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Check prices for these dates

Next weekend
26 Sep - 28 Sep
In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov

B&B in Winchester

Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (318)
"We stayed one night. We were able to get checked early, enjoyed breakfast, quiet and charming atmosphere. Owners are very friendly. "
The price is SAR 549
SAR 604 total
includes taxes & fees
28 Sep - 29 Sep
Colonel Williams Inn
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (270)
"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
8.4 out of 10, Very Good, (7)
"The area is beautiful and the inn is lovely. I would highly recommend to anyone visiting the area. "
The price is SAR 901
SAR 983 total
includes taxes & fees
29 Sep - 30 Sep
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, (155)
"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 SAR 712
SAR 773 total
includes taxes & fees
1 Oct - 2 Oct
The Carriage Barn Inn
Centennial House
Free daily full breakfast

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (163)
"Great breakfast, friendly staff"
The price is SAR 755
SAR 798 total
includes taxes & fees
21 Sep - 22 Sep
Centennial House
Four Columns Inn
Dining

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
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 SAR 1,362
SAR 1,498 total
includes taxes & fees
28 Sep - 29 Sep
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, (76)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is SAR 1,058
SAR 1,164 total
includes taxes & fees
25 Sep - 26 Sep
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 SAR 1,134
SAR 1,134 total
includes taxes & fees
8 Oct - 9 Oct
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
"Very convenient location. Facility is clean and attractive. Very comfortable. "
Jane 1-night trip
Posted 2 days ago
The Colonial 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, 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 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: 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 downtown core. Enjoy the deli and patio area. Monadnock Inn: 11 rooms. Situated 17.2 mi (27.6 km) from the heart of Winchester. Centennial House: 5 rooms. 6.4 mi (10.3 km) from the heart of downtown. Enjoy the free full breakfast and unique décor. The Carriage Barn Inn: 4 rooms. Located 11.8 mi (18.9 km) from the core of Winchester.
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, Rhododendron State Park and Ashuelot River are some notable spots. You might put Pisgah State Park and New England Sweetwater Farm & Distillery on your list if you want to see more of the area.