockbridge vacation rentals

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

2. Berkshire Mountain Lodge

3. Vacation Village in the Berkshires

4. Cozy 1-bedroom studio in serene Great Barrington with AC

5. Riverside Retreat in the Berkshires

6. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

7. Home in Great Barrington

8. NEW RENO - Chalet-style farm loft near Tanglewood

9. Sweet Cozy Victorian in Housatonic. Close to everything.

10. Real Estate: Therapy - Lake, Laundry, Love it

11. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

12. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

13. Cozy Camper tucked into the woods

14. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

15. Treetop Hideaway in Tyringham

16. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

17. 1800s Carriage house in Berkshires / Hudson Valley

18. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

19. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

20. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Find vacation rentals that suit your style

Top Stockbridge Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Stockbridge

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