Holiday rentals with a pool in Shenandoah Valley

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Top-rated rentals with a pool in Shenandoah Valley

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

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Top guest favourite
Cabin in Dayton
4.99 out of 5 average rating, 222 reviews

Luxurious Cabin By the Creek! Inground pool! Spa!

Rest&Relax with the whole family at this peaceful place to stay while sitting beside the stream. Recently Renovated! Close to many hiking and mountain biking trails. If you love nature, or enjoy time by the water there are many lakes near by. 25 minutes from Harrisonburg and JMU. Close to natural chimney campground. 20 minutes from the West Virginia line. Also has a covered deck with a outdoor bar and a TV. Hot tub conveniently located right off from the bar and deck. Pool open Mar.13-Sep.30!

Top guest favourite
The exterior of the converted barn and silo is softly illuminated by string lights at dusk. A serene pond, framed by smooth stones, reflects the warm glow of light. The porch invites relaxation with its spacious seating and rustic charm, creating a peaceful outdoor setting.
Barn in Louisa
4.99 out of 5 average rating, 138 reviews

Unique OASIS - Silo Barn - Swim Pond- 5 Miles Trai

4 unique rentals available (click our profile)! Unwind at this Central VA Country Paradise! Stay in a converted Barn & Silo w/ private natural swim pond and waterfall tucked into the woods on 140 Acres! Your own Oasis awaits, step out on your porch for coffee/drinks with the farm animals. Take a hike around the Lake on the 5+ miles of trails before cooling off in the pond while you gaze up at the stars. Sheep, Dwarf Fainting goats(next to silo 10' away), Chickens, Ducks, Bunnies, & Turkeys.

Top guest favourite
A round green yurt stands surrounded by a grassy area, accented by a flower bed of daffodils in bloom. A wooden deck leads to the entrance, while a fire pit with log seating is positioned nearby. Bare trees provide a serene mountain backdrop.
Yurt in Stanardsville
4.96 out of 5 average rating, 1,286 reviews

Yurt*FARM*horses*goats*woods*STARS*Hotub*Hiking

Come experience living in a round structure filled with amenities-fully equipped kitchen, deep tub, heating and AC, hot tub and in-ground pool. Great for couples, friends, and families. A 10 minute hike gets you into Shenandoah National Park, explore our 58 acres on numerous walking trails, visit Charlottesville, historical sites, caves, or play in rivers. Child friendly- no pets.( PRIVATE hot tub Nov 20- March 1.) Check out Cair Paravel Farmstead on FB/the web to see all we have to offer.

Top guest favourite
A private deck offers unobstructed views of rolling hills and distant mountains, framed by bare trees and open fields. The white railing complements the natural landscape, creating a serene outdoor space to enjoy the surrounding scenery.
Cottage in Stanardsville
4.95 out of 5 average rating, 293 reviews

Farm Studio with Blue Ridge views 20 mins from SNP

The Carriage House Studio is perfect for a romantic getaway or quiet escape. Enjoy stunning mountain views from the deck. Hike our private trails. Fish in pond or South River. Enjoy pool. Delight in farm animals including our miniature horses. Less than 20 mins from Shenandoah National Park and Appalachian Trail. Located 2 hours southwest of Washington, DC; 1 1/2 hours east of Richmond; and 25 minutes north of Charlottesville, VA. Near wineries; Monticello, Montpelier, Ash Lawn, and UVA.

Guest favourite
A spacious living area features a brick fireplace as a focal point, surrounded by natural light from windows. Comfortable sofas are arranged for conversation, with soft cushions added for support. A wooden floor complements the neutral tones, creating a cozy and inviting space.
Cabin in McGaheysville
4.94 out of 5 average rating, 139 reviews

Cozy Cabin in Massanutten Resort, Private Yard

Enjoy the perfect blend of relaxation and adventure close to everything the Massanutten Resort area has to offer. Just 5 minutes from the resort’s top attractions: ski slopes, water park, outdoor pools, golf courses, mountain biking trails, and much more. Located only 15 miles from downtown Harrisonburg and James Madison University, easy access to local shops, restaurants, museums, and entertainment. Discover the scenic caverns, wineries, breweries, hiking, and endless outdoor adventures.

Top guest favourite
The living area features large two-story windows that offer views of the surrounding wooded landscape. A cozy leather sofa and armchair are complemented by a wooden dining table with seating for six. Warm lighting and natural textures enhance the inviting atmosphere.
Cabin in Hedgesville
5 out of 5 average rating, 128 reviews

Cozy Secluded A-Frame Cabin Retreat

Visit us on IG @almostheavenwvcabin for the latest photos and cabin moments! Welcome to Almost Heaven Cabin, our beloved A-frame escape tucked away on a private, wooded acre in the heart of the Sleepy Creek Wildlife Management area. Surrounded by 23,000 acres of protected wilderness, this cabin was created as a peaceful family retreat from city life-yet it's just a scenic 1.5-hour drive from DC and Baltimore. Expect quiet mornings, fresh mountain air, and a true West Virginia getaway.

Top guest favourite
An open living area features high wooden ceilings with exposed beams, creating a spacious atmosphere. A large kitchen island with bar seating is situated near a dining table. Two spiral staircases lead to upper levels, while large windows frame views of the surrounding nature.
Home in Robertson
4.93 out of 5 average rating, 245 reviews

One Of A Kind Home in VA Wine Country on 50 acres

Welcome to Lumusa Lodge. Leave your cares behind as you turn onto the windy road that leads you to this beautiful 50-acre retreat. We are proud to share our home and hope your time here is rejuvenating. Designed/built by a Hollywood actor and situated in wine country, this home is an hour from Dulles, 45 minutes from Charlottesville & 15 minutes from Culpeper. We have an adjacent farmhouse if you need additional space. Great venue for weddings, bachelorettes, and other special events.

Top guest favourite
A spacious yurt is surrounded by lush greenery, with trees framing its exterior. The entrance is marked by a set of steps leading up to the door. Natural stone borders the well-maintained pathway, enhancing the connection to the countryside.
Yurt in Afton
4.96 out of 5 average rating, 112 reviews

Mountain View Getaway Yurt

Come enjoy country living in beautiful western Albemarle county. Our yurt is on a 13 acre property on a quiet country road. (My husband and I also have our home about 200 ft away from yurt). The yurt features a relaxing outdoor claw foot tub/shower with beautiful country views. The private bathroom is situated on the deck of the yurt. The pool is a shared space directly behind our home. The wooded part of the property is private with a beautiful walking trail for you to enjoy.

Guest favourite
Tiny home in New Market
4.94 out of 5 average rating, 145 reviews

Lakefront Escape w/ Retreat, Fish, Swim, Pets okay

Private lakefront, vintage Airstream, with firepit, stargazing, and a full game room—perfect for a peaceful escape. Unplug, relax, and enjoy quiet waterfront views just steps from your door. Perfect for 2–3 guests, this "weekend escape" features a private firepit, waterfront, plus access to a fun game room. Relax under incredible dark-sky stargazing just minutes from Shenandoah National Park, wineries, and hiking trails. Pet-friendly. Great for last minute trips!

Top guest favourite
Double doors framed by potted plants and embellished with decorative wreaths welcome guests into the home. The brick exterior and pathway provide a warm entryway, hinting at the charm within.
Guest suite in Penn Laird
5 out of 5 average rating, 163 reviews

On Cottonwood Pond

A beautiful country setting just minutes from Harrisonburg and JMU, winter snow sports (skiing/tubing/ice skating) at Massanutten Resort, Shenandoah National Park, hiking, other local universities and countless Shenandoah Valley attractions! You won't want to miss the new features in this home with a full kitchen, updated fixtures, plush accommodations and thoughtful touches throughout. Enjoy a quaint getaway in this meticulously designed home away from home!

Guest favourite
A cascading waterfall is observed flowing over rocks and creating a series of smaller falls. Surrounding trees provide a natural setting, with clear water collecting in a serene pool at the base. The sky is partly cloudy, enhancing the tranquil atmosphere.
Cottage in Covington
4.94 out of 5 average rating, 285 reviews

Beaverdam Falls, Earlehurst Cottage

Built for $500.00 dollars "back-in-the-day," the Earlehurst Cottage was inhabited by The Carters, a humble, cute old country couple. Here, they raised two daughters. Today, the house is tastefully appointed where expected - & comfortable to modern standards - yet, it has been left as charming, rustic & cozy as it had always been: with elements of the original decor, windows, plaster walls, etc., being preserved. Pets stay for free!

Top guest favourite
A bright game room features a blue pool table at the forefront, surrounded by a variety of games like foosball and air hockey. Comfortable seating is arranged near large windows, allowing natural light to fill the space. Tall bar stools add extra seating options.
Home in Nellysford
5 out of 5 average rating, 105 reviews

Family Fun on 151: Game Room+Screen Porch+Hot Tub

Luxury meets location at this spacious golf-course retreat—minutes to Nelson 151’s vineyards, breweries, and hiking. Fun for adults & kids with garage game room, board games and books. Enjoy summer fun with screened porch, BBQ, lawn games, and gas fire pit. Great layout for groups and families. 2 King beds, 1 Queen, 2 Doubles. EV charger Community pool access Discounted weekly/monthly stays, and just 35 mins to UVA.

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