A snow-covered town with a river running through it, surrounded by mountains and trees.

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Check prices for these dates

Next weekend
25 Sep - 27 Sep
In two weeks
2 Oct - 4 Oct
In one month
16 Oct - 18 Oct
In two months
13 Nov - 15 Nov

Our top choices for Winchester bed & breakfast

Front of property

1. Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (180 reviews)
"The owner was excellent in showing us around. Recommending local things to do and restaurants. It was a very nice stay."
United States
Lauren
The price is AED 620
AED 655 total
includes taxes & fees
20 Sep - 21 Sep
Centennial House
Free daily continental breakfast

2. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (176 reviews)
"Perfectly clean and quaint. Friendly owner, great location"
United States
Jonathan
The price is AED 561
AED 609 total
includes taxes & fees
20 Sep - 21 Sep
The Carriage Barn Inn
Front of property

3. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (359 reviews)
"A very historic and well maintained bed and breakfast. The owners are wonderful and the rooms were cozy. The hand made breakfast was a highlight"
United States
Robert
The price is AED 555
AED 611 total
includes taxes & fees
20 Oct - 21 Oct
Colonel Williams Inn
Property entrance

4. The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.8 out of 10, Exceptional, (81 reviews)
"Breakfast was fantastic Did not need any shops Hosts were super friendly We enjoyed our short stay"
United States
marjie
The price is AED 1,102
AED 1,212 total
includes taxes & fees
23 Sep - 24 Sep
The One Cat B&B
Exterior

5. Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (61 reviews)
"Helpful staff, wonderful breakfast and homey ambiance."
United States
Karla
The price is AED 1,334
AED 1,467 total
includes taxes & fees
21 Sep - 22 Sep
Inn on Putney Road
Exterior

6. Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.8 out of 10, Good, (292 reviews)
"Very nice, clean, and a good vibe. An older building but very charming. Would certainly stay again."
United States
Jed
The price is AED 620
AED 673 total
includes taxes & fees
20 Sep - 21 Sep
Monadnock Inn
Land view from property

7. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (55 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is AED 541
AED 589 total
includes taxes & fees
20 Sep - 21 Sep
Four Columns Inn
Outdoor dining

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

Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Guilford
The price is AED 1,010
AED 1,292 total
includes taxes & fees
26 Sep - 27 Sep
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Terrace/patio

9. The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The price is AED 1,122
AED 1,122 total
includes taxes & fees
23 Sep - 24 Sep
The Maguire House Bed & Breakfast
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

Deerfield Inn

Deerfield Inn

8/10 Good
"The inn was in a perfect location for many activities. The room was very nice with a super comfy king size bed. The bathroom was fine. In the hallway they had a coffee machine for your morning routine. Our only comment is that the TV was very small. Parking was right onsite and convenient. The restaurant was nice and the morning coffee with muffins was a nice touch."
Patrice 1-night trip
Posted 1 hour ago
Deerfield Inn

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 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: Centennial House: 5 rooms. 6.4 mi (10.3 km) from the heart of Winchester. Enjoy the free full breakfast and private yard. Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the downtown core. The Carriage Barn Inn: 4 rooms. 11.8 mi (18.9 km) from the heart of downtown.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, Birch Point and Cass Pond are some notable spots. You might put Winchester Speedpark and New England Sweetwater Farm & Distillery on your list if you want to see more of the area.

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