Search Deals onOrwell Vacation Packages
Orwell Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast
Price was $750, price is now $656 per person
$656
per person
Sep 28 - Oct 2
found 1 day 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 pleasant.
Reviewed on Aug 13, 2026
Mountain Green Resort
Save 100% on your flight
Price was $4,631, price is now $3,656 per person
$3,656
per person
Sep 20 - Sep 27
found 9 hours ago
Roundtrip non-stop flight included
New York (NYC) 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
The Mountain Inn at Killington
Price was $1,474, price is now $1,203 per person
$1,203
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Fun location with a distillery on site. Lots of dining opportunities close by
Reviewed on Aug 15, 2026
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Price was $1,387, price is now $1,140 per person
$1,140
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this 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.
Nice area, clean and kitchen was well equipped. We used the air fryer for dinner one night.
Reviewed on Aug 15, 2026
The Suites at Killington Center
Price was $1,353, price is now $1,128 per person
$1,128
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Stay at this condo in Killington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Killington Resort and Killington School for Tennis are located nearby.
Days Inn by Wyndham Rutland/Killington Area
Price was $1,275, price is now $1,087 per person
$1,087
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Green Mountain Shopping Plaza and Spartan Arena are located nearby.
The Landgrove
Price was $987, price is now $844 per person
$844
per person
Sep 28 - Oct 2
found 1 day 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.
Greenbrier Inn
Price was $1,236, price is now $1,063 per person
$1,063
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Stay at this hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Killington Resort and Gifford Woods State Park are located nearby.
Nice place. Rooms are large, and there is ample space in the common areas. Breakfast was simple but sufficient. My room had a small balcony.
Reviewed on Aug 3, 2026
Orwell Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Orwell Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
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