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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sep - 28 Sep

B&B in Winchester

Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (310)
"Excellent. Wonderful breakfast. "
The price is SAR 514
SAR 560 total
includes taxes & fees
5 Aug - 6 Aug
Colonel Williams Inn
Centennial House
Free daily full breakfast

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (157)
"Great breakfast, friendly staff"
The price is SAR 680
SAR 719 total
includes taxes & fees
3 Aug - 4 Aug
Centennial House
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (265)
"It was very personable. They were very flexible with check-in. Quiet and homie. "
Monadnock Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (153)
"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 SAR 709
SAR 770 total
includes taxes & fees
20 Aug - 21 Aug
The Carriage Barn Inn
Green River Bridge Inn
Exterior

Green River Bridge Inn

3.0 star property
8.0 out of 10, Very Good, (6)
"The area is beautiful and the inn is lovely. I would highly recommend to anyone visiting the area. "
The price is SAR 760
SAR 828 total
includes taxes & fees
3 Aug - 4 Aug
Green River Bridge Inn
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (49)
"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 SAR 1,106
SAR 1,216 total
includes taxes & fees
3 Aug - 4 Aug
Inn on Putney Road
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is SAR 1,130
SAR 1,226 total
includes taxes & fees
4 Aug - 5 Aug
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 SAR 699
SAR 769 total
includes taxes & fees
6 Aug - 7 Aug
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
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
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

Latchis Hotel

Latchis Hotel

10/10 Excellent
"Staff were friendly and efficient and went out of their way to help me in a difficult situation at a local restaurant!! Very compassionate and supportive through my ordeal!! I will definitely stay again when in Brattleboro!"
Deborah 1-night trip
Posted 2 days ago
Latchis Hotel

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: Green River Bridge Inn: 4 rooms. 14.4 mi (23.1 km) from the heart of Winchester. Enjoy the deli and patio area. Centennial House: 5 rooms. 6.4 mi (10.3 km) from the downtown core. Enjoy the free full breakfast and unique décor. Monadnock Inn: 11 rooms. Situated 17.2 mi (27.6 km) from the heart of Winchester. The Carriage Barn Inn: 4 rooms. 11.8 mi (18.9 km) from the heart of downtown.Colonel Williams Inn: 9 rooms. Located 18.2 mi (29.3 km) from the core of Winchester. Enjoy the local cuisine breakfast and library.
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 New England Sweetwater Farm & Distillery and Pisgah State Park on your list if you want to see more of the area.