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Bed and Breakfast in Winchester

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Featured B&B in Winchester

Monadnock Inn
Exterior
Monadnock Inn
2.5 star property
7.6 out of 10, Good, 256 reviews
"Wonderful place."
The price is NZ$278
includes taxes & fees
5 Jul - 6 Jul
Monadnock Inn
Colonel Williams Inn
Front of property
Colonel Williams Inn
3.0 star property
9.6 out of 10, Exceptional, 267 reviews
"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 NZ$245
includes taxes & fees
12 Jun - 13 Jun
Colonel Williams Inn
Centennial House
Exterior detail
Centennial House
3.5 star property
9.4 out of 10, Exceptional, 128 reviews
"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 NZ$340
includes taxes & fees
6 Jun - 7 Jun
Centennial House
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The One Cat B&B
Exterior detail
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, 68 reviews
"A wonderful B&B that could use a thorough cleaning. Cute, full of books, great owners and their two cats!"
The price is NZ$352
includes taxes & fees
13 Jun - 14 Jun
The One Cat B&B
The Carriage Barn Inn
Free daily continental breakfast
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, 123 reviews
"Great nights stay and very walkable to the center of town. The host Joe was awesome!"
The price is NZ$373
includes taxes & fees
6 Jun - 7 Jun
The Carriage Barn Inn
Inn on Putney Road
Exterior
Inn on Putney Road
4.0 star property
9.8 out of 10, Exceptional, 39 reviews
"The Inn is charming and beautifully furnished. The gardens are beautiful. The innkeeper and staff were gracious and our room was decked out with complimentary Vermont treats. The breakfast was lavish - muffins, fruit, eggs, potatoes, sausage, freshly ground coffee and fresh-squeezed juice. We only did a quick overnight visit but next time it would be fun to stay longer to take advantage of the game room and the many books."
The price is NZ$476
includes taxes & fees
16 Jun - 17 Jun
Inn on Putney Road
The Maguire House Bed & Breakfast
Fountain
The Maguire House Bed & Breakfast
3.5 star property
10.0 out of 10, Exceptional, 31 reviews
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
The price is NZ$420
includes taxes & fees
23 Jun - 24 Jun
The Maguire House Bed & Breakfast
Chesterfield Inn
Lobby
Chesterfield Inn
4.0 star property
9.0 out of 10, Wonderful, 100 reviews
"A true find!"
The price is NZ$528
includes taxes & fees
6 Jun - 7 Jun
Chesterfield Inn
Four Columns Inn
Deluxe Room | Living area
Four Columns Inn
3.0 star property
8.6 out of 10, Excellent, 3 reviews
"Friendliest Staff Ever!"
Four Columns Inn
The Engel House
Exterior
The Engel House
3.0 star property
9.4 out of 10, Exceptional, 6 reviews
"Last minute reservation for trip to see the eclipse. Very nice a"
The price is NZ$274
includes taxes & fees
6 Jun - 7 Jun
The Engel House
The Brattleboro
Seasonal outdoor pool
The Brattleboro
3.0 star property
10.0 out of 10, Exceptional, 4 reviews
"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

Charming Waterfront Log Cabin
Interior
Charming Waterfront Log Cabin
9.8 out of 10, Exceptional, 27 reviews
"This cabin is so wonderful. The linens are exquisite and the beds are super comfortable. It is decorated so cute. There is everything you need! My favorite activity was sitting in the wooden rocking chair on the front porch each morning, drinking coffee, listening to nature (frogs, fish), and watching the lovely pond (which is so big it should be called a lake!) The owner responded to all my questions within minutes. You can even have pizza (regular AND gluten free) delivered!! If you visit, you...
The price is NZ$641
includes taxes & fees
18 Jun - 19 Jun
Charming Waterfront Log Cabin
Cozy Cottage Along Idyllic Green River
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, 34 reviews
"Charming house with everything we needed!"
Cozy Cottage Along Idyllic Green River
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Exterior
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
10.0 out of 10, Exceptional, 54 reviews
"Great location for our destination wedding nearby. Spacious home with a nice sunroom. Loved how you felt away from it all yet were very close to groceries, shops and restaurants."
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
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
826
Accommodation
11 B&B
Lowest Price
NZ$245
Highest Price
NZ$528

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, 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 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: Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the heart of Winchester. Colonel Williams Inn: 9 rooms. 18.2 mi (29.3 km) from the city centre. Enjoy the local cuisine breakfast and library. Centennial House: 5 rooms. Situated 6.4 mi (10.3 km) from the heart of Winchester. Enjoy the free full breakfast and library. The Carriage Barn Inn: 4 rooms. 11.8 mi (18.9 km) from the city centre. 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 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, April and February, with each month seeing an average of 28 cm 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 should put Rhododendron State Park and Ashuelot River on your list if you want to see more of the area.

Recent Reviews in Winchester
Expedia verified reviews

Latchis Hotel

Latchis Hotel

5/5 Excellent
Vintage View thats Fabulous
"We travel a lot... hands down this was my favorite hotel stay ever! It was like we stepped into 1940 to vacation for the night. The record player and albums were an amazing touch that will bring me back if I am ever in the area again"
A verified traveller stayed at Latchis Hotel
Posted 6 hours ago
Latchis Hotel