Holiday rentals with a pool in Culpeper County

4.99 out of 5 average rating, 153 reviews

Cottage in Locust Grove

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.

5 out of 5 average rating, 8 reviews

Home in Madison

NEW l Near Shenandoah ~ Pool ~ Hot Tub ~ Fire Pit

Welcome to Emerald Retreat! Tucked away on 10 peaceful acres in Virginia's scenic countryside, this is your ultimate escape into nature. Perfect for a family reunion or a friends’ retreat, this spacious 6-bedroom, 4.5-bath home offers a pool, hot tub, fire pit and more. Designed for unforgettable memories. Just minutes from Shenandoah National Park, local wineries, craft breweries, University of Virginia, and Charlottesville - this property offers outdoor adventure and wine-country relaxation.

4.99 out of 5 average rating, 127 reviews

Farm stay in Elkwood

The Garden View Suite—Zero In Hidden Fees!

Luxury on the farm! This private guest suite is situated on a 43-acre farm--Bees & Trees--and is attached to the North end of the main farmhouse. A private garden-gate guides you to the suite. Enjoy a magical sky full of stars while relaxing in the hot tub or enjoy the saltwater pool--all to yourself! You'll have breathtaking sunrise views from the front windows and gorgeous sunsets from your back porch! Be sure to visit the Farm Store where, as a guest, you'll get 10% off your purchases.

4.91 out of 5 average rating, 254 reviews

Apartment in Madison

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*

4.71 out of 5 average rating, 63 reviews

Lakefront Getaway | Close to DC | Near Winery

This Lake House features a delightful open floor plan and modern design with direct access to water from the backyard. Perfect for swimming, fishing and enjoying sunsets. Included: Awesome work-from-home setup with dual monitors, universal docking station, keyboard and mouse, so you can spend as much time out of the office as possible. The community offers a number of amenities including a pool, beaches, golfing and more! If none of those strike your fancy, our favorite winery is 5 min away.

4.92 out of 5 average rating, 66 reviews

Beach, Arcade, Hot Tub, 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

4.98 out of 5 average rating, 97 reviews

Home in Aroda

Sunset Retreat a cabin off the beaten path

Relaxation and quiet are two words that come to mind at Sunset Retreat. Close enough to stores for convenience but far enough away for solitude. Large yard, fire pit and concrete area if children want to create a masterpiece in chalk, there is also a tree swing next to woods. Close to many wineries, breweries and hiking. No WIFI or satellite tv, we have antenna only. You are welcome to bring your own hotspot . We have one smart tv. There is also a private in ground pool for summer time use.

4.92 out of 5 average rating, 25 reviews

Hummingbird Lakehouse

Hummingbird Lakehouse in Locus Grove, VA, offers stunning waterfront views 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.

5 out of 5 average rating, 53 reviews

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.

4.96 out of 5 average rating, 154 reviews

Home in Boston

Peacefield - Blue Ridge views near Culpeper

Welcome to the Peacefield! This retreat is nestled in the rolling foothills of the Blue Ridge Mountains in the shadow of Old Rag, overlooking Hazel River Farm (160 acres). The spacious estate is perfect for escaping the city. There are many options for relaxing with a deck, hot tub, pool (summer only), home theater, and an open kitchen connecting the dining and family rooms. The beauty of the estate includes walking trails, glimpses of sheep, and local art (watercolor and photography).