Vacation rentals with a pool in Shenandoah Valley

4.99 out of 5 average rating, 80 reviews

Home in Moneta

Lake View Farm Retreat -Private Pickleball & Pool

Very private lake front oasis with lots of amenities and WiFi. Beautiful lake view with an in ground heated swimming pool, private stocked pond, walking trail, game room, playground, theater room, basketball court, workout room, and indoor pickleball court. This retreat would be perfect for multi-generational or multi family gatherings. The main house has 3 bedrooms and 3 and 1/2 bathrooms and a bunk room for children. A separate detached space has a bedroom and full bathroom. (8 Adults Max)

4.89 out of 5 average rating, 36 reviews

Home in Mineral

Lakefront Pool, Water Slide, Sauna, Dock, Hot Tub, Peloton

Lake Anna Lakefront: Private pool, 50-foot water slide, barrel sauna, Peloton, kayaks, ping-pong/pool table, game room... Gather 'round fire pit under starlit sky. Relax in the sauna or soak in a secluded hot tub, both overlooking the lake. No steps to primary bedroom on 1st floor. Private Dock: 3 kayaks, floats Game Room: foosball, air hockey, hoops, arcade Sleeps 12 in 5BR+loft: K, K, K, Q, Q, 2x bunk (twin/full) 3-Car Garage w/EV charger (standard/Tesla) $150 Dog fee, $150/day pool heating

4.83 out of 5 average rating, 107 reviews

Home in Lovettsville

Cozy 3500sf Private 10ac. pickleball-hot tub-pool

5/6 (6th bedroom has queen sofa bed) Bedrooms furnished w/linens and all your needs 10 private acres in Farm land views of horses Remodeled fully equipped Kitchen w/new appliances 5 full baths w/spa like showers 7 person hot tub 35,000 gallon in ground private pool opens May 25 Private Tennis Court (basic)/Basketball Court 2 Fire pits Picnic area with grills and patio furniture Kiddos play area w/swing sets and slides Large great room/family room 10 acres with 4 acres a forest Dining for 8+

4.94 out of 5 average rating, 17 reviews

Home in McHenry

NEW~Indoor Pool & Hot Tub~Game RM~Near Wisp~Dock!

The Big Dipper - Brand new construction with seasonal lake views & everything for your Deep Creek vacation. The perfect, all suite, 5 bedroom (including bunk room), INDOOR POOL cabin with a hot tub, fire pit, game room (pool table, shuffleboard & arcades), outdoor living room & fireplace, EV charger and more! This home is 5 minutes to Wisp Resort (Skiing), Lodestone Golf Course, local marinas, the grocery store, restaurants & across the street from Deep Creek Lake and a private dock space.

Home in Wintergreen Resort

4.93 out of 5 average rating, 58 reviews

Wintergreen Condo~ 1 Minute To Four Seasons Resort

You're sure to have a blast at this incredible mountain condo! Condo is walking distance to the Wintergreen Resort Ski Lodge, Restaurants, The Market, and much more! This is the only condo neighborhood at Wintergreen that has it's own private outdoor pool. If you are up for a short drive down the mountain; check out the quality breweries, restaurants, distilleries, golf, and other fun activities near by! The Charlottesville area has been named 2023 Wine Region of the Year by Wine Enthusiast!

Home in Wintergreen Resort

4.86 out of 5 average rating, 107 reviews

Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard

Sweeping views year round. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and walking distance to three great hiking trails. Sleeps 16: K, K, Q, 2 DBL,4 twin, 1PO ★Dogs OK ★2,714sqft ★HOT TUB for 7 ★Sound system ★2-Story vaulted ceiling, gas fireplace, 60"TV ★Dining table for 6 + breakfast bar ★Workspace w/ FAST Wi-Fi ★Shuffleboard ★Pool table Seasonal pool/tennis. Resort access not included. Pet fee $150. 8min walk or 3min drive to ski.

4.96 out of 5 average rating, 142 reviews

Guesthouse in Monrovia

Poolside Paradise in Monrovia, Maryland.

Enjoy your stay in this fabulous pool house located in a quiet neighborhood. Relax poolside during the day and enjoy the outdoor bar and kitchen for cocktails at sunset. Breathtaking views all around. Just 50 minutes from Baltimore and Washington DC and 10 minutes to historic downtown Frederick. Private entrance to backyard with a large green space on the backside of the pool house. We consider ourselves a couples retreat and don’t host gatherings. We look forward to hosting you soon:)

4.93 out of 5 average rating, 121 reviews

Guest suite in Warrenton

Lakeside 2-Bedroom Suite

Waiting to welcome you to our treasured peaceful lakeside living. Hot tub, swimming pool and canoe available to complete a family adventure. Two bedrooms joining a bath (more suitable for children and parents or 2 cozy couples); private sunny living room overlooking gardens and bird sanctuary on lake. Fish from property or by our canoe. Friendly, quiet suburb in beautiful Virginia countryside, but one hour drive to Washington DC for city life and adventures. Relaxation at its best!

4.89 out of 5 average rating, 137 reviews

Home in Woodstock

Sunset Ranch: Hot Tub! Mountain Views! Pool

If you want to bask in the beauty of the Shenandoah Valley, this is the perfect spot! Dip in the pool and watch the sun dip behind the mountains for some of the most gorgeous sunsets you will ever see! Soak in your own private hot tub. Dine on the patio underneath the market lights. Enjoy the scenery of the rolling hills with awesome mountain views. Inside this updated farmhouse has everything you need to relax and refresh. Venture out to the caverns, hiking, and wineries.

Home in Town of Rockingham

4.78 out of 5 average rating, 260 reviews

Stone Spring - Heated Salt Pool - on 2.5 Acres

Heated Salt water pool and hot tub on 2.5 Acres. Lawn games & outdoor living room! New for '21 - Stove, Upstairs Flooring, Foosball Table, Board Games, paint New for '20 - Antimicrobial door handles, kitchen items Completely separate owner/caretakers quarters onsite, occupied by our property manager. Pool, hot-tub, grilling, etc are private spaces for guests and NOT shared *entrance and egress through pool area* *playhouse removed, gas fireplaces inoperable *no pets

4.95 out of 5 average rating, 58 reviews

Villa in Luray

Private Indoor Pool~WiFi~ Arcade~Fire Pit~Views

Enjoy a beautiful spring escape! The villa features spacious and tastefully decorated interiors, providing ample space for relaxation and enjoyment. With its huge 20ft by 40ft heated indoor salt water pool you and your family can indulge in refreshing swims and soak up the sun in complete privacy. Whether you're seeking a rejuvenating getaway or quality time with your friends our villa rental is the perfect choice for a memorable and enjoyable vacation.