Search Deals onRupert Vacation Packages
Rupert Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast
Price was $651, price is now $556 per person
$556
per person
Sep 29 - Oct 2
found 23 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this golf B&B in Poultney. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Poultney Public Library and Slate Quarry Park are located nearby.
very clean, very friendly, good breakfast, very nice Victorian style house
Reviewed on Aug 25, 2026
The Shire Woodstock
Price was $1,322, price is now $1,048 per person
$1,048
per person
Nov 5 - Nov 8
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.
Lake Bomoseen Lodge
Price was $717, price is now $570 per person
$570
per person
Sep 29 - Oct 2
found 23 hours ago
Roundtrip flight included
New York (NYC) 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.
Sinclair Inn Bed and Breakfast
Price was $903, price is now $758 per person
$758
per person
Nov 20 - Nov 25
found 20 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.
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
The Landgrove
Price was $714, price is now $600 per person
$600
per person
Sep 29 - Oct 2
found 23 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this family-friendly inn in Londonderry. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hapgood Pond and Wild Wings Ski Touring Center are located nearby.
Latchis Hotel
Price was $1,096, price is now $923 per person
$923
per person
Oct 9 - Oct 12
just found
Roundtrip non-stop flight included
New York (JFK) 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.
Mountain Green Resort
Price was $1,154, price is now $983 per person
$983
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Book a stay at this business-friendly apartment in Killington. Enjoy free WiFi, free parking, and in-room washers/dryers. Popular attractions Killington Resort and Black Dog Sports are located nearby.
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.
Reviewed on Jan 28, 2026
My Place Hotel-Randolph VT
Price was $883, price is now $755 per person
$755
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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.
Very pleasant experience from checking in to when we left. Very helpful front desk staff and hotel was very clean.
Reviewed on Aug 30, 2026
Rupert Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Rupert Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
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