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Bed and Breakfast in Winchester

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Check prices for these dates

Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec
In one month
19 Dec - 21 Dec
In two months
16 Jan - 18 Jan

Featured B&B in Winchester

Front of property
Colonel Williams Inn

Colonel Williams Inn

3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (339)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is NZ$285
includes taxes & fees
19 Nov - 20 Nov
Colonel Williams Inn
Exclusive Room
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (11)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
The price is NZ$220
includes taxes & fees
24 Nov - 25 Nov
Four Columns Inn
Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is NZ$270
includes taxes & fees
1 Dec - 2 Dec
The Carriage Barn Inn
Free daily full breakfast
Centennial House

Centennial House

3.5 star property
Northfield
9.6 out of 10, Exceptional, (172)
"The property was wonderful and the hosts exceptional❤️"
United States
Susan
The price is NZ$318
includes taxes & fees
1 Dec - 2 Dec
Centennial House
Exterior
Inn on Putney Road

Inn on Putney Road

4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is NZ$517
includes taxes & fees
24 Nov - 25 Nov
Inn on Putney Road
Exterior
The One Cat B&B

The One Cat B&B

2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is NZ$479
includes taxes & fees
24 Nov - 25 Nov
The One Cat B&B
Exterior
Monadnock Inn

Monadnock Inn

2.5 star property
Jaffrey
7.6 out of 10, Good, (274)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
United States
Sharon-Ann C
Monadnock Inn
Exterior
The Engel House

The Engel House

3.0 star property
Jacksonville
9.2 out of 10, Wonderful, (17)
"A very quaint property. The room was comfortable and clean."
United States
Frank
The Engel House
Exterior
Green River Bridge Inn

Green River Bridge Inn

3.0 star property
Guilford
8.4 out of 10, Very good, (13)
"Beautiful Inn and property"
United States
JaDean
The price is NZ$469
includes taxes & fees
2 Dec - 3 Dec
Green River Bridge Inn
Lobby
Chesterfield Inn

Chesterfield Inn

4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
The price is NZ$575
includes taxes & fees
24 Nov - 25 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.

Guilford
The price is NZ$621
includes taxes & fees
24 Nov - 25 Nov
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

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
" Very nice hotel. "
JoAnn 1-night trip
Posted 5 days ago
The Colonial Hotel

Find out more about Winchester

Winchester B&B information

Number of reviews
1,027
Accommodation
12 B&B
Lowest Price
NZ$220
Highest Price
NZ$621

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, Loring Field and Richmond Wildlife Manangement Area 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 B&Bs in the area: Colonel Williams Inn: 9 rooms. Situated 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 city centre. Centennial House: 5 rooms. Located 6.4 mi (10.3 km) from the core of Winchester. Enjoy the free full breakfast and unique decor.
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, Birch Point and Ashuelot River are some notable spots. You should put New England Sweetwater Farm & Distillery and Pisgah State Park on your list if you want to see more of the area.

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