Vacation 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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Guest favorite

Bungalow in Stanardsville

4.93 out of 5 average rating, 241 reviews

Romantic, Carriage House Studio at Fairhill Farm

Delight in the bold views of the Blue Ridge Mountains while lounging on your private deck at the Carriage House on Fairhill Farm. Spring has sprung. We are open. Stroll on 300 acres Hike our private trails. Fish in private pond or river. Enjoy pool. Delight in farm animals including our miniature horses. Located 2 hours southwest of Washington, DC, 1 1/2 hours east of Richmond and 25 minutes north of Charlottesville, VA. Near Shenandoah National Park, Monticello, Montpelier,Ash Lawn, and UVA

Mar 28 – Apr 4

ﺩ.ﺇ598 per night

Guest favorite

Apartment in Madison

4.9 out of 5 average rating, 229 reviews

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*

Jun 17 – 24

ﺩ.ﺇ307 per night

Guest favorite

Farm stay in Stanardsville

4.96 out of 5 average rating, 514 reviews

GreeneHouse.POOL*HotTub*MTNviews*FarmGOATS*Hiking

The private, adults 18+only, Greene House apartment is located at ground level of the main farmhouse. Views out the kitchen windows and private patio overlook the piedmont valley. Great for couples or a gathering of 4 adult friends. Private hot tub on porch+shared in-ground pool. A ten minute hike gets you into Shenandoah National Park Back Country. 20 min. to Swift Run Gap SNP. Walking trails. No pets. Check out Cair Paravel Farmstead on FB/the web to see all we have to offer. High speed WiFi

Aug 30 – Sep 6

ﺩ.ﺇ574 per night

Guest favorite

Cabin in Gordonsville

4.82 out of 5 average rating, 228 reviews

1700's Summer Kitchen Cottage #147 Pool & WIFI

Escape from city life on a beautiful historic 250-acre estate. It is close to historic attractions and wineries. You’ll love it because of the gorgeous outdoors and historic charm. This place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). There is WIFI. This is only 20 minutes away from Jefferson's Monticello, and James Madison's "Montpelier" or play golf (5 min) away. Treat yourself to an onsite certified massage wellness therapist.

Feb 24 – Mar 3

ﺩ.ﺇ516 per night

Guest favorite

Condo in Wintergreen Resort

4.95 out of 5 average rating, 201 reviews

Eight Minute Walk to Everything

This one-bedroom, one-bath condo is centrally located. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within an 8 minute walk. It's a one-story, downstairs unit that includes a back porch with just a few steps down to the ground. Perfect for taking the dog outside in the pet-friendly space. Full kitchen and dishes, wood-burning fireplace, balcony, and all towels and linens are provided for your convenience. Sleeps 3.

Oct 18 – 25

ﺩ.ﺇ392 per night

Guest favorite

Home in Robertson

4.92 out of 5 average rating, 184 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.

Feb 11 – 18

ﺩ.ﺇ2,514 per night

Guest favorite

Cabin in Culpeper

4.97 out of 5 average rating, 159 reviews

Comfortable and unique 1790's log cabin

Recently restored 1790's log cabin with modern amenities on a 30 acre horse farm. Secluded wooded setting with pond view, less than 1,000 feet from main house and only 5 miles from downtown Culpeper with it's fine dining and quaint shops. Take a short drive to scenic Shenandoah hiking & biking trails, local vineyards and distilleries, Civil War sites, Commonwealth Equestrian Park, stroll around the farm or just unwind on the front porch or in front of the wood stove with a good book.

Jun 12 – 19

ﺩ.ﺇ465 per night

Guest favorite

Guesthouse in Troy

4.99 out of 5 average rating, 121 reviews

Beaver Pond Farm - Near Charlottesville

Relax at this unique and tranquil getaway. Sit on the screened in porch and enjoy the sights and sounds of nature while you enjoy a beverage. Take a walk on miles of trails that are adjacent to the property. Visit the Downtown Mall, Monticello, a Winery, a Brewery, or UVA (20 min). Enjoy a dip in the pool (JUN-AUG) or relax by the firepit - perhaps joined by the horses for cocktails. Feel like staying in - SmartTVs and Gig-speed Internet await. Easy checkout. No cleaning fee.

Jan 26 – Feb 2

ﺩ.ﺇ504 per night

Guest favorite

Home in Lost City

5.0 out of 5 average rating, 108 reviews

Mountain Retreat-Stunning Views/Pool/Hot tub

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 fiberoptic internet ideal for remote work Hot tub with mountain views. Pool is open from 5/27/24 - 9/30/24. Min 7 day booking in June, July, August and September from from Friday to Friday.

Sep 6 – 13

ﺩ.ﺇ1,784 per night

Guest favorite

Farm stay in Barboursville

4.98 out of 5 average rating, 178 reviews

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!

Sep 21 – 28

ﺩ.ﺇ503 per night

Guest favorite

Townhouse in Wintergreen Resort

4.94 out of 5 average rating, 141 reviews

Fantastic retreat in ideal location, dogs welcome!

Wintergreen Resort is a fantastic, all season destination, with adventures for everyone! We are a pet and kid friendly, 2br/2ba townhome, located in the heart of all the action. Ski check-in, Mountain Inn, restaurants, & the Market stocked with all the essentials located right next to our community. Come hike, golf, play tennis, swim in our private pool or lakes, ski, snowboard, tube, and vineyard, brewery, distillery, or cider hop. We have it all!

Dec 5 – 12

ﺩ.ﺇ415 per night

Guest favorite

Farm stay in Crozet

4.95 out of 5 average rating, 155 reviews

Refreshed '24, Mt Views & Pool: Sunset Farm Studio

2024 Upgrades! Sunny, spacious Q bed/living room upstairs (wood stove); mini-kitchen & bath downstairs on a 10-acre farm with 180-degree views of Blue Ridge Mts. A floor mattress is available for an extra fee. Quiet, private, big-sky, 5 min from Crozet. I have a blind dog; no visitor dogs. It is a perfect place to be on retreat/ wine country or get work done (WiFi and a printer). NEW 50" TV.

Aug 16 – 23

ﺩ.ﺇ517 per night