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Bed and Breakfast in Winchester

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Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Featured B&B in Winchester

Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (326)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
The price is NZ$276
includes taxes & fees
6 Oct - 7 Oct
Colonel Williams Inn
Monadnock Inn
Exterior

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
Green River Bridge Inn
Exterior

Green River Bridge Inn

3.0 star property
8.6 out of 10, Excellent, (8)
"The area is beautiful and the inn is lovely. I would highly recommend to anyone visiting the area. "
The price is NZ$437
includes taxes & fees
22 Oct - 23 Oct
Green River Bridge Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (156)
"Very quiet and peaceful but at the same time it's right down the street from Main Street. Joe the owner was so nice! "
The price is NZ$355
includes taxes & fees
26 Oct - 27 Oct
The Carriage Barn Inn
Centennial House
Free daily full breakfast

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (166)
"The property was wonderful and the hosts exceptional❤️"
The price is NZ$367
includes taxes & fees
27 Oct - 28 Oct
Centennial House
Four Columns Inn
Dining

Four Columns Inn

3.0 star property
9.0 out of 10, Wonderful, (4)
"Great place to stay. People were Friendly and the service was great. The pizza was great and the service was outstanding."
Four Columns Inn
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (54)
"Outstanding breakfast in a charming home. A 15 minute walk excellent to restaurants and art galleries."
The price is NZ$586
includes taxes & fees
1 Nov - 2 Nov
Inn on Putney Road
The One Cat B&B
Exterior

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 NZ$547
includes taxes & fees
6 Oct - 7 Oct
The One Cat B&B
The Engel House
Exterior

The Engel House

3.0 star property
9.4 out of 10, Exceptional, (13)
"The perfect Vermont Bed and Breakfast. "
The Engel House
The Maguire House Bed & Breakfast
Property grounds

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 Maguire House Bed & Breakfast
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
Chesterfield Inn
The Brattleboro
Hiking

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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Top Winchester Hotel Reviews

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"Great"
Alice 1-night trip
Posted 3 days ago
The Colonial Hotel

Find out more about Winchester

Find out more about Winchester

Winchester B&B information

Number of reviews
978
Accommodation
12 B&B
Lowest Price
NZ$276
Highest Price
NZ$586

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. 14.4 mi (23.1 km) from the city centre. Enjoy the snack bar/deli and patio area. The Carriage Barn Inn: 4 rooms. Situated 11.8 mi (18.9 km) from the heart 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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