21 Amazing Airbnb & Vacation Rentals in Northern Virginia’s Wine Country

April 29, 2021


Just a short drive from Washington, DC, Northern Virginia's wine country is a picturesque spot offering the perfect escape from everyday life. Whether you're looking for a romantic getaway, a family vacation, or a trip with friends, finding the right place to stay only enhances the experience. To help you find the best accommodations, I've curated a list of amazing Northern Virginia vacation rentals and Airbnbs in the heart of wine country. 

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Visiting Northern Virginia Wine Country

When I lived in Washington, DC, I spent many weekends touring Northern Virginia's beautiful wine country. Nothing helped me unwind more than sipping a glass of local Virginia wine while admiring the rows of vines and rolling green hills of the surrounding landscape.

In addition to dozens of wineries - good luck trying them all! - the region is home to beautiful parks, rivers, and lakes that are wonderful for hiking and other outdoor activities. 

Vineyard in Northern Virginia's wine country

Whether you're local to DC or are on a road trip through Northern Virginia, spending time in Virginia wine country is such an experience you shouldn't miss.  

Northern Virginia Vacation Rentals and Airbnbs

Since the way to really soak in the relaxing vibes of Northern Virginia's wine country is to stay for a couple days, I've compiled a list of amazing vacation rentals from Airbnb and VRBO that I think are perfect getaway spots. 

Scattered throughout Northern Virginia, each vacation home is close to a variety of wineries, breweries, parks, and other fantastic attractions. These vacation rentals and Airbnbs range from cozy, romantic getaways to larger accommodations suitable for a family, multiple couples, or a group of friends.

All of these Virginia vacation rentals are "entire house" accommodations so your privacy is ensured no matter which one you pick! Plus, they all come highly recommend by guests who have stayed there.

Things to Know about the Quoted Nightly Rates

  • All prices listed are in USD and are average or approximate prices per night.
  •  Nightly rates vary (sometimes greatly) depending on the season or day(s) of the week you are booking the vacation rental. 
  • Please click on the Airbnb or VRBO listing using the Booking button and enter your trip info to see the actual costs for your travel date(s).

Spacious, modern home with a large deck overlooking the Shenandoah River.

Location: Berryville, VA
Avg. Price per Night$444
Guests: 6 guests
Beds/Baths: 2 bedrooms · 4 beds · 2 baths

Pet-friendly: No
Special Features: Riverfront property with kayaks provided by host, wraparound deck, indoor fireplace, large kitchen. washer/dryer. 

This beautiful, recently renovated home with a wrap-around deck on the banks of the Shenandoah River is a perfect retreat. The inside of the home is light and spacious with incredible views of the river. In the winter, keep warm by the fire while curling up with a good book. In the summer, take advantage of the kayaks provided by the host or go swimming in the river! 

Riverfront Getaway in Northern Virginia

Photo courtesy of VRBO

Perfect stay for: Couple, Family, Friend trip

Gorgeous English-style country cottage in Virginia's Hunt Country.

Location: Bluemont, VA
Avg. Price per Night$205
Guests: 6 guests
Beds/Baths: 3 bedrooms · 5 beds · 1 bath

Pet-friendly: No
Special Features: Fireplace, heated garage, luxury bathroom with heated floor, washer/dryer, spiral staircase, Inkjet printer, stocked fishing pond, fire pit.

After years of travel, innkeepers Jennifer and Eric Singleton wanted to create the perfect space to escape from it all and so the Windswept Inn was born. This quaint English-style country cottage is set amidst the rolling green hills of Virginia's Hunt country.

Windswept Inn Virginia vacation rental

Photo courtesy of VRBO

It offers the perfect spot to relax, fish in the property's pond, and explore the nearby wineries and breweries. The little treehouse on the property offers a bit of adventure for the kids as well.

Windswept Inn pond vacation rental in Virginia

Photo courtesy of VRBO

Perfect stay for: Couple, Family

Sprawling French country estate nestled in the Blue Ridge Mountains.

Location: Bluemont, VA
Avg. Price per Night$582
Guests: 8 guests
Beds/Baths: 4 bedrooms · 4 beds · 3.5 baths

Pet-friendly: Yes
Special Features: Fireplace, washer/dryer, music library, balcony, fire pit, BBQ grill, outdoor furniture.

This spacious 1896 French country estate nestled in the Blue Ridge Mountains offers the perfect spot for a family reunion or a group of friends that want to get away. Its large living areas offer plenty of space for a group but the home also has plenty of nooks where you can have your own space.

French country estate living room in Blueridge Mountains Virginia

Photo courtesy of VRBO

Outside, enjoy views of the Shenandoah Valley from the day beds, sip a glass of wine beside the large fit pit, or walk to the nearby pond. 

French country estate firepit - Virginia vacation rental

Photo courtesy of VRBO

Perfect stay for: Family, Friend trip

Historic home with outdoor pool and views of Shenandoah River.

Location: Boyce, VA
Avg. Price per Night$495
Guests: 9 guests
Beds/Baths: 3 bedrooms · 4 beds · 2 full baths · 2 half baths

Pet-friendly: Yes
Special Features: Fireplace, washer/dryer, swimming pool, lawn games, kayaks, bicycles, BBQ grill, verandah with river views.

This recently-renovated historic home is right in the heart of Virginia's horse and hunt country. Its living spaces are nicely decorated which gives the space a comfortable and charming vibe.

The Play Garden bedroom - Virginia vacation rental

Photo courtesy of VRBO

Due to its location atop a plateau, this Virginia vacation rental offers amazing views of the Shenandoah River from the verandah. Imagine sipping a glass of wine with this view - especially in autumn with those fall colors!

The Play Garden verandah with views of Shenandoah River

Photo courtesy of VRBO

Other amenities include indoor fireplaces, an outdoor pool, and various lawn games and sports gear that are available to guests.

The Play Garden pool - Virginia Vacation Home

Photo courtesy of VRBO

The Play Garden is the perfect jumping off spot for hiking in Sky Meadows State Park or Shenandoah National Park. Or perhaps for visiting local wineries and breweries. If you have a larger group, you may also want to rent the small guest house on the property in addition to the main house. 

Perfect stay for: Family, Friend trip

Spacious studio retreat with large pool and incredible valley views.

Location: Bluemont, VA 
Approx. Price per Night: $260
Guests: 2 guests
Beds/Baths: 1 bedroom · 1 bed · 1 bath

Pet-friendly: No
Special Features: Pool, valley views, private balcony, kitchen, BBQ grill

When you enter Foxglove Retreat, you'll immediately be drawn to the large window overlooking the incredible valley views and the pool below. During the summer, hang out at the pool or perhaps explore the surrounding trails of the Blue Ridge Mountains. This retreat is also the perfect jumping off point for local wineries and breweries.  

Foxglove Retreat Airbnb with pool

Photo courtesy of Airbnb

Perfect stay for: Couple

Spacious, restored historic log house with rustic charm and pond views.

Location: Flint Hill, VA
Avg. Price per Night: $240
Guests: 4 guests
Beds/Baths: 1 bedroom · 1 bed · 1.5 baths

Pet-friendly: No
Special Features: Pond and mountain views, historic charm, BBQ grill, horse pastures nearby.

This historic log house was originally built as a tavern in 1790. In 1990, the house was moved to Windsor Lodge where you'll find incredible views of the large pond and the Blue Ridge Mountains. Despite its rustic charm, you'll find all the modern amenities you need and the house is spacious enough for a family. Many reviewers noted that the horses nearby are friendly, so be sure to stop and say 'hi'!

Camelot at Windsor Lodge Airbnb

Photo courtesy of VRBO

Perfect stay for: Couple, Family

Bright, modern space in the forest with huge windows, sunset views, and hot tub.

Location: Front Royal, VA
Avg. Price per Night: $375
Guests: 6 guests
Beds/Baths: 3 bedrooms · 4 beds · 1 bath

Pet-friendly:  No
Special Features: Hot tub, wood-burning stove, grill, firepit, sunset views

This quiet oasis in the treetops of the Blue Ridge Mountains is a beautiful forest escape! The interior is beautifully decorated and large windows let in plenty of light. Warm up in the hot tub or beside the wood-burning stove on cooler nights. In the summer, enjoy lounging on the large deck with family or friends while grilling up some dinner.

Royal A Frame vacation rental with hot tub

Photo courtesy of VRBO

Perfect stay for: Family, Friend trip

A chic riverfront home with beautiful design elements and a large deck.

Location: Front Royal, VA
Approx. Price per Night: $203
Guests: 4 guests 
Beds/Baths: 2 bedrooms · 2 beds · 1 bath

Pet-friendly: Permitted on case-by-case basis
Special Features: Riverfront property with large deck, BBQ grill, firepit, washer/dryer, EV charging station.

This stylish riverfront home on the bank of the Shenandoah River is the perfect getaway for a couple or a group of friends. Sleek Danish-modern design elements will make you feel like you're living in luxury for the weekend. Plus, bring your kayaks and access the Shenandoah River from the backyard! 

Skyhouse Airbnb in Northern Virginia

Photo courtesy of Airbnb

Perfect stay for: Couple, Friend trip

Beautifully-designed waterfront home with incredible views plus a hot tub and kayaks.

Location: Front Royal, VA
Avg. Price per Night: $549
Guests: 10 guests
Beds/Baths: 3 bedrooms · 5 beds · 2.5 baths

Pet-friendly: Yes
Special Features: Washer/dryer, fireplace, BBQ grill, hot tub, multiple decks with incredible views of the Shenandoah River, fire pit, kayaks, boat dock.

A spectacular waterfront cottage with views of the Shenandoah River from multiple decks as well as the hot tub - what more could you ask for? The interior is beautifully designed with wood beamed ceilings and a stone fireplace on the main floor which give it a cozy feel. The windows allow the natural light to brighten the space and the open floor plan is perfect for hanging out as you cook. 

Spectacular Cottage overlooking Shenandoah River

Photo courtesy of VRBO

And the wow factor doesn't stop as you head outside! Multiple decks offer incredible views of the Shenandoah River, including one with a hot tub. Since the property is right on the water, head down to the river for kayaking or fishing. If you have a boat, you can bring it along and dock it at the floating boat dock.

Spectacular Cottage with hot tub in northern Virginia wine country

Photo courtesy of VRBO

Perfect stay for: Family, Multiple families, Friend trip

Bright, charming house with large outdoor area and fire pit.

Location: Front Royal, VA
Avg. Price per Night: $257
Guests: 4 guests
Beds/Baths: 2 bedrooms · 3 beds · 1 bath

Pet-friendly: Yes
Special Features: Sunroom, large outdoor area with picnic table, fire pit, BBQ grill.

This charming cottage in the woods near Front Royal is the perfect jumping off point to exploring local vineyards and breweries or going hiking in Shenandoah National Park. During the summer, take advantage of its nearby access to two private lakes and the Shenandoah River for kayaking and swimming. In the winter, head out to the fire pit for some smores and stargazing. 

Sweet Pea Cottage Airbnb Northern Virginia

Photo courtesy of VRBO

Perfect stay for: Couple, Family, Friend trip

Cozy, modern home with gorgeous river views plus a hot tub, foosball, and kayaks.

Location: Front Royal, VA
Avg. Price per Night: $562
Guests: 8 guests
Beds/Baths: 3 bedrooms · 3 beds · 3.5 baths

Pet-friendly: Yes
Special Features: Washer/dryer, fireplace, game room with foosball, spiral staircase, BBQ grill, hot tub, multiple decks with incredible views of the Shenandoah River, fire pit, kayaks.

The Snug is a cozy and elegant home along the Shenandoah River that would be an incredible retreat from city life. Its large windows bring the natural beauty of the outdoors inside and the river views from multiple decks are stunning. On the lower level, the media room is an excellent place for the kids to play while the adults are cooking, drinking wine from local Virginia wineries, and hanging out upstairs.

Country Elegance VA vacation rental exterior

Photo courtesy of VRBO

Another perk of The Snug is the private access to the Shenandoah River. Enjoy the river using the kayaks provided or just admire it from the hot tub. You're sure to have an excellent time no matter what! 

Perfect stay for: Family, Multiple families/couples, Friend trip

Renovated historic schoolhouse with bright, open floor plan and fire pit.

Location: Leesburg, VA
Avg. Price per Night: $350
Guests: 4 guests
Beds/Baths: 2 bedrooms · 3 beds · 1 bath

Pet-friendly: No
Special Features: Washer/dryer, Outdoor fire pit.

This renovated historic schoolhouse is now a cozy cottage that's a unique place for a couple or a family to stay as you explore northern Virginia. Watson Hall's open floor plan is bright with lots of natural light and the outdoor fire pit is the perfect spot to sit and have a glass of wine at night. Plus, it's close to many fun outdoor activities as well as local breweries and wineries. 

Watson Hall vacation rental nothern virginia

Photo courtesy of VRBO

Perfect stay for: Couple, Family

Cozy cottage within walking distance of downtown Historic Leesburg.

Location: Leesburg, VA
Avg. Price per Night: $275
Guests: 4 guests
Beds/Baths: 2 bedrooms · 2 beds · 1 bath

Pet-friendly: Yes (pet fee)
Special Features: Washer/dryer, Outdoor patio, parking.

A charming cottage in the heart of downtown Historic Leesburg, this is the perfect place for anyone who loves a colonial old town feel and wants to be within walking distance of great restaurants, cafes, boutique shops, and more. Plus, the cozy vibe and thoughtful decorative touches in this cottage will make you feel right at home.

Cottage on King Street - Virginia vacation rental

Photo courtesy of VRBO

Perfect stay for: Couple, Family

Looking for other charming USA towns? Check out Traverse City, Michigan!

Appalachian-style log cabin with vaulted ceilings nestled in the forest.

Location: Linden, VA
Avg. Price per Night: $217
Guests: 5 guests
Beds/Baths: 3 bedrooms · 3 beds · 2 baths

Pet-friendly: Yes
Special Features: Washer/dryer, wood stove, BBQ grill, outdoor fire pit, multiple decks.

This Appalachian-style log cabin is nestled amidst beautiful poplar trees which makes it a peaceful spot in any season. Inside, the vaulted ceilings, wood accents, and wood stove give it a rustic feel, yet the space is updated and modern at the same time. Sit outside one of the decks or beside the fire pit to enjoy the serenity of nature. Alternatively, walk to the Appalachian Trail which is only minutes away or visit Sky Meadows State Park to enjoy a beautiful hike.

Blue Mountain Log Cabin exterior

Photo courtesy of VRBO

Perfect stay for: Couple, Family, Friend trip

Cozy cottage surrounded by forests with large hot tub on the back deck.

Location: Linden, VA
Avg. Price per Night: $213
Guests: 6 guests
Beds/Baths: 3 bedrooms · 3 beds · 2.5 baths

Pet-friendly: Yes
Special Features: Washer/dryer, fireplace, BBQ grill, front patio and back deck, hot tub.

This bright and cozy cottage is perfect for anyone who'd like to do a little forest bathing! Sip a glass of wine outside on the porch or in the hot tub while soaking in the pure forest air. Although this cottage sleeps 6 guests, its cozy living areas and secluded location seem ideal for a romantic getaway for a couple as well. 

Beavers Hill Cottage northern Virginia vacation rental

Photo courtesy of VRBO

Perfect stay for: Couple, Family, Friend trip

Spacious modern house with incredible views and a pool table for game night.

Location: Linden, VA
Avg. Price per Night: $425
Guests: 10 guests
Beds/Baths: 4 bedrooms · 6 beds · 4 baths

Pet-friendly: Yes
Special Features: Washer/dryer, fireplace, game room with pool table, BBQ grill, backyard deck with incredible views, fire pit.

Since this spacious Virginia Wine Country Retreat is just an hour away from DC, it's a great spot for a group of friends to get out of the city for a few days. With plenty of bedrooms, as well as multiple areas throughout the house to hang out, your group won't feel cramped.

Plus, the large game room and pool table will keep you entertained as you enjoy a glass of wine and those amazing views of Virginia's green hills.

Wine Country Retreat in Northern Virginia

Photo courtesy of VRBO

Perfect stay for: Family reunion, Friend trip

Beautifully-designed manor with large outside deck and lawn.

Location: Middleburg, VA
Avg. Price per Night: $339
Guests: 8 guests
Beds/Baths: 4 bedrooms · 5 beds · 2 baths

Pet-friendly: No
Special Features: Washer/dryer, BBQ grill, outdoor patio and furniture, large lawn.

Mosby Manor is a luxuriously-designed home just outside of historic Middleburg. Convenient to wineries, shopping, and excellent restaurants. But this home is also a great space to just relax and grill up some dinner while enjoying the backyard after a day of hiking or wine tasting.  

Mosby Manor vacation home in Virginia

Photo courtesy of VRBO

Perfect stay for: Couple, Family, Friend trip

Spacious farm house with stables for horses, hot tub, fitness room. 

Location: Middleburg, VA
Avg. Price per Night: $268
Guests: 6 guests
Beds/Baths: 3 bedrooms · 4 beds · 2.5 baths

Pet-friendly: Yes
Special Features: Washer/dryer, wood stove, fireplace, BBQ grill, Jacuzzi tub, fitness room with treadmill + weights, outdoor fire pit, hot tub, and horse stables.

The Dutch Barn is a spacious farm house located a couple miles from historic Middleburg. With plenty of room for the whole family to spread out both indoors and out, this is the perfect place for you to relax while the kids run around the huge lawn. Or, if you want to get in a workout of your own, try out the fitness room!

The Dutch Barn farm house in Virginia horse country

Photo courtesy of VRBO

An added bonus to the Dutch Barn is that you can bring along your horses as the property's stable has 5 indoor stalls where they can rest comfortably. Since the Dutch Barn is located in the middle of Virginia's Horse and Hunt Country - you'll find plenty of trails to explore with your horses. Don't have a horse? That's okay, me neither - you can explore the various hiking trails and wineries in the area instead! 

Perfect stay for: Couple, Family, Friend trip

Country farmhouse with a charming design, pond views, and Clydesdale horses.  

Location: Purcellville, VA
Avg. Price per Night: $154
Guests: 2 guests
Beds/Baths: 1 bedroom · 1 bed · 1 bath

Pet-friendly: No
Special Features: Garden, BBQ grill, animal interactions, horse stalls available

Have the run of the farm and meet some new (animal) friends at this country farmhouse on Sylvanside farm. Beautifully landscaped with charming interiors that look out onto the nearby pond as well as grazing horses. It's a great space for wedding photos or exploring country life in between your winery visits.

Country Cottage on Horse Farm VRBO

Photo courtesy of VRBO

Perfect stay for: Family, Multiple Families or Couples, Friend trip

A spacious family home perfect for family or friend gatherings in wine country.

Location: The Plains, VA
Avg. Price per Night$192
Guests: 8 guests
Beds/Baths: 3 bedrooms · 7 beds · 2 baths

Pet-friendly: Yes
Special Features: Lots of family-friendly amenities, washer/dryer, BBQ grill, firepit, large lawn, barn available for artist studio

This spacious family home is perfect place for a family gathering or for a group of friends to get away. With lots of rooms, family-friendly amenities like a crib and baby monitor, plus an expansive lawn where children can run - it's a great find! The fire pit outside is an excellent place to sit and roast s'mores after a day of wine tasting. 

Fox Cross Cottage Airbnb in Virginia Wine Country

Photo courtesy of VRBO

Perfect stay for: Family, Friend trip

Spacious studio in a restored historic church with an impressive library.

Location: Waterford, VA
Approx. Price per Night: $199
Guests: 6 guests
Beds/Baths: 1 bedroom · 3 beds · 1 bath

Pet-friendly: No
Special Features: High ceilings, library, baby grand piano

A unique Airbnb stay for sure - Grace Cottage is a restored church in Waterford Village - a National Historic Landmark. The town was given this distinction due to its well-preserved 18th and 19th century architecture so be sure to take a stroll around town during your stay. On its interior, Grace Cottage is a stylish and elegant space with an impressive library with 1,000 books, large windows, and a baby grand piano. 

Grace Cottage Restored Church Airbnb

Photo courtesy of Airbnb

Perfect stay for: Couple, Family

Tips for Finding the Perfect Northern Virginia Vacation Rental

With all the excellent vacation rental properties on VRBO and Airbnb these days, choosing your perfect home away from home can be tough!

Though I hope you've found some good options on this list, here are a few tips to keep in mind when choosing the best vacation rental for you: 

1) Use the Airbnb or VRBO Filters

Not only can you filter for the type of accommodation (i.e. private room vs entire house), but you can filter by price, type of house, specific amenities, etc.

Filtering is especially useful if you're looking for a property with special features like a hot tub or a swimming pool. Or perhaps you want to bring your dogs on your Virginia vacation and are looking for a pet-friendly vacation rental? You can filter to find only pet-friendly homes.  

2) Check Cancellation Policy

If your plans may change, it's important to check the cancellation policy carefully. Since Airbnb and VRBO allow hosts to choose their own cancellation policy, it tends to vary significantly from host to host. Though I've often found VRBO hosts to be a bit more flexible with cancellation policies. 

3) Read Reviews Thoroughly

Although pictures can make a place look spectacular, the reviews will tell the true story. Be sure to read them thoroughly, especially if you're interested in a particular amenity. For example, as I looked at a property recently, I noticed a fireplace in the photos. However, a guest review mentioned that guests cannot use it. This detail would be important to know if you're booking a place solely to use that fireplace. 

Final Thoughts

I hope you'll decide to discover Northern Virginia's incredible wine country and book one of these amazing Airbnb or VRBO rentals. With the number of wineries, breweries, and hiking trails to explore in this region, you'll be sure to have an amazing time!

Which of these vacation homes would you like to try? Let me know in the comments below!

Other Articles You Might Enjoy

If you're planning a trip to northern Virginia and the DC area, you might also find these articles helpful:

Happy travels!


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USA travel 21 Vacation Rentals in Northern Virginia wine country
21 Amazing Vacation Rentals in Northern Virginia Wine Country
21 Amazing Vacation Rentals in Northern Virginia
    • Thanks so much! I hope you’ll get the chance to try one of these Airbnbs out. You’ll have to let me know what you think if you do. 🙂 Virginia wine country definitely makes a good weekend trip.

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