Search Deals onWardsboro Vacation Packages
Wardsboro Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast
Price was $852, price is now $764 per person
$764
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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 Mills Riverside Park and Waters Memorial Library are located nearby.
Holy and Kyle were awesome! Such wonderful breakfasts each day we were there, delicious! So close to everything we wanted to see. We look forward to coming back for our next Vermont getaway!
Reviewed on Jun 19, 2026
The Shire Woodstock
Price was $1,782, price is now $1,451 per person
$1,451
per person
Aug 20 - Aug 24
found 20 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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 Quechee Gorge Bridge and Billings Park and Trail are located nearby.
Very nice property. Would be great to have coffee in the rooms. Also very limited hot water. Ran out a few times even after a quick shower.
Reviewed on Jul 12, 2026
Greenbrier Inn
Price was $954, price is now $835 per person
$835
per person
Aug 20 - Aug 24
found 20 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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 Fire Tower are located nearby.
The hotel was very nice, quaint and clean. It is in a great location just prior to the entry of the access road. Large room. Small hotel with only about 20 rooms. Breakfast included. I would recommend a stay.
Reviewed on Jul 16, 2026
The Mountain Inn at Killington
Price was $922, price is now $835 per person
$835
per person
Aug 20 - Aug 24
found 20 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Good location. Small pool and no chairs around pool
Reviewed on Jul 16, 2026
Jackson Gore Village, A Vail Resorts Property
Price was $978, price is now $888 per person
$888
per person
Aug 20 - Aug 24
found 20 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Timber Ripper Mountain Coaster are located nearby.
Great family friendly location!
Reviewed on Jul 11, 2026
Bentley House Bed and Breakfast
Price was $898, price is now $820 per person
$820
per person
Aug 20 - Aug 24
found 20 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.
Great place, friendly owners. I will be coming back.
Reviewed on Jul 11, 2026
Winterplace at Okemo, A Vail Resorts Property
Price was $1,149, price is now $1,051 per person
$1,051
per person
Aug 20 - Aug 24
found 20 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty
Reviewed on Dec 1, 2025
Solitude Village at Okemo by Vail Resorts
Price was $1,050, price is now $967 per person
$967
per person
Aug 20 - Aug 24
found 20 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and 2 hot tubs. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Wardsboro Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
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