Search Deals onCastleton Vacation Packages
Castleton Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast
Price was $941, price is now $820 per person
$820
per person
Dec 16 - Dec 21
found 4 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Mountain Green Resort
Price was $5,334, price is now $4,111 per person
$4,111
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Price was $1,892, price is now $1,469 per person
$1,469
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Stay at this resort in Brownsville. Enjoy a business center, a fireplace in the lobby, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions T-Bar and Rope Tow are located nearby.
The Suites at Killington Center
Price was $1,814, price is now $1,467 per person
$1,467
per person
Dec 16 - Dec 21
found 4 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Price was $5,424, price is now $4,656 per person
$4,656
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
It is a wonderful place to stay at any time for coming foliage or ski. The location is excellent, quiet and very clean inside. We felt like at home, We will stay again when we visit woodstook area next time.
Reviewed on Oct 15, 2026
Days Inn by Wyndham Rutland/Killington Area
Price was $1,067, price is now $923 per person
$923
per person
Dec 16 - Dec 21
found 4 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Nice place good breakfast
Reviewed on Oct 27, 2026
Lake Bomoseen Lodge
Price was $1,038, price is now $903 per person
$903
per person
Dec 16 - Dec 21
found 4 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
I love staying here!
Reviewed on Oct 27, 2026
The Vermont Inn
Price was $1,350, price is now $1,181 per person
$1,181
per person
Dec 16 - Dec 21
found 4 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this family-friendly B&B in Rutland. Enjoy free WiFi, free parking, and a conference center. Popular attractions Killington Resort and Golden Express Quad are located nearby.
Our room was large and comfortable, with a large, well-supplied bathroom. The fellow at the front desk was friendly and helpful. It feels like a very nice rural country inn. There isn't a lot else there, as there aren't 24-hour onsite staff or a fitness room or many other lobby amenities. I wouldn't hesitate to come back.
Reviewed on Oct 15, 2026
Castleton Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Castleton Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
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