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Wintergreen Vacation Packages

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Wintergreen Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Holiday Inn Express & Suites Charlottesville - Ruckersville, an IHG Hotel

per person

Jan 25 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charlottesville (CHO)

Book a stay at this business-friendly hotel in Ruckersville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Preddy Creek Trail Park and Montefalco Vineyard are located nearby.

Postcard Cabins Shenandoah

per person

Jan 25 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charlottesville (CHO)

Stay at this cabin in Stanardsville. Enjoy free parking, patios, and climate control. Popular attractions Green Hills Golf Course and Greene County Library are located nearby.

Lafayette Inn

per person

Jan 25 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charlottesville (CHO)

Stay at this 3-star B&B in Stanardsville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Greene County Library and Greene County Park are located nearby.

Round Hill Inn

per person

Jan 25 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charlottesville (CHO)

Book a stay at this business-friendly hotel in Orange. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions The Arts Center in Orange and St. Thomas Episcopal Church are located nearby.

Bliss Point Farm and B&B

per person

Jan 25 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charlottesville (CHO)

Stay at this 3-star B&B in Dyke. Enjoy free WiFi, free parking, and an attached winery. Popular attractions Autumn Hill Winery and Kilaurwen Winery are located nearby.

Kimpton The Forum Hotel, an IHG Hotel

per person

Feb 8 - Feb 10

found 22 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

Stay at this 4-star business-friendly hotel in Charlottesville. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Monticello and Klockner Stadium are located nearby.

Little Mod Hotel at the University

per person

Feb 8 - Feb 10

found 22 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

Stay at this 3-star hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a picnic area. Our guests praise the helpful staff in our reviews. Popular attractions Downtown Mall and Monticello are located nearby.

Rooted Land Company

per person

Jan 25 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charlottesville (CHO)

Stay at this farm stay in Madison. Enjoy free WiFi, free parking, and a garden. Popular attractions Early Mountain Vineyards and Sweely Estate Winery are located nearby.

Wintergreen Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.