
Holiday rentals with a pool in Shenandoah Valley
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Top-rated rentals with a pool in Shenandoah Valley
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House rentals with a pool

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat
We had the absolute best time staying here. We had two families staying together, 10 total. With more than enough space! The location was perfect. The space was clean and cozy. We had the best time and made some amazing memories with our friends. Also we slept at night on the third floor with a window opened and it was so quiet outside! Thank you for opening your home to us!

Mountain Retreat-Stunning Views/Pool/Hot tub
We had an incredibly relaxing, peaceful, quiet getaway. The house is more than enough space for 2 people, well stocked kitchen, amazing scenery. Beautiful Mountain View’s, screened in porch, super serene.

Peaceful 3-BR Mountain home w/Fireplace + Hot tub
Our family of four needed a quiet get away, and we enjoyed the beautiful days and evenings, inside and on the deck! Hikes nearby, spa nearby, restaurants, grocery, gas also nearby. Great resort year round! Lots of activities if you want them, and lots of peaceful nature if you want. Great!

Walnut Lane
My husband, brother, and two of our friends spent the weekend at Brad’s house and we had a lovely time. It was extremely conducive to relaxing. We cooked our meals there. The kitchen was very clean and we had found everything we needed for our meals. We were able to use lies the front porch. The pool was closed, but it looked very nice. Brad is an amazing host. He will answer your questions quickly. I would highly recommend staying at Brad’s place to anyone.

Bear's Mountain Escape
Great stay! Perfect location and space was great. A tad smaller than what it looked like in the photos, but overall, great! The kitchen did not have any pantry space, but we made do with a shelf above the microwave and bins on top of the fridge. A day prior to check-in, I received an email stating the pool in the complex was closed for repairs. A bit disappointed at first, but it ended up working out really well. We had access to the SPA indoor and outdoor pools and the outdoors ended up being too cold to swim in. The indoor pool was no problem at all and they were very accommodating with lettings us have access throughout our stay. We would stay here again for sure!

Mt. RelaxCATION~on resort~hottub~pool table~arcade
Our stay was everything we could have wanted for a weekend with friends. James was extremely helpful, flexible, and communicative, and the house is clean, well stocked, and packs a lot of space & fun into a small footprint.

Historic Peace and Plenty Farm: Pool House
Duane and Matt were absolutely wonderful hosts! They helped make our quick weekend getaway truly unforgettable. Every amenity at the property was thoughtfully provided, and our daughters enjoyed every bit of it. Even while traveling internationally, Duane remained incredibly attentive and responsive, going above and beyond to ensure our stay was perfect. One of the highlights for our girls was getting to meet a baby sheep—such a thoughtful and special touch! They were especially taken with little Pinky Pie and are still talking about her. Thank you again, Duane, for sharing your beautiful property and creating such a memorable experience for our family!

Sunset Ranch: Hot Tub! Mountain Views! Pool
Great place to stay! We enjoyed our time there. Easy to separate dogs in the house. Wonderful yard to play with the pups in. If you have pups be aware the few cars that do travel the road do so quite fast. We didn’t get to take advantage of the pool or hot tub, but they appeared well maintained. Would absolutely stay here again. Out far enough with pretty views, but convenient to lots of things. Highly recommend!
Apartment rentals with a pool

The Modern Mountain Condo
We had an absolutely wonderful stay at Randolph’s mountain getaway! The space was peaceful, clean, and beautifully located—just the perfect escape from the noise and busyness of everyday life. Randolph was a fantastic host—warm, responsive, and helpful! He made sure we had everything we needed for a comfortable stay and offered great local tips in his guidebook. If you're looking for a relaxing, private retreat in the mountains with a thoughtful and welcoming host, this is the place. We’ll definitely be back!

Mtn/Firework Views from Private Deck ~ King Suite
Susie’s place was PERFECT for my weekend of solitude and peace. I was able to relax and just take it easy in a comfortable home with a beautiful view. The home was clean and felt so comfortable. There were lots of personal touches that really show Susie put a lot of thought into the space. For example, the motion sensor nightlights in the bathrooms. And the dimmable lights in the bedroom. Check in and check out instructions were very clear and easy to follow, she even included a map of where to park! I can’t say enough great things about this experience.

Five Minute Walk to Everything!
This place was great! Conveniently located with tons of things to do, many walkable from the condo. The photos and descriptions were super accurate and our dogs even felt welcomed! We appreciated the convenience of The Market, The Edge, Upper Crust, and really enjoyed all of the Memorial Day activities that Dave ad Paige let us know were happening. It was the perfect place to unwind after a day of adventuring. Dave and Paige were super hosts all the way around. We'd love to come back here again!

Eight Minute Walk to Everything
beautiful mountain top and away from the hustle and bustle. The place was very clean and peaceful, but the oven temp was a little off other then taht the place was perfect.

Ski-in/Ski-out Wintergreen Highlands Condo -Views!
Fantastic place to stay and a very good host. Communication from the host was always extremely fast, detailed, and helpful. The space itself is fantastic - perfect view of the Blue Ridge Mountains skyline and sunset. Also, especially in the skiing off-season (which it was for our visit), it’s very close to Devil’s Backbone, Bold Rock, Three Notch’d, etc, but you are still far enough away to feel like you’ve gotten away from everything. There’s also a solid-looking pizza restaurant in walking distance, though we did not make it there during our visit. The condo has 2 stories that both serve their purpose very nicely - the upstairs has a nice living space and a clean, very usable kitchen. The downstairs has bunk beds and you could walk from the downstairs patio to the slopes. In the offseason, there is a nice hiking trail that is no more than 100 yards away. Overall, we had a blast and would love to return! Thank you!

Cozy, clean, quiet mountain condo- King bed
Super clean condo with everything we needed. Perfect for a stay in Wintergreen!

2-min drive from hiking/resort, seasonal HOA pool
Very clean and a great place to sit back and relax after a long day out. The living room features two sliding glass doors with screens, which was perfect for the weather in early-June. That and the covered balcony was where we sat back and relaxed.

King Bed Slope Side Retreat in Village Central
Unit was perfect for our long weekend! We had one small hiccup at check in but the host was quick to answer/reply and got it resolved right away! The home was clean and location is perfect for staying in the village! Would definitely rent again!
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