What's it like in Chestnut Springs?

Travellers are sure to enjoy a stay in Wintergreen's Chestnut Springs neighbourhood. Consider a visit to Wintergreen Resort as part of your Chestnut Springs travel plans.

How many hotels are there in Chestnut Springs?

Expedia has 74 hotels and other accommodation options in Chestnut Springs to choose from, making this an ideal home base for exploring the greater Wintergreen area.

If I need to cancel my hotel reservation in Chestnut Springs, will I receive a refund?

Yes! The majority of hotel bookings are fully refundable if you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, you might be able to still cancel and receive a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to view the top deals on offer in Chestnut Springs.

What can I see and do in this Wintergreen neighbourhood?

Wintergreen Resort is an attraction you might want to check out while you're in Chestnut Springs. While you're out sightseeing in Wintergreen, make sure that you visit other sights such as Raven's Roost Overlook or Humpback Rocks.

The Best Hotels in Chestnut Springs, Roseland - 2026 Updated Prices

A waterfall in a forest with autumn leaves.

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Our top choices for Chestnut Springs hotels

A multi-story hotel with a covered entrance, parking lot, and a clear sky.

1. Holiday Inn Express & Suites Staunton by IHG

23.4 km from Chestnut Springs

John

₹12,023 total

includes taxes & fees

27 Sept - 28 Sept

A Best Western Plus hotel with a covered entrance, multiple floors, and a landscaped area with trees.

2. Best Western Plus Waynesboro Inn & Suites Conference Center

14.6 km from Chestnut Springs

Danforth

₹12,274 total

includes taxes & fees

29 Sept - 30 Sept

A hotel room with two single beds and a larger bed, all with white bedding.

3. Days Inn by Wyndham Staunton

20.1 km from Chestnut Springs

Toni

₹6,835 total

includes taxes & fees

27 Sept - 28 Sept

A modern living room with a large sectional sofa, a fireplace, and a view of the mountains.

4. Firefly on The Ridge

0.7 km from Chestnut Springs

₹32,743 total

includes taxes & fees

27 Sept - 28 Sept

A swimming pool area with four lounge chairs and large windows offering a view of trees.

5. Hampton Inn Waynesboro/Stuarts Draft

17.5 km from Chestnut Springs

Sade

₹13,020 total

includes taxes & fees

4 Oct - 5 Oct

A hotel room with two beds, a desk with a chair, a lamp, and a large landscape painting on the wall.

6. Super 8 by Wyndham Waynesboro

14.7 km from Chestnut Springs

Brian

₹7,417 total

includes taxes & fees

27 Sept - 28 Sept

A modern cafe with a self-serve coffee station, refrigerated display case, and a variety of food items on the counter.

7. Quality Inn Waynesboro - Skyline Drive

16 km from Chestnut Springs

Ignacio

₹7,531 total

includes taxes & fees

27 Sept - 28 Sept

A modern hotel reception area with a curved wooden counter, a digital screen, and a view of the outdoors through large windows.

8. Tru By Hilton Staunton

23.8 km from Chestnut Springs

George

₹11,764 total

includes taxes & fees

30 Sept - 1 Oct

A hotel room with two beds, a desk, a chair, and a TV.

9. Comfort Inn & Suites Staunton

23.6 km from Chestnut Springs

Shawn

₹9,351 total

includes taxes & fees

25 Oct - 26 Oct

A reception desk with a 'Sleep Inn' sign, a 'Welcome!' sign, a 'Manager On Duty' sign, a 'Check Out' sign, and a 'Check In' sign.

10. Sleep Inn Staunton

22.9 km from Chestnut Springs

Marilyn

₹10,779 total

includes taxes & fees

25 Oct - 26 Oct

A modern hotel with a flat roof, large windows, and a covered entrance area with stone pillars.

11. Holiday Inn Express & Suites Waynesboro East by IHG

14.4 km from Chestnut Springs

John

₹11,384 total

includes taxes & fees

28 Sept - 29 Sept

A hotel with a modern design, featuring a prominent 'spark by Hilton' sign, multiple flagpoles, and a well-maintained landscaped garden.

12. Spark by Hilton Waynesboro

14.5 km from Chestnut Springs

John

₹9,510 total

includes taxes & fees

30 Sept - 1 Oct

A hotel room with a large bed, two bedside tables with lamps, and a mountain landscape painting above the bed.

13. Days Inn by Wyndham Waynesboro

14.5 km from Chestnut Springs

Preston

₹6,150 total

includes taxes & fees

27 Sept - 28 Sept

A modern living room with a gray sectional sofa, a small coffee table, and a flat-screen TV mounted on the wall. Large windows provide a view of the cityscape.

14. Mountain View Vista

0.8 km from Chestnut Springs

₹24,584 total

includes taxes & fees

27 Sept - 28 Sept

A two-story building with a porch and a yellow door.

15. Basecamp151

9.5 km from Chestnut Springs

Matthew

₹13,816 total

includes taxes & fees

27 Sept - 28 Sept

A swimming pool with four lounge chairs and a view of trees through large windows.

16. avid hotel Staunton by IHG

23.2 km from Chestnut Springs

Sumanjit

₹11,597 total

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen with dark wood cabinets, a marble countertop, and a mosaic backsplash.

17. Quality Inn Verona - Staunton North

29.7 km from Chestnut Springs

Pramod

₹7,531 total

includes taxes & fees

27 Sept - 28 Sept

A modern lobby with a stone accent wall, a flat-screen TV, and comfortable seating including a yellow armchair and a grey sofa.

18. Clarion Pointe Staunton East

24.1 km from Chestnut Springs

Andrea

₹8,880 total

includes taxes & fees

30 Sept - 1 Oct

A covered walkway leading to a registration lobby with a sign, surrounded by landscaped areas with various shrubs and trees.

19. Motel 6 Staunton, VA

26.5 km from Chestnut Springs

Diana

₹6,701 total

includes taxes & fees

4 Oct - 5 Oct

A clean, modern reception area with a wooden reception desk, a refrigerated display case, and shelves stocked with snacks.

20. Fairfield Inn & Suites by Marriott Staunton

23.7 km from Chestnut Springs

Willim

₹14,676 total

includes taxes & fees

30 Sept - 1 Oct

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Where to stay in Chestnut Springs

Find the best Chestnut Springs areas for the activities you enjoy most.

Laurel Ridge

A mountainous landscape with autumn foliage and a layer of fog.

Laurel Ridge

Laurel Ridge might not have many top sights, but Wintergreen Resort and Raven's Roost Overlook are two attractions nearby that you can check out.

See properties

Top Chestnut Springs Hotel Reviews

Spark by Hilton Waynesboro

8/10 Good

"The property was recently refurbished and done well. My room was clean though it could have been scrubbed a bit better in the bathroom. The AC unit worked but I believe the unit should have been replaced. All in all a good stay."