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

Exterior
Monadnock Inn
2.5 star property
7.6 out of 10, Good, (256)
"Wonderful place."
The price is $158
$176 total
includes taxes & fees
Jun 1 - Jun 2
Monadnock Inn
Exterior detail
Centennial House
3.5 star property
9.4 out of 10, Exceptional, (127)
"The owners of this historic home are exceptionally helpful with all of the details for a pleasant visit. The particular highlight is the marvelous and creative breakfasts, in our case especially the frittatas and raspberry turnovers, which we wished we could take home by the dozen."
The price is $199
$210 total
includes taxes & fees
May 26 - May 27
Centennial House
Free daily continental breakfast
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (122)
"Great nights stay and very walkable to the center of town. The host Joe was awesome!"
The price is $197
$214 total
includes taxes & fees
May 26 - May 27
The Carriage Barn Inn
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Front of property
Colonel Williams Inn
3.0 star property
9.6 out of 10, Exceptional, (266)
"The owners are very friendly and hospitable. The property has a lot of history and it's charm makes you feel comfortable and at home. Wonderful stay and would highly recommend!"
The price is $148
$162 total
includes taxes & fees
Jun 4 - Jun 5
Colonel Williams Inn
Exterior detail
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, (68)
"A wonderful B&B that could use a thorough cleaning. Cute, full of books, great owners and their two cats!"
The price is $166
$183 total
includes taxes & fees
Jun 24 - Jun 25
The One Cat B&B
Exterior
Inn on Putney Road
4.0 star property
9.8 out of 10, Exceptional, (38)
"The Inn was so warm and comforting that it felt like home. It's beautifully decorated and you have access to the common areas where you can enjoy a game of pool, play piano, play a board game or find a nice book to read. The grounds are beautiful with flowers and plenty of seating. The owner Paul was very welcoming and included local snacks and sodas as well as waters in the room which I thought was a nice touch. The breakfast each morning was out of this world! Will definitely stay here again...
The price is $268
$295 total
includes taxes & fees
Jun 16 - Jun 17
Inn on Putney Road
Lobby
Chesterfield Inn
4.0 star property
9.0 out of 10, Wonderful, (100)
"A true find!"
The price is $301
$327 total
includes taxes & fees
May 28 - May 29
Chesterfield Inn
Front of property
The Maguire House Bed & Breakfast
3.5 star property
10.0 out of 10, Exceptional, (31)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
The price is $258
$258 total
includes taxes & fees
Jun 5 - Jun 6
The Maguire House Bed & Breakfast
Deluxe Room | Living area | TV
Four Columns Inn
3.0 star property
8.6 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
Exterior
The Engel House
3.0 star property
9.4 out of 10, Exceptional, (6)
"Last minute reservation for trip to see the eclipse. Very nice a"
The price is $107
$117 total
includes taxes & fees
May 29 - May 30
The Engel House
Seasonal outdoor pool
The Brattleboro
3.0 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
Don't see what you're looking for?
See all available properties in Winchester
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.

Other property types in Winchester

Interior
Charming Waterfront Log Cabin
10.0 out of 10, Exceptional, (24)
"Wonderful place it’s are 3rd time staying there an you can’t beat the location, pond view or the nature surrounding you. An a very fast response. I will be staying agsin!"
The price is $189
$407 total
includes taxes & fees
Jun 11 - Jun 12
Charming Waterfront Log Cabin
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (24)
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (33)
"Charming house with everything we needed!"
Cozy Cottage Along Idyllic Green River
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.

Winchester B&B information

Number of reviews
824
Accommodation
11 B&B
Lowest Price
$107
Highest Price
$301

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: Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the heart of Winchester.Centennial House: 5 rooms. 6.4 mi (10.3 km) from the downtown core. Enjoy the free full breakfast and library. The Carriage Barn Inn: 4 rooms. Situated 11.8 mi (18.9 km) from the heart of Winchester. Colonel Williams Inn: 9 rooms. 18.2 mi (29.3 km) from the heart of downtown. Enjoy the local cuisine breakfast and library. The One Cat B&B: 2 rooms. Located 10.3 mi (16.6 km) from the core of Winchester. Enjoy the free full breakfast and unique décor.
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, April, and February, with each month seeing an average of 11 inches of snowfall.
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.

Recent reviews of Winchester hotels
Expedia verified reviews

The Putney Inn

The Putney Inn

5/5 Excellent
"Easy, quick check in, friendly staff. Some noise from neighbors to be expected. Very clean, good sleep, pleasant stay. Would return. "
A verified traveler stayed at The Putney Inn
Posted 3 days ago
The Putney Inn