Search Deals onCharlestown Vacation Packages
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Charlestown Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Shire Woodstock
Price was $448, price is now $363 per person
$363
per person
Jan 3 - Jan 5
found 10 hours ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
Stay at this 3-star 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.
Killington Mountain Lodge, Tapestry Collection by Hilton
Price was $1,107, price is now $852 per person
$852
per person
Jan 16 - Jan 19
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
Stay at this 3.5-star ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Price was $795, price is now $618 per person
$618
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Lebanon (LEB)
Stay at this 3-star resort in Brownsville. Enjoy an outdoor pool, a business center, and a fireplace in the lobby. Our guests praise the helpful staff in our reviews. Popular attractions Mount Ascutney and Mt Ascutney State Park are located nearby.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Save 100% on your flight
Price was $2,294, price is now $1,834 per person
$1,834
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Stay at this 3-star ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage I are located nearby.
Mount Snow Grand Summit Resort
Price was $1,621, price is now $1,355 per person
$1,355
per person
Dec 25 - Dec 28
found 12 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stay at this 3-star 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.
Golden Stage Inn B&B
Price was $1,088, price is now $910 per person
$910
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)
Stay at this 3.5-star B&B in Cavendish. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Emrose Luxury Cabins
Price was $1,653, price is now $1,392 per person
$1,392
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)
Stay at this hotel in Brandon. Enjoy free WiFi, free parking, and 8 hot tubs. Popular attractions Otter Valley Winery and Stephen A Douglas Birthplace are located nearby.
Summit Lodge
Price was $951, price is now $804 per person
$804
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Stay at this 3-star inn in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Killington Resort and Killington School for Tennis are located nearby.
Charlestown Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Charlestown Vacation Packages 5-7 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, Feb 10 - Tue, Feb 10
JFK
John F. Kennedy Intl.
LEB
Lebanon Municipal
$294 Roundtrip, found 12 hours ago
$294
Roundtrip
found 12 hours ago
Sun, Dec 7 - Wed, Dec 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$304 Roundtrip, found 14 hours ago
$304
Roundtrip
found 14 hours ago
Thu, Dec 4 - Mon, Dec 8
LGA
LaGuardia
RUT
Rutland Southern Vermont Regional
$321 Roundtrip, found 1 day ago
$321
Roundtrip
found 1 day ago
Sun, Dec 7 - Mon, Dec 8
EWR
Newark Liberty Intl. Airport
RUT
Rutland Southern Vermont Regional
$344 Roundtrip, found 17 hours ago
$344
Roundtrip
found 17 hours ago
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