Nestled in the heart of Virginia’s picturesque Wine Region, these six charming cottages offer the perfect blend of relaxation, adventure, and natural beauty. Whether you’re here to explore the scenic vineyards, embark on a hike through rolling hills, or simply unwind in a cozy retreat, these cottages are ideally located to make the most of everything this renowned region has to offer. From wine-tasting tours to tranquil walks in the woods, each cottage promises a unique experience. So, how do you choose the right one for your getaway? Let’s explore the options!

Cottage 1: The Wine Cottage

For a peaceful retreat in the heart of Virginia’s Wine Region, The Wine Cottage is the perfect escape. Nestled in a tranquil valley, this spacious cottage offers a serene setting surrounded by lush vineyards and rolling hills. While it doesn’t feature panoramic mountain views, the beauty of the valley and its natural surroundings create a quiet, picturesque atmosphere ideal for relaxation.

The cottage boasts 5 comfortable bedrooms, 3 bathrooms, and a fully stocked kitchen, making it perfect for families or groups. Whether you’re cooking up a meal with local ingredients or simply enjoying a quiet evening by the fire, the spacious layout offers plenty of room for everyone to unwind. After a day of wine tasting at nearby vineyards — just minutes away — gather around the fire pit and soak in the peaceful surroundings. Deer, rabbits, and other small wildlife are often seen meandering through the area, adding to the tranquil charm of the setting.

The Wine Cottage offers a perfect blend of comfort and convenience, with a prime location near the best wineries in the region and all the amenities you need for a relaxing getaway. Whether you’re a wine enthusiast or simply looking for a peaceful retreat, this cottage provides a welcoming atmosphere to make the most of your time in Virginia’s Wine Region.

Cottage 2: The Cheval Circle

For a touch of elegance and adventure, The Cheval Circle is the perfect choice. Nestled at the end of a private driveway, shared

with a nearby horse farm, this charming cottage offers both seclusion and easy access to the best that Virginia’s Wine Region has to offer. Located just a short drive from some of the area’s most popular vineyards, this peaceful retreat allows you to enjoy the serenity of nature while being close to all the wine-tasting action.

The cottage features 5 spacious bedrooms and 3 full bathrooms, comfortably accommodating larger groups or families. With two distinct common spaces, there’s plenty of room for everyone to relax, unwind, and enjoy time together. The fully stocked kitchen is perfect for preparing meals with fresh, local ingredients, and the inviting living areas offer cozy spots to gather. Outdoors, you’ll find a large deck with a propane grill — ideal for cooking up a delicious meal while enjoying the beautiful surroundings. Whether you’re dining al fresco or sipping a glass of wine on the deck, the fresh air and scenic views provide the perfect backdrop for relaxation.

One of the highlights of The Cheval Circle is its outdoor amenities, including a hot tub and two fire pits.

Unwind after a day of adventure by soaking in the hot tub or gathering around the fire pit under the stars. The tranquil atmosphere and peaceful surroundings make it an unforgettable place to relax.

As an added bonus, The Cheval Circle is located next to Rebel’s Run, a horse farm that offers horseback riding tours through the stunning Afton Mountain Vineyard. Take a ride through the picturesque landscape and experience the vineyards from a unique perspective.

Cottage 3: The Little Farmhouse

For a cozy and charming retreat, The Little Farmhouse offers the perfect blend of comfort and rustic elegance. This inviting cottage features 3 bedrooms and 2 full bathrooms, making it an ideal choice for smaller groups or families. Whether you’re seeking a weekend escape or a longer stay, The Little Farmhouse provides a peaceful sanctuary with all the amenities you need to feel right at home.

One of the standout features of this cottage is the spacious wrap-around deck, offering plenty of room to relax, enjoy a meal, or simply take in the beautiful surroundings. The outdoor fire pit is perfect for gathering around in the evening, roasting marshmallows, and enjoying the peaceful atmosphere. There’s also a propane grill, ideal for cooking up a delicious dinner with fresh, local ingredients from nearby markets.

The interior of The Little Farmhouse is designed with a farmhouse modern-style decor, blending rustic charm with contemporary touches. The open living spaces are both stylish and comfortable, with clean lines and a warm, welcoming feel. Whether you’re curling up by the fire or enjoying meals together at the dining table, the interior offers the perfect balance of coziness and modern elegance.

If you’re looking for a charming, peaceful getaway with a touch of countryside charm and modern style, The Little Farmhouse is a perfect choice for those wanting to enjoy both the beauty of Virginia’s Wine Region and the comforts of a cozy, stylish home.

Cottage 4: Meme’s Cottage

For those seeking a quiet, peaceful getaway with plenty of space to unwind, Meme’s Cottage is the perfect choice. This spacious 2-bedroom, 1-bathroom property offers a relaxing escape with all the comforts of home. Whether you’re here for a short weekend or a longer retreat, the peaceful ambiance and cozy interior make it a perfect spot to recharge. Located just minutes away from Virginia’s most celebrated vineyards, it offers easy access to the area’s renowned wine scene.

The cottage features a large dining area, ideal for enjoying meals together or gathering with loved ones. The open, spacious interior provides a welcoming atmosphere, allowing you to enjoy quiet moments in comfort. Whether you’re curled up with a good book or enjoying a meal with friends, Meme’s Cottage offers a serene environment for relaxation.

Outside, you’ll find a fire pit, perfect for cozying up on cooler evenings, roasting marshmallows, or simply enjoying the stars above. The peaceful setting and spacious layout make this cottage an ideal choice for a calm and laid-back retreat.

If you’re looking for a simple yet charming escape with the perfect balance of comfort and tranquility, Meme’s Cottageoffers a warm and inviting place to stay in Virginia’s Wine Region.

Cottage 5: Papa’s Cottage

For those looking for an intimate and cozy retreat, Papa’s Cottage is the perfect escape. Located adjacent to Meme’s Cottage, this charming 2-bedroom, 1-bathroom property offers a peaceful, welcoming space for couples or small groups. Whether you’re celebrating a special occasion or just enjoying a quiet getaway, Papa’s Cottage provides the ideal setting for relaxation.

The cottage features a cozy dining area and a comfortable living space, perfect for winding down after a day of exploring Virginia’s Wine Region. Though the dining area is more intimate, it’s perfect for enjoying meals together or spending time with close friends or family in a warm, inviting atmosphere. One of the highlights of Papa’s Cottage is its year-round hot tub, ideal for relaxing after a day of wine tasting or simply enjoying some peaceful moments under the stars.

With a charming interior and the addition of a fire pit outside, Papa’s Cottage is the perfect spot for an intimate celebration, a romantic getaway, or a cozy escape with friends. Its serene setting and proximity to Virginia’s celebrated vineyards make it a great choice for those looking to enjoy both nature and local wine culture.

Whether you’re staying alone or with a partner, Papa’s Cottage offers a unique space for creating lasting memories in Virginia’s Wine Region.

Cottage 6: Carter’s Cottage

Nestled in the heart of Nellysford, Virginia, Carter’s Cottage offers a perfect retreat just 15 minutes from the popular Wintergreen Resort. Whether you’re seeking outdoor adventure or a peaceful escape, this 3-bedroom, 2-bathroom cottage provides the ideal blend of comfort and convenience.

The cottage boasts a spacious interior with cozy living areas perfect for gathering or relaxing after a day of exploring. The fully equipped kitchen ensures you can easily prepare meals, while the dining area provides a comfortable spot to enjoy them. The outdoor space includes both a fire pit and a year-round hot tub, giving you the option to unwind under the stars in the hot tub or gather around the fire pit for a cozy evening.

Carter’s Cottage is the ideal location for those who love nature. Whether you’re spending the day skiing at Wintergreen Resort,

hiking along the nearby trails, or exploring local vineyards, distilleries, and breweries, this cottage offers a peaceful retreat to return to at the end of your day. The surrounding area is rich in both outdoor activities and scenic beauty, ensuring you’ll have a memorable time.

For those seeking a getaway that balances relaxation with outdoor adventure, Carter’s Cottage is the perfect choice for families, friends, or anyone looking to experience the best of Nellysford and the nearby Wintergreen Resort