Holiday 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

Top Guest favourite
Home in Hedgesville
5 out of 5 average rating, 29 reviews

'Little Blue Bungalow' in The Woods-pool access

IgorRating, 5 starstoday
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!
Top Guest favourite
Home in Sabillasville
4.93 out of 5 average rating, 121 reviews

Stoney Spring Overlook

TracyRating, 5 stars1 week ago
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!
Guest favourite
Home in Berkeley Springs
4.93 out of 5 average rating, 27 reviews

Cabin w/King Bed, Hot Tub

AdamRating, 5 stars1 week ago
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.
Top Guest favourite
Home in Gettysburg
5 out of 5 average rating, 255 reviews

Civil War Farm House w/Heated (seasonal) Pool

JamesRating, 5 stars4 days ago
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!
Superhost
Home in Strasburg
4.76 out of 5 average rating, 270 reviews

Cedar Creek Wayside Castle

TraceyRating, 5 stars4 weeks ago
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.
Top Guest favourite
Home in Luray
4.98 out of 5 average rating, 102 reviews

Walnut Lane

LynneRating, 5 stars1 month ago
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.
Guest favourite
Home in Leesburg
4.97 out of 5 average rating, 121 reviews

Potomac Overlook Farms: 6 BR, 10 Acre River Estate

MelissaRating, 5 stars1 month ago
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.
Top Guest favourite
Home in Harpers Ferry
5 out of 5 average rating, 27 reviews

*NEW* Riverview Rtrt Pool/HotTub/FirePit & View

CaitlinRating, 5 stars2 days ago
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

Guest favourite
Condo in Somerset County
4.94 out of 5 average rating, 231 reviews

Beautiful, 2 bedroom condo

DanielRating, 5 stars1 day ago
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
Guest favourite
Condo in Champion
4.88 out of 5 average rating, 146 reviews

Spring Special - Book 2 Nights Get a 3rd FREE

MorganRating, 5 stars3 months ago
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!
Top Guest favourite
Condo in McHenry
4.96 out of 5 average rating, 130 reviews

Lake Access/2BR/2Bath/kitchen/pool/5m to Wisp

RobertRating, 5 stars3 months ago
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!
Top Guest favourite
Condo in Champion
5 out of 5 average rating, 116 reviews

Free shuttle to 7springs Full Kitchen CalKing Bed

NickRating, 5 stars3 weeks ago
Kara was amazing and very responsive! Great stay.
Guest favourite
Condo in Farmington
4.91 out of 5 average rating, 135 reviews

A Cozy, Quiet Getaway

TuckerRating, 5 stars3 weeks ago
Elizabeth’s condo was excellent - cleanly, organized & in a wonderful location. Would definitely recommend.
Superhost
Condo in West Springfield
4.83 out of 5 average rating, 218 reviews

Beautiful 2BR/1BA Renovated Condo near DC

DakotaRating, 5 stars6 days ago
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!
Top Guest favourite
Condo in Oakland
5 out of 5 average rating, 15 reviews

Landlocked@DCL Lakefront with Dock, and Pool

KierstenRating, 5 stars1 week ago
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!
Top Guest favourite
Condo in Champion
4.98 out of 5 average rating, 102 reviews

Laurel Highlands, Seven Springs Condo 1 Bed, 1 Bth

ShawnRating, 5 stars3 months ago
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.

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