Hotels in Chestnut Springs

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Property class

Top 10 Hotels in Chestnut Springs

Hike, Bike & Explore: Wintergreen Resort Condo

3.0 star property
9.0 out of 10, Wonderful, (4)
"Close to everything we needed for a nice ski getaway. The property was clean and as described. We would love this place again with friends "
The price is S$279
includes taxes & fees
14 Jun - 15 Jun
Hike, Bike & Explore: Wintergreen Resort Condo

Blackwood Chalet

2.0 star property
10.0 out of 10, Exceptional, (2)
"Everything was amazing. "
The price is S$498
includes taxes & fees
16 Jun - 17 Jun
Blackwood Chalet

Piedmont Grove

2.0 star property
9.2 out of 10, Wonderful, (25)
"Our stay at Piedmont Grove was awesome. We enjoyed the breweries and the wineries. It’s a quiet stay. We plan to go back so we can hike. I wish the cabins had microwaves. Other than that, our stay was perfect. "
The price is S$343
includes taxes & fees
22 Jun - 23 Jun
Piedmont Grove

Stoney Creek Cottage Off The VA 151 Wine Trail

2.0 star property
The price is S$863
includes taxes & fees
16 Jun - 17 Jun
Stoney Creek Cottage Off The VA 151 Wine Trail

Love Ridge Mountain Lodging

3.0 star property
10.0 out of 10, Exceptional, (11)
"Amazing stay I had, very peaceful and very quiet. "
The price is S$336
includes taxes & fees
16 Jun - 17 Jun
Love Ridge Mountain Lodging

Basecamp151

3.0 star property
9.4 out of 10, Exceptional, (71)
"conveniently located between Wintergreen Spa and a multitude of wineries and breweries. "
The price is S$182
includes taxes & fees
15 Jun - 16 Jun
Basecamp151

Afton Mountain Inn

3.0 star property
9.8 out of 10, Exceptional, (62)
"Enjoyed our stay at your beautiful. Only negative, we couldn’t get the fireplace to work. "
The price is S$279
includes taxes & fees
15 Jun - 16 Jun
Afton Mountain Inn

Afton Mountain Vineyards

2.5 star property
The price is S$485
includes taxes & fees
18 Jun - 19 Jun
Afton Mountain Vineyards

The Farmhouse at Veritas

4.0 star property
9.8 out of 10, Exceptional, (31)
"Nice location a staff. Dining in the vineyard was excellent."
The price is S$467
includes taxes & fees
14 Jul - 15 Jul
The Farmhouse at Veritas

Grey Pine Lodge

2.0 star property
9.6 out of 10, Exceptional, (94)
"Property is newly updated with great location. Would definitely recommend."
The price is S$170
includes taxes & fees
15 Jun - 16 Jun
Grey Pine Lodge

Holiday Inn Express And Suites Waynesboro East by IHG

2.5 star property
9.2 out of 10, Wonderful, (348)
"Nice location, lots of restaurants nearby, friendly staff. "
The price is S$162
includes taxes & fees
8 Jul - 9 Jul
Holiday Inn Express And Suites Waynesboro East by IHG

Days Inn by Wyndham Waynesboro

2.0 star property
7.2 out of 10, Good, (1003)
"The owners have upgraded the property, though it is still a roadside motel. We appreciated the breakfast, friendly staff, and availability of a wheelchair-accessible room. All in all, we had a nice stay."
The price is S$83
includes taxes & fees
6 Jul - 7 Jul
Days Inn by Wyndham Waynesboro

Comfort Inn

2.5 star property
8.4 out of 10, Very good, (904)
"Convenient location "
The price is S$114
includes taxes & fees
29 Jun - 30 Jun
Comfort Inn

Residence Inn Marriott Waynesboro

3.0 star property
9.2 out of 10, Wonderful, (427)
"Beautiful place to stay , the room was way better than we expected "
The price is S$192
includes taxes & fees
7 Jul - 8 Jul
Residence Inn Marriott Waynesboro

Best Western Plus Waynesboro Inn & Suites Conference Center

2.5 star property
8.6 out of 10, Excellent, (1003)
"Nice, clean hotel. Lots of good food options within walking distance. I would stay here again for sure. "
The price is S$150
includes taxes & fees
7 Jul - 8 Jul
Best Western Plus Waynesboro Inn & Suites Conference Center

Super 8 by Wyndham Waynesboro

2.0 star property
7.6 out of 10, Good, (885)
"Convenient to highway, comfy beds, wonderful staff"
The price is S$89
includes taxes & fees
22 Jun - 23 Jun
Super 8 by Wyndham Waynesboro

Econo Lodge Waynesboro - Skyline Drive

2.0 star property
7.2 out of 10, Good, (76)
"Room was nice! Breakfast buffet was pretty good."
The price is S$74
includes taxes & fees
14 Jul - 15 Jul
Econo Lodge Waynesboro - Skyline Drive

Quality Inn Waynesboro - Skyline Drive

2.5 star property
7.0 out of 10, Good, (775)
"Was good place for what I needed "
The price is S$96
includes taxes & fees
13 Jul - 14 Jul
Quality Inn Waynesboro - Skyline Drive

Royal Inn Motel

2.0 star property
6.2 out of 10, (67)
"Not the best place to stay! Doesn’t allow pets or service animals without "
The price is S$111
includes taxes & fees
14 Jun - 15 Jun
Royal Inn Motel

Skyline Motel By OYO Waynesboro US 250

2.0 star property
6.0 out of 10, (8)
"Nice and quiet stay. Convenient location "
The price is S$74
includes taxes & fees
22 Jun - 23 Jun
Skyline Motel By OYO Waynesboro US 250
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.
Save an average of 15% on thousands of hotels when you're signed in

Where to stay in Chestnut Springs

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

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.

Frequently asked questions

What's it like in Chestnut Springs?

Travellers are sure to enjoy a stay in Roseland'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 69 hotels and other accommodation options 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 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 Roseland neighbourhood?

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