Hotels in Chestnut Springs

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Filter by

Guest rating
Guest rating
Property class

Top 10 Hotels in Chestnut Springs

The Crossroads Inn

4.5 star property
10.0 out of 10, Exceptional, (21)
"This was our second time here. It will definitely become an annual stay. Our favorite place to stay in Charlottesville and our favorite Virginia winery Pippin Hill. "
The price is S$283
includes taxes & fees
19 Feb - 20 Feb
The Crossroads Inn

Basecamp151

3.0 star property
9.4 out of 10, Exceptional, (63)
"Great location. Within 10 minutes from popular vineyards and breweries. "
The price is S$190
includes taxes & fees
12 Mar - 13 Mar
Basecamp151

Afton Mountain Inn

3.0 star property
9.8 out of 10, Exceptional, (57)
"Amazing stay! There are plenty of great amenities. "
The price is S$276
includes taxes & fees
12 Mar - 13 Mar
Afton Mountain Inn

The Farmhouse at Veritas

4.0 star property
9.8 out of 10, Exceptional, (29)
"An amazing experience, would definitely recommend."
The price is S$331
includes taxes & fees
24 Feb - 25 Feb
The Farmhouse at Veritas

Village Inn

2.0 star property
9.0 out of 10, Wonderful, (183)
"It’s clean and it’s warm, what else can I ask from a hotel? Nothing extra, but nice for a night"
The price is S$135
includes taxes & fees
19 Feb - 20 Feb
Village Inn

Stoney Creek Cottage Off The VA 151 Wine Trail

2.0 star property
The price is S$634
includes taxes & fees
19 Feb - 20 Feb
Stoney Creek Cottage Off The VA 151 Wine Trail

Afton Mountain Vineyards

2.0 star property
The price is S$362
includes taxes & fees
23 Feb - 24 Feb
Afton Mountain Vineyards

Grey Pine Lodge

2.0 star property
9.4 out of 10, Exceptional, (70)
"Stayed here while skiing at Wintergreen, an easy 30 minutes away. The rooms were comfortable, and we really enjoyed having an outdoor fire and smores in a lovely wooded ambiance after our ski days. I can imagine this would be a perfect place in summer/fall too if you’re traveling to the mountains. Will absolutely stay again. "
The price is S$151
includes taxes & fees
20 Feb - 21 Feb
Grey Pine Lodge

Red Hill Bed and Breakfast

3.0 star property
8.2 out of 10, Very good, (21)
"Wonderful stay! "
The price is S$451
includes taxes & fees
27 Feb - 28 Feb
Red Hill Bed and Breakfast

Piedmont Grove

2.0 star property
9.4 out of 10, Exceptional, (22)
"Very happy with our stay..."
The price is S$254
includes taxes & fees
5 Mar - 6 Mar
Piedmont Grove

Quality Inn Waynesboro - Skyline Drive

2.5 star property
7.0 out of 10, Good, (749)
"Great stay for a great price"
The price is S$89
includes taxes & fees
19 Feb - 20 Feb
Quality Inn Waynesboro - Skyline Drive

Econo Lodge Waynesboro - Skyline Drive

2.0 star property
7.6 out of 10, Good, (54)
"Wonderful staff who upgraded our reservation for a larger room very quickly."
The price is S$71
includes taxes & fees
11 Mar - 12 Mar
Econo Lodge Waynesboro - Skyline Drive

Blackwood Chalet

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is S$558
includes taxes & fees
19 Feb - 20 Feb
Blackwood Chalet

Wingate by Wyndham Waynesboro

2.5 star property
8.6 out of 10, Excellent, (777)
"Stayed here after snowboarding with my boys. We hit some tall beers at the Outback Steakhouse next door, then kept the party going at the 24-hour indoor pool. Feel like I've never been to a hotel where the pool is actually open, so it felt like something out of a dream. Truly beautiful night. Maybe bring your own pillow though. Coffee in the morning was good too."
The price is S$99
includes taxes & fees
24 Feb - 25 Feb
Wingate by Wyndham Waynesboro

Comfort Inn

2.5 star property
8.4 out of 10, Very good, (856)
"Room was cleanliness, many options for breakfast and staffs were gentle and friendly. I will be come back again"
The price is S$113
includes taxes & fees
19 Feb - 20 Feb
Comfort Inn

Residence Inn Marriott Waynesboro

3.0 star property
9.2 out of 10, Wonderful, (415)
"This was such a beautiful and clean hotel. My two year old had a blast in the pool. Super clean and the beds were so comfy. Room was clean and ALL the staff was so sweet. Rosa who was cleaning the rooms was absolutely sweet and helpful and so kind. Would stay again in a heartbeat. The breakfast was amazing as well. Highly recommend!"
The price is S$176
includes taxes & fees
17 Mar - 18 Mar
Residence Inn Marriott Waynesboro

Holiday Inn Express And Suites Waynesboro East by IHG

2.5 star property
9.2 out of 10, Wonderful, (267)
"Location is great, complimentary breakfast is really good and the heated pool is very nice. I can’t say enough good things about the facility itself, very nice. The only downside I can say is that the floors/ceiling are fairly “thin” and not noise proof. Between someone above us apparently running laps and them having a dog also it was not a peaceful stay at all. I did make the front desk person aware and they assured me they would address this with those above us. That worked for the majority...
The price is S$165
includes taxes & fees
24 Feb - 25 Feb
Holiday Inn Express And Suites Waynesboro East by IHG

Days Inn by Wyndham Waynesboro

2.0 star property
7.2 out of 10, Good, (1005)
"Just the icy conditions in parking lot"
The price is S$75
includes taxes & fees
23 Feb - 24 Feb
Days Inn by Wyndham Waynesboro

Super 8 by Wyndham Waynesboro

2.0 star property
7.6 out of 10, Good, (849)
"It’s one of the better Super 8’s that I’ve stayed in. The bed was comfy, pretty decent pillows, good size TV, and the staff was friendly and helpful. "
The price is S$77
includes taxes & fees
23 Feb - 24 Feb
Super 8 by Wyndham Waynesboro

Best Western Plus Waynesboro Inn & Suites Conference Center

2.5 star property
8.6 out of 10, Excellent, (1003)
"The ceiling need work and the bathroom shower wasn’t greats "
The price is S$147
includes taxes & fees
23 Feb - 24 Feb
Best Western Plus Waynesboro Inn & Suites Conference Center
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.
Don't see what you're looking for?
See all available properties in Chestnut Springs
Save an average of 15% on thousands of hotels when you're signed in

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.