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Wintergreen Resort Vacation Packages

A waterfall in a forest with autumn leaves.

Wintergreen Resort Flight + Hotel Packages

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

Days Inn by Wyndham Charlottesville/University Area

$751

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

Book a stay at this business-friendly motel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Downtown Mall and Monticello are located nearby.

Oakhurst Inn at the University

$915

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a sauna. Our guests praise the helpful staff in our reviews. Popular attractions Downtown Mall and Monticello are located nearby.

Little Mod Hotel at the University

$855

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

Stay at this 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.

The Doyle Hotel

$831

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Downtown Mall and Monticello are located nearby.

Shenandoah Wilderness Traveler

$825

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

Stay at this hotel in Gordonsville. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attraction Graves Fine Art Gallery is located nearby.

English Inn of Charlottesville

$862

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

Book a stay at this business-friendly hotel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Downtown Mall and Monticello are located nearby.

Afton Mountain Vineyards

$1,406

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

Stay at this cabin in Afton. Enjoy free WiFi, free parking, and bathrobes. Popular attractions Afton Mountain Vineyards and Veritas Vineyard and Winery are located nearby.

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

$853

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

Book a stay at this business-friendly hotel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Downtown Mall and Monticello are located nearby.

The Estate at Meander

$1,225

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

Stay at this B&B in Locust Dale. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Cedar Mountain and Rapidian Historic District are located nearby.

Round Hill Inn

$854

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop 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 James Madison Museum are located nearby.

Sonesta ES Suites Charlottesville University

$817

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

Book a stay at this business-friendly hotel in Charlottesville. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Downtown Mall and Monticello are located nearby.

Basecamp151

$1,114

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

Stay at this motel in Afton. Enjoy free WiFi, free parking, and an in-room coffeemaker. Popular attractions Wintergreen Resort and Flying Fox Vineyard are located nearby.

3-4 Night Vacations in Wintergreen Resort

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