Best Villas in Stockbridge 2026

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Recommended hotels in Stockbridge

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

1. The Red Lion Inn

Stockbridge

Patricia

includes taxes & fees

29 Sept - 30 Sept

2. The Inn at Stockbridge

Stockbridge

includes taxes & fees

13 Sept - 14 Sept

A two-story house with a brick entrance and a white facade.

3. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

Philippe

includes taxes & fees

28 Sept - 29 Sept

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

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

Stockbridge

Anonymous traveller

includes taxes & fees

28 Sept - 29 Sept

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

5. The Yankee Inn

Lenox

Karen

includes taxes & fees

27 Sept - 28 Sept

A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

6. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Claudia

includes taxes & fees

7 Sept - 8 Sept

A lodge with a large building and a dock by a lake, surrounded by forest.

7. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

James

includes taxes & fees

21 Sept - 22 Sept

A hotel room with two beds, a desk, a TV, and a window with curtains.

8. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

BJORN

includes taxes & fees

7 Sept - 8 Sept

A Super 8 motel with a two-story building, a parking lot, and a picnic table.

9. Quality Inn Lee - Lenox South

Lee

Christine

includes taxes & fees

20 Sept - 21 Sept

A round metal table with chairs, a grill, and a view of a lake.

10. Berkshire Lake Lodge

Lee

mike

includes taxes & fees

29 Sept - 30 Sept

A red building with a sign reading "Shaker Mill Inn."

11. Shaker Mill Inn

West Stockbridge

Mervin

includes taxes & fees

9 Sept - 10 Sept

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

12. Monument Mountain Motel

Great Barrington

John

includes taxes & fees

1 Sept - 2 Sept

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

13. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Lisa

includes taxes & fees

7 Sept - 8 Sept

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

14. Berkshire Mountain Lodge

Pittsfield

Robert

includes taxes & fees

31 Aug - 1 Sept

A motel with a gravel driveway leading to a parking area, surrounded by lush green trees and a clear blue sky.

15. East Rock Inn

Great Barrington

ERIK

includes taxes & fees

22 Sept - 23 Sept

A two-story building with a gabled roof and a chimney.

16. The Little Lion

Great Barrington

Anne

includes taxes & fees

1 Sept - 2 Sept

17. Inn at Silver Maple Farm

East Chatham

Erdem

includes taxes & fees

1 Sept - 2 Sept

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Pittsfield

Ken

includes taxes & fees

8 Sept - 9 Sept

A Quality Inn sign, a brick building, and a parking lot with cars.

19. Quality Inn Great Barrington

Great Barrington

Sisile

includes taxes & fees

20 Sept - 21 Sept

A wooden deck with a table and chairs, overlooking a road with a sign for 'Holliday Lodge'.

20. Econo Lodge Lee - Great Barrington

Lee

Anna

includes taxes & fees

7 Sept - 8 Sept

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Top Stockbridge Hotel Reviews

Berkshires Untold

10/10 Excellent

"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

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

10/10 Excellent

"Nice, well-maintained property, everything was very clean. The breakfast nook was not overly crazy crowded, which is really good traveling with young children. The staff even apologized for not having the waffle maker as a new one was being delivered. The hot tub was also a plus!"

Find out more about Stockbridge

Stockbridge Villas information

Number of reviews	9,325
Accommodation	2 Villas
Lowest Price	£57
Highest Price	£327

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Stockbridge

1. The Red Lion Inn

2. The Inn at Stockbridge

3. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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

5. The Yankee Inn

6. Holiday Inn Club Vacations Oak 'n Spruce Resort

7. The Black Swan Lee - Lenox, an Ascend Collection Hotel

8. Holiday Inn Express Hotel & Suites Great Barrington by IHG

9. Quality Inn Lee - Lenox South

10. Berkshire Lake Lodge

11. Shaker Mill Inn

12. Monument Mountain Motel

13. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

14. Berkshire Mountain Lodge

15. East Rock Inn

16. The Little Lion

17. Inn at Silver Maple Farm

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

19. Quality Inn Great Barrington

20. Econo Lodge Lee - Great Barrington

Find holiday rentals that suit your style

Top Stockbridge Hotel Reviews

Berkshires Untold

The Yankee Inn

Vacation Village in the Berkshires

Quality Inn Great Barrington

Quality Inn Lee - Lenox South

Holiday Inn Club Vacations Oak 'n Spruce Resort

Hotel On North

The Red Lion Inn

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

Find out more about Stockbridge

Stockbridge Villas information

Explore a world of travel with Expedia

Search Villas in Stockbridge

Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Stockbridge

1. The Red Lion Inn

2. The Inn at Stockbridge

3. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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

5. The Yankee Inn

6. Holiday Inn Club Vacations Oak 'n Spruce Resort

7. The Black Swan Lee - Lenox, an Ascend Collection Hotel

8. Holiday Inn Express Hotel & Suites Great Barrington by IHG

9. Quality Inn Lee - Lenox South

10. Berkshire Lake Lodge

11. Shaker Mill Inn

12. Monument Mountain Motel

13. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

14. Berkshire Mountain Lodge

15. East Rock Inn

16. The Little Lion

17. Inn at Silver Maple Farm

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

19. Quality Inn Great Barrington

20. Econo Lodge Lee - Great Barrington

Find holiday rentals that suit your style

Top Stockbridge Hotel Reviews

Berkshires Untold

Find out more about Stockbridge

Stockbridge Villas information

Explore a world of travel with Expedia