Search Deals onCharlestown Vacation Packages
Charlestown Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast
Price was $787, price is now $742 per person
$742
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) 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.
Had an amazing time here, everyone was so friendly and welcoming and the property itself was beautiful! Breakfast was delicious and we were a huge fan of the late night snacks too! We’re looking forward to staying again the next time we visit the area!
Reviewed on Aug 27, 2026
My Place Hotel-Randolph VT
Price was $1,190, price is now $1,001 per person
$1,001
per person
Oct 21 - Oct 25
just found
Roundtrip non-stop flight included
San Antonio (SAT) to Rutland (RUT)
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Whale Dance Sculpture and Montague Golf Club are located nearby.
Castle Hill Resort And Spa
Price was $1,030, price is now $893 per person
$893
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Rutland (RUT)
Book a stay at this luxury hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
The Landgrove
Price was $900, price is now $833 per person
$833
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Rutland (RUT)
Book a stay at this family-friendly inn in Londonderry. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bromley Mountain Ski Resort and Hapgood Pond are located nearby.
Lots to like about this Inn: Accurate web descriptions including of their many tasty breakfast options; Very clean, Comfortable mattress with quality linens, Great bath products, Hot showers, Individual temp controls for room, Tasty tap water, Pretty landscaping. Every staff member is very pleasant – shout out to Audrey. Other things to expect: Bring a sleep mask if sensitive to light, no cell service nearby but inn offers unsecured Wi-Fi; stairs to 2nd flr rooms are shallow & steep-typical for age of building; and its easy to take country walks on the road.
Reviewed on Sep 1, 2026
Lake Bomoseen Lodge
Price was $835, price is now $778 per person
$778
per person
Oct 14 - Oct 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Rutland (RUT)
Book a stay at this beach lodge in Bomoseen. Enjoy free parking, an outdoor pool, and a private beach. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Prospect Bay Country Club and Lake Bomoseen are located nearby.
Another excellent visit with impeccable rooms, customer service, and convenient location.
Reviewed on Sep 8, 2026
1846 Inn and Tavern
Price was $877, price is now $823 per person
$823
per person
Oct 14 - Oct 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
Chalet 239
Price was $819, price is now $774 per person
$774
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) 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.
Perfect boutique stay
Reviewed on Aug 29, 2026
Latchis Hotel
Price was $790, price is now $751 per person
$751
per person
Oct 14 - Oct 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
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.
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