Name: Luxury 5Bd 4Ba Sleeps 16+ Hot-tub/Dog Friendly
Address: Wintergreen Resort
Rating: 10

The Latest Chestnut Springs Vacation Packages

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

Mayhurst Inn

$945

per person

Nov 28 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

Providence (PVD) to Charlottesville (CHO)

9.2/10 Wonderful! (287 reviews)

A perfect spot with the delicious breakfast. Highly recommend staying here.

Reviewed on Sep 4, 2025

The Doyle Hotel

Starr Hill

$1,157

per person

Nov 28 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

Providence (PVD) to Charlottesville (CHO)

8.6/10 Excellent! (907 reviews)

The hotel was minimal staff and self check in/out on line. For an old baby boomer I prefer a fully human staffed facility. Not sure I would have booked the hotel. Luckily I found a human in the lobby who helped me. When we left, the valet was nowhere to be found. Had to walk to the car. Hotel manager was unhappy and told me he would refund the parking cost. Have yet to see that money

Reviewed on Oct 12, 2025

Little Mod Hotel at the University

Venable

$1,067

per person

Nov 28 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

Providence (PVD) to Charlottesville (CHO)

9.2/10 Wonderful! (255 reviews)

Mod Pod foot truck on-site was an unexpected treat!

Reviewed on Oct 7, 2025

Oakhurst Inn at the University

Jefferson Park Avenue

$1,054

per person

Nov 28 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

Providence (PVD) to Charlottesville (CHO)

9.2/10 Wonderful! (485 reviews)

Staff was so kind and the property was gorgeous. I travel for work and this was one of my favorite places I have stayed.

Reviewed on Sep 30, 2025

Kimpton The Forum Hotel by IHG

UVA

$1,158

per person

Nov 28 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

Providence (PVD) to Charlottesville (CHO)

9.6/10 Exceptional! (375 reviews)

Wonderful hotel and restaurants for a football weekend!

Reviewed on Sep 28, 2025

Chestnut Springs Hotel Deals

New Build! Log Cabin with Hot Tub in Wintergreen

Wintergreen Resort, VA

$1,144 nightly

$1,284 total

Oct 16 - Oct 17

Total with taxes and fees

10/10 Exceptional! (1 review)

"House was beautiful and spacious! Plenty of rooms and main lifting room was gorgeous. The bedrooms did not have any king size beds which might have been a problem but since there were so many rooms we just spread out more. We stayed in the late summer and there were countless beautiful hikes nearby ..."

Reviewed on Sep 27, 2025

4 BR cabin mins to trails & breweries pets welcome

Roseland

$552 nightly

$620 total

Nov 11 - Nov 12

Total with taxes and fees

9.6/10 Exceptional! (28 reviews)

"Nice place and very clean"

Reviewed on Aug 22, 2025

Luxury 5Bd 4Ba Sleeps 16+ Hot-tub/Dog Friendly

Wintergreen Resort

10/10 Exceptional! (14 reviews)

Good Stay

"Nice place with great amenities."

Reviewed on Jul 4, 2025

Get rates

See all 1,223 properties in Chestnut Springs

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.