Stockbridge Vacation Rentals from ￥15,942: Search Short-Term Rentals

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Our top choices for Stockbridge vacation rentals

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

1. Berkshire Mountain Lodge

Pittsfield

Kathleen

￥18,735 total

includes taxes & fees

Nov 9 - Nov 10

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

2. Vacation Village in the Berkshires

Williamstown

Pofen

￥15,942 total

includes taxes & fees

Nov 1 - Nov 2

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

3. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

￥110,220 total

includes taxes & fees

Oct 20 - Oct 21

A staircase with a wooden handrail and a white wall with a light switch.

4. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

￥44,649 total

includes taxes & fees

Oct 26 - Oct 27

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

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

Housatonic

Peter S.

￥55,526 total

includes taxes & fees

Oct 18 - Oct 19

A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

6. Stylish Mid-century Modern Berkshires Cape

Lee

￥138,195 total

includes taxes & fees

Oct 18 - Oct 19

A modern living room with a sofa, armchair, coffee table, and TV.

7. Spacious Central Berkshires Home for Groups

Lee

Beth S.

￥101,678 total

includes taxes & fees

Nov 9 - Nov 10

A living room with a sofa, armchairs, a coffee table, and a television.

8. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

￥100,565 total

includes taxes & fees

Oct 14 - Oct 15

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

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

Great Barrington

Marc R.

￥52,167 total

includes taxes & fees

Oct 14 - Oct 15

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

10. Home in Great Barrington

Great Barrington

Janet G.

￥56,656 total

includes taxes & fees

Oct 26 - Oct 27

A modern kitchen with a central island, stainless steel appliances, and a ceiling fan.

11. Urban Peak Escape, Lenox, MA

Lenox

Nancy H.

￥120,618 total

includes taxes & fees

Oct 14 - Oct 15

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

12. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mark M.

￥111,227 total

includes taxes & fees

Oct 19 - Oct 20

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

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

Great Barrington

Deborah S.

￥26,083 total

includes taxes & fees

Oct 30 - Oct 31

A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

14. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

Roberta

￥211,365 total

includes taxes & fees

Oct 14 - Oct 15

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.

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

Sherwood Forest

Sharon K.

￥59,381 total

includes taxes & fees

Oct 14 - Oct 15

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

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

New Lebanon

Joanna P.

￥32,929 total

includes taxes & fees

Oct 14 - Oct 15

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

17. 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.

￥89,189 total

includes taxes & fees

Nov 9 - Nov 10

A white two-story house with a porch, surrounded by trees and a hill.

18. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

￥75,153 total

includes taxes & fees

Oct 14 - Oct 15

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

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

Sherwood Forest

Frank M.

￥65,782 total

includes taxes & fees

Oct 28 - Oct 29

A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

20. Ellie’s Overlook, best view in the Berkshires!

Richmond

￥109,412 total

includes taxes & fees

Oct 18 - Oct 19

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Top Stockbridge Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Amazing pool and great full kitchens in rooms."

The Red Lion Inn

8/10 Good

"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."

Berkshires Untold

8/10 Good

"First this is a gorgeous property, the outdoor areas are wonderful, with comfy furniture, flowers and fire pits. The main area is an intimate restaurant and bar, with a seating area with books and plants. We enjoyed drinks and dinner there and it was excellent, particularly with the sunset and fire pit to begin our evening, Absolutely lovely! Upon checking in, we were assigned a “premium” room, which sounded great, however it turned out to be on the second floor, at the end of a very long outside corridor, parking and lobby quite distant. They have no elevator. We did lug our bags and a cooler to the room, which was lovely, but we knew we would be much more comfortable on the first floor closer to the lobby, as we are somewhat older. We asked to be moved, and we accommodated, found the room the same, but lacking the coffee service and luggage rack. We were brought a luggage rack, and complimentary coffee was available in the lobby in the morning, but it seemed odd that those would be considered premium in such a nice place. The star of the place is the beautiful outdoor space, and restaurant, we just loved that!"

Find out more about Stockbridge

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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.

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Check prices for these dates

Our top choices for Stockbridge vacation rentals

1. Berkshire Mountain Lodge

2. Vacation Village in the Berkshires

3. Secluded Family Home in Serene Stockbridge Woods

4. Leaf-Peeper Paradise in the Berkshires

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

6. Stylish Mid-century Modern Berkshires Cape

7. Spacious Central Berkshires Home for Groups

8. Sun Filled Lenox Retreat - Minutes to Tanglewood!

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

10. Home in Great Barrington

11. Urban Peak Escape, Lenox, MA

12. Cozy. Clean. Free bagel shop. 3 Fireplaces.

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

14. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

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

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

17. Treetop Hideaway in Tyringham

18. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

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

20. Ellie’s Overlook, best view in the Berkshires!

Find vacation rentals that suit your style

Top Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Hotel On North

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Yankee Inn

Quality Inn Great Barrington

Berkshire Mountain Lodge

The Cornell Inn, Lenox & The Berkshires

The Red Lion Inn

Berkshires Untold

Find out more about Stockbridge

Frequently asked questions

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