
Vacation rentals with a pool in Western Maryland
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Western Maryland
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
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.

Magic Mountain Retreat - Mountain View, EV charger
This is by far the best Airbnb experience I’ve had yet. Rana was extremely welcoming and responsive. We even left items and she messaged me to let me know and arranged to get them back to me. The home is immaculate, beautiful, charming, and had even more room than we anticipated. It was a perfect place for family dinner and game nights. I grew up in this area, so coming back is always fun, in addition to the handful of need to do things, like Creekside Market, Berkeley Springs State Park, Cacapon State Park, Lot 12 restaurant, The Naked Olive…. We had 8 people in our party and we were more than comfortable. I will 100% come back here!!

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.

Lake View Home w/Fire Pit, Indoor Pool, Dogs OK!
Great vacation. Wendy was the best host we have ever had—responsive and generous. The house itself was one of the best stocked rentals we have ever been in. We loved the use of the kayaks and would absolutely come back to enjoy Alpine Lake here again. Very relaxed, friendly vibe within the whole community.

The Dacha. Rebirth sauna experience
This place is incredibly high tech, super cozy and well worth the price! Roman is a talented artist with a knack for hosting. His level of communication was just right and always super responsive. His home is in an old, historical town. Do your research for this to do before you stay as we were unable to book what we wanted since it sold out. With that said, there is so much entertainment right at the house that we didn't feel the slightest bit of disappointment! He also far exceeds any other host when it comes to making you feel at home and offers a slew of toiletries in addition to your standard toothbrush and toothpaste. I would come back to Cumberland just to stay at this house again!!

*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
Wonderful Stay – Perfect for Families! This place was clean and very nice. My kids absolutely loved staying in the lofted area—it was a fun and cozy space for them. I really appreciated having a usable washer and dryer, especially after our amazing time at the pool. The pool itself was a highlight, featuring a bar that also served food, which made it easy to relax and enjoy. The shuttle service was prompt and took us straight to the pool when we called. The beds were very comfortable, including the pull-out couch, which made for a great night’s sleep. Overall, a fantastic stay—we’d definitely come back!

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.

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.

1-Bedroom Condo 4701 Swiss Mountain Seven Springs
The condo was beautiful, clean, and conveniently located with close proximity to the resort and available shuttle services. Barrett was always responsive. A great place to stay!
Destinations to explore
- Pittsburgh Vacation rentals
- Laurel Highlands Vacation rentals
- Western North Carolina Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- Pocono Mountains Vacation rentals
- Mississauga Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- South Jersey Vacation rentals
- Jersey Shore Vacation rentals
- New York Vacation rentals
- East River Vacation rentals
- Guesthouse rentals Western Maryland
- Rentals with breakfast Western Maryland
- Private suite rentals Western Maryland
- Tiny house rentals Western Maryland
- Kid-friendly rentals Western Maryland
- Apartment rentals Western Maryland
- Bed and breakfasts Western Maryland
- Smoking-friendly rentals Western Maryland
- Rentals with a sauna Western Maryland
- Rentals with a washer and dryer Western Maryland
- Cabin rentals Western Maryland
- Fitness-friendly rentals Western Maryland
- Rentals with an EV charger Western Maryland
- Farmstay rentals Western Maryland
- Cottage rentals Western Maryland
- Rentals with outdoor seating Western Maryland
- Rentals with a home theater Western Maryland
- Waterfront rentals Western Maryland
- Rentals with a fire pit Western Maryland
- Townhouse rentals Western Maryland
- Condo rentals Western Maryland
- Ski-in/ski-out rentals Western Maryland
- Rentals with a hot tub Western Maryland
- Family-friendly rentals Western Maryland
- Rentals with lake access Western Maryland
- Hotel rentals Western Maryland
- House rentals Western Maryland
- Pet-friendly rentals Western Maryland
- Rentals with a kayak Western Maryland
- Rentals with a fireplace Western Maryland
- Rentals with a patio Western Maryland
- Chalet rentals Western Maryland
- Rentals with pools Maryland
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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
- Pikewood National Golf Club
- Shawnee State Park
- Bella Terra Vineyards
- White Grass
- Lodestone Golf Course
- Lakeview Golf Resort
- Canaan Valley Ski Resort
- Laurel Mountain Ski Resort
- Warden Lake
- Clear Shade Creek
- Winter Experiences at The Peak
- Mountain Dragon Mazery Fine Honey Wine