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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

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
9.8 out of 10, Exceptional, (291)
"The owners were so kind. My boyfriend and I woke up a little late for breakfast the second day of our ski trip, and one of the hosts still made us a beautiful spread. Truly it was some of the best French toast I’ve had in years! The Christmas decorations were charming and sweet, not to mention the property itself is beautiful. They also had this amazing studio Ghibli gingerbread house that they made themselves! It’s located about 25 minutes from Mount snow. The rooms themselves are spacious and...
The price is AED 492
AED 536 total
includes taxes & fees
6 Feb - 7 Feb
Colonel Williams Inn
The Carriage Barn Inn
Exterior

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (143)
"Perfect for our one night getaway to Keene. Clean, great location, friendly inkeeper (Joe) and many nice touches such as the breakfast."
The price is AED 520
AED 564 total
includes taxes & fees
26 Jan - 27 Jan
The Carriage Barn Inn
Centennial House
Breakfast area

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (149)
"We had a great stay at Centennial House! Myself and my 14 year old son stayed for one night -- the bed was very comfortable and breakfast was fabulous!!"
The price is AED 657
AED 694 total
includes taxes & fees
18 Feb - 19 Feb
Centennial House
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (264)
"owners are very nice "
The price is AED 607
AED 658 total
includes taxes & fees
24 Jan - 25 Jan
Monadnock Inn
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (44)
"Great stop on our way out of N Vermont. Nice warm room on a cold night."
The price is AED 862
AED 948 total
includes taxes & fees
26 Jan - 27 Jan
Inn on Putney Road
The Engel House
Exterior

The Engel House

3.0 star property
9.2 out of 10, Wonderful, (11)
"The "
The price is AED 435
AED 474 total
includes taxes & fees
30 Jan - 31 Jan
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, (74)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is AED 735
AED 808 total
includes taxes & fees
26 Jan - 27 Jan
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...
The price is AED 1,129
AED 1,225 total
includes taxes & fees
28 Jan - 29 Jan
Chesterfield Inn
Four Columns Inn
Garden

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
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 973
AED 973 total
includes taxes & fees
30 Jan - 31 Jan
The Maguire House Bed & Breakfast
The Brattleboro
Room

The Brattleboro

4.0 star property
10.0 out of 10, Exceptional, (5)
"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
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.
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Other property types in Winchester

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
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Charming Waterfront Log Cabin
Exterior

Charming Waterfront Log Cabin

9.6 out of 10, Exceptional, (37)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
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: Colonel Williams Inn: 9 rooms. 18.2 mi (29.3 km) from the heart of Winchester. Enjoy the local cuisine breakfast and library. Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the downtown core. The Carriage Barn Inn: 4 rooms. Situated 11.8 mi (18.9 km) from the heart of Winchester. Centennial House: 5 rooms. 6.4 mi (10.3 km) from the heart of downtown. Enjoy the free full breakfast and unique décor. 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. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.
What is there to do in Winchester?
When you want to spend some time in the great outdoors, Pisgah State Park and Ashuelot River are some notable spots. You might put Birch Point and Rhododendron State Park on your list if you want to see more of the area.