
Holiday rentals with a pool in Western Maryland
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Top-rated rentals with a pool in Western Maryland
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Popular amenities for Western Maryland rentals with a pool
House rentals with a pool

'Little Blue Bungalow' in The Woods-pool access
We stayed at this beautiful home and couldn’t have asked for a better getaway. The house was spotless, cozy, and beautifully decorated — every detail was thoughtfully done. It’s incredibly quiet and peaceful, making it the perfect place to relax and unwind. The host was beyond responsive and helpful, answering every question promptly and making us feel truly welcome. You can tell they genuinely care about their guests’ experience. We’ve stayed in many places, but this one stands out. We can’t recommend it highly enough — everything was perfect!

Stoney Spring Overlook
This BnB is in contention for my FAVORITE stay of all time. Family of 6 adults and 1 child had more than enough space, and Jeanne really made our stay effortless. We felt right at home and we didn't have to make that last minute trip to the store you sometimes have to make bc the host skimped on providing toilet paper or dish soap, because she honestly thought of EVERYTHING ❤️ My granddaughter loved the pool and dips in the hot tub after swimsmade the adults happy. The location and view are to die for, and the two pups were ecstatic playing in the large fenced area. We spent a lot of time outside, plenty of furniture, fire pit, just eating dinner on the deck. (Missing NOTHING in the kitchen either!) Our last night we spent sitting and talking on the deck trying to identify the multitude of frog voices from the pond, before we parted ways to our various home states. I am most grateful for memories made and we are definitely considering a repeat! ❤️Thank you!

Cabin w/King Bed, Hot Tub
Cabin was extremely clean. Had all the amenities needed. We were only there for one night but was definitely worth the drive. Very close to town. We ate at the Naked Olive i recommend giving it a try. We also stopped by Berkley Springs brewery also enjoyed.

Civil War Farm House w/Heated (seasonal) Pool
We really enjoyed the stay at your farm house while we attended the Civil War Institute at Gettysburg College. The place was clean and comfortable. The hosts were always quick in replying. I would definitely stay there again. Thanks again for everything!

Cedar Creek Wayside Castle
I needed a place that my family, from out of state, could stay while attending a graduation. The house was perfect! I told Bob what I wanted to do and he was encouraging and helpful. He made sure we had propane for grilling and answered all my questions. He was very prompt when I reached out to him. We had an amazing time. I would stay there again.

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.

Potomac Overlook Farms: 6 BR, 10 Acre River Estate
We had a wonderful family reunion here with 3 generations. Each family had their own private space but there was tons to do on the property together as well. The hosts were very responsive to our questions and made sure we were comfortable and happy! We appreciated that the kitchen was well stocked, too.

*NEW* Riverview Rtrt Pool/HotTub/FirePit & View
the stay was wonderful!! we thoroughly enjoyed the pool and hot tub. from photos, the house seemed very secluded but it’s not (no biggie!) it’s also close to nearby towns and the house was well stocked for us. we did lose power due to storms, but Michelle was very responsive and polite. Also, if you have a low riding vehicle beware that you’ll scrape bottom coming out of the driveway. The hot tub was nice, but the accessibility leaves a lot to be desired. the stairs are terrifying lol but once we got the nerve to climb them, it was lovely! the pool was amazing with a lot of provided floats, tubes etc. they also left out their vacuum and skimmers for us to use which was so helpful as a lot of frogs, turtles and bugs got into the pool throughout the night & the storms. overall, we had a great time and i would highly recommend booking. we would absolutely visit again.
Condo rentals with a pool

Beautiful, 2 bedroom condo
Stayed a night here as we played two rounds at the golf course that is right there. Place met all of our needs,and communication was clear

Spring Special - Book 2 Nights Get a 3rd FREE
We had an amazing stay at this cabin for our après-ski weekend this year! The location was perfect—easy to find and ski and ski out. The cabin itself was spotless, well-maintained, and had everything we needed for a comfortable stay. The amenities were great, from the fully stocked kitchen to the cozy living room and hot tub, making it the perfect spot to unwind after a day on the mountain. Parking was a breeze, and check-in was seamless. We would absolutely stay here again—highly recommend!

Lake Access/2BR/2Bath/kitchen/pool/5m to Wisp
I wish there was an extra star for the Host! Lorena was super helpful, always responded less than 30 minutes, and made us feel welcome into her home. Personal touches say a lot, and she had written us a nice thank you card that was on the table when we arrived. It was also nice that we did not have to run out and get toiletries immediately as they were readily available upon our arrival. Lorena was also upfront with an issue involving the oven, however there was a toaster oven readily available if we so choose. I highly recommend her condo to anyone with a small group of people/small family that plans on staying in the Deep Creek area!

Free shuttle to 7springs Full Kitchen CalKing Bed
Kara was amazing and very responsive! Great stay.

A Cozy, Quiet Getaway
Elizabeth’s condo was excellent - cleanly, organized & in a wonderful location. Would definitely recommend.

Beautiful 2BR/1BA Renovated Condo near DC
Our stay was perfect! The place was private, clean, and spacious—plenty of room for three people to relax comfortably. It was in a great location, just about a 20-minute drive to the metro station we used daily to get into DC. Everything was easy and convenient, which made our trip even better. We’ll definitely be booking this place again the next time we’re in the area. Highly recommend!

Landlocked@DCL Lakefront with Dock, and Pool
An incredible hidden gem with all the amenities you could ask for. The small touches are what made a difference here, like the provided s’mores and snacks, fireplace prepared, and clean and sustainable shower products. We will definitely be returning! Only thing is if you are somebody that prefers their home on the cooler side, the thermostat is locked on 73!

Laurel Highlands, Seven Springs Condo 1 Bed, 1 Bth
I can’t say enough about the entire experience. For a first timer it was wonderful and a perfect experience! The condo was better than described and much more affordable than the surrounding options! Will be booking yearly!!! Patricia is quick to respond and very resourceful. They have a tons of ideas and resources available for you to explore. I highly encourage you to check it out.
Destinations to explore
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- Seven Springs Mountain Resort
- Fallingwater
- Canaan Valley Resort & Conference Center
- Blackwater Falls State Park
- Idlewild & SoakZone
- Flight 93 National Memorial
- Timberline Mountain
- Hidden Valley Resort
- Ohiopyle State Park
- Wisp Resort
- Shawnee State Park
- Pikewood National Golf Club
- Bella Terra Vineyards
- White Grass
- Lakeview Golf Resort
- Lodestone Golf Course
- Laurel Mountain Ski Resort
- Canaan Valley Ski Resort
- Warden Lake
- Clear Shade Creek
- Mountain Dragon Mazery Fine Honey Wine
- Winter Experiences at The Peak