Vacation rentals with a pool in Orange County

The Studio at Dark Run Retreat

Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*

Hummingbird Lakehouse

Hummingbird Lakehouse in Locus Grove, VA, offers waterfront access to the lake and various outdoor activities like golfing, kayaking, swimming, fishing, and horseback riding. Guests can gather around the fire pit and access community amenities like the pool and beaches. Nearby historic sites & hiking trails provide additional exploration opportunities. If you're looking for a peaceful getaway or an adventure-filled vacation, this lake house offers an idyllic setting for making lasting memories.

Bloomingdale Honeymoon Cabin w/Mountain/Barn Views

Relax in the rustic cabin retreat set on the hill crest of our 14 acre farm. With mountain views and vintage vibes, it's the perfect getaway for those who want to unplug, or need a change of scenery while working remote! We are near some of the top wineries in VA. There are plenty of options for hiking, antiquing, sightseeing and eating in all directions: 5 min. from the Market at Grelen and Montpelier; minutes to Orange and Gordonsville; 30 min. to Charlottesville & Shenandoah. Come and see!

La Petite Maison at Hedgeapple Hollow

La Petite Maison (our guest house) is the perfect place to simply get away from the hustle and bustle and relax! Sit in the private screen porch and watch the sun melt into the mountains. Deer, hummingbirds, bluebirds, and the occasional turkey like to hang out on the 8 acres of the property, perfect for any wildlife lover. Enjoy the fenced in common area featuring a seasonal in-ground pool. Conveniently situated near award-winning wineries, Montpelier, and historic downtown Gordonsville.

Beach, Hot Tub, Arcade, Golf, Pub: The Lucky Duck!

Unforgettable retreat with partial lake view, luxurious 7-person Jacuzzi, custom pub featuring a retro 4-player arcade with 7,500+ games and trackball, cozy woodstove, and delightful surprises! Ideal for epic family vacations, The Lucky Duck in the exclusive gated Lake of the Woods offers year-round fun—two lakes, eight pristine beaches, two pools, a golf course, an equestrian center, and scenic parks with fitness trails await! Come experience lakeside fun and relaxation! #TheLuckyDuckLOW

Experience Luxury, Historic Manor, Private Pool

Enjoy the elegance of a bygone era in a residence designed to sweep you off your feet. Beautifully decorated and updated with modern amenities and rich details, the home is a once-in-a-lifetime experience. Lounge on the front veranda, pour a drink in the pub and stroll down Main Street for Fine Dining, Wine Bistros, and excellent boutique shopping. In historic Gordonsville, you're just minutes from award-winning vineyards, wedding venues, the Blue Ridge Mountains, Woodberry Forest, and UVA.

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.

Secluded Lakefront | Private Pool | Dock | Hot Tub

**Discover Ultimate Luxury at LesLee at the Lake: a Deep Water Lakefront Haven with Private Inground Pool, Hot Tub, and Dock** Nestled on the public side of Lake Anna, this picturesque 2.63-acre secluded property offers stunning waterfront views, a boat house for easy water access, and a lakefront fire pit. Our expansive and luxurious 9,000 sq. ft. home with game room, spacious kitchen, and movie theater, is ideal for an unforgettable escape and perfect for accommodating large groups.

Sauna & Game Room: Lake House in Locust Grove!

Spa Room | Community Amenities (Paid + Complimentary) Experience lake livin' at this welcoming Locust Grove vacation rental! The 2-bedroom, 2-bath home is ideal for groups yearning for recreation and relaxation. Explore the area's historic sites, then return home to let your worries melt away in the infrared sauna and steam shower, unwind by the wood-burning stove, or enjoy a game night in the rec room. Stay on-site and enjoy optional access to community pools, a playground, and more!

Brewery Manor Sleeps 10 Hot Tub

Woodbourne Estate, circa 1810, is a National and Virginia historic registered landmark Manor House and farm nestled in the foothills of the Blue Ridge Mountains in Madison, Virginia. The 53-acre Estate is also home to our award-winning Bald Top Brewing Company which sits just a comfortable stroll beyond the Manor house. This magical Manor, with its gorgeous grounds, gardens, barns, ruins, pool, stream and vistas awaits! The Manor at Bald Top: Drink in the Moment!

Lakefront Access | Hour from DC | Kayaks Provided

Welcome to Lakeside Serenity, located in the Locust Grove gated community of Lake of the Woods. This charming residence, situated in a quiet cove, features a spacious backyard with direct lake access perfect for swimming, fishing, kayaking, or lounging lakeside. Enjoy the convenience of an on-site grill for delightful barbecues and dine al fresco in our outdoor seating area overlooking the lake. This home is a haven for anyone looking for a peaceful getaway!

Panorama Shores

Take a break and unwind at this peaceful expansive oasis. This lake front retreat boasts more lake access than you can imagine. Your own, pool, tennis court and huge yard to create memories with your friends and family. All linens provided including a set of outdoor towels for your use. The kitchen has been newly expanded and completely upgraded with 3 ovens, 2 islands and 2 sinks. This property was formerly listed as Anna Breeze. Now managed privately.