Vacation rentals with a pool in Orange County

NEW 7BR Lakefront Lake Anna, Pool, Spa, Dock

Your backyard opens directly to Lake Anna. From the main deck, the trees part and the cove appears—quiet water, private dock, heated pool and spa (seasonal), and a boathouse that feels like your own waterfront clubhouse. Inside, you’ll find a chef’s kitchen, multiple lounge spaces, a dedicated theater, karaoke room, full game floor, kids’ treehouse loft, office/den, and beautifully styled bedrooms (plus an optional 2-bedroom guest house above the carriage garage). This home was designed for mult

Blue House and a Pool

Relax at Lake Anna with friends and family at your own pool, hot tub and dock. Blue house boasts numerous spaces for entertaining and private chill time. House features 4 bedrooms, 3 large couches and 3 full bathrooms. The gourmet kitchen is fully stocked and ready for a home cooked meal after a full day on the lake. Tim's at Lake Anna is a short car ride or boat ride to enjoy a meal and cocktail. The Cove and Lake Anna Plaza at the 208 bridge are close by including boat and jet ski rentals.

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!

3 Acre 5BR Resort: private pool, hot tub boat dock

Gather your loved ones at a secluded 5BR lakehouse on 3 lush acres at Lake Anna. Dive into the new heated Salt-Water Infinity pool & hilltop lake view hot tub, soothe muscles in the sauna, or spark friendly rivalries in the game room and volleyball court. Cook up joy in the fully stocked kitchen and unwind by the fire under crystal clear starry skies. Serene water views, fireside chats, and room for every adventure, this is where cherished memories are made—your ultimate private escape awaits!

Near Lake Anna: Gem w/ Saltwater Pool & Arcade!

You may never want to leave this 5-bedroom, 3-bath vacation rental located just a short distance from Lake Anna! Watch a movie on the 110" projector, swim day or night in the heated saltwater pool, and unwind in the 8-person hot tub under the stars. Grill or smoke your favorite meats, then kick back in comfort. If you're looking to venture, visit wineries on the Monticello Wine Trail or head to James Madison's Montpelier for guided tours, gardens, and walking trails. Book your next escape now!

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.

Hot Tub, Arcade, Golf, Pub, Beach: 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.

2 Bdrm Private Suite @ Sunshine Acres

Charming guest suite in our home located in the Central Virginia countryside on 18 partially wooded acres. We offer early check in and late checkout, perfect for wedding guests & overnight trips. Relax to the sights and sounds of nature while exploring the area's many historic landmarks and award winning wineries. Due to the nature of our work as an active sanctuary for senior dogs, our space is not suitable for children under 15. We are able to accommodate infants upon request.