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

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Our top choices for Winchester bed & breakfast

1. Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (178 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
$197 nightly
The price is $209
Sep 17 - Sep 18
Total with taxes and fees
Centennial House

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
$197 nightly
The price is $214
Sep 17 - Sep 18
Total with taxes and fees
The Carriage Barn Inn

3. 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
$300 nightly
The price is $330
Sep 20 - Sep 21
Total with taxes and fees
The One Cat B&B

4. 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
$158 nightly
The price is $173
Sep 22 - Sep 23
Total with taxes and fees
Colonel Williams Inn

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
$363 nightly
The price is $399
Sep 17 - Sep 18
Total with taxes and fees
Inn on Putney Road

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
$183 nightly
The price is $198
Sep 23 - Sep 24
Total with taxes and fees
Monadnock Inn

7. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (54 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
$128 nightly
The price is $140
Sep 29 - Sep 30
Total with taxes and fees
Four Columns Inn

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
$314 nightly
The price is $352
Sep 23 - Sep 24
Total with taxes and fees
Private bedroom in the Green River Bridge Inn. A full breakfast is included.

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
$283 nightly
The price is $283
Sep 24 - Sep 25
Total with taxes and fees
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

Find out more about Winchester

Winchester B&B information

Number of reviews
1,179
Accommodation
13 B&B
Lowest Price
$140
Highest Price
$399

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Winchester?
Prices for B&Bs in Winchester often vary, but you can find a great deal from $140 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Winchester?
The best time to book a B&B in Winchester is during the vibrant spring months of April to June, when the region comes alive with blooming flowers and outdoor activities. This period is particularly attractive to travelers seeking a mix of history and nature, as the comfortable temperatures, ranging from the mid-50s to the low 80s Fahrenheit, create ideal conditions for exploring the scenic landscapes and historic sites.

April marks the start of a delightful season, with many visitors drawn to Winchester for its picturesque gardens and nearby hiking trails. The famous Appalachian Trail, which runs close to Winchester, offers opportunities for both leisurely walks and more challenging hikes, making it a haven for outdoor enthusiasts. Additionally, spring festivals celebrating local culture add to the charm of the area.

For those looking to enjoy a quieter experience while still taking in the beauty of the region, consider visiting in November. This month often features stunning autumn foliage, ideal for scenic drives and peaceful strolls through Winchester's historic downtown. The fewer crowds create a more relaxed atmosphere, superb for savoring the local cuisine and exploring the rich history of the town.
What is the difference between a Winchester Bed and Breakfast and a hotel?
Every Winchester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winchester B&Bs.

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