Hot Wintergreen Cottage Rates

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Featured Cottages in Wintergreen

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

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

Nellysford Virginia
The price is NZ$822 per night from 14 Jan to 15 Jan
NZ$822
14 Jan - 15 Jan 2026
includes taxes & fees
Stay at this cottage in Wintergreen. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Wintergreen Resort and Bold Rock Hard ...
Opens in a new windowPine Cottage: Hot Tub, 2 mins to Bold Rock!
Wintergreen Resort Home w/ 2 Decks + Ski Access!

Wintergreen Resort Home w/ 2 Decks + Ski Access!

3 out of 5
Nellysford VA
Stay at this business-friendly cottage in Wintergreen. Enjoy free parking, a garden and an in-room coffee maker. Popular attractions Wintergreen Resort and Raven's ...
Opens in a new windowWintergreen Resort Home w/ 2 Decks + Ski Access!
Grand Chalet w/ Hot Tub - Near Wintergreen Resort

Grand Chalet w/ Hot Tub - Near Wintergreen Resort

3 out of 5
Nellysford VA
Stay at this cottage in Wintergreen. Enjoy free parking, a sauna and in-room fireplaces. Popular attractions Wintergreen Resort and Raven's Roost Overlook are ...
Opens in a new windowGrand Chalet w/ Hot Tub - Near Wintergreen Resort
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Mountain Mindset: Pup Friendly + Trail

Mountain Mindset: Pup Friendly + Trail

Wintergreen Resort VA
Stay at this cottage in Wintergreen. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Wintergreen Resort and Raven's Roost Overlook are located ...
Opens in a new windowMountain Mindset: Pup Friendly + Trail
Golf Course-view Cabin: Deck in Wintergreen Resort

Golf Course-view Cabin: Deck in Wintergreen Resort

3 out of 5
Roseland VA
Stay at this cottage in Wintergreen. Enjoy free parking, balconies and in-room fireplaces. Popular attractions Wintergreen Resort and Raven's Roost Overlook ...
Opens in a new windowGolf Course-view Cabin: Deck in Wintergreen Resort
Cozy Cottage with beautiful Mountain View’s - close to wineries

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

Wintergreen Resort VA
Stay at this cottage in Wintergreen. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Wintergreen Resort and Reids Gap Trailhead are located ...
Opens in a new windowCozy Cottage with beautiful Mountain View’s - close to wineries
Walk to Ski Slopes: Wintergreen Resort Treehouse

Walk to Ski Slopes: Wintergreen Resort Treehouse

3 out of 5
Nellysford VA
Stay at this cottage in Wintergreen. Enjoy free parking, in-room fireplaces and air conditioning. Popular attractions Wintergreen Resort and Raven's Roost Overlook ...
Opens in a new windowWalk to Ski Slopes: Wintergreen Resort Treehouse
Cozy 'hillside Hideaway' in Wintergreen Resort!

Cozy 'hillside Hideaway' in Wintergreen Resort!

3 out of 5
Roseland VA
Stay at this 3-star business-friendly cottage in Wintergreen. Enjoy free parking, balconies and in-room fireplaces. Popular attractions Wintergreen Resort and ...
Opens in a new windowCozy 'hillside Hideaway' in Wintergreen Resort!
Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit

Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit

3 out of 5
Nellysford VA
Stay at this cottage in Nellysford. Enjoy free parking and air conditioning. Popular attractions Wintergreen Resort and Stoney Creek Golf Course are located ...
Opens in a new windowStoney Creek Cottage: Waterfront Hot Tub, Fire Pit
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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
34 Cottages
Lowest Price
NZ$445
Highest Price
NZ$1,774
Popular accommodation
Pine Cottage: Hot Tub, 2 mins to Bold Rock!, Wintergreen Resort Home w/ 2 Decks + Ski Access!, Grand Chalet w/ Hot Tub - Near Wintergreen Resort, Mountain Mindset: Pup Friendly + Trail, Golf Course-view Cabin: Deck in Wintergreen Resort, Cozy Cottage with beautiful Mountain View’s - close to wineries, Walk to Ski Slopes: Wintergreen Resort Treehouse, Cozy 'hillside Hideaway' in Wintergreen Resort!, Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit

Top trending hotels in Wintergreen

Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

Wintergreen VA
Stay at this condo in Wintergreen. Enjoy free Wi-Fi, private pools and a sauna. Our guests praise the helpful staff in their reviews. Popular attractions Wintergreen ...
Opens in a new windowBest views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
RARE 3B/2B Mountain Top Condo Walk to the Slopes and Resturants! Slope Views!

RARE 3B/2B Mountain Top Condo Walk to the Slopes and Resturants! Slope Views!

Wintergreen Resort VA
Stay at this condo in Wintergreen. Enjoy laundry facilities, patios and cable/satellite TV service. Popular attractions Wintergreen Resort and Raven's Roost ...
Opens in a new windowRARE 3B/2B Mountain Top Condo Walk to the Slopes and Resturants! Slope Views!
New Build! Log Cabin with Hot Tub in Wintergreen

New Build! Log Cabin with Hot Tub in Wintergreen

Wintergreen Resort VA
The price is NZ$1,774 per night from 7 Jan to 8 Jan
NZ$1,774
7 Jan - 8 Jan 2026
includes taxes & fees
Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Wintergreen Resort and Raven's Roost Overlook are located nearby.
Opens in a new windowNew Build! Log Cabin with Hot Tub in Wintergreen
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2br/2ba:  Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Roseland VA
The price is NZ$445 per night from 4 Jan to 5 Jan
NZ$445
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this condo in Wintergreen. Enjoy a water park, laundry facilities and tennis courts. Popular attractions Wintergreen Resort and Raven's Roost Overlook ...
Opens in a new window2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Don't see what you're looking for?
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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.