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Check prices for these dates

Next weekend
May 29 - May 31
In two weeks
Jun 5 - Jun 7
In one month
Jun 19 - Jun 21
In two months
Jul 17 - Jul 19

Our top choices for Winchester guest houses

Exterior

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.2 out of 10, Wonderful, (73 reviews)
"Property was just as described, it was great staying there, outdoors was beautiful."
United States
Tami
The price is CA $268
CA $295 total
includes taxes & fees
May 24 - May 25
The Inn At Quail Run
Exterior

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (167 reviews)
"Self check-in and checkout. Room was very clean but a bit too much potpourri for my allergies. Will stay here again when in Keene. "
United States
Charles
The price is CA $182
CA $203 total
includes taxes & fees
May 25 - May 26
The Burrell House
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (136 reviews)
"The room was clean and comfortable. It was a quiet night's sleep as I believe I was the only one there. Breakfast was very plain and simple: English muffins and cinnamon toast, with no fruit or juice. Coffee was plentiful"
United States
Sarah
The price is CA $147
CA $232 total
includes taxes & fees
May 27 - May 28
Blooming Inn
Property grounds

In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony
Shelburne Falls
10.0 out of 10, Exceptional, (125 reviews)
"set up great! very clean great location, WONDERFUL"
United States
laurie p.
The price is CA $155
CA $243 total
includes taxes & fees
May 31 - Jun 1
In town, newly remodeled studio with private balcony
Exterior

Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing

Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing
Munsonville
10.0 out of 10, Exceptional, (16 reviews)
"Great little place to stay. Minimal living style away from it all."
United States
Ryan W.
The price is CA $309
CA $467 total
includes taxes & fees
May 22 - May 23
Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing
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
"Nice place, great staff, convenient to downtown Keene."
Barry 1-night trip
Posted 4 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

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