Search Deals onCharlestown Vacation Packages
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Charlestown Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

North Star Lodge and Resort
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip flight included
New York (LGA) to Rutland (RUT)
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Killington Resort and Fire Tower are located nearby.

The Shire Woodstock
Save 100% on your flight
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip flight included
New York (LGA) 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.

The Quechee Inn at Marshland Farm
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip flight included
New York (LGA) to Rutland (RUT)
Stay at this 3-star golf hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Wilderness Trails and Vermont Institiute of Natural Science are located nearby.

Jackson Gore Village
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip flight included
New York (LGA) to Springfield (VSF)
Stay at this 3-star 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.

Okemo Mountain Lodging
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip flight included
New York (LGA) to Springfield (VSF)
Stay at this 3.5-star vacation home in Ludlow. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.

Mountain Lodge at Okemo
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip flight included
New York (LGA) to Springfield (VSF)
Stay at this 3-star ski hotel in Ludlow. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.


Farm Road Estate
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip flight included
New York (LGA) to Springfield (VSF)
Stay at this 3-star golf hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Mount Snow and Mount Snow Golf Course 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, Jun 3 - Sat, Jun 7
IAD
Washington Dulles Intl.
RUT
Rutland Southern Vermont Regional
$454 Roundtrip, found 6 days ago
$454
Roundtrip
found 6 days ago

Tue, Jun 3 - Sat, Jun 7
IAD
Washington Dulles Intl.
RUT
Rutland Southern Vermont Regional
$463 Roundtrip, found 6 days ago
$463
Roundtrip
found 6 days ago

Thu, Jun 5 - Wed, Jun 11
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$474 Roundtrip, found 3 days ago
$474
Roundtrip
found 3 days ago

Thu, Jun 5 - Fri, Jun 13
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$498 Roundtrip, found 3 days ago
$498
Roundtrip
found 3 days ago
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