Search Deals onWinchester Vacation Packages
Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Chalet 239
Price was $729, price is now $599 per person
$599
per person
Oct 10 - Oct 13
found 22 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (VSF)
Stay at this motel in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
Beautifully renovated, and well designed property unlike anything I’ve ever seen!
Reviewed on Aug 7, 2026
Latchis Hotel
Price was $752, price is now $601 per person
$601
per person
Oct 10 - Oct 13
found 22 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (VSF)
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. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
Jackson Gore Village, A Vail Resorts Property
Price was $721, price is now $600 per person
$600
per person
Oct 10 - Oct 13
found 22 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Timber Ripper Mountain Coaster are located nearby.
Everything was great, inside and outside clean and well-maintained. Air conditioner did not work well. Room wasn't hot, but not cool either - only issue we have. We would stay again.
Reviewed on Aug 19, 2026
1846 Inn and Tavern
Price was $861, price is now $719 per person
$719
per person
Oct 10 - Oct 13
found 22 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (VSF)
Stay at this inn in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
Grand Summit Resort, A Vail Resorts Property
Price was $710, price is now $616 per person
$616
per person
Oct 10 - Oct 13
found 22 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (VSF)
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and a free area shuttle. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
Hampton Inn Brattleboro
Price was $767, price is now $701 per person
$701
per person
Oct 10 - Oct 13
found 22 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (VSF)
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 helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Breakfast was mediocre in choices and quality but the area was clean and well stocked. Orange juice clearly watered down excessively.
Reviewed on Aug 19, 2026
Sinclair Inn Bed and Breakfast
Price was $753, price is now $698 per person
$698
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this B&B in Jericho. Enjoy free breakfast, free WiFi, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Mills Riverside Park and Waters Memorial Library are located nearby.
Everything about Sinclair Inn Bed and Breakfast was exceptional. Holly and Kyle were welcoming hosts the property is very well maintained and the gardens are beautiful with areas to sit and relax. Breakfast was delicious with a variety of options with fresh berries, yogurt and granola to build your own parfait, delicious quiche, fresh baked goods. And delicious cookies for Night time snack.
I would highly recommend this establishment for your next trip to the area.
Reviewed on Aug 10, 2026
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Price was $1,009, price is now $935 per person
$935
per person
Oct 10 - Oct 13
found 22 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (VSF)
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 staff in our reviews. Popular attractions Brattleboro Bowl and New England Center for Circus Arts are located nearby.
Clean room, very nice front desk staff. Breakfast was good - nice variety and the coffee machine delivered great fresh coffee. It was worth paying the extra cost for this hotel vs the others in the area that seemed a bit sketchy.
Reviewed on Aug 16, 2026
Winchester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Oct 20 - Tue, Oct 27
LAX
Los Angeles Intl.
BOS
Logan Intl.
$218 Roundtrip, found 10 hours ago
$218
Roundtrip
found 10 hours ago
Wed, Sep 16 - Sat, Sep 19
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$223 Roundtrip, found 4 days ago
$223
Roundtrip
found 4 days ago
Sat, Sep 5 - Sat, Sep 26
LAX
Los Angeles Intl.
ALB
Albany Intl.
$261 Roundtrip, found 6 days ago
$261
Roundtrip
found 6 days ago
Tue, Nov 3 - Sat, Nov 7
PDX
Portland Intl.
BOS
Logan Intl.
$301 Roundtrip, found 23 hours ago
$301
Roundtrip
found 23 hours ago
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