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Discover 1,182 Chestnut Springs hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

The Crossroads Inn
Set amidst rolling hills, this charming hotel offers a serene escape amidst lush gardens.

The Crossroads Inn

5.0 star property
10.0 out of 10, Exceptional, (31)
"Wonderful stay! "
The Crossroads Inn
Modern Nellysford Getaway on 40 Private Acres!
House (3 Bedrooms) | Interior

Modern Nellysford Getaway on 40 Private Acres!

3.0 star property
The price is ￥40,700
￥86,588 total
includes taxes & fees
Aug 4 - Aug 5
Modern Nellysford Getaway on 40 Private Acres!
Basecamp151
Relax on the covered deck with comfortable sofas and tables, surrounded by trees and a serene atmosphere.

Basecamp151

3.0 star property
9.4 out of 10, Exceptional, (75)
"Thought it was going to be more of a hotel and then realizing it was like a full apartment was quite nice"
Basecamp151
Afton Mountain Inn
Enjoy a cozy evening by the outdoor fireplace, surrounded by lush greenery and shaded by two umbrellas.

Afton Mountain Inn

3.0 star property
9.8 out of 10, Exceptional, (63)
"Great place!"
The price is ￥20,953
￥31,060 total
includes taxes & fees
Aug 26 - Aug 27
Afton Mountain Inn
The Farmhouse at Veritas
Stately two-story building with a central entrance and manicured lawn.

The Farmhouse at Veritas

4.0 star property
9.8 out of 10, Exceptional, (32)
"Nice location a staff. Dining in the vineyard was excellent."
The price is ￥48,991
￥55,016 total
includes taxes & fees
Aug 5 - Aug 6
The Farmhouse at Veritas
Village Inn
Covered parking area with a bench and views of the surrounding green landscape.

Village Inn

2.0 star property
9.0 out of 10, Wonderful, (197)
"Itvwas a good place. It was just what we wre looking for. We were traveling thru the area and need a place to crash for the night"
The price is ￥14,739
￥16,552 total
includes taxes & fees
Aug 5 - Aug 6
Village Inn
Stoney Creek Cottage Off The VA 151 Wine Trail
Relax by the pool surrounded by lounge chairs and umbrellas, with a hot tub nearby.

Stoney Creek Cottage Off The VA 151 Wine Trail

2.0 star property
The price is ￥31,372
￥104,673 total
includes taxes & fees
Aug 6 - Aug 7
Stoney Creek Cottage Off The VA 151 Wine Trail
Afton Mountain Vineyards
Relax in a spacious lounge area with sofas, chairs, and a small table, offering scenic views of a vineyard and distant hills.

Afton Mountain Vineyards

2.5 star property
The price is ￥50,875
￥57,133 total
includes taxes & fees
Aug 3 - Aug 4
Afton Mountain Vineyards
Grey Pine Lodge
Guests can dine al fresco at the lodge's outdoor tables, surrounded by nature.

Grey Pine Lodge

2.0 star property
9.4 out of 10, Exceptional, (100)
"We had a great stay! Clean & cozy, we would definitely recommend staying here to others and would stay here again!"
The price is ￥17,652
￥22,330 total
includes taxes & fees
Aug 3 - Aug 4
Grey Pine Lodge
Waynesboro Home Near Wintergreen Charlottesville
Enjoy cooking in this well-lit kitchen with a refrigerator, dishwasher, sink, and ample countertop space.

Waynesboro Home Near Wintergreen Charlottesville

2.0 star property
The price is ￥23,742
￥85,442 total
includes taxes & fees
Aug 6 - Aug 7
Waynesboro Home Near Wintergreen Charlottesville
Piedmont Grove
Suite, Private Bathroom (Suite 3) | Exterior

Piedmont Grove

2.0 star property
9.4 out of 10, Exceptional, (26)
"Lovely place"
The price is ￥36,027
￥40,459 total
includes taxes & fees
Aug 3 - Aug 4
Piedmont Grove
Quality Inn Waynesboro - Skyline Drive
Two single beds with matching headboards and footboards, a desk, chair, and telephone.

Quality Inn Waynesboro - Skyline Drive

2.5 star property
7.0 out of 10, Good, (781)
"Was good place for what I needed "
The price is ￥9,798
￥10,905 total
includes taxes & fees
Aug 3 - Aug 4
Quality Inn Waynesboro - Skyline Drive
Econo Lodge Waynesboro - Skyline Drive
Enjoy meals in this functional kitchen and dining area, featuring a central island, pendant lights, and a long dining table.

Econo Lodge Waynesboro - Skyline Drive

2.0 star property
7.2 out of 10, Good, (88)
"Room was nice! Breakfast buffet was pretty good."
The price is ￥7,848
￥8,736 total
includes taxes & fees
Aug 31 - Sep 1
Econo Lodge Waynesboro - Skyline Drive
Iris Inn and Cabins
Family Cottage | 1 bedroom, blackout drapes, soundproofing, free WiFi

Iris Inn and Cabins

4.0 star property
10.0 out of 10, Exceptional, (2)
"Every thing , extraordinary place ."
The price is ￥42,152
￥46,915 total
includes taxes & fees
Aug 5 - Aug 6
Iris Inn and Cabins
Royal Inn Motel
Two single beds with matching headboards, a desk, and a window with curtains.

Royal Inn Motel

2.0 star property
6.2 out of 10, (70)
"The place was great for obe night stay "
The price is ￥11,788
￥13,120 total
includes taxes & fees
Aug 2 - Aug 3
Royal Inn Motel
Comfort Inn
Classic hotel with a central entrance and beautifully maintained grounds.

Comfort Inn

2.5 star property
8.4 out of 10, Very Good, (930)
"Nice clean hotel, friendly staff."
The price is ￥12,814
￥14,262 total
includes taxes & fees
Aug 31 - Sep 1
Comfort Inn
Residence Inn Marriott Waynesboro
Relax by the fire pit in our outdoor patio area, surrounded by a pergola and adjacent to a pool.

Residence Inn Marriott Waynesboro

3.0 star property
9.2 out of 10, Wonderful, (433)
"I was impressed and loved the stay. Sometimes a hotel thats dog friendly have a smell. This place very clean no smell. I loved my stay here will recommend "
The price is ￥22,912
￥25,501 total
includes taxes & fees
Aug 24 - Aug 25
Residence Inn Marriott Waynesboro
Holiday Inn Express And Suites Waynesboro East by IHG
Experience the grand entrance of this hotel, featuring a striking overhang and stone pillars.

Holiday Inn Express And Suites Waynesboro East by IHG

2.5 star property
9.2 out of 10, Wonderful, (385)
"Great place to stay"
The price is ￥17,034
￥18,959 total
includes taxes & fees
Aug 21 - Aug 22
Holiday Inn Express And Suites Waynesboro East by IHG
Days Inn by Wyndham Waynesboro
Relax in a spacious room with a large bed, two nightstands, and a stunning panoramic painting above.

Days Inn by Wyndham Waynesboro

2.0 star property
7.2 out of 10, Good, (1001)
"Check-in was fast and easy."
The price is ￥8,712
￥9,695 total
includes taxes & fees
Aug 17 - Aug 18
Days Inn by Wyndham Waynesboro
Super 8 by Wyndham Waynesboro
Enjoy a comfortable stay with two single beds, a desk, and a flat-screen TV.

Super 8 by Wyndham Waynesboro

2.0 star property
7.6 out of 10, Good, (898)
"Very convenient and plenty of restaurants very close by! Nice front desk help!"
The price is ￥9,866
￥10,982 total
includes taxes & fees
Aug 31 - Sep 1
Super 8 by Wyndham Waynesboro
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.
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Where to stay in Chestnut Springs

Find the best Chestnut Springs areas and neighborhoods for the activities you enjoy most.
Laurel Ridge map

Laurel Ridge

When in Laurel Ridge, you can plan a visit to Wintergreen Resort and Raven's Roost Overlook, some noteworthy sights in the nearby area.

Top Chestnut Springs Hotel Reviews

The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

10/10 Excellent
"Great bed and convenient location "
Joseph 3-night trip
Posted 2 days ago
The Blackburn Inn and Conference Center

Frequently asked questions

What's it like in Chestnut Springs?

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

What's a favorite place to stay in Chestnut Springs?

For your stay in Chestnut Springs, 4 BR cabin mins to trails & breweries pets welcome is one of the top choices based on our traveler data.

How many hotels will I find in Chestnut Springs?

Expedia has 71 hotels and other accommodations in Chestnut Springs to choose from, making this an ideal home base for exploring the greater Roseland 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 cancelled prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within 24 hours of your booking. Enter dates in and click on "Search", then you can use the "fully refundable" filter to get top deals in Chestnut Springs.

Where can I learn more about changing or cancelling my trip to Chestnut Springs?

To access more information about rescheduling or cancelling your trip to Chestnut Springs, head over to our customer service page.

What can I see and do in this Roseland neighborhood?

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