Cottage holiday rentals in Lake of the Woods

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Top-rated cottage rentals in Lake of the Woods

Guests agree: these cottages are highly rated for location, cleanliness and more.

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Top guest favourite
The exterior of the cottage features a welcoming red door framed by white clapboard siding and black shutters. Flower pots with pink blooms are hung on either side, adding a touch of color. A set of steps leads up to the entrance, surrounded by green foliage.
Cottage in Fredericksburg
4.88 out of 5 average rating, 559 reviews

Rappahannock River Cottage Near I-95 Sleeps 6!

Charming 3-Bedroom with rustic charm Built in 1895. Ideal location for shopping, entertainment, history, and outdoor adventures. Discover all things Fredericksburg! Your cozy haven awaits! 🏡✨ New for 2026!! —Updated hardwood flooring throughout the whole house. Also, a small fenced in front yard (3 1/2 foot tall) AND screened in front door complete with doggie door for the fur babies! 🐕 🐾 Please see last 2 photos in photo gallery for IMPORTANT INFORMATION about insects/wildlife. 🐛 🐞🦟🪲🐜

Top guest favourite
A quaint outdoor seating area is presented under a covered porch, featuring two wooden chairs and a small round table. A decorative cushion adds a touch of color. The surrounding scenery includes lush green fields and distant hills, creating a serene backdrop.
Cottage in Madison
4.93 out of 5 average rating, 101 reviews

Spectacular Mountain Retreat

Cottage is the guest house of our country home. Situated on a mountain with spectacular views of the Blue Ridge and access to many hiking trails; biking; fishing and swimming in private pond only steps from the door. Cottage is located within easy driving distance of multiple wineries, Sky Line Drive and Shenandoah National Park; Montpelier; and restaurants and shops. We can accommodate no more than one dog, with prior permission. In April 2023, we again upgraded our internet (see below).

Guest favourite
An aerial view captures the surrounding countryside, featuring sprawling green fields and distant mountains under a partly cloudy sky. The image shows a mix of residential buildings, including cottages and a red-roofed structure, situated amidst lush trees.
Cottage in Madison
4.91 out of 5 average rating, 172 reviews

Robinson River Roost - Cottage near Shenandoah NP

Enjoy a slice of country life in our rustic 2 BR, 1.5 bath cottage nestled along the Blue Ridge in Madison County. Great for a family or small group. Minutes to scenic hikes at White Oak and Old Rag in Shenandoah National Park, plus wineries, breweries and festivals at Graves Mountain Lodge. Steps away from trout fishing and swimming holes of the peaceful Robinson River, plus Possum's Store across the street. Convenient to Charlottesville, Culpeper, Blue Ridge Pkwy, Luray Caverns, Camp Varsity.

Guest favourite
Cottage in Orange
4.89 out of 5 average rating, 224 reviews

Willie's Place Country Cottage Pets Allowed

Step out your front door and pet horses located next door. Willie's place is newly renovated and has all the amenities you need. Located close to wineries, shopping, wedding venues, Historic Montpelier, Corn Maze, Town of Orange, Woodberry Forest School, 10 minutes to Gordonsville, 30 minutes to Charlottesville. Kayak the Rapidan, take a horseback ride at Oakland Heights or see a play at Barboursville. Exposed beams throughout, a beautiful Loft and back porch for sitting. You won't go wrong.

Guest favourite
Cottage in Leon
4.94 out of 5 average rating, 107 reviews

Comfy Cottage Near SNP, Hiking, & Wineries

This cottage at Grateful View is conveniently located in beautiful Madison Co. Accessible to Rt 29 and centrally located to local breweries, wineries (across from Prince Michel), and hiking. A few local places to visit include: Bald Top Brewing Company, Early Mountain Vineyard, the Skyline Drive in Shenandoah National Park (Old Rag Mtn and White Oak Falls). An easy 15-minute drive to Culpeper or 35-minute drive to Charlottesville with historical sites, restaurants, and antique shops not far.

Top guest favourite
A charming cottage with a steeply pitched roof is surrounded by a tranquil winter landscape. Fresh snow covers the ground, and soft flakes fall gently, contrasting with the dark wood exterior. The entrance features a decorative door, framed by colorful window accents.
Cottage in Bentonville
4.97 out of 5 average rating, 575 reviews

The Cottage

Need some time to refresh? Spending time in the foothills of the Skyline Drive at our cozy cottage may be for you. Well behaved dogs are welcome but not on furniture. The driveway is long and home is very secluded. Winter access will be subject to weather conditions. Driveway does not get plowed and gets rutty during rainy periods. Cell service is spotty on Browntown road. The cottage has a landline and wifi. Use your wifi calling feature for cell phone use. More info under photos.

Top guest favourite
Cottage in Orange
4.96 out of 5 average rating, 499 reviews

Private Fenced Yard for Dogs/Horses - 2BR Cottage

2BR Hen and Hound Cottage is located just outside Orange, VA and has a private fenced yard for pets and walk-in access to adjacent James Madison's Montpelier and its many walking trails. In addition, we are minutes away from all of the popular wedding venues in Orange and a short drive to Shenandoah National Park. Our house on Whistle Stop Farm (so named for the train that passes by) is next to the cottage if you need us. Otherwise, the place is yours. Come enjoy some time in country!

Top guest favourite
A view from an open doorway reveals a covered porch with white rocking chairs. A welcome mat lies on the wooden floor, leading to a scenic landscape of rolling hills adorned with autumn foliage. A glimpse of black chairs is visible in the distance.
Cottage in Gordonsville
5 out of 5 average rating, 205 reviews

Merry View Cottage

Our newly renovated farm cottage sits at the edge of a grove of giant hardwoods. Enjoy year round mountain views, including Merry Mountain. Ease into the morning while watching wildlife from a front porch rocker. Visit local wineries, breweries, restaurants, museums, shops, hiking trails or wedding venues. Unwind in the hammock or practice yoga on the back deck. Prepare dinner in our full size kitchen. Then, star gaze around the fire-pit after dark. This peaceful oasis awaits you.

Guest favourite
Cottage in Fredericksburg
4.89 out of 5 average rating, 187 reviews

“Little Sligo” Historic Downtown Cottage Near I-95

“Little Sligo” a charming cottage built in 1760 and lovingly restored less than 5 years ago. Our unique property blends old-world charm with modern amenities, sits on a beautiful 2-acre historic site adjacent to a 46-acre public park, perfect for morning walks, sports, & family activities. Public swimming pool is OPEN Memorial Day to Labor Day. 1 minute walk from the cottage. Enjoy the convenience of being just 3 minutes from the heart of Downtown FXBG and 3 miles from I-95.

Top guest favourite
Cottage in Warrenton
4.96 out of 5 average rating, 372 reviews

The Soper House-A Quaint & Lovely Country Getaway

The Soper House is a 1,000 sq.ft. ranch-style home with 3 bedrooms & 1 bath perfectly situated on a 5 acre farmette. Located in Fauquier County, VA. also known as Hunt, Horse & Wine country, each of the bedrooms uniquely displaying these historical themes. This charming cottage has a fully functional eat-in kitchen, a living room & a mudroom with W/D for your use. There are a few neighbors that are visible & we live in the adjacent property & can be easily available.

Top guest favourite
A charming historic cottage is featured, showcasing a white exterior with a red metal roof. The front porch is framed by a small staircase and surrounded by well-maintained greenery. Tall trees provide shade on the side, set against a backdrop of an expansive blue sky.
Cottage in Spotsylvania Courthouse
4.9 out of 5 average rating, 193 reviews

Bond House: Historic Retreat at Walnut Grove

Escape from the city to a historic 1740s cottage with a distant view of the Blue Ridge Mountains and peaceful surroundings with the opportunity to experience the slower pace of country living. Spend the day at Lake Anna to swim/ kayak/ boat or visit the state park, just 5 minutes away. Enjoy local wineries, and explore historic Civil War battlefields. After a fun filled day, return to your private oasis with a fully equipped kitchen.

Top guest favourite
A charming cottage surrounded by lush greenery and trees in autumn colors. The red structure with a sloped roof sits in a serene area, offering a peaceful retreat, while a dirt path leads towards it, under a clear blue sky.
Cottage in Ruckersville
4.9 out of 5 average rating, 374 reviews

Lake Haven Cottage

Make yourself at home at our peaceful 1-bedroom cottage that has everything you need for your trip to the Blue Ridge Mountains. The cottage comes with heating, AC, Washer+Dryer and DIRECTV. During your stay, you can also enjoy using a convenient private bathroom, kitchen, and living room. Our Airbnb is within driving distance to UVA, the Skyline Drive & Shenandoah National Park, local wineries, craft breweries and much more!

Popular amenities for cottage rentals in Lake of the Woods