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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Browse Select Winchester B&B

Our top choices for Winchester bed & breakfast

Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (267)
"It was very personable. They were very flexible with check-in. Quiet and homie. "
Monadnock Inn
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (315)
"I enjoyed my stay and found the room more than adequately furnished. Wished the bed could be firmer and they could supply meals other than just breakfast."
The price is Rp2.562.840
Rp2.819.287 total
includes taxes & fees
31 Aug - 1 Sept
Colonel Williams Inn
Green River Bridge Inn
Exterior

Green River Bridge Inn

3.0 star property
8.4 out of 10, Very good, (7)
"The area is beautiful and the inn is lovely. I would highly recommend to anyone visiting the area. "
The price is Rp3.587.976
Rp3.910.894 total
includes taxes & fees
24 Aug - 25 Aug
Green River Bridge Inn
Centennial House
Free daily full breakfast

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (160)
"Lovely property and innkeepers, I was in the area for an event and hope to come back. "
The price is Rp3.276.774
Rp3.463.550 total
includes taxes & fees
13 Sept - 14 Sept
Centennial House
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (50)
"The folks were nice and accommodating. The breakfast was absolutely fantastically delicious. We would recommend this B&B to all our family and friends."
The price is Rp4.796.009
Rp5.275.708 total
includes taxes & fees
26 Aug - 27 Aug
Inn on Putney Road
The One Cat B&B
Exterior

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 Rp3.295.080
Rp3.624.588 total
includes taxes & fees
27 Aug - 28 Aug
The One Cat B&B
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (153)
"Loved our stay. Beautifully decorated and I was able to play the house guitar in common room which was a unique touch I really enjoyed. Would gladly stay here again."
The price is Rp2.882.389
Rp3.127.392 total
includes taxes & fees
2 Sept - 3 Sept
The Carriage Barn Inn
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is Rp4.900.150
Rp5.316.713 total
includes taxes & fees
31 Aug - 1 Sept
Chesterfield Inn
The Engel House
Exterior

The Engel House

3.0 star property
9.4 out of 10, Exceptional, (13)
"The perfect Vermont Bed and Breakfast. "
The Engel House
The Maguire House Bed & Breakfast
Property grounds

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 Rp4.474.800
Rp4.474.800 total
includes taxes & fees
10 Sept - 11 Sept
The Maguire House Bed & Breakfast
Four Columns Inn
Standard Room | 1 bedroom, free WiFi, bed sheets

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
The Brattleboro
Hiking

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
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

Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"We were blown away by this property! The theme-ing was on point but never in a way that sacrificed quality. The craftsmanship and attention to detail were extraordinary throughout the property. A highlight was reading with my morning coffee overlooking the sheep herd. Can’t wait to come back!"
Katherine 1-night trip
Posted 2 days ago
Vikings Villages Resort

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, Richmond Wildlife Manangement 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 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 well-liked B&Bs in the area: Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the heart of Winchester. Green River Bridge Inn: 4 rooms. 14.4 mi (23.1 km) from the city centre. Enjoy the snack bar/deli and patio area. Colonel Williams Inn: 9 rooms. Situated 18.2 mi (29.3 km) from the heart of Winchester. Enjoy the local cuisine breakfast and library. Centennial House: 5 rooms. 6.4 mi (10.3 km) from the city centre. Enjoy the free full breakfast and unique decor. Inn on Putney Road: 6 rooms. Located 10.7 mi (17.3 km) from the core of Winchester. Enjoy the free full breakfast and on-site spa services.
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, Richmond Wildlife Manangement Area and Rhododendron State Park are some notable spots. You should put New England Sweetwater Farm & Distillery and Pisgah State Park on your list if you want to see more of the area.