Photo by Rebecca Brent

Search Cottages in Wintergreen

Start date: Check-in selected.
To Date
End date: Check-out
    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Cottages in Wintergreen

Unique Cypress cottage, close to Charlottesville with mountain views.
Exterior

Unique Cypress cottage, close to Charlottesville with mountain views.

10.0 out of 10, Exceptional, (39)
"The cabin was beautiful and a perfect place for us to relax. The location was phenomenal and closely located to Shenandoah and many amazing towns to explore."
The price is AED 588
AED 1,092 total
includes taxes & fees
27 Oct - 28 Oct
Unique Cypress cottage, close to Charlottesville with mountain views.
Isolated cottage with good view close to many winery and Brewers.
Exterior

Isolated cottage with good view close to many winery and Brewers.

9.0 out of 10, Wonderful, (22)
"It was great thank you"
The price is AED 661
AED 961 total
includes taxes & fees
1 Oct - 2 Oct
Isolated cottage with good view close to many winery and Brewers.
Mechum Hill Cottage: Central to Crozet & Cville
Outdoor dining

Mechum Hill Cottage: Central to Crozet & Cville

9.6 out of 10, Exceptional, (16)
"Very quiet and peaceful. Large, secluded property. Good base from which to explore area wineries, local beer, food, and hike im the Shenandoah National Park."
The price is AED 474
AED 1,029 total
includes taxes & fees
1 Oct - 2 Oct
Mechum Hill Cottage: Central to Crozet & Cville
Bluebird Cottage: Near 151 + Appalachian Trail
Terrace/patio

Bluebird Cottage: Near 151 + Appalachian Trail

2.0 star property
8.0 out of 10, Very Good, (8)
"I contacted the owners to see if my family and I could check in earlier and they were about to accommodate for us. The home was clean, spacious, and had everything we needed for our stay."
The price is AED 422
AED 1,072 total
includes taxes & fees
29 Oct - 30 Oct
Bluebird Cottage: Near 151 + Appalachian Trail
Birds and Bees Cottage
Terrace/patio

Birds and Bees Cottage

10.0 out of 10, Exceptional, (44)
"Loved staying at the Birds and Bees Cottage. It was so peaceful waking up each day, sitting on the porch and enjoying the views of the farm. This cottage was the perfect spot to unwind after visiting some local wineries. It was quiet and very easy to relax on the porch with a good book in the evening. Hope to return in the fall. "
Birds and Bees Cottage
The Cottage @ Afton Mountain- Close to Wineries!
Outdoor dining

The Cottage @ Afton Mountain- Close to Wineries!

10.0 out of 10, Exceptional, (14)
"Great place"
The price is AED 592
AED 1,238 total
includes taxes & fees
1 Oct - 2 Oct
The Cottage @ Afton Mountain- Close to Wineries!
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.
Exterior

Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.

9.8 out of 10, Exceptional, (141)
"This was our fourth visit and we love the house, the property and the area. We are already booked for next year "
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Terrace/patio

Pine Cottage: Hot Tub, 2 mins to Bold Rock!

10.0 out of 10, Exceptional, (21)
"The house was super cute and accommodated our whole group. It was close to a good amount of breweries and wineries. "
The price is AED 694
AED 1,708 total
includes taxes & fees
1 Oct - 2 Oct
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.
Property grounds

Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.

10.0 out of 10, Exceptional, (20)
"We had a great time starting here on spring break."
Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.
Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors
Exterior

Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors

10.0 out of 10, Exceptional, (48)
"Very peaceful and comfortable place to stay."
Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors
Cozy Getaway | Near Veritas & Blue Ridge Tunnel | Modern Comforts
Exterior

Cozy Getaway | Near Veritas & Blue Ridge Tunnel | Modern Comforts

10.0 out of 10, Exceptional, (4)
" Cleanest rental we've ever stayed in and the kitchen was very well stocked."
Cozy Getaway | Near Veritas & Blue Ridge Tunnel | Modern Comforts
Rosé All Day: Wine Country Getaway! Walk to Dining
Exterior

Rosé All Day: Wine Country Getaway! Walk to Dining

2.0 star property
10.0 out of 10, Exceptional, (15)
"Excellent location close to a variety of restaurants and not far from many wineries along the Monticello Wine Trail. The house is the perfect size with lots of thoughtful touches. We will definitely be back!"
Rosé All Day: Wine Country Getaway! Walk to Dining
Cozy Cottage with beautiful Mountain View’s - close to wineries
Terrace/patio

Cozy Cottage with beautiful Mountain View’s - close to wineries

10.0 out of 10, Exceptional, (16)
"The cottage was extremely well equipped, clean and comfortable. We will definitely stay here again "
Cozy Cottage with beautiful Mountain View’s - close to wineries
Charming Mountain Escape | Hot Tub & Scenic Views
Outdoor spa tub

Charming Mountain Escape | Hot Tub & Scenic Views

10.0 out of 10, Exceptional, (3)
"We had a wonderful stay! The house is conveniently located near many popular wineries. We absolutely loved the house amenities, including the hot tub and fire pits. Beds were comfortable and kitchen was well stocked with essentials."
Charming Mountain Escape | Hot Tub & Scenic Views
Serene Roseland Retreat Near Wintergreen Resort!
House (3 Bedrooms) | Interior

Serene Roseland Retreat Near Wintergreen Resort!

3.0 star property
Serene Roseland Retreat Near Wintergreen Resort!
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
Exterior

Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

10.0 out of 10, Exceptional, (61)
"We all loved the cottage in Alhambra. The setting was amazing and peaceful tucked in among the mountains and overlooking the creek. The inside was lovely and our hosts had the place outfitted to fill all of our needs. This was one of our favorite stays!"
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
Brand new serene luxury cottage just off the Brew Ridge Trail
Exterior

Brand new serene luxury cottage just off the Brew Ridge Trail

10.0 out of 10, Exceptional, (1)
"Cute, tiny house with everything we could have needed. Perfect location for a weekend touring Nelson County sites. We will be back."
The price is AED 275
AED 577 total
includes taxes & fees
1 Oct - 2 Oct
Brand new serene luxury cottage just off the Brew Ridge Trail
Cozy Cottage at Frogmorton
Property grounds

Cozy Cottage at Frogmorton

2.0 star property
10.0 out of 10, Exceptional, (4)
"Everything was just as stated in the write up. Beautiful, quaint little cottage, very clean and easy check-in, check out process. We thoroughly enjoyed our stay."
The price is AED 496
AED 756 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Cottage at Frogmorton
High Street | Walk to Everything Crozet | Pet-Friendly
Terrace/patio

High Street | Walk to Everything Crozet | Pet-Friendly

9.8 out of 10, Exceptional, (102)
"reaturants walking distance, just wish the water pressure was better"
The price is AED 735
AED 1,223 total
includes taxes & fees
1 Oct - 2 Oct
High Street | Walk to Everything Crozet | Pet-Friendly
Quiet Blue Ridge Mountain Cottage
Terrace/patio

Quiet Blue Ridge Mountain Cottage

9.6 out of 10, Exceptional, (88)
"We greatly enjoyed our stay! It was located near the areas we planned to visit. Owner was friendly, and the pool was great! The listing was accurate, too!"
Quiet Blue Ridge Mountain Cottage
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 Wintergreen Hotel Reviews

The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

10/10 Excellent
"I’ve stayed at the Blackburn many times now. Each and every visit has been peaceful and amazing. The rooms are always impeccable, the staff is always friendly and helpful, and the surrounding area is beautiful."
James 1-night trip
Posted 4 days ago
The Blackburn Inn and Conference Center

Frequently asked questions

Why book your cottage in Wintergreen with Expedia?
We think that vacays should be easy, so if you're seeking cottages in Wintergreen at a nice price, Expedia has you covered. Keep the budget under control and choose a wallet-friendly option surrounded by wilderness, or splurge on a luxury cottage to treat your loved ones.
How can I find cheap cottages in Wintergreen?
With Expedia's useful filter tool, comparing cheap cottages in Wintergreen is a snap. To discover stays that are friendly on the wallet, tailor your search results by amenities, star rating and budget.