
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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Popular amenities for Shenandoah Valley rentals with a pool
House rentals with a pool

Cliffs Edge- Hike, Play & Splash into Summer!
Amazing place! My family and I thoroughly enjoyed our stay. Great home with breathtaking views of the Blue Ridge Mtns and tranquility for days! Julie was a superb host. Her hospitality, directions and communication were second to none. Thank you and we look forward to visiting again.

Wizard's Escape | Sleep15+ | Pool | 2 EscapeRooms
Our experience at the Wizards Escape was amazing! Nate, our host, was the best. He checked in to make sure that we were getting the best experience out of the house. The atmosphere is unreal! We really felt we were at Hogwarts Castle. The bedrooms are so full of detail. The kitchen is stocked with everything you could imagine. The Great Hall is magical! The escape rooms.. fantastic. We only stayed 2 days but tried to get in all the activities that were available. We played quidditch golf, did escape rooms, had a scavenger hunt, made great meals in the Weasley's kitchen. We had dinner in the Great Hall under the levitating candles while listening to the Harry Potter music in the background. This house is a home to be experienced. We are definitely coming back!

Afton Awaits: Pool & Hot Tub/Central to Wineries
Beautiful place! Surrounded with mountain views, horses and a peaceful atmosphere. Loved the pool and porch! The master suite bed was absolutely amazing! Best sleep ever!! Highly recommend stay in beautiful tranquil Afton area.

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.

Hottub Ski In/Ski Out Renovated Chalet Lower Tyro
Joes property was absolutely beautiful! The views are amazing from the cozy hot tub on the back porch. Everything was super clean and the beds were super comfortable! This airbnb would be great for a family stay or a friends getaway. It was everything we needed and more! Joe was quickly responsive when i had questions. This air bnb is stocked with EVERYTHING you may need. Beautiful spot, 10/10!

Incredible views with hot tub & swimming pool
Patricia’s home was a fantastic getaway for a long weekend! Absolutely stunning views, a relaxing pool, a well equipped and a thoughtfully put together home for anything you might need. The kitchen might be one of the best equipped we’ve ever seen! Could not recommend the home more for a place to relax and switch off! We hope to be back!
Condo 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!

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.

Panoramic Mountain View~ Summer Pool~ First Floor
Wintergreen is a gorgeous area with so much to do all around. Hikes, wineries, and of course just sitting on the deck and taking in the beautiful mountain view. Condo is spacious and comfortable. Kitchen well stocked and everything very clean. Plenty of firewood for some evening fires in the fireplace. Loved every minute of our time there!

New Construction! 1 Bed/2 Bath, pet friendly
We really enjoyed our stay at your condo. It was nice to be in a newer unit. It was very clean and comfortable. The location is great being walkable to Fire and Frost, a coffee/wood fired pizza restaurant, and we prefer the upper mountain location also being walkable to golf, tennis and trails. We hope to come back to Wintergreen soon. It is a great place to relax!

Tips Up: Cozy Slopeside Retreat w/ Fireplace
Nice home, in an ideal location. Great communication and quick to respond as needed. Recommend the home and location!

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.
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