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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

B&B in Winchester

Centennial House
Free daily full breakfast

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (155)
"Elegant 200-year-old home updated with an en suite BR, AC. Wonderful hosts, Joan & Steve; excellent gourmet breakfast served in their historic dining area. Highly recommend for a quiet, historic, picturesque, comfortable, friendly stay."
The price is AED 639
AED 675 total
includes taxes & fees
20 Jul - 21 Jul
Centennial House
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (265)
"Hi it’s a beautiful inn and very comfortable "
Monadnock Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (152)
"Loved our stay. Beautifully decorated and I was able to play the house guitar in common room which was a unique touch I really enjoyed. Would gladly stay here again."
The price is AED 624
AED 677 total
includes taxes & fees
30 Jul - 31 Jul
The Carriage Barn Inn
Green River Bridge Inn
Exterior

Green River Bridge Inn

3.0 star property
10.0 out of 10, Exceptional, (2)
"Such a peaceful, beautiful area and inn! The host is wonderful and an amazing cook. The quintessential Vermont inn with an international flair. Can’t wait to go back!"
The price is AED 744
AED 811 total
includes taxes & fees
20 Jul - 21 Jul
Green River Bridge Inn
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (48)
"The folks were nice and accommodating. The breakfast was absolutely fantastically delicious. We would recommend this B&B to all our family and friends."
The price is AED 974
AED 1,072 total
includes taxes & fees
20 Jul - 21 Jul
Inn on Putney Road
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (307)
"The inn keepers are always super friendly and the place is kept well. The breakfast is delicious. Great for families who prefer quiet and quaint."
The price is AED 509
AED 555 total
includes taxes & fees
23 Jul - 24 Jul
Colonel Williams Inn
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (103)
"Great stay"
The price is AED 1,106
AED 1,200 total
includes taxes & fees
21 Jul - 22 Jul
Chesterfield Inn
The One Cat B&B
Exterior

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (75)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is AED 785
AED 864 total
includes taxes & fees
23 Jul - 24 Jul
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 price is AED 1,010
AED 1,010 total
includes taxes & fees
30 Jul - 31 Jul
The Maguire House Bed & Breakfast
Four Columns Inn
Deluxe Room | Living area | 20-inch TV with cable channels

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Outdoor dining

Private bedroom in the Green River Bridge Inn. A full breakfast is included.

The price is AED 808
AED 1,037 total
includes taxes & fees
24 Jul - 25 Jul
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
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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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, Richmond Wildlife Manangement Area 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: Centennial House: 5 rooms. 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 downtown core. The Carriage Barn Inn: 4 rooms. Situated 11.8 mi (18.9 km) from the heart of Winchester. Colonel Williams Inn: 9 rooms. 18.2 mi (29.3 km) from the heart of downtown. Enjoy the local cuisine breakfast and library. 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, Richmond Wildlife Manangement Area and Rhododendron State Park are some notable spots. You might put Winchester Speedpark and Pisgah State Park on your list if you want to see more of the area.