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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 11 B&B in Winchester with updated reviews, rates, and availability.

Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (304)
"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 579
AED 631 total
includes taxes & fees
20 May - 21 May
Colonel Williams Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (146)
"This is a great place to stay. Host, Joe, was very friendly and helpful. The room was clean and cozy , and nicely furnished. Common areas were very comfortable and welcoming. We will definitely come back! "
The price is AED 723
AED 784 total
includes taxes & fees
19 May - 20 May
The Carriage Barn Inn
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 "
The price is AED 646
AED 701 total
includes taxes & fees
18 May - 19 May
Monadnock Inn
Centennial House
Exterior detail

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (152)
"This historic property is very nice. Beds are comfortable. The hosts are very welcoming and communication was very good. Breakfast was outstanding! I highly recommend this property and hope to return for another visit someday. "
The price is AED 710
AED 751 total
includes taxes & fees
1 Jun - 2 Jun
Centennial House
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (46)
"Excellent"
The price is AED 1,043
AED 1,148 total
includes taxes & fees
19 May - 20 May
Inn on Putney Road
The Maguire House Bed & Breakfast
Building design

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
4 Jun - 5 Jun
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 Engel House
Exterior

The Engel House

3.0 star property
9.2 out of 10, Wonderful, (12)
"The perfect Vermont Bed and Breakfast. "
The price is AED 572
AED 624 total
includes taxes & fees
19 May - 20 May
The Engel House
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (101)
"Charming place with friendly staff and owners."
The price is AED 1,106
AED 1,200 total
includes taxes & fees
20 May - 21 May
Chesterfield Inn
The One Cat B&B
Exterior detail

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (75)
"Such nice innkeepers! And a bespoke breakfast to boot. I hope I'm back in Brattleboro soon so I can spend another night at the One Cat B&B. Next time I hope to meet the cat."
The price is AED 826
AED 909 total
includes taxes & fees
19 May - 20 May
The One Cat B&B
The Brattleboro
Seasonal outdoor pool

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
Unique people and pet welcoming haven
Interior

Unique people and pet welcoming haven

Unique people and pet welcoming haven
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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Other property types in Winchester

Story Book Lake Front Chateau with Private Beach!
Miscellaneous

Story Book Lake Front Chateau with Private Beach!

10.0 out of 10, Exceptional, (6)
"We loved staying here! The property was sparkling clean and very well stocked with everything you need. Comfortable beds and space. The view was beautiful and the privacy and yard created great memories for our family. Thank you sharing your beautiful house with us!"
Story Book Lake Front Chateau with Private Beach!
Lovely 2nd Floor Apartment
Interior

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (23)
"Easy stay, good location for us. Would stay again. "
The price is AED 422
AED 734 total
includes taxes & fees
20 May - 21 May
Lovely 2nd Floor Apartment
GAMERS HAVEN, River Wine Inn!
Game room

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"The property is very large. Lots of sleeping area. Many activities within the rental to keep everyone off all ages busy, kept finding new things in nooks and crannies. Lots of property got our dog to run. "
GAMERS HAVEN, River Wine Inn!
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.

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, Loring Field 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: Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the heart of Winchester.Centennial House: 5 rooms. 6.4 mi (10.3 km) from the downtown core. Enjoy the free full breakfast and unique décor. Colonel Williams Inn: 9 rooms. Situated 18.2 mi (29.3 km) from the heart of Winchester. Enjoy the local cuisine breakfast and library. Inn on Putney Road: 6 rooms. 10.7 mi (17.3 km) from the heart of downtown. Enjoy the free full breakfast and onsite spa services. 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, Loring Field and Birch Point 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.