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Featured Cottages in Wintergreen

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

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

Roseland
When you stay at this cottage in Roseland, you'll be on the waterfront and steps from George Washington National Forest.
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!

❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!

Nellysford
The price is AU$707 per night from 8 Apr to 9 Apr
AU$707
includes taxes & fees
8 Apr - 9 Apr
With a stay at this cottage in Nellysford, you'll be steps from George Washington National Forest and a 4-minute drive from Stoney Creek Golf Course.
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.

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

Roseland
When you stay at this cottage in Roseland, you'll be on the waterfront and steps from George Washington National Forest.
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.
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Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.

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

Tyro
With a stay at this cottage in Tyro, you'll be on the waterfront, just a 1-minute walk from George Washington National Forest and 15 minutes by foot from Crabtree ...
Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.
Unique Cypress cottage, close to Charlottesville with mountain views.

Unique Cypress cottage, close to Charlottesville with mountain views.

Charlottesville
The price is AU$464 per night from 6 Apr to 7 Apr
AU$464
includes taxes & fees
6 Apr - 7 Apr
Located in Charlottesville, this cottage is within a 15-minute drive of University of Virginia and University of Virginia Hospital.
Unique Cypress cottage, close to Charlottesville with mountain views.
Peaceful Raphine Cottage w/ Deck & Fireplace!

Peaceful Raphine Cottage w/ Deck & Fireplace!

Raphine
Located in Raphine, this cottage is in a rural location, within a 10-minute drive of George Washington National Forest and Rockbridge Vineyard.
Peaceful Raphine Cottage w/ Deck & Fireplace!
Charming Mountain Escape | Hot Tub & Scenic Views

Charming Mountain Escape | Hot Tub & Scenic Views

Afton
With a stay at this cottage in Afton, you'll be in the mountains, within a 10-minute drive of Shenandoah National Park and Afton Mountain Vineyards.
Charming Mountain Escape | Hot Tub & Scenic Views
Mountain View Meadow Cottage - Blue Ridge Mountains and Virginia wine country

Mountain View Meadow Cottage - Blue Ridge Mountains and Virginia wine country

Afton
The price is AU$553 per night from 7 Apr to 8 Apr
AU$553
includes taxes & fees
7 Apr - 8 Apr
With a stay at this cottage in Afton, you'll be in the mountains, within a 15-minute drive of Shenandoah National Park and George Washington National ...
Mountain View Meadow Cottage - Blue Ridge Mountains and Virginia wine country
Quiet Blue Ridge Mountain Cottage

Quiet Blue Ridge Mountain Cottage

Schuyler
This ski cottage is 3.6 mi (5.8 km) from Walton's Mountain Museum and 3.9 mi (6.3 km) from Simpson Park.
Quiet Blue Ridge Mountain Cottage
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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.

Wintergreen Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Wintergreen will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Wintergreen definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Wintergreen, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Wintergreen Cottages essential information

Accommodation
105 Cottages
Lowest Price
AU$464
Highest Price
AU$707
Popular accommodation
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!, ❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!, Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains. , Cottage with stream, mountains, peaceful, quite, secluded, dog friendly. , Unique Cypress cottage, close to Charlottesville with mountain views., Peaceful Raphine Cottage w/ Deck & Fireplace!, Charming Mountain Escape | Hot Tub & Scenic Views, Mountain View Meadow Cottage - Blue Ridge Mountains and Virginia wine country, Quiet Blue Ridge Mountain Cottage

Top trending hotels in Wintergreen

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Roseland
The price is AU$675 per night from 13 Apr to 14 Apr
AU$675
includes taxes & fees
13 Apr - 14 Apr
When you stay at this vacation home in Nellysford, you'll be on a lake, just steps from Wintergreen Resort and George Washington National Forest.
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Roseland
When you stay at this condo in Nellysford, you'll be in the mountains, just steps from Wintergreen Resort and George Washington National Forest.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Best views on Mountain! Breathtaking 5 Star. APRIL-Spring available! BOOK NOW!

Best views on Mountain! Breathtaking 5 Star. APRIL-Spring available! BOOK NOW!

Wintergreen
With a stay at this condo in Nellysford, you'll be in the mountains, just a 1-minute walk from George Washington National Forest and 8 minutes by foot from Bold ...
Best views on Mountain! Breathtaking 5 Star. APRIL-Spring available! BOOK NOW!
Save an average of 15% on thousands of hotels when you're signed in
Custom Builder just completely  remodeled this Mountain Chalet! ...with Hot Tub!

Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

Wintergreen Resort
With a stay at this vacation home in Nellysford (Treeloft), you'll be steps from Wintergreen Resort and George Washington National Forest.
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
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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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^Subject to availability and chosen travel dates.