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Search B&B in Winchester

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Check prices for these dates

Next weekend
14 Rab. I - 16 Rab. I
In two weeks
21 Rab. I - 23 Rab. I
In one month
4 Rab. II - 6 Rab. II
In two months
2 Jum. I - 4 Jum. I

Compare 11 B&B in Winchester with updated reviews, rates, and availability.

Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.6 out of 10, Exceptional, (300)
"It is about 30 mins from Mount Snow. The room was gorgeous and king bed so comfortable. Brian was welcoming and the breakfast tacos to go were amazing!"
The price is SAR 508
SAR 554 total
includes taxes & fees
6 Apr - 7 Apr
Colonel Williams Inn
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (264)
"owners are very nice "
The price is SAR 571
SAR 619 total
includes taxes & fees
13 Mar - 14 Mar
Monadnock Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (144)
"I was in town for the Harris Hill Ski Jump Challenge in Brattleboro, VT and decided to stay in Keene, NH a town I always wanted to visit. I couldn't have picked a better location. What a lovely place and a brisk 5-minute walk got me into town with a great bakery, running store and restaurants. I'll be back, so much more to do and see. Even got an afternoon of skiing in at Granite Gorge."
The price is SAR 579
SAR 628 total
includes taxes & fees
1 Apr - 2 Apr
The Carriage Barn Inn
Centennial House
Exterior detail

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (150)
"We had a great stay at Centennial House! Myself and my 14 year old son stayed for one night -- the bed was very comfortable and breakfast was fabulous!!"
The price is SAR 761
SAR 804 total
includes taxes & fees
11 Mar - 12 Mar
Centennial House
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (44)
"Great stop on our way out of N Vermont. Nice warm room on a cold night."
The price is SAR 880
SAR 968 total
includes taxes & fees
12 Mar - 13 Mar
Inn on Putney Road
The Engel House
Exterior

The Engel House

3.0 star property
9.2 out of 10, Wonderful, (12)
"The perfect Vermont Bed and Breakfast. "
The price is SAR 630
SAR 686 total
includes taxes & fees
9 Mar - 10 Mar
The Engel House
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (101)
"Lots of things were lovely; fantastic room service food (unbelievably fresh and delicious, better than anywhere I’ve ever eaten in a hotel while traveling), beautiful serene natural setting, and wonderful design of the buildings plus COOKIES and tea in the afternoon. The service was also fantastic. The paint could use freshening and the bathroom grout needs redoing (or consider retiling). A piece of one window pane, a wood bit, fell off… so I stuck it back, obviously needs a proper repair. With...
The price is SAR 1,153
SAR 1,251 total
includes taxes & fees
19 Mar - 20 Mar
Chesterfield Inn
The Maguire House Bed & Breakfast
Building design

The Maguire House Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (34)
"Terry was an amazing host. She was so hospitable and made my stay here that much more comfortable. She not only cooks really amazing breakfast but she was so helpful when I wanted to check out the town. Her house is really truly beautiful and the lake is a little walk away from the house. I highly recommend coming here."
The price is SAR 994
SAR 994 total
includes taxes & fees
14 Mar - 15 Mar
The Maguire House Bed & Breakfast
Four Columns Inn
Deluxe Room | Living area | 20-inch TV with cable channels

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
The One Cat B&B
Exterior detail

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (74)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is SAR 844
SAR 928 total
includes taxes & fees
1 Apr - 2 Apr
The One Cat B&B
The Brattleboro
Seasonal outdoor pool

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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Other property types in Winchester

Secluded Lakefront Vacation Home
Smart TV, fireplace, books, printers

Secluded Lakefront Vacation Home

9.8 out of 10, Exceptional, (69)
"Once again I was placed into a state of memories starting from childhood when I used to swim in Lake Sunshine(now lake Contoocook! The scenery is mesmerizing and I love staring at the trees and lake which takes me back to days of freedom and wonderment. The sunrises are spectacular and make me begin a new day with energy and hope for this unsettled world."
Secluded Lakefront Vacation Home
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Outdoor dining

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (46)
"The cabin is cozy and sweet- we have a dog and small family and wanted to ski at Mt Snow. Cabin is short 20 minute drive to ski. Super cute town of Wilmington just a few minutes away. Go to Dots or Alpen Glow! Shaws grocery 2 minutes away. House has Pottery Barn vibes. Decent sized kitchen sitting and dining area. 2Bedroom 2 bath. This is not a house for a large crew but for a family getaway it was perfect. Street is quiet and residential. Neighbors seem really friendly. We would love to come...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cozy 2-bedroom Unit with private backyard
Fridge, microwave, oven, stovetop

Cozy 2-bedroom Unit with private backyard

10.0 out of 10, Exceptional, (21)
"Small but very clean and had everything we needed for our stay "
Cozy 2-bedroom Unit with private backyard
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.

Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find a place to stay with fewer rooms than a hotel and a cozy environment, a B&B might be just the right fit for your trip to Winchester. While you’re enjoying your trip to Winchester, Rhododendron State Park and Loring Field are perfect spots to get in some fresh air and greenery.
How do you know if a B&B is the best choice for your stay?
Every B&B has its own unique feel. Whether it’s a cozy reading space or a beautiful breakfast room, the tiny 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: Colonel Williams Inn: 9 rooms. 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 downtown core. Enjoy the free full breakfast and unique décor. Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the heart of downtown.The Carriage Barn Inn: 4 rooms. Located 11.8 mi (18.9 km) from the core of Winchester.
What's the best time of year to book my B&B in Winchester?
When you’re dreaming of a escape to Winchester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.
What is there to do in Winchester?
When you want to spend some time in the great outdoors, Birch Point and Rhododendron State Park are some notable spots. You might put Pisgah State Park and Ashuelot River on your list if you want to see more of the area.