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Winchester Vacation Packages

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Winchester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Mountain Lodge at Okemo, A Vail Resorts Property

Mountain Lodge at Okemo, A Vail Resorts Property

3 out of 5
Price was $803, price is now $765 per person
$765
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $1,210, price is now $1,009 per person
$1,009
per person
Jul 17 - Jul 24
found 22 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 Veterans' Park and Mills Riverside Park are located nearby.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,030, price is now $895 per person
$895
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
Price was $1,175, price is now $1,043 per person
$1,043
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $883, price is now $807 per person
$807
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Deer Brook Inn

Deer Brook Inn

3 out of 5
Price was $922, price is now $861 per person
$861
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and climate control. Popular attractions Ottaquechee River and Union Arena Community Center are located nearby.
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $806, price is now $768 per person
$768
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and 2 hot tubs. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
Price was $805, price is now $805 per person
$805
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.

Winchester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $982, price is now $910 per person
$910
per person
Jul 2 - Jul 6
found 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)

Winchester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $1,210, price is now $1,009 per person
$1,009
per person
Jul 17 - Jul 24
found 22 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Sat, Oct 17 - Wed, Oct 21
LAX
Los Angeles Intl.
BOS
Logan Intl.
$237 Roundtrip, just found
$237
Roundtrip
just found
Select American Airlines flight, departing Sat, Oct 17 from Los Angeles Intl. to Logan Intl., returning Wed, Oct 21, priced at $237 just found
American Airlines
Tue, Aug 18 - Sun, Aug 23
LAX
Los Angeles Intl.
PVD
T.F. Green
$297 Roundtrip, just found
$297
Roundtrip
just found
Select American Airlines flight, departing Tue, Aug 18 from Los Angeles Intl. to T.F. Green, returning Sun, Aug 23, priced at $297 just found
Bargain Flight
Sat, Jun 6 - Sat, Jun 13
PDX
Portland Intl.
BOS
Logan Intl.
$302 Roundtrip, just found
$302
Roundtrip
just found
Select Bargain Flight flight, departing Sat, Jun 6 from Portland Intl. to Logan Intl., returning Sat, Jun 13, priced at $302 just found
Delta
Wed, Jul 22 - Wed, Jul 29
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$336 Roundtrip, found 12 hours ago
$336
Roundtrip
found 12 hours ago
Select Delta flight, departing Wed, Jul 22 from Los Angeles Intl. to Bradley Intl., returning Wed, Jul 29, priced at $336 found 12 hours ago