Search Deals on
Winchester Vacation Packages

Build your package with 2 more options

Winchester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $695, price is now $524 per person
$524
per person
Mar 4 - Mar 8
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) 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 United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $1,113, price is now $866 per person
$866
per person
Mar 4 - Mar 8
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Stay at this B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bonnie's Bundles Dolls and DaVallia Art & Accents are located nearby.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Price was $1,937, price is now $1,618 per person
$1,618
per person
Mar 4 - Mar 8
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
Chalet 239

Chalet 239

2 out of 5
Price was $895, price is now $751 per person
$751
per person
Mar 4 - Mar 8
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was $1,221, price is now $1,036 per person
$1,036
per person
Mar 4 - Mar 8
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Book a stay at this spa resort in West Dover. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.
Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Price was $816, price is now $697 per person
$697
per person
Mar 4 - Mar 8
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Stay at this B&B in West Dover. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
Windham Hill Inn

Windham Hill Inn

4 out of 5
Price was $816, price is now $719 per person
$719
per person
Mar 4 - Mar 8
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Stay at this B&B in West Townshend. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Hot Glass Works and Ball Mountain State Park are located nearby.
COHO Inn & Motor Lodge

COHO Inn & Motor Lodge

2 out of 5
Price was $766, price is now $706 per person
$706
per person
Mar 4 - Mar 8
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Stay at this motel in Weston. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Weston Playhouse and Mill Museum are located nearby.

Winchester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $695, price is now $524 per person
$524
per person
Mar 4 - Mar 8
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $1,113, price is now $866 per person
$866
per person
Mar 4 - Mar 8
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $1,937, price is now $1,618 per person
$1,618
per person
Mar 4 - Mar 8
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Chalet 239

Chalet 239

2 out of 5
Price was $895, price is now $751 per person
$751
per person
Mar 4 - Mar 8
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)

Top Flight Deals

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

American Airlines
Mon, Apr 20 - Tue, Apr 28
PDX
Portland Intl.
BOS
Logan Intl.
$180 Roundtrip, just found
$180
Roundtrip
just found
Select American Airlines flight, departing Mon, Apr 20 from Portland Intl. to Logan Intl., returning Tue, Apr 28, priced at $180 just found
United
Tue, Mar 10 - Wed, Mar 18
LAX
Los Angeles Intl.
BOS
Logan Intl.
$185 Roundtrip, just found
$185
Roundtrip
just found
Select United flight, departing Tue, Mar 10 from Los Angeles Intl. to Logan Intl., returning Wed, Mar 18, priced at $185 just found
American Airlines
Wed, Feb 25 - Tue, Mar 3
PDX
Portland Intl.
PVD
T.F. Green
$255 Roundtrip, found 8 hours ago
$255
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Wed, Feb 25 from Portland Intl. to T.F. Green, returning Tue, Mar 3, priced at $255 found 8 hours ago
JetBlue Airways
Tue, Mar 10 - Tue, Mar 17
LAX
Los Angeles Intl.
PVD
T.F. Green
$273 Roundtrip, found 12 hours ago
$273
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Tue, Mar 10 from Los Angeles Intl. to T.F. Green, returning Tue, Mar 17, priced at $273 found 12 hours ago