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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

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, (302)
"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
30 Mar - 31 Mar
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 567
AED 615 total
includes taxes & fees
1 Apr - 2 Apr
The Carriage Barn Inn
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (264)
"owners are very nice "
The price is AED 559
AED 607 total
includes taxes & fees
5 Apr - 6 Apr
Monadnock Inn
Centennial House
Exterior detail

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (150)
"We had a great stay at Centennial House! Myself and my 14 year old son stayed for one night -- the bed was very comfortable and breakfast was fabulous!!"
The price is AED 789
AED 834 total
includes taxes & fees
28 Mar - 29 Mar
Centennial House
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (44)
"Great stop on our way out of N Vermont. Nice warm room on a cold night."
The price is AED 862
AED 948 total
includes taxes & fees
30 Mar - 31 Mar
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)
"Terry was an amazing host. She was so hospitable and made my stay here that much more comfortable. She not only cooks really amazing breakfast but she was so helpful when I wanted to check out the town. Her house is really truly beautiful and the lake is a little walk away from the house. I highly recommend coming here."
The price is AED 973
AED 973 total
includes taxes & fees
29 Mar - 30 Mar
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 528
AED 575 total
includes taxes & fees
6 Apr - 7 Apr
The Engel House
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (101)
"Lots of things were lovely; fantastic room service food (unbelievably fresh and delicious, better than anywhere I’ve ever eaten in a hotel while traveling), beautiful serene natural setting, and wonderful design of the buildings plus COOKIES and tea in the afternoon. The service was also fantastic. The paint could use freshening and the bathroom grout needs redoing (or consider retiling). A piece of one window pane, a wood bit, fell off… so I stuck it back, obviously needs a proper repair. With...
The price is AED 1,129
AED 1,225 total
includes taxes & fees
8 Apr - 9 Apr
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)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is AED 826
AED 909 total
includes taxes & fees
1 Apr - 2 Apr
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

Cozy Home Near Downtown, Shops, and Restaurants.
Exterior

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Online info was accurate. Nice spot to rent with family."
The price is AED 1,102
AED 1,901 total
includes taxes & fees
8 Apr - 9 Apr
Cozy Home Near Downtown, Shops, and Restaurants.
The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (46)
"Stayed for sugar season. Spring thaw makes river road a bit sketch but place and hosts were great! Will b back. "
The Jelly Mill-A River Retreat
Riverfront 2 Bedroom Unit 2
Property grounds

Riverfront 2 Bedroom Unit 2

9.8 out of 10, Exceptional, (16)
"We had a lovely time in central Mass"
Riverfront 2 Bedroom Unit 2
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, Barden State Wildlife Management 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: Colonel Williams Inn: 9 rooms. 18.2 mi (29.3 km) from the heart of Winchester. Enjoy the local cuisine breakfast and library. The Carriage Barn Inn: 4 rooms. 11.8 mi (18.9 km) from the downtown core. Monadnock Inn: 11 rooms. Situated 17.2 mi (27.6 km) from the heart of Winchester. 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. Centennial House: 5 rooms. Located 6.4 mi (10.3 km) from the core of Winchester. Enjoy the free full breakfast and unique décor.
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, Ashuelot River and Barden State Wildlife Management Area 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.