Holiday rentals with a pool in Shenandoah County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Shenandoah County

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Cabin in Woodstock

4.92 out of 5 average rating, 105 reviews

Luxury Cabin: Pool, Hot Tub, Romance & Family Fun

Escape to a romantic retreat featured in The Washingtonian as a top DC-area getaway. This enchanting three-bedroom cabin in the Shenandoah Valley offers everything you need for a perfect stay. Surrounded by lush woods with stunning mountain views and a short walk to the peaceful river, you'll experience nature at its best. Relax in king-size beds, swim in the indoor pool, or unwind in the hot tub. Savor the fire pit with a glass of wine under the starry sky. Book your unforgettable escape today!

Top Guest favourite

Home in New Market

4.97 out of 5 average rating, 128 reviews

Peaceful Shenandoah Valley Getaway

Our woodsy cabin is great for couples, families and groups. 2700 sf cabin has it all. Great location for wine tasting or golf weekends, ( Local course is one mile away) , antique shopping - cavern explorations! History buffs, nature lovers and people looking for relaxation will be pleased here. Very private! Small above ground pool (weather permitting) and hot tub for star gazing! Wi-Fi is available - Up to 2 pets allowed ($50/pet). Max number of guests for property use is 8.

Top Guest favourite

Cottage in New Market

4.97 out of 5 average rating, 141 reviews

Amazing coffee bar, pool, lake, fish, relax!

PET FRIENDLY Come experience Reel and Relax!! Hike, explore the trails, fish, float, go rafting, read, enjoy a fire, grill, shop/eat in super cute country towns... Whether its the river, the rolling mountains, the whispering breeze or the cozy cottage, this property offers all of the feels you are searching for without ever leaving! Every season is magical and offers its own reason to visit!!! "This place is amazing; you have literally thought of EVERYTHING! -past guest.

Superhost

Home in Strasburg

4.76 out of 5 average rating, 272 reviews

Cedar Creek Wayside Castle

1930 Stone House 'Mini Castle' on 9 private acres near Strasburg Virginia bordering Cedar Creek Battlefield and Belle Grove Plantation National Park. Home was built by Otis Elevator company in 1930 for their daughter. You have nature trails and fire pit, swimming pool (opened April 15th), deer and wildlife too. Short walk to historic Ceder Creek. Full estate is yours to play and relax. No dogs in pool. Pool is open into October usually. Hot tub is year round

Guest favourite

Home in Quicksburg

4.92 out of 5 average rating, 138 reviews

Overbank Riverfront Estate~Hot Tub~Pool~Views

This renovated farmhouse on the Shenandoah River is the ultimate vacation spot. Relax on the new massive deck sitting above the Shenandoah River with the blue ridge mountains as your backdrop. Play in your own private pool. Dine on the wrap around screened porch. Paddle under historic Meems Bottom Covered Bridge. This 100 year old farmhouse has been renovated to add modern comfort to timeless charm. Venture out to the caverns, hiking, and wineries nearby.

Guest favourite

Condo in Mount Jackson

4.87 out of 5 average rating, 98 reviews

Bike,Hike,Relax in Lux! at Bryce Resort

This recently renovated, modern condo offers the latest amenities, including WIFI and Smart TVs. The true charm lies in its outdoor options. Sip a hot drink on the balcony, watch the sunset, or cozy up by the fireplace. In the season, enjoy the Community Pool, explore slopes, lifts, dining, and shops nearby. Golfing, skiing, biking, ziplining, swimming, and canoeing at Lake Laura are a short walk away. Embrace modern comfort and thrilling outdoor adventures!

Top Guest favourite

Home in Luray

4.98 out of 5 average rating, 104 reviews

Walnut Lane

This house was purchased and furnished to be a vacation rental, from the coffee maker to the outdoor pool with a view. Luray has been our home, our escape, and our happy place for some time and we are excited to be able to share this town with you and your family. The house is large with 4 bedrooms and 3 bathrooms, beautiful views, and an above-ground pool. We are conveniently located near Lake Arrowhead, Luray Caverns, and Shenandoah National Park.

Guest favourite

Condo in Basye

4.79 out of 5 average rating, 131 reviews

Multi-Level Mountain Stay w/ Pool

Relax and recharge in this 2-bedroom multi-level condo at Chalet High, just 2 miles from Bryce Resort in Virginia’s scenic Shenandoah Valley. Featuring a full kitchen, fireplace, and private balcony, it’s ideal for families or couples seeking a cozy mountain escape. Enjoy access to an indoor pool, sauna, hot tub, and fitness center. Whether you're hiking, skiing, or simply unwinding, this peaceful retreat offers year-round comfort and convenience.

Guest favourite

Condo in Mount Jackson

4.93 out of 5 average rating, 140 reviews

Ski and Golf Condo Aspen East Condos Unit 212

Newly renovated condo located at Bryce Resort on ski slopes and golf course. This second floor condo faces the golf course with mountain views. Ski in and ski out. Walk to all of Bryce Resort’s amenities including events at the Shenandoah Center. Fully equipped kitchen with Keurig. 2 queen beds and 1 single bed. Wood burning fireplace. Smart TV’s in living room and bedroom. Washer and dryer. Walk-in shower. Wi-fi. Outdoor pool open seasonally.

Top Guest favourite

Home in Lost City

5 out of 5 average rating, 134 reviews

Mountain Retreat-Stunning Views/Pool/Hot tub

Pool is open from 5/26/25 - 9/30/25. Our secluded 5 acre mountain retreat in Lost City s a perfect space for couples, families (with older kids), and groups looking to get away from urban life and unplug. Plenty of outdoor excursions nearby, or just come to relax, unwind and enjoy the breathtaking views. Modern amenities and fiber optic internet ideal for remote work Hot tub with mountain views. 7 day rental from fri - fri from June - Aug.

Superhost

Tiny home in Fort Valley

4.8 out of 5 average rating, 285 reviews

Tiny Cabin Retreat 1 @ Camp Shenandoah Meadows

The Cabin sits on 40 acres in the heart of Fort Valley with views of the blue ridge mountains Across the property. The Cabin is part of the larger Shenandoah Meadows Camp with great amenities as the summer camps only operates June-August. Within a short drive there are hiking, biking, rock climbing, and many local attractions like Luray Caverns, Skyline Drive, vineyards and breweries. Firewood is included! *Pet Fee of $20.00

Top Guest favourite

Guesthouse in Strasburg

5 out of 5 average rating, 31 reviews

Shenandoah Valley cottage & private pool

This IG-worthy poolside cottage is located on the grounds of the historic Snapp House. It overlooks formal gardens, a wisteria-covered pergola (with swinging daybeds), barn, and a rolling landscape. This custom-designed space is modern, whimsical, and light-filled. Every detail has been considered. Window walls open up on both ends to provide a glorious through-breeze all year long. The perfect glamping experience!