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Top 10 Winchester hotels and places to stay
Lakefront Orange Vacation Rental - Pet Friendly!
Lakefront Orange Vacation Rental - Pet Friendly!
10.0 out of 10, Exceptional, (6)
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
10.0 out of 10, Exceptional, (130)
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
10.0 out of 10, Exceptional, (22)
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Charming Waterfront Log Cabin
Charming Waterfront Log Cabin
10.0 out of 10, Exceptional, (24)
The price is CA $238
CA $530 total
includes taxes & fees
Jun 11 - Jun 12
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
10.0 out of 10, Exceptional, (8)
Penthouse, Steps to the Sandy Beach & clear water
Penthouse, Steps to the Sandy Beach & clear water
10.0 out of 10, Exceptional, (5)
Historic Home w/ Modern Updates on 3.5 Acres
Historic Home w/ Modern Updates on 3.5 Acres
10.0 out of 10, Exceptional, (5)
Waterfont log home nestled in the pines
Waterfont log home nestled in the pines
10.0 out of 10, Exceptional, (43)
Historic Home w/ Modern Updates on < 4 Acres
Historic Home w/ Modern Updates on < 4 Acres
10.0 out of 10, Exceptional, (1)
Spectacular Mountain views with all the amentities nearby
Spectacular Mountain views with all the amentities nearby
9.8 out of 10, Exceptional, (39)
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford
9.8 out of 10, Exceptional, (22)
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat
9.8 out of 10, Exceptional, (8)
The Carriage Barn Inn
The Carriage Barn Inn
9.6 out of 10, Exceptional, (121)
The price is CA $253
CA $275 total
includes taxes & fees
May 23 - May 24
The One Cat B&B
The One Cat B&B
9.6 out of 10, Exceptional, (66)
The price is CA $269
CA $296 total
includes taxes & fees
May 28 - May 29
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Cozy Updated Log Cabin with Mountain Views close to Monadnock
9.6 out of 10, Exceptional, (18)
The price is CA $212
CA $422 total
includes taxes & fees
May 28 - May 29
"The Murdock Suite @ The Large House"
"The Murdock Suite @ The Large House"
9.6 out of 10, Exceptional, (4)
Centennial House
Centennial House
9.4 out of 10, Exceptional, (127)
The price is CA $271
CA $286 total
includes taxes & fees
May 19 - May 20
Downtown Hot Tub Escape
Downtown Hot Tub Escape
9.4 out of 10, Exceptional, (3)
The price is CA $245
CA $471 total
includes taxes & fees
May 20 - May 21
Waterfront Cottage on Scenic Sportsman Pond
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, (34)
The Inn At Crumpin Fox
The Inn At Crumpin Fox
9.2 out of 10, Wonderful, (223)
The price is CA $231
CA $258 total
includes taxes & fees
Jun 2 - Jun 3
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.
More cheap stays in Winchester
The Covered Bridge Inn
1043 Putney Road, Brattleboro, VT
The price is CA $105 per night from May 19 to May 20
CA $105
CA $117 total
includes taxes & fees
May 19 - May 20
8.2/10 Very Good! (1,000 reviews)
Frequently asked questions
Recent Reviews in WinchesterExpedia verified reviews
5/5 Excellent
Wonderful staff.
"The hotel was clean and the staff was very welcoming. The hotel was a bit dated, but the mattresses were comfortable and I enjoyed my stay there."
A verified traveller stayed at Black Mountain Inn
Posted 2 days ago
Hotels near Popular Winchester Attractions
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Explore more hotels
- Comfort Inn & Suites Brattleboro I-91
- Fairfield Inn & Suites by Marriott Keene Downtown
- Black Mountain Inn
- Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
- Holiday Inn Express Keene, an IHG Hotel
- Riverhouse by Weekender (Formerly Jack Daniels Inn)
- The Inn At Crumpin Fox
- Blooming Inn
- Monadnock Inn
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