20 Best B&B in Stephentown, NY - Bed and Breakfast from AED 505

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Our top choices for Stephentown bed & breakfast

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

1. Inn at Silver Maple Farm

East Chatham

Linda

AED 675 total

includes taxes & fees

3 Dec - 4 Dec

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

2. Shaker Mill Inn

West Stockbridge

Mahadeva

AED 584 total

includes taxes & fees

8 Nov - 9 Nov

A snow-covered outdoor area with a patio, seating, and a covered dining area.

3. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

AED 716 total

includes taxes & fees

9 Nov - 10 Nov

A garden with a white gazebo, a brick pathway, and various plants and flowers.

4. Whistler's Inn Bed & Breakfast

Lenox

George

AED 565 total

includes taxes & fees

8 Nov - 9 Nov

A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

5. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

AED 706 total

includes taxes & fees

8 Dec - 9 Dec

A historic building with a wooden door, two wreaths, and a sign that reads "Old Judge Mansion."

6. Olde Judge Mansion

Troy

Sallie

AED 566 total

includes taxes & fees

23 Nov - 24 Nov

A garden with a stone wall, various plants, and a small shed.

7. Gardner Farm Inn

Troy

Karon

AED 700 total

includes taxes & fees

8 Nov - 9 Nov

8. The Inn at Stockbridge

Stockbridge

Kimberly

AED 1,151 total

includes taxes & fees

8 Nov - 9 Nov

A two-story building with a sign reading "Chambéry Inn".

9. Chambery Inn

Lee

Alexandra

AED 760 total

includes taxes & fees

10 Nov - 11 Nov

A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

10. Experience Timeless Elegance in The Edith Wharton Room!

Lenox

AED 1,242 total

includes taxes & fees

9 Nov - 10 Nov

A dining table with a view of trees and parked cars through a window with wooden shutters.

11. The Morgan State House

Albany

Michael

AED 1,144 total

includes taxes & fees

12 Nov - 13 Nov

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

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

Stockbridge

Philippe

AED 1,697 total

includes taxes & fees

26 Nov - 27 Nov

A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

13. Harbour House Inn

Cheshire

Gregory

AED 926 total

includes taxes & fees

12 Nov - 13 Nov

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

14. Devonfield Inn B&B

Lee

Sebastien

AED 1,514 total

includes taxes & fees

13 Nov - 14 Nov

A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

15. Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Lenox

AED 1,242 total

includes taxes & fees

9 Nov - 10 Nov

A room with a dark green sofa, a small table with a vase of flowers, a desk with a lamp, and a window with curtains.

16. Elegant Carriage House room with a queen bed and private patio.

Lenox

AED 1,305 total

includes taxes & fees

8 Nov - 9 Nov

A porch with a white railing, a potted plant, and a view of a garden.

17. Cozy Carriage House room with a double bed and private balcony

Lenox

AED 1,385 total

includes taxes & fees

15 Nov - 16 Nov

A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

18. Historic Susan B. Anthony Room - Cozy & Charming Stay

Lenox

AED 1,452 total

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a bed, a fireplace, a ceiling fan, and a door.

19. Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Lenox

AED 1,788 total

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a bed, a television, a fireplace, and a window.

20. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

Lenox

AED 1,877 total

includes taxes & fees

8 Nov - 9 Nov

View all properties

Top reviews in Stephentown

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Michelle

Harbour House Inn

Cheshire

10/10 Excellent

Anonymous traveler

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lawrence

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

Brook Farm Inn

Lenox

10/10 Excellent

roberta

The Trail in Adams - Berkshires’ Art Hotel

Adams

10/10 Excellent

Esther

Gardner Farm Inn

Troy

10/10 Excellent

My daughter and I were in town for one night to tour RPI. We certainly chose well with our overnight accommodations. Although the house is quaint, extra clean, and decorated perfectly, the star of our stay was the innkeeper, John. From the moment we walked in, it was like seeing an old friend. John was friendly, kind and took excellent care of us. His hospitality made us want to come back again....very soon.

Victoria

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

Chambery Inn

Lee

10/10 Excellent

Elaine

The Inn at Stockbridge

Stockbridge

10/10 Excellent

Kevin

Whistler's Inn Bed & Breakfast

Lenox

10/10 Excellent

eli

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

Stockbridge

10/10 Excellent

Charles

The Morgan State House

Albany

10/10 Excellent

Ganesh

Olde Judge Mansion

Troy

10/10 Excellent

Anonymous traveler

Frequently Asked Questions

Searching for B&Bs in Stephentown?

Whether you're on a family vacation and want a small, cozy place to stay, or you're traveling solo and hoping to meet fellow tourists, B&Bs can be a great choice for many travelers. When you want to explore some attractions in town, Zema's Nursery and Taconic Ridge State Forest are worth a stop.

How do you know if a B&B is the right choice for your stay?

With attentive service, opportunities to socialize with other guests, and delectable breakfasts, B&Bs provide a truly one-of-a-kind setting.

What are the best bed and breakfasts in Stephentown?

Here are some well-liked B&Bs in the area: Berkshire Mountain House: 7 rooms. 2.4 mi (3.9 km) from the heart of Stephentown. Enjoy the free buffet breakfast and rooftop terrace. The Cornell Inn, Lenox & The Berkshires: 14.2 mi (22.8 km) from the downtown core. Enjoy the free full breakfast and unique décor. Inn at Silver Maple Farm: 11 rooms. 10 mi (16.1 km) from the heart of downtown. Enjoy the free buffet breakfast and designer toiletries. Shaker Mill Inn: 9 rooms. Located 15.2 mi (24.4 km) from the core of Stephentown.

What's the best time of year to book my B&B in Stephentown?

When you're dreaming of a trip to Stephentown, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Stephentown are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

What is there to do in Stephentown?

When you want to check out some attractions in town, you might consider a visit to Zema's Nursery and Taconic Ridge State Forest. Jiminy Peak Mountain Resort and Hancock Shaker Village are also some sites to visit if you want to see more of the area.

How can I get to and around Stephentown?

You can plan your excursions in and around Stephentown ahead of time with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 10.3 mi (16.6 km) away from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 24.2 mi (38.9 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

Search B&B in Stephentown

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Stephentown bed & breakfast

1. Inn at Silver Maple Farm

2. Shaker Mill Inn

3. The Cornell Inn, Lenox & The Berkshires

4. Whistler's Inn Bed & Breakfast

5. The Trail in Adams - Berkshires’ Art Hotel

6. Olde Judge Mansion

7. Gardner Farm Inn

8. The Inn at Stockbridge

9. Chambery Inn

10. Experience Timeless Elegance in The Edith Wharton Room!

11. The Morgan State House

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

13. Harbour House Inn

14. Devonfield Inn B&B

15. Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

16. Elegant Carriage House room with a queen bed and private patio.

17. Cozy Carriage House room with a double bed and private balcony

18. Historic Susan B. Anthony Room - Cozy & Charming Stay

19. Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

20. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

Top reviews in Stephentown

Inn at Silver Maple Farm

10/10 Excellent

Frequently Asked Questions

Searching for B&Bs in Stephentown?

How do you know if a B&B is the right choice for your stay?

What are the best bed and breakfasts in Stephentown?

What's the best time of year to book my B&B in Stephentown?

What is there to do in Stephentown?

How can I get to and around Stephentown?

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