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Search B&B in Winchester

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Compare 11 B&B in Winchester with updated reviews, rates, and availability.

Colonel Williams Inn
Front of property
Colonel Williams Inn
3.0 star property
9.6 out of 10, Exceptional, (275)
"Beautiful property with outstanding customer service! Highly recommend for a weekend getaway or for spending time in beautiful Vermont. "
The price is AED 538
AED 586 total
includes taxes & fees
24 Sep - 25 Sep
Colonel Williams Inn
The Carriage Barn Inn
Exterior
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (134)
"Clean, quiet and owner is very pleasant!"
The price is AED 723
AED 784 total
includes taxes & fees
24 Sep - 25 Sep
The Carriage Barn Inn
Centennial House
Breakfast area
Centennial House
3.5 star property
9.4 out of 10, Exceptional, (139)
"Beautiful antiques and historical home. It was very clean and beautifully restored. A step back in time except thankfully with air conditioning. The breakfast was delicious!"
The price is AED 621
AED 656 total
includes taxes & fees
24 Sep - 25 Sep
Centennial House
The Maguire House Bed & Breakfast
Front of property
The Maguire House Bed & Breakfast
3.5 star property
10.0 out of 10, Exceptional, (34)
"Terry was an amazing host. She was so hospitable and made my stay here that much more comfortable. She not only cooks really amazing breakfast but she was so helpful when I wanted to check out the town. Her house is really truly beautiful and the lake is a little walk away from the house. I highly recommend coming here."
The price is AED 974
AED 974 total
includes taxes & fees
25 Sep - 26 Sep
The Maguire House Bed & Breakfast
Inn on Putney Road
Exterior
Inn on Putney Road
4.0 star property
9.8 out of 10, Exceptional, (42)
"A lovely four day stay in Vermont. Inn was perfect, with gardens to enjoy and lots of lounges and nooks to spend time and read. We had a suite with a separate sitting room, which allowed us to have our daughter accompany us on a last minute visit. Paul and his staff are super accommodating and are genuinely friendly hosts. Paul also cooks all the breakfasts which are superb! Different breakfasts each day, beautifully presented and absolutely delicious!"
The price is AED 1,334
AED 1,467 total
includes taxes & fees
25 Sep - 26 Sep
Inn on Putney Road
The Engel House
Exterior
The Engel House
3.0 star property
9.0 out of 10, Wonderful, (7)
"Last minute reservation for trip to see the eclipse. Very nice a"
The price is AED 572
AED 624 total
includes taxes & fees
25 Sep - 26 Sep
The Engel House
The One Cat B&B
Property entrance
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, (75)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is AED 1,010
AED 1,111 total
includes taxes & fees
25 Sep - 26 Sep
The One Cat B&B
Chesterfield Inn
Lobby
Chesterfield Inn
4.0 star property
9.0 out of 10, Wonderful, (101)
"Lots of things were lovely; fantastic room service food (unbelievably fresh and delicious, better than anywhere I’ve ever eaten in a hotel while traveling), beautiful serene natural setting, and wonderful design of the buildings plus COOKIES and tea in the afternoon. The service was also fantastic. The paint could use freshening and the bathroom grout needs redoing (or consider retiling). A piece of one window pane, a wood bit, fell off… so I stuck it back, obviously needs a proper repair. With...
Chesterfield Inn
Monadnock Inn
Exterior
Monadnock Inn
2.5 star property
7.6 out of 10, Good, (261)
"The place is over coming new ownership so it has work being done but the new owners seem nice and our room was nice a clean and the bed was super comfy. I would love to see it in a year to see all the renovations done. "
The price is AED 546
AED 593 total
includes taxes & fees
3 Oct - 4 Oct
Monadnock Inn
Four Columns Inn
Garden
Four Columns Inn
3.0 star property
8.6 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
The Brattleboro
Room
The Brattleboro
4.0 star property
10.0 out of 10, Exceptional, (4)
"Peaceful, comfortable, great views. We were made welcome and had wonderful beverage and snack options and the Breakfast were Superior. We will definitely return. "
The Brattleboro
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Other property types in Winchester

Beautiful, private log cabin with huge, relaxing screened porch
Exterior
Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, (30)
"We had a wonderful, quiet and relaxing time. Plenty of rooms for every guest. The veranda is very special. We will go back again and we would recommend it. The Host, Beth, was welcoming and helpful."
Beautiful, private log cabin with huge, relaxing screened porch
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Vernon Vacation Rental | 1BR | 1BA | 800 Sq Ft | 3 Steps Required
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
10.0 out of 10, Exceptional, (28)
"We had a wonderful time staying at the cabin. Enjoyed the space itself and the property. Quiet, private and peaceful. Looking forward to returning in the winter. "
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Exterior
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
10.0 out of 10, Exceptional, (6)
"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family air hockey tournaments. A lovely experience and we hope to return at some point. Thank you for sharing your beautiful home with us!"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find a place to stay with fewer rooms than a hotel and a cozy environment, a B&B might be just the right fit for your trip to Winchester. While you’re enjoying your trip to Winchester, Pisgah State Park and Rhododendron State Park are perfect spots to get in some fresh air and greenery.
How do you know if a B&B is the best choice for your stay?
Every B&B has its own unique feel. Whether it’s a cozy reading space or a beautiful breakfast room, the tiny details are what make bed and breakfasts a fun place to get away.
What are the best B&Bs in Winchester?
Below are some well-liked B&Bs in the area: The Carriage Barn Inn: 4 rooms. 11.8 mi (18.9 km) from the heart of Winchester.Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the downtown core. Centennial House: 5 rooms. Situated 6.4 mi (10.3 km) from the heart of Winchester. Enjoy the free full breakfast and unique décor. Colonel Williams Inn: 9 rooms. 18.2 mi (29.3 km) from the heart of downtown. Enjoy the local cuisine breakfast and library. Inn on Putney Road: 6 rooms. Located 10.7 mi (17.3 km) from the core of Winchester. Enjoy the free full breakfast and onsite spa services.
What's the best time of year to book my B&B in Winchester?
When you’re dreaming of a escape to Winchester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. Average annual precipitation for Winchester is 50 inches.
What is there to do in Winchester?
When you want to spend some time in the great outdoors, Birch Point and Pisgah State Park are some notable spots. You might put Rhododendron State Park and Ashuelot River on your list if you want to see more of the area.