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Check prices for these dates

Next weekend
7 Saf. - 9 Saf.
In two weeks
14 Saf. - 16 Saf.
In one month
28 Saf. - 2 Rab. I
In two months
28 Rab. I - 30 Rab. I

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, (292)
"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 SAR 520
SAR 567 total
includes taxes & fees
9 Feb - 10 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 SAR 579
SAR 628 total
includes taxes & fees
4 Feb - 5 Feb
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 SAR 806
SAR 852 total
includes taxes & fees
4 Feb - 5 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 SAR 571
SAR 619 total
includes taxes & fees
4 Feb - 5 Feb
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 SAR 880
SAR 968 total
includes taxes & fees
5 Feb - 6 Feb
Inn on Putney Road
The Engel House
Exterior

The Engel House

3.0 star property
9.2 out of 10, Wonderful, (12)
"The perfect Vermont Bed and Breakfast. "
The price is SAR 630
SAR 686 total
includes taxes & fees
4 Feb - 5 Feb
The Engel House
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 SAR 1,153
SAR 1,251 total
includes taxes & fees
4 Feb - 5 Feb
Chesterfield Inn
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 SAR 675
SAR 743 total
includes taxes & fees
9 Feb - 10 Feb
The One Cat B&B
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 SAR 994
SAR 994 total
includes taxes & fees
5 Feb - 6 Feb
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

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
Winter wonderland!

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (112)
"Great place to stay with friends and family. Will be visiting again!"
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Plenty of private open space to explore with the whole family!

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (51)
"This place was just about perfect with excellent hosts that were easy to communicate to. My only ask would be to get shades to block the sun in the morning in the bedroom to the left of the upstairs bathroom. We did not use that bedroom because of this reason. That being said, we loved this place so much that we already booked again for next year. "
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

6.8 out of 10, (13)
"We enjoyed our stay. AWD is a must for the driveway. The number of security cameras around the property is uncomfortable."
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
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. The Carriage Barn Inn: 4 rooms. 11.8 mi (18.9 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. Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the heart of downtown.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.