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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct
Colonel Williams Inn
Stunning hotel set amidst a serene autumn landscape.

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (310)
"Excellent. Wonderful breakfast. "
The price is HK$1,137
HK$1,251 total
includes taxes & fees
14 Aug - 15 Aug
Colonel Williams Inn
Centennial House
Enjoy meals in a beautifully lit dining area with arched windows and a view of the outdoors.

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (159)
"Lovely property and innkeepers, I was in the area for an event and hope to come back. "
The price is HK$1,423
HK$1,504 total
includes taxes & fees
10 Aug - 11 Aug
Centennial House
Monadnock Inn
Stroll up to this charming residence, featuring a covered porch with white columns and a small railing, surrounded by lush greenery.

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (265)
"It was very personable. They were very flexible with check-in. Quiet and homie. "
Monadnock Inn
The Carriage Barn Inn
Enjoy a meal with a view from this dining table near a window.

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 HK$1,350
HK$1,464 total
includes taxes & fees
2 Sept - 3 Sept
The Carriage Barn 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 HK$1,590
HK$1,733 total
includes taxes & fees
7 Aug - 8 Aug
Green River Bridge Inn
Inn on Putney Road
Classic two-story house with a gabled roof and symmetrical facade, surrounded by a well-maintained garden and a white fence.

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (49)
"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 HK$2,314
HK$2,545 total
includes taxes & fees
14 Aug - 15 Aug
Inn on Putney Road
Chesterfield Inn
Cozy living room with a rustic fireplace, large windows, and classic furnishings.

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is HK$2,364
HK$2,565 total
includes taxes & fees
12 Aug - 13 Aug
Chesterfield Inn
The One Cat B&B
Stroll through the serene garden, surrounded by vibrant blooms and a whimsical cat-themed sign.

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 HK$1,432
HK$1,575 total
includes taxes & fees
27 Aug - 28 Aug
The One Cat B&B
The Engel House
Guests can enjoy a warm welcome on the porch with outdoor seating.

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
Relax in a serene garden setting surrounded by lush foliage and vibrant flowers.

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 HK$2,237
HK$2,237 total
includes taxes & fees
4 Sept - 5 Sept
The Maguire House Bed & Breakfast
Four Columns Inn
Relax in this stylish room with two armchairs, a coffee table, and a large window overlooking a charming view.

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

Blooming Inn

Blooming Inn

10/10 Excellent
"The Blooming Inn is in a perfect location for visiting Shelburne Falls. There is ample parking, and the hosts are gracious, welcoming, and accommodating. I look forward to returning next time with my wife."
MARK 2-night trip
Posted 1 day ago
Blooming Inn

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: Green River Bridge Inn: 4 rooms. 14.4 mi (23.1 km) from the heart of Winchester. Enjoy the snack bar/deli and patio area. Centennial House: 5 rooms. 6.4 mi (10.3 km) from the city centre. Enjoy the free full breakfast and unique decor. Monadnock Inn: 11 rooms. Situated 17.2 mi (27.6 km) from the heart of Winchester. The Carriage Barn Inn: 4 rooms. 11.8 mi (18.9 km) from the city centre. Colonel Williams Inn: 9 rooms. Located 18.2 mi (29.3 km) from the core of Winchester. Enjoy the local cuisine breakfast and library.
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.