Holiday rentals in Orange County

Quaint & Cozy LakeView Cottage - Lake of the Woods

Welcome to Brent and Carla's Lake View Cottage! Our beautifully renovated, fully furnished, unique and luxurious home is stocked with everything you need to enjoy your stay in beautiful Lake of the Woods. Our cozy cottage is a perfect get-away for your next vacation, visit with family, work trip, staycation or weekend getaway. You will instantly be set at ease as you enter our home featuring wonderful décor, detailed craftsmanship and lots of amenities to make your stay relaxing and memorable.

Whippoorwill Cottage

1500' gorgeous panoramic water frontage on 5 acres. Private dock/boat launch. Enjoy a fully-appointed property with the comforts of home. Open floor plan, & ceiling fans in almost every room for that tropical feel. 3 bedrooms/2 baths with expansive waterfront views. Enjoy the day with a gorgeous sunrise and coffee on the deck and end your perfect day at the dock in Adirondack chairs. Spacious private cove for boating & easy travel to lakeside restaurants. Boat & jet ski rental available on-site.

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.

Lakefront at Turtle Cove

Enjoy the lake life in a peaceful quiet cove on the gorgeous large lake within Lake of the Woods. When not enjoying the newly renovated home with a vaulted ceiling great room, huge screened porch, and a desk and flat screen TV in each room, you can swim, float, kayak, or paddleboard in the quiet, secluded cove, or enjoy the 9 beaches or 2 community pools. Catch fish off the dock in one of the best fishing coves on the lake, and then warm up at night by the fire pit . Great for families.

Beachwalk Hideaway

Escape to our delightful Beachwalk Hideaway, a cozy retreat that offers easy access to the serene beach on the shimmering lake. Walk just 6 houses down to Ramsey Beach for sandy shores on the lake. Lounge by Ramsey Beach water's edge, build sandcastles, swim, and immerse yourself in the calm of lakeside living. As evening falls, enjoy breathtaking sunsets and starlit skies from your piece of paradise. Book your stay now and experience the ultimate in lakeside relaxation and recreation.

Waterfront retreat w/private dock/hot tub/kayaks

Homeport Harbor is the ultimate lake vacation home! Unwind in this spacious, cozy waterfront retreat located on the public side of Lake Anna! This 1,800 sq ft. home is located on one acre and is beautifully decorated; including completely all brand new furniture, kitchen upgrades and new mattresses throughout. Spend your days relaxing at the water’s edge on the private dock, screened in porch or large deck and your evenings roasting marshmallows gathered around the built-in fire-pit.

Private Couples getaway with HOT TUB.

Welcome to the exquisite location, conveniently situated only 15 minutes away from Lake Anna. Our family has invested significant effort into creating this splendid, contemporary A-frame cabin, nestled on our 110 acre family farm. Strategically positioned to offer a breathtaking view of the creek that traverses our property, this private retreat is located just one hour from Washington, D.C. Immerse yourself in the tranquil ambiance and soothing sounds of nature.

Stunning Modern Cabin w WiFi near Shenandoah Park

My family lovingly restored this log cabin and it was recently featured in the Washingtonian as one of the top places to visit in the DC region! We’re so excited to share it with you! It is one of the only houses in the area with reliable high speed xfinity wifi. It is a short drive to so many of the popular Shenandoah National Park hikes and it's centrally located to so many of the popular breweries, wineries, restaurants, and adorable small towns.

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.