Sheffield Bed and Breakfast Inns | Places to Stay in Sheffield

April 21, 2023 Deane Carmody

Discover the best Bed and Breakfast Inns in Sheffield, Massachusetts including Staveleigh House Bed and Breakfast, Race Brook Lodge, Sheffield Lodge, B&B at Howden Farm, Berkshire Manor, Sheffield 1802 House.
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1. Staveleigh House Bed and Breakfast

59 Main St, Sheffield, MA 01257-9555
Excellent
88%
Good
10%
Satisfactory
1%
Poor
1%
Terrible
0%
Overall Ratings

5 based on 176 reviews

Staveleigh House Bed and Breakfast

Warm, gracious hospitality in circa 1821 home in Historic Sheffield. 7 Comfortable AC guestrooms w/private baths. Splendid breakfast.

Delightful Berkshire Weekend

Reviewed By Richard G

We needed a weekend away and had a beautiful stay at the Staveleigh House. This is a terrific bed and breakfast in a great region with so much to see and do. Located on the main road in Sheffield, you can easily drive a short distance to Great Barrington and Stockbridge where you can find a great choice of restaurants. We have stayed at many B & Bs and Inns over the years, and Chris and Mike are exceptional hosts. They take a great deal of pride in what they do, and they execute flawlessly. We were in Room 1 which is spacious and comfortable with a private bath. Every detail is thought through in a meticulous way. Breakfast is served between 8 and 10 am and the two meals we enjoyed were wonderful. Delicious coffee, juice and fruit followed by one of Chris' creative main courses: we had a delicious homemade quiche one morning and a scrambled eggs and goat cheese dish served atop the local sourdough bread on Sunday. Both excellent. And, by the way, really good coffee and an incredible selection of tea. Great way to start the day. They serve the bread from the local bakery (Berkshire Mountain Bakery). Good stuff: we came home with two Berkshire loaves purchased at the Great Barrington farmers market. The Staveleigh has been there since 1820 and Mike will be happy to tell you the complete history. He and Chris became custodians of this hospitality legacy seven years ago (after serious careers elsewhere) and they certainly seem to love what they do. Mike was very helpful in recommending local restaurants, hikes, shopping and sightseeing. I must point out that they are absolutely COVID compliant. Masks, gloves, contactless check-in and check-out, but somehow they do not lose the personal touch in the process. You feel like you are staying with good friends, albeit at an acceptable social distance. Highly recommend. Next time we are in the Berkshires, we will return without hesitation.

2. Race Brook Lodge

864 S Undermountain Rd, Sheffield, MA 01257-9641
Excellent
56%
Good
27%
Satisfactory
7%
Poor
5%
Terrible
6%
Overall Ratings

4 based on 135 reviews

Race Brook Lodge

Nestled at the foot of Mount Race in Sheffield MA, Race Brook Lodge welcomes you to a place of peaceful respite and outstanding hospitality in alignment with local sustainability and inner harmony right here in the Berkshires. When you step outside your room, you’ll be greeted with breathtaking hiking trails that will lead you to the must-see views from the top of Race Brook Falls. From there, you have direct access to The Appalachian Trail and just across the brook, you’ll find our farm garden, which grows much of the produce for our restaurant. Our family-run space is founded on a deep commitment to serving the unique needs of each of our guests. We host couples seeking a tranquil, romantic Berkshires getaway for anniversaries weddings, or just because. We also host wellness and yoga retreats, corporate events and family gatherings. Regardless of your needs, we are here to provide you with an unforgettable, easeful experience that will leave you feeling rejuvenated, refreshed, and more connected to yourself, nature and any new friends you made along the way.

A great experience!

Reviewed By F2136TGgeorgeh

We had a wonderful stay. The staff is wonderful, the room was cozy, and the meal at the tavern excellent. We had the great pleasure to meet the owner and had a fun conversation. The prices may seem high but it is so they can pay staff a fair wage. We support this effort and love this idea. Bravo!

3. Sheffield Lodge

400 S Undermountain Rd, Sheffield, MA 01257-9640
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5 based on 5 reviews

Sheffield Lodge

Sheffield Lodge is a quaint, rustic Bed & Breakfast located in the Southern Berkshires of Massachusetts. Secluded in a quiet forest of tall pine and maple trees, it offers delicious breakfasts, and quick access to nearby restaurants, outdoor activities, shopping, theaters and museums. Enjoy a visit to the tranquil atmosphere, away from day-to-day city life, and reconnect with nature and family.

ideal long weekend getaway

Reviewed By Mary M

We had a wonderful long weekend at Susan’s cozy lodge. Her hospitality is unparalleled and she is full of suggestions for what to do in the area if you need ideas. She provides a large hot breakfast every morning and there are snacks available in the afternoon and evening. Our room was very comfortable and spacious for two and came with an electric blanket which was a perfect touch for an unseasonably cool, rainy weekend. There are plenty of books and games to keep yourself occupied, in addition to a large TV in the living room. The wifi also works great if you’re looking to get work done. Susan also provides a large list of dining recommendations in the area. I highly recommend a stay at Sheffield Lodge and we hope to return again when the weather is nicer!

4. B&B at Howden Farm

303 Rannapo Rd, Sheffield, MA 01257-9619
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5 based on 2 reviews

B&B at Howden Farm

Welcome to B&B at Howden Farm, your Sheffield “home away from home.” B&B at Howden Farm aims to make your visit as relaxing and enjoyable as possible, which is why so many guests continue to come back year after year. Rooms at B&B at Howden Farm provide air conditioning. While staying in Sheffield, you can check out a popular cafe like The Marketplace Cafe, which is serving up some great dishes. Sheffield is also home to Thom Reed UFO Monument Park, a popular history museum that is not too far from B&B at Howden Farm. B&B at Howden Farm puts the best of Sheffield at your fingertips, making your stay both relaxing and enjoyable.

Warm Welcome & Great Breakfasts

Reviewed By Kristi S

My husband and I spent a few days here this past summer at this comfortable B & B while attending an event at Lime Rock. Our hosts where genial and welcoming with any information we needed on the area. The farm was a great retreat from the noisy activity at the convention site and the peace and quiet was glorious. Breakfast was fresh, well made and interesting with lively conversation to start the day. Thanks again for a wonderful stay!

5. Berkshire Manor

175 Main St, Sheffield, MA 01257-9564
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5 based on 1 reviews

Historic 1800 home built for the first physician in the region. Upscale accommodations, Jacuzzi, Italian marble, heated floors, 21st century retaining historic charm. Only minutes from downtown Great Barrington. "RELAXED ELEGANCE"

what a place, a true jewel

Reviewed By pegmagyar

Beautiful room, immaculate and luxurious. A super breakfast, and a knockout made to order picnic basket for our day at Tanglewood. I want to return in the fall or winter to enjoy the fireplaces. I loved the showcase of jewelry and gifts, and bought a nice piece home as a memento of our stay. I also liked their website.

6. Sheffield 1802 House

48 South Main Street, Sheffield, MA 01257-9696
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5 based on 9 reviews

Sheffield 1802 House

Luxury bed and breakfast in the Southern Berkshires with mostly king beds, modern private bathrooms, wonderful sitting areas, and a host of free amenities. A hot breakfast is included. Located on beautifully landscaped 2 acre grounds.

Awesome b&b

Reviewed By 6cindyk

We don't typically stay at b&bs but we're so glad we stayed at this one. so welcoming and pretty we wanted to stay longer! Breakfasts were great, going above and beyond to accommodate my AIP diet. Hotel level amenities, great innkeeper, books to read and a cute kitten. (The cat's not allowed in the bed rooms; we asked for her company in the living room. ) The place is very clean and quiet.

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