Winchester Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Top Hotel Deals
The Colonial Hotel
625 Betty Spring Road Gardner MA
Book a stay at this business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
Colonial Motel
889 Putney Rd Brattleboro VT
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Latchis Hotel
50 Main Street Brattleboro VT
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Gardner Inn
22 Pearson Blvd Gardner MA
Stay at this hotel in Gardner. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Dunn State Park and 1761 Old Mill Gift Shop are located ...
The Putney Inn
57 Putney Landing Rd Putney VT
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Comfort Inn & Suites Brattleboro I-91
1186 Putney Road Brattleboro VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Hampton Inn & Suites Greenfield
184 Shelburne Rd Greenfield MA
Book a stay at this business-friendly hotel in Greenfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Vikings Villages Resort
360 Viking Village Drive Guilford VT
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions ...
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
The Inn At Crumpin Fox
71 Northfield Rd Bernardston MA
Book a stay at this business-friendly hotel in Bernardston. Enjoy free WiFi, free parking, and a conference center. Our guests praise the helpful staff and the ...
Riverside Hotel, an Ascend Collection Hotel
20 Riverside Drive West Chesterfield NH
Book a stay at this business-friendly hotel in West Chesterfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful ...
Windmill Motel Restaurant
497 Northfield Rd Bernardston MA
Stay at this hotel in Bernardston. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Bennett Meadows Wildlife Management Area and ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Nov 3 - Tue, Nov 10
LAX
Los Angeles Intl.
BOS
Logan Intl.
$258
Roundtrip
found 2 days ago
Sun, Nov 1 - Sat, Nov 14
LAX
Los Angeles Intl.
BOS
Logan Intl.
$288
Roundtrip
found 11 hours ago
Mon, Oct 26 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$343
Roundtrip
found 4 days ago
Wed, Dec 2 - Sat, Dec 12
LAX
Los Angeles Intl.
BOS
Logan Intl.
$357
Roundtrip
found 4 days ago
Fri, Dec 4 - Tue, Dec 15
LAX
Los Angeles Intl.
BOS
Logan Intl.
$367
Roundtrip
found 1 day ago
Best points of interest in Winchester
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