Vacation rentals with a pool in Orange County

Lakefront retreat with huge screened-in porch

Kick back on the screened-in porch or the dock and take in the view, or enjoy our kayaks. Community's amenities: golf course, 2 lakes, 8 beaches, outdoor pools, horseback riding, walking trails, parks/playgrounds, and a clubhouse for dinner, drinks, and Sunday brunch, all with a fabulous view of the 550-acre “big lake.” For history buffs, the area is rich in Civil War history and battlefields. Local wineries offer tastings and live music. [Due to health conditions, no pets or service animals.]

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!

Historic Bloomingdale Farmhouse w/Mountain Views

Situated on the crest of our 14 acre farm with beautiful mountain views on all sides, our 1840's farmhouse is the perfect location for a friends getaway, family retreat or wedding weekend. Conveniently located near several wedding venues including Market at Grelen (5 min), Castle Hill (15 min) and Barboursville (15 min). Plenty of options for hiking, antiquing, sightseeing and eating in all directions: Montpelier; 8 min to Orange; 15 min to Gordonsville; 30 min. to C'ville & Shenandoah Park.

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.

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

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.

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.

Moonfire Farm cozy Shenandoah Region Getaway

Experience charm and nature at Moonfire Farm! Our finished basement on a 5-acre hobby farm offers delightful animal encounters with chickens, ducks, alpacas, and hilarious goats. Our active family of three, including our 7-year-old daughter Piper, welcomes you. High-speed Internet and nearby wineries, breweries, hiking trails, and pick-your-own fruit locations await you. Explore our guidebook for recommendations. Book now for a memorable farm getaway!