Search Guest Houses in Winchester

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Dec 12 - Dec 14
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Guest Houses in Winchester

Front of property
Blooming Inn

Blooming Inn

3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (123)
"When visiting the friends that live in Shelburne Falls; I wouldn't stay anywhere else."
United States
christian
$117 nightly
The price is $124
Dec 7 - Dec 8
Total with taxes and fees
Blooming Inn
Exterior
The Burrell House

The Burrell House

2.5 star property
Keene
9.6 out of 10, Exceptional, (155)
"Very helpful, kind staff"
United States
Paitris
$121 nightly
The price is $132
Dec 7 - Dec 8
Total with taxes and fees
The Burrell House
Seasonal outdoor pool
The Inn At Quail Run

The Inn At Quail Run

2.5 star property
Wilmington
9.0 out of 10, Wonderful, (71)
"Property was just as described, it was great staying there, outdoors was beautiful."
United States
Tami
$185 nightly
The price is $204
Dec 6 - Dec 7
Total with taxes and fees
The Inn At Quail Run
Smart TV, Netflix, streaming services
In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony

Shelburne Falls
10.0 out of 10, Exceptional, (119)
"We had a great visit! Easy to access, clean and comfortable. The studio had everything we needed!Great host!"
United States
Marina G.
$131 nightly
The price is $146
Dec 8 - Dec 9
Total with taxes and fees
In town, newly remodeled studio with private balcony
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"The customer service at this hotel is consistently exceptional. Every staff member is friendly, professional, and welcoming, creating an atmosphere that feels truly comfortable. The property is impeccably clean, and the breakfast offerings are always enjoyable. I have had an excellent experience during each of my visits, and I highly recommend this hotel to others"
qader 2-night trip
Posted 5 days ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Winchester

Winchester Guest Houses information

Number of reviews
467
Accommodation
7 Guest Houses
Lowest Price
$124
Highest Price
$204

Frequently asked questions

What is the nightly rate for a guest house in Winchester?
Rates for Winchester guest houses vary, but travelers can find great-value prices from $124 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Winchester guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Winchester guest house and a B&B?
A guest house in Winchester is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

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