Winchester Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
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Winchester Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Shire Woodstock
Price was $1,334, price is now $1,038 per person
$1,038
per person
Feb 15 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Jackson Gore Village
Jackson Gore Base Area
Save 100% on your flight
Price was $5,073, price is now $3,429 per person
$3,429
per person
Feb 15 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Book a stay at this spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Jackson Gore Parking are located nearby.
Woodstock Inn & Resort
Price was $2,864, price is now $2,643 per person
$2,643
per person
Feb 15 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
Lincoln Inn & Gallery
West Woodstock
Price was $1,228, price is now $1,228 per person
$1,228
per person
Feb 15 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Stay at this inn in Woodstock. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Union Arena Community Center and Ottaquechee River are located nearby.
Top Hotel Deals
The Colonial Hotel
625 Betty Spring Road Gardner MA
42.31 km from city center
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 ...
Comfort Inn & Suites Brattleboro I-91
1186 Putney Road Brattleboro VT
18.95 km from city center
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. ...
The Covered Bridge Inn
1043 Putney Road Brattleboro VT
18.68 km from city center
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
19.03 km from city center
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 ...
The Putney Inn
57 Putney Landing Rd Putney VT
23.92 km from city center
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 ...
Latchis Hotel
50 Main Street Brattleboro VT
16.67 km from city center
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. ...
Econo Lodge Brattleboro
515 Canal St Brattleboro VT
16.53 km from city center
Stay at this motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Vermont Marketplace and Estey Organ Museum are located ...
Hampton Inn & Suites Greenfield
184 Shelburne Rd Greenfield MA
28.52 km from city center
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. ...
Gardner Inn
22 Pearson Blvd Gardner MA
40.24 km from city center
Stay at this hotel in Gardner. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Dunn State Park and 1761 Old Mill Gift Shop are located ...
Vikings Villages Resort
360 Viking Village Drive Guilford VT
18.58 km from city center
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 ...
Colonial Motel And Spa
889 Putney Rd Brattleboro VT
18.53 km from city center
Book a stay at this spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
Holiday Inn Express Hotel & Suites Brattleboro by IHG
100 Chickering Drive Brattleboro VT
18.8 km from city center
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
18.3 km from city center
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 ...
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, Mar 24 - Sat, Apr 4
PDX
Portland Intl.
BOS
Logan Intl.
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Sat, Mar 28 - Sat, Apr 4
PDX
Portland Intl.
BOS
Logan Intl.
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Wed, May 13 - Sat, May 23
PDX
Portland Intl.
BOS
Logan Intl.
$292 Roundtrip, found 5 hours ago
$292
Roundtrip
found 5 hours ago
Wed, Jun 10 - Tue, Jun 16
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$299 Roundtrip, found 2 days ago
$299
Roundtrip
found 2 days ago
Wed, Jun 10 - Tue, Jun 16
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$340 Roundtrip, found 2 days ago
$340
Roundtrip
found 2 days ago