Compare Vacation Rentals with Pools in Virginia

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Virginia vacation rentals
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Choose from Top-Rated Vacation Rentals with Swimming Pools in Virginia

1 Mi To Slopes! Family-friendly Massanutten Cabin - Virginia
9.5 135 reviews
Virginia
07/10 – 07/12
$478/nighttotal: $956 (2 )

1 Mi To Slopes! Family-friendly Massanutten Cabin

3 8
cabin, Massanutten
This cabin offers a prime Massanutten location, just 1 mile from the ski slopes and 1.9 miles from the Water Park, with James Madison University 14 miles away.
Enjoy family-friendly comfort in this 3-bedroom cabin with a swimming pool, spa, tennis court, and a fully equipped kitchen, providing convenient access to outdoor recreation and relaxation.
Hikers Paradise!  Come Relax This Summer!!! - Virginia
9.8 192 reviews
Virginia
07/03 – 07/05
$893/nighttotal: $1786 (2 )

Hikers Paradise! Come Relax This Summer!!!

5 12
apartment, Wintergreen
Just yards from the Blue Ridge Parkway and Appalachian Trail, this Wintergreen mountain apartment offers unparalleled access to outdoor adventures and is close to Wintergreen Resort and Sherando Lake Recreation Area.
This spacious 2850 square foot apartment, perfect for families and groups of up to 14, features 5 bedrooms, 3 bathrooms, and a swimming pool, alongside amenities like a full kitchen, air conditioning, and a relaxing den fireplace.
17-seat Theater, Hot Tub & Game Room: Ideal Home! - Virginia
9.7 69 reviews
Virginia
07/16 – 07/19
$899/nighttotal: $2697 (3 )

17-seat Theater, Hot Tub & Game Room: Ideal Home!

7 15
house, Massanutten
This Massanutten house offers a private swimming pool experience, conveniently located just 4.8 miles from Massanutten Resort Water Park and 17 miles from James Madison University attractions like Bridgeforth Stadium.
Boasting 2800 square feet, this family-friendly home features 7 bedrooms, a 17-seat theater, a game room, and a spa, ensuring entertainment for all guests with free WiFi and parking.
Stylish 7br/16 Pp Wintergreen Resort Home Ski/hike - Virginia
9.8 134 reviews
Virginia
07/16 – 07/19
$734/nighttotal: $2202 (3 )

Stylish 7br/16 Pp Wintergreen Resort Home Ski/hike

1 15
cabin, Wintergreen
Enjoy a mountain escape at this spacious cabin, located in the woods on a half-acre, less than 5 minutes from Wintergreen Resort's skiing, hiking, spa, pool, and tennis.
This family-friendly cabin accommodates 16 guests with 7 bedrooms and 6.5 bathrooms, offering a swimming pool, a deck with a grill, a 75” TV, ping pong, and easy access to neighborhood amenities like the Chestnut Springs Pool.
Massanutten Log Home Near Slopes, 2 Master Suites,  Hot Tub, Pool Table, Views - Virginia
9.8 333 reviews
Virginia
07/09 – 07/13
$615/nighttotal: $2460 (4 )

Massanutten Log Home Near Slopes, 2 Master Suites, Hot Tub, Pool Table, Views

5 12
chalet, Massanutten
Located in McGaheysville, this chalet is just a short drive from Massanutten Ski Resort and Massanutten Water Park, offering panoramic mountain views from its multiple decks.
This 2900 sq ft custom log chalet, built in 2012, sleeps 12 guests and features a private seven-person hot tub, an entertainment room with a pool table and wet bar, and a fully equipped kitchen, perfect for a getaway with a pool.
Cozy Mountain Chalet (#102) - Quiet Location | Summertime Secluded | Great Winter Views! - Virginia
9.2 45 reviews
Virginia
07/10 – 07/12
$294/nighttotal: $588 (2 )

Cozy Mountain Chalet (#102) - Quiet Location | Summertime Secluded | Great Winter Views!

3 8
chalet, Basye
Located within the Bryce Resort community, this chalet offers golf course and mountain views, approximately one mile from the main lodge and lifts and 2.5 miles from the Basye Community Store.
Enjoy a comfortable stay in this 1500 sq ft chalet, featuring 3 bedrooms, 2 bathrooms, and a guest capacity of 10, complete with a Jacuzzi tub and sauna, plus unlimited summer swimming pool access.
Where The Trail Ends - Virginia
9.9 303 reviews
Virginia
08/08 – 08/17
$154/nighttotal: $1386 (9 )

Where The Trail Ends

1 4
apartment, Wintergreen
Breathtaking mountain views are yours from this recently renovated condo at the 4-season Wintergreen Resort, offering convenient access to Shenandoah National Park and the Rockfish Gap Entrance.
Enjoy this family-friendly, 700 sq ft apartment with a cozy wood-burning fireplace, a fully equipped kitchen, and a private patio, all complemented by an on-site swimming pool perfect for a getaway with a pool.
Wintergreen Resort Cabin: Near The Slopes! - Virginia
9.9 91 reviews
Virginia
06/18 – 06/21
$324/nighttotal: $972 (3 )

Wintergreen Resort Cabin: Near The Slopes!

3 5
cabin, Wintergreen
Conveniently located near the Wintergreen Resort slopes, this 1700 square foot cabin offers easy ski access and is approximately 43 miles from Shenandoah Valley Regional Airport.
Enjoy family-friendly accommodations with three bedrooms, three bathrooms, and a fully equipped kitchen, plus a refreshing swimming pool perfect for your getaway.
Charming 4-bedroom Cottage With Ac In Williamsburg - Virginia
Virginia
12/27 – 12/30
$513/nighttotal: $1539 (3 )

Charming 4-bedroom Cottage With Ac In Williamsburg

4 16
cottage, Williamsburg
This cottage in Williamsburg is conveniently located just 1 mile from Williamsburg Premium Outlets and offers easy access to Water Country USA and Busch Gardens Williamsburg.
Enjoy a spacious getaway with 4 bedrooms, 3 bathrooms, and sleeping accommodations for up to 16 guests, complete with air conditioning, heating, and a refreshing swimming pool for your enjoyment.
The Bear's Den At Wintergreen- 6 Bedroom - Virginia
10 26 reviews
Virginia
08/07 – 08/09
$686/nighttotal: $1372 (2 )

The Bear's Den At Wintergreen- 6 Bedroom

6 14
cabin, Wintergreen
Located in Chestnut Springs within Wintergreen Resort, this cabin is nestled in the mountains, just 1 mile from George Washington National Forest and Reids Gap Trailhead, offering a perfect mountain getaway with a pool.
This spacious, family-friendly cabin accommodates up to 15 guests with 6 bedrooms, featuring two living rooms, two kitchens, a game room, and a large deck, all within easy reach of Wintergreen's outdoor activities and attractions.
Bluegreen Vacations Parkside Williamsburg, An Ascend Collection Resort - Virginia
9.1 1270 reviews
Virginia
12/27 – 12/30
$499/nighttotal: $1497 (3 )

Bluegreen Vacations Parkside Williamsburg, An Ascend Collection Resort

3 16
resort, Williamsburg
Directly across from Busch Gardens, this resort offers unparalleled convenience for theme park enthusiasts.
Enjoy a relaxing stay with a swimming pool, tennis courts, and self-catering villas featuring modern kitchens and private balconies with landscape views.
Relax In Style | 2 King Beds - *Pool* - Pacman! - Virginia
9.9 74 reviews
Virginia
07/22 – 07/31
$160/nighttotal: $1440 (9 )

Relax In Style | 2 King Beds - *Pool* - Pacman!

1 3
apartment, Lynchburg
This stylish apartment is located in Downtown Lynchburg, offering convenient access to universities and hospitals, with Liberty University 5.6 miles away and the University of Lynchburg 3.6 miles away.
Enjoy a unique stay with a PACMAN gaming center and a swimming pool, perfect for travelers seeking a getaway with a pool.

Find a Luxury Vacation Rental with a Private Pool in Virginia

Romantic Cottage With Blue Ridge Mountain Views - Virginia
9.9 287 reviews
Virginia
07/06 – 07/09
$168/nighttotal: $504 (3 )

Romantic Cottage With Blue Ridge Mountain Views

1 2
apartment, Stanardsville
Secluded on 150 acres with mountain views, this Stanardsville apartment is just minutes from Shenandoah National Park, Skyline Drive, and the Appalachian Trail, offering easy access to hiking and a fishing pond.
This apartment features a private kitchen, air conditioning, and a swimming pool, making it ideal for romantic getaways and quiet escapes year-round with wineries and antique shops nearby.

Top cities

Best Family-Friendly Vacation Rentals with Pools in Virginia

Among the 53117 accommodations in Virginia, here are the 8 best family friendly rentals

Mt. Relaxcation~on Resort~hottub~pool Table~arcade - Virginia
9.8 220 reviews
Virginia
12/27 – 12/30
$1828/nighttotal: $5484 (3 )

Mt. Relaxcation~on Resort~hottub~pool Table~arcade

6 16
resort, Massanutten
Located in McGaheysville, this resort is surrounded by George Washington National Forest, 2.0 miles from Massanutten Overlook and Massanutten Ridge Trail, and 16.0 miles from Shenandoah National Park.
This 2,700 square foot resort accommodates up to 16 guests and features a seasonal community swimming pool, a bonus fun room with arcades, and a hot tub for a perfect getaway with a pool.
Holiday Inn Club Vacations Williamsburg Resort - Virginia
9.0 1038 reviews
Virginia
08/15 – 08/16
$184/nightfor 1 night

Holiday Inn Club Vacations Williamsburg Resort

1 3
resort, Williamsburg
Just 1 mile from Cedar Valley Shopping Center and Williamsburg Marketcenter, this resort offers easy access to shopping and is within 12 miles of Water Country USA and Busch Gardens.
Enjoy a family-friendly resort experience with an outdoor and an indoor swimming pool, complete with free Wi-Fi and on-site parking.
Holiday Inn Express & Suites Williamsburg By Ihg - Virginia
8.4 1485 reviews
Virginia
07/06 – 07/11
$162/nighttotal: $810 (5 )

Holiday Inn Express & Suites Williamsburg By Ihg

1 1
resort, Williamsburg
Minutes from Colonial Williamsburg, this resort offers convenient access to historical immersion and is a short drive from Busch Gardens and Water Country USA.
Enjoy relaxation and recreation with the resort's indoor swimming pool, complimentary hot breakfast, and on-site fitness center, perfect for a getaway with a pool.
Spacious Family Retreat-hot Tub & Game Room - Virginia
Virginia
08/07 – 08/09
$560/nighttotal: $1120 (2 )

Spacious Family Retreat-hot Tub & Game Room

5 14
house, Wintergreen
Located in Wintergreen, this vacation home is approximately 35 miles from Shenandoah Valley Regional Airport.
This spacious 3050 square foot house with 5 bedrooms and 3 bathrooms offers a seasonal outdoor swimming pool, a hot tub, a game room with table tennis and darts, and is ideal for families and winter sports enthusiasts with on-site ski amenities.
Bright 3rd-floor Courtyard Condo With Balcony, Pools, Gym, & Ac - Virginia
9.4 23 reviews
Virginia
11/27 – 12/05
$220/nighttotal: $1760 (8 )

Bright 3rd-floor Courtyard Condo With Balcony, Pools, Gym, & Ac

2 5
apartment, Virginia Beach
Directly on the beach in Sandbridge, Virginia Beach, this waterfront condo offers stunning ocean views and is a short drive from the Neptune Statue and Ocean Breeze Waterpark.
This 1400 square foot apartment features two bedrooms and two bathrooms, comfortably sleeping up to five guests, and includes access to three swimming pools and free parking for two vehicles, making it an ideal family getaway with a pool.
One Of The Best Views In Wintergreen! - Virginia
9.9 67 reviews
Virginia
07/05 – 07/12
$436/nighttotal: $3052 (7 )

One Of The Best Views In Wintergreen!

4 8
apartment, Wintergreen
Experience unparalleled panoramic views of the Shenandoah Valley and surrounding mountains from this apartment, perfectly situated within Wintergreen Resort, just a short walk to High Country Park and only one mile from the Blue Ridge Parkway.
This family and pet-friendly apartment offers four bedrooms accommodating up to nine guests, featuring a fully stocked kitchen, a stone fireplace, and access to a luxurious indoor swimming pool, ideal for a pool getaway.
Tumnus Mtn Cabin *Pool*pvt Hot Tub *Snp*farmtours - Virginia
9.9 648 reviews
Virginia
09/01 – 09/08
$171/nighttotal: $1197 (7 )

Tumnus Mtn Cabin *Pool*pvt Hot Tub *Snp*farmtours

1 1
gîte, Stanardsville
Secluded in the Blue Ridge Mountains near Stanardsville, this gîte offers a peaceful escape with private trails on 58 acres, just a 10-minute hike to Shenandoah National Park Back Country and a short drive to Monticello.
This family-friendly gîte accommodates 8 guests and features a private hot tub, a seasonal outdoor swimming pool, and a well-equipped kitchen, making it an ideal getaway with a pool.
Wolf Creek Farm B&b And Motorcycle Manor At Wolf Creek Farm, Llc - Virginia
9.4 67 reviews
Virginia
08/08 – 08/17
$169/nighttotal: $1521 (9 )

Wolf Creek Farm B&b And Motorcycle Manor At Wolf Creek Farm, Llc

2 4
glamping, Cana
Experience a glamping getaway in Ararat, offering tranquil mountain views and located 60 miles from Piedmont Triad Airport.
This family-friendly glamping provides a swimming pool, air conditioning, and a kitchen with a fridge and microwave, along with wellness packages and abundant outdoor activities like hiking and cycling.

Find places to stay

Explore Our Top Pet-Friendly Vacation Rentals with a Pool in Virginia

Among the 53117 accommodations in Virginia, here are the 8 best pet friendly rentals

Private Mountain Condo - Virginia
9.3 3 reviews
Virginia
09/01 – 09/08
$147/nighttotal: $1029 (7 )

Private Mountain Condo

1 1
house, Wintergreen
Enjoy a mountain retreat at this house in Wintergreen, located approximately 35 miles from Shenandoah Valley Regional Airport.
This accommodation features a seasonal outdoor swimming pool, a garden, and a terrace, perfect for outdoor enthusiasts with access to hiking and skiing opportunities.
Massanutten Family Retreat: Hike, Lounge & Game On - Virginia
9.8 53 reviews
Virginia
07/03 – 07/05
$653/nighttotal: $1306 (2 )

Massanutten Family Retreat: Hike, Lounge & Game On

1 12
apartment, Massanutten
Located within the Massanutten Resort in the Shenandoah Valley, this apartment offers prime access to year-round activities and is just miles from Shenandoah National Park.
This family and pet-friendly apartment, accommodating up to 14 guests, features five bedrooms, three bathrooms, and a fully stocked kitchen, making it an ideal group getaway with a swimming pool.
Jmu, Dog Friendly, Rec Passes, Hiking! - Virginia
8.6 20 reviews
Virginia
06/18 – 06/21
$220/nighttotal: $660 (3 )

Jmu, Dog Friendly, Rec Passes, Hiking!

3 5
apartment, Massanutten
Located in Keezletown at the base of Massanutten Mountain, this apartment is a 20-minute drive to Massanutten Resort and a 30-minute drive to Shenandoah National Park.
This 1740 sq ft, 3-bedroom, 2-bathroom apartment comfortably sleeps up to ten guests and offers access to an indoor pool, hot tubs, and fitness rooms at Massanutten Resort, perfect for a getaway with a pool.
House On The Slopes  Ski-in/out - Virginia
9.4 51 reviews
Virginia
10/09 – 10/11
$418/nighttotal: $836 (2 )

House On The Slopes Ski-in/out

3 10
chalet, Wintergreen
Direct ski-in/ski-out access to the Tyro slopes is available from this chalet, located in the Pedlars Edge neighborhood of Wintergreen, offering breathtaking sunrise mountain views and proximity to Shenandoah National Park.
This family-friendly chalet accommodates up to 10 guests and features a swimming pool, a fully stocked kitchen, complimentary Wi-Fi, and provided essentials, making it an excellent choice for a getaway with a pool.
Cozy Condo On The Slope At Bryce Resort! - Virginia
9.7 155 reviews
Virginia
07/31 – 08/03
$218/nighttotal: $654 (3 )

Cozy Condo On The Slope At Bryce Resort!

1 2
apartment, Basye
This ground-level apartment in Mount Jackson offers prime access, just 350 kid steps from Bryce Resort's ski lift, community swimming pool, and golf course, with parking directly across the unit.
Enjoy a comfortable stay with a wood-burning fireplace, a private balcony with panoramic vistas, and 300 mbps WiFi, perfect for year-round Shenandoah Valley adventures including mountain biking and cavern tours, all within this pet-friendly accommodation with a pool.
Mcgaheysville Home W/ Screened Porch & Gas Grill! - Virginia
9.5 18 reviews
Virginia
07/10 – 07/12
$483/nighttotal: $966 (2 )

Mcgaheysville Home W/ Screened Porch & Gas Grill!

4 8
house, Massanutten
Located in McGaheysville, this house offers convenient access to Massanutten Resort Water Park, just 2.3 miles away, and is within 15 miles of James Madison University.
This 2000 square foot home with a pool accommodates up to 17 guests across 4 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, air conditioning, a fitness center, and tennis courts for an enjoyable stay.
Swimming Under The Stars In The Historical District - Virginia
9.0 13 reviews
Virginia
07/06 – 07/11
$149/nighttotal: $745 (5 )

Swimming Under The Stars In The Historical District

2 1
apartment, Lynchburg
Experience Lynchburg's Historical District in this 2-bedroom apartment, conveniently located 3.9 miles from Lynchburg College and 8.7 miles from Liberty University.
This family-friendly apartment offers 1130 square feet of space, air conditioning, a full kitchen, and a private swimming pool for a unique recreational experience, with free WiFi and parking available.
Hot Tub Pool Pac Man Foosball Dogs Ok Tennis Golf - Virginia
9.8 18 reviews
Virginia
07/05 – 07/12
$277/nighttotal: $1939 (7 )

Hot Tub Pool Pac Man Foosball Dogs Ok Tennis Golf

4 8
apartment, Wintergreen
Just 4 minutes from Wintergreen ski slopes, this apartment offers a prime rural mountain location, a short walk to trails and only 1 mile from Founder's Overlook for spectacular sunrises.
This 1300 square foot apartment accommodates up to 9 guests and features a hot tub with a forest view, Foosball, PAC-MAN, and access to an outdoor swimming pool with a tennis court, perfect for a getaway with a pool.
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