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
28 Aug - 30 Aug
In two weeks
4 Sept - 6 Sept
In one month
18 Sept - 20 Sept
In two months
16 Oct - 18 Oct

Our top choices for Winchester bed & breakfast

Free daily continental breakfast

1. 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 HK$1,147
HK$1,244 total
includes taxes & fees
18 Aug - 19 Aug
The Carriage Barn Inn
Front of property

2. 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 HK$1,962
HK$2,158 total
includes taxes & fees
24 Aug - 25 Aug
The One Cat B&B
Front of property

3. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (358 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 HK$1,236
HK$1,359 total
includes taxes & fees
23 Aug - 24 Aug
Colonel Williams Inn
Front of property – evening/night

4. Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (106 reviews)
"Great stay"
United States
Wayne
The price is HK$2,363
HK$2,564 total
includes taxes & fees
18 Aug - 19 Aug
Chesterfield Inn
Exterior

5. Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (59 reviews)
"Helpful staff, wonderful breakfast and homey ambiance."
United States
Karla
The price is HK$2,313
HK$2,544 total
includes taxes & fees
20 Aug - 21 Aug
Inn on Putney Road
Land view from property

6. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (50 reviews)
"Can’t go wrong with this place."
United States
John
The price is HK$1,229
HK$1,339 total
includes taxes & fees
18 Aug - 19 Aug
Four Columns Inn
Exterior

7. Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.8 out of 10, Good, (290 reviews)
"Castine is a great host, and the inn has a lot of New England charm. Great place to stay!"
United States
Saif
The price is HK$1,291
HK$1,401 total
includes taxes & fees
18 Aug - 19 Aug
Monadnock 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 HK$2,158
HK$2,768 total
includes taxes & fees
24 Aug - 25 Aug
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, (38 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 HK$2,236
HK$2,236 total
includes taxes & fees
26 Aug - 27 Aug
The Maguire House Bed & Breakfast
Children’s activities

10. Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (176 reviews)
"David was incredibly hospitable. I thoroughly enjoyed my stay. "
United States
Amy
The price is HK$1,408
HK$1,489 total
includes taxes & fees
18 Aug - 19 Aug
Centennial House
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

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

8/10 Good
"Friendly staff, clean lobby and adequate rooms."
Michelle 2-night trip
Posted 12 hours ago
Hampton Inn & Suites Greenfield

Find out more about Winchester

Winchester B&B information

Number of reviews
1,334
Accommodation
12 B&B
Lowest Price
HK$1,244
Highest Price
HK$2,768

Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find a place to stay with fewer rooms than the traditional hotel and a cosy environment, a bed and breakfast might be just the right fit for your trip to Winchester. While you're enjoying your trip to Winchester, Loring Field and Richmond Wildlife Manangement Area are perfect spots to get in some fresh air and greenery.
How do you know if a B&B is a good option for your stay?
Every B&B has its own unique feel — whether it's a comfy common area with a fireplace or a beautiful breakfast room, the little details are what make bed and breakfasts a fun place to get away.
What are the best B&Bs in Winchester?
Below are some B&Bs in the area: Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the city centre. Colonel Williams Inn: 9 rooms. Situated 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 city centre. Centennial House: 5 rooms. Located 6.4 mi (10.3 km) from the core of Winchester. Enjoy the free full breakfast and unique decor.
When should I book my B&B in Winchester?
When you're dreaming of a trip to Winchester, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.
What is there to do in Winchester?
When you want to spend some time in the great outdoors, Cass Pond and Loring Field are some notable spots. You should put Winchester Speedpark and Pisgah State Park on your list if you want to see more of the area.

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