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Check prices for these dates

Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec

Featured B&B in Winchester

Front of property
Colonel Williams Inn
Colonel Williams Inn
3.0 star property
9.8 out of 10, Exceptional, (332)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
The price is AU$250
includes taxes & fees
3 Nov - 4 Nov
Colonel Williams Inn
Dining
Four Columns Inn
Four Columns Inn
3.0 star property
9.6 out of 10, Exceptional, (8)
"Lovely staff, amazing ambiance!"
Four Columns Inn
Free daily continental breakfast
The Carriage Barn Inn
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (158)
"Great BB. Very charming and cozy! Will definitely stay again! "
The price is AU$310
includes taxes & fees
26 Oct - 27 Oct
The Carriage Barn Inn
Exterior
Green River Bridge Inn
Green River Bridge Inn
3.0 star property
8.8 out of 10, Excellent, (10)
"Beautiful Inn and property"
The price is AU$340
includes taxes & fees
2 Nov - 3 Nov
Green River Bridge Inn
Exterior
The One Cat B&B
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, (77)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is AU$409
includes taxes & fees
6 Nov - 7 Nov
The One Cat B&B
Free daily full breakfast
Centennial House
Centennial House
3.5 star property
9.6 out of 10, Exceptional, (169)
"The property was wonderful and the hosts exceptional❤️"
The price is AU$317
includes taxes & fees
31 Oct - 1 Nov
Centennial House
Exterior
Inn on Putney Road
Inn on Putney Road
4.0 star property
9.8 out of 10, Exceptional, (55)
"Outstanding breakfast in a charming home. A 15 minute walk excellent to restaurants and art galleries."
The price is AU$450
includes taxes & fees
2 Nov - 3 Nov
Inn on Putney Road
Exterior
Monadnock Inn
Monadnock Inn
2.5 star property
7.6 out of 10, Good, (271)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
Monadnock Inn
Exterior
The Engel House
The Engel House
3.0 star property
9.4 out of 10, Exceptional, (14)
"The perfect Vermont Bed and Breakfast. "
The Engel House
Property grounds
The Maguire House Bed & Breakfast
The Maguire House Bed & Breakfast
3.5 star property
10.0 out of 10, Exceptional, (34)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
The price is AU$422
includes taxes & fees
6 Nov - 7 Nov
The Maguire House Bed & Breakfast
Lobby
Chesterfield Inn
Chesterfield Inn
4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is AU$501
includes taxes & fees
2 Nov - 3 Nov
Chesterfield Inn
Outdoor dining
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
The price is AU$544
includes taxes & fees
21 Oct - 22 Oct
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
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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Top Winchester Hotel Reviews

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

8/10 Good
"The room HVAC worked but is noisy. I don't mind because i like to sleep to white noise. Decent hotel. Not fancy at all. Seasonal prices were high compared to what i usually pay around the country. Vermont hotels seem to always be expensive Only bare essentials in room. Good tv channel selection."
Dan 2-night trip
Posted 2 days ago
Travelodge by Wyndham Brattleboro VT

Find out more about Winchester

Winchester B&B information

Number of reviews
994
Accommodation
12 B&B
Lowest Price
AU$250
Highest Price
AU$501

Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find a place to stay with fewer rooms than the traditional hotel and a cosy environment, a bed and breakfast might be just the right fit for your trip to Winchester. While you're enjoying your trip to Winchester, Rhododendron State Park and Loring Field are perfect spots to get in some fresh air and greenery.
How do you know if a B&B is a good option for your stay?
Every B&B has its own unique feel — whether it's a comfy common area with a fireplace or a beautiful breakfast room, the little 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. Green River Bridge Inn: 4 rooms. Situated 14.4 mi (23.1 km) from the heart of Winchester. Enjoy the snack bar/deli and patio area. The Carriage Barn Inn: 4 rooms. Located 11.8 mi (18.9 km) from the core of Winchester.
When should I book my B&B in Winchester?
When you're dreaming of a trip to Winchester, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.
What is there to do in Winchester?
When you want to spend some time in the great outdoors, Rhododendron State Park and Ashuelot River are some notable spots. You should put Pisgah State Park and New England Sweetwater Farm & Distillery on your list if you want to see more of the area.

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