A lush green landscape with rolling hills and a distant view of a valley.

Search Condos Rentals in Grottoes from CA $356

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Grottoes condo rentals

Property grounds

1. New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (159 reviews)
"We had a calm and relaxing mountain get a way. The property was charming and perfect for us, clean and organized. The location was great. We loved to go for walks nearby and visit the gnomes and fairies in the trees. We would love to make it an annual trip and would definitely stay here again."
United States
Michelle
The price is CA $152
CA $343 total
includes taxes & fees
Sep 8 - Sep 9
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Exterior

2. 1 Bedroom | Free Daily Breakfast + Indoor Pool

1 Bedroom | Free Daily Breakfast + Indoor Pool
Hollymead
10.0 out of 10, Exceptional, (1 review)
"The room was very clean. The bed was comfortable. My only suggestion would be to have a couple more towels and washcloths in the room."
United States
Maura
The price is CA $178
CA $229 total
includes taxes & fees
Oct 5 - Oct 6
1 Bedroom | Free Daily Breakfast + Indoor Pool
Interior

3. Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Roseland
9.8 out of 10, Exceptional, (34 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
The price is CA $125
CA $292 total
includes taxes & fees
Sep 8 - Sep 9
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Dining

4. Updated! Cozy and clean two bedroom condo.

Updated! Cozy and clean two bedroom condo.
Wintergreen Resort
9.2 out of 10, Wonderful, (35 reviews)
"Everything was great! Very accommodating host and lovely place!"
United States
Jason S.
The price is CA $137
CA $350 total
includes taxes & fees
Sep 8 - Sep 9
Updated! Cozy and clean two bedroom condo.
Fireplace

5. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (60 reviews)
"Nice resort"
United States
Diana J.
The price is CA $65
CA $243 total
includes taxes & fees
Sep 9 - Sep 10
Where the Trail Ends
Property grounds

6. Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (48 reviews)
"Wonderful stay, wonderful place!! The view, the fireplace, well appointed, comfortable bed, comfortable furniture, very clean...will definitely stay again! Thank you!!"
United States
Art P.
The price is CA $192
CA $402 total
includes taxes & fees
Sep 8 - Sep 9
Panoramic Peak: Wintergreen Condo with Views
Exterior

7. Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Wintergreen Resort
10.0 out of 10, Exceptional, (122 reviews)
"Great home, very clean and well stocked."
United States
Rob H.
The price is CA $230
CA $451 total
includes taxes & fees
Sep 8 - Sep 9
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Exterior

8. Mountain Retreat in Wintergreen!

Mountain Retreat in Wintergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (25 reviews)
"Super clean and equipped with everything you need (just bring your own hangars). Very comfortable bed. "
United States
Pam M.
The price is CA $173
CA $397 total
includes taxes & fees
Sep 8 - Sep 9
Mountain Retreat in Wintergreen!
Outdoor dining

9. Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (128 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
The price is CA $161
CA $354 total
includes taxes & fees
Sep 8 - Sep 9
Escape to the Blue Ridge Mountains at Wine-tergreen!
Coffee/tea maker, fridge, microwave, oven

10. "Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining

"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
Wintergreen Resort
10.0 out of 10, Exceptional, (42 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
The price is CA $143
CA $428 total
includes taxes & fees
Sep 8 - Sep 9
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
Property grounds

11. Luxury Condo in the Sky! Finest in Wintergreen!

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (43 reviews)
"Views from the porch are beautiful!Essentials ar all there Well thought out for a rentalHope to be back for another anniversary"
United States
rodney f.
The price is CA $188
CA $437 total
includes taxes & fees
Sep 9 - Sep 10
Luxury Condo in the Sky! Finest in Wintergreen!
1 bedroom, in-room safe, iron/ironing board, WiFi (free)

12. Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.6 out of 10, Exceptional, (15 reviews)
"Relaxing, scenic, quiet during the week, clean, modern, great communication with the host."
United States
Darlene
The price is CA $192
CA $402 total
includes taxes & fees
Sep 8 - Sep 9
Mountain View Vista: Resort Condo w/ Views
Terrace/patio

13. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (36 reviews)
"Great place to stay for our family of 4 for a wedding weekend. Easy check-in and close to the Inn."
United States
Scott M.
The price is CA $158
CA $368 total
includes taxes & fees
Sep 8 - Sep 9
Wintergreen Condo -Steps to Ski and restaurants
Coffee/tea maker, fridge, microwave, oven

14. Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Wintergreen Resort
9.4 out of 10, Exceptional, (15 reviews)
"The condo was beautiful and clean and worked perfectly for our group."
United States
Eric W.
The price is CA $187
CA $454 total
includes taxes & fees
Sep 10 - Sep 11
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
1 bedroom, iron/ironing board, WiFi (free), bed sheets

15. First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (17 reviews)
"Had a great stay, location was perfect! Condo was very nice. "
United States
Alicia K.
The price is CA $144
CA $342 total
includes taxes & fees
Sep 9 - Sep 10
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Exterior

16. Pet-Friendly Retreat Walk to Slopes & Village!

Pet-Friendly Retreat Walk to Slopes & Village!
Wintergreen Resort
10.0 out of 10, Exceptional, (1 review)
"A wonderful place to stay comfortable beds. The place was nice and clean "
United States
Denise P.
The price is CA $154
CA $404 total
includes taxes & fees
Sep 9 - Sep 10
Pet-Friendly Retreat Walk to Slopes & Village!
Condo, Private Bathroom (Firefly on The Ridge) | Lounge

17. Firefly on The Ridge

Firefly on The Ridge
2.0 star property
Nellysford
The price is CA $249
CA $474 total
includes taxes & fees
Sep 8 - Sep 9
Firefly on The Ridge
Outdoor pool, a heated pool

18. 2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.

2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
Wintergreen Resort
10.0 out of 10, Exceptional, (4 reviews)
"This is a warm and inviting condo. We enjoyed our stay. The host provided excellent communication!"
United States
Shannon T.
The price is CA $166
CA $475 total
includes taxes & fees
Sep 8 - Sep 9
2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
Coffee/tea maker, fridge, microwave, oven

19. Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (39 reviews)
"We had an incredible stay this past week. The condo "
United States
Holly M.
The price is CA $225
CA $587 total
includes taxes & fees
Sep 13 - Sep 14
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Exterior

20. Highridge Court 30 with Wintergreen Advantage

Highridge Court 30 with Wintergreen Advantage
Chestnut Springs
10.0 out of 10, Exceptional, (1 review)
The price is CA $282
CA $493 total
includes taxes & fees
Sep 8 - Sep 9
Highridge Court 30 with Wintergreen Advantage
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Grottoes Hotel Reviews

Holiday Inn Charlottesville-Univ Area by IHG

Holiday Inn Charlottesville-Univ Area by IHG

10/10 Excellent
"Staff was amazing and so helpful which made my stay very comfortable and enjoyable"
Grace 1-night trip
Posted 2 hours ago
Holiday Inn Charlottesville-Univ Area by IHG

Find out more about Grottoes

Grottoes Condo Rentals information

Number of reviews
Accommodation
426 Condo Rentals
Lowest Price
CA $356
Highest Price
CA $474

Frequently asked questions

Why book your condo in Grottoes with Expedia?
Vacationing should be stress-free, so if you're looking for condos at a competitive price, Expedia can help. Keep costs down and check in to something small and cozy, or book a 5-star condo and really spoil your crew. Use our search filters to secure a property in Grottoes that meets your needs.
How can I find cheap condos in Grottoes?
A great way to score cheap condos in Grottoes is with Expedia's useful filter tool. Narrow down your search results by budget, star rating and amenities to land unbeatable prices in just a few keystrokes.
What is there to do in Grottoes near my condo?
Once you've unpacked and settled in, set out and discover the wonderful things Grottoes has for you to experience. Grand Caverns is a great attraction to add to your travel itinerary.

Explore a world of travel with Expedia