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Bed and Breakfast in Winchester

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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured B&B in Winchester

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, (156)
"Great breakfast, friendly staff"
The price is NZ$262
includes taxes & fees
28 July - 29 July
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 NZ$361
includes taxes & fees
28 July - 29 July
The Carriage Barn Inn
Green River Bridge Inn
Exterior

Green River Bridge Inn

3.0 star property
8.6 out of 10, Excellent, (4)
"The area is beautiful and the inn is lovely. I would highly recommend to anyone visiting the area. "
The price is NZ$365
includes taxes & fees
27 July - 28 July
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, (48)
"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 NZ$483
includes taxes & fees
28 July - 29 July
Inn on Putney Road
Colonel Williams Inn
Stunning hotel set amidst a serene autumn landscape.

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (307)
"The inn keepers are always super friendly and the place is kept well. The breakfast is delicious. Great for families who prefer quiet and quaint."
The price is NZ$247
includes taxes & fees
14 Aug - 15 Aug
Colonel Williams Inn
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 NZ$540
includes taxes & fees
30 July - 31 July
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 NZ$346
includes taxes & fees
30 July - 31 July
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 price is NZ$351
includes taxes & fees
20 Aug - 21 Aug
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 NZ$455
includes taxes & fees
30 July - 31 July
The Maguire House Bed & Breakfast
Four Columns Inn
Surrounded by lush greenery, this tranquil outdoor space features a beautiful blooming tree.

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Outdoor dining

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

The price is NZ$467
includes taxes & fees
31 July - 1 Aug
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
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
"Christine greeted me personally and reached out afterwards to learn about my experience. Love, love, love this place and can't wait to stay again!"
Gloria 1-night trip
Posted 15 hours 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: Centennial House: 5 rooms. 6.4 mi (10.3 km) from the heart of Winchester. Enjoy the free full breakfast and unique decor. Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the city centre. The Carriage Barn Inn: 4 rooms. Situated 11.8 mi (18.9 km) from the heart of Winchester. Colonel Williams Inn: 9 rooms. 18.2 mi (29.3 km) from the city centre. Enjoy the local cuisine breakfast and library. 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 Winchester Speedpark and Pisgah State Park on your list if you want to see more of the area.