Search Deals onWardsboro Vacation Packages
Wardsboro Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast
Price was $1,078, price is now $868 per person
$868
per person
Dec 25 - Jan 2
found 15 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.
Very unique house with lovely furnishings. Owners were very helpful and breakfast was delicious.
Reviewed on Oct 9, 2026
Vikings Villages Resort
Save 100% on your flight
Price was $1,725, price is now $1,204 per person
$1,204
per person
Dec 25 - Jan 2
found 15 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Sweet Pond State Park and Shattuck Brook Wildlife Management Area are located nearby.
Love our stay in Vikings. Staff was amazing and very attentive and helpful. The cabins were beautiful, clean and had everything we needed. Very recommended. Hope to go back in the future.
Reviewed on Oct 13, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Price was $1,946, price is now $1,369 per person
$1,369
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) 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 Mount Ascutney and Mt Ascutney State Park are located nearby.
Ij kii it
Reviewed on Oct 16, 2026
Mountain Green Resort
Save 100% on your flight
Price was $5,037, price is now $3,606 per person
$3,606
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) 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 Suites at Killington Center
Save 100% on your flight
Price was $4,475, price is now $3,220 per person
$3,220
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) 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.
Latchis Hotel
Price was $1,119, price is now $869 per person
$869
per person
Dec 25 - Jan 2
found 15 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
The Landgrove
Price was $1,643, price is now $1,285 per person
$1,285
per person
Dec 26 - Jan 2
found 6 hours ago
Roundtrip flight included
Orlando (MCO) 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.
1846 Inn and Tavern
Price was $1,464, price is now $1,162 per person
$1,162
per person
Dec 26 - Jan 2
found 6 hours ago
Roundtrip flight included
Orlando (MCO) 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.
The Inn also has an adjacent nice food tavern and music this weekend. Friendly host - embodied the helpful spirit of old inns. Helped with allowing a late dinner due to late arrival. Adjusted the heat for us and allowed us to set a bit extra in their library.
Very welcoming. A ++ for hospitality and making us welcome!
Reviewed on Oct 12, 2026
Wardsboro Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Wardsboro Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
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