Vacation rentals with a pool in Berkeley County

4.94 out of 5 average rating, 119 reviews

Dog-friendly, boutique & chic + fireplace

A cool, retro, dog-friendly, Mid-Century modern A-frame cabin in a woodsy, secluded setting near DC and Baltimore! Free firewood! Sleeps 10 in SUPER COMFY beds w/high-quality sheets + a pull out cushy sofa bed in LR + futon in loft. Lux pillows & towels. Deck w/Grill & free propane. Modern ultra-stocked kitchen. High speed wifi + work space. Screened-in porch. Generator w/transfer switch. Basic supplies provided. Hike + golf + swim + ski+ fish + spa + shopping + breweries + farm markets nearby.

4.94 out of 5 average rating, 117 reviews

Modern Cabin: Hot Tub, Arcade, FirePit, Pets+Pool

Experience the epitome of luxury in our breathtaking A-frame cabin, nestled amidst the serene woods. This modern retreat offers lavish amenities and a stunning open living space with floor-to-ceiling windows, immersing you in nature's beauty. Indulge in the private hot tub, relax by the fire pit, and unleash your culinary skills in our fully equipped kitchen. The large screened porch provides a tranquil oasis, while nearby hiking trails, golf courses, and a spa offer an unforgettable getaway!

4.93 out of 5 average rating, 262 reviews

Bear Pines Retreat ~ Game Room ~ Screened Porch

Come enjoy this 3 bedroom/2 bath A frame cabin in The Woods. Bear Pines Retreat features 2 bedrooms on the lower level with 4 beds and full bathroom. The Master Suite loft has a queen bed with mountain spa bathroom. You can connect to the built in Bluetooth speaker and play some relaxing music while looking out the skylight above. The living area has plenty of seating with wood burning fireplace and 55” TV mounted above. You can enjoy over 100 cable channels, music and streaming services.

4.94 out of 5 average rating, 141 reviews

Starcatcher Chalet, The Woods Resort

Enjoy a fun, relaxing stay at our completely renovated chalet in The Woods Resort in beautiful Berkeley County, WV--a 90-minute drive from the Washington DC-Baltimore Metro Area. You'll be in the heart of the WV Eastern panhandle, close to Sleepy Creek, Berkeley Springs, Cacapon State Park, Antietam National Battlefield, and more. The Woods Resort amenities (fees apply) include a spa, restaurant, and two golf courses, three swimming pools, tennis, pickleball, fitness, and a playground.

4.94 out of 5 average rating, 183 reviews

Hot Tub, Dog Friendly Boho Cabin in The Woods

Unwind at our secluded A-frame cabin in The Woods! Feel transported into the trees as you enjoy coffee on the screened-in porch, roast marshmallows by the fire pit, relax in the hot tub, or simply look out the expansive windows. Furry friends will feel at home with a built-in dog bowl station and two-acres for exploring. Just under two hours from the D.C./Baltimore area with a ChargePoint EV station in the driveway, it's the perfect all-seasons getaway for families and groups of friends.

5 out of 5 average rating, 26 reviews

Home in Hedgesville

'Little Blue Bungalow' in The Woods-pool access

Escape from the hustle-and-bustle of everyday life at The Little Blue Bungalow! The perfect getaway spot located in The Woods community in Hedgesville, WV, just under two hours from the D.C./Baltimore area. It’s the ideal place for couples, families, or groups of friends. Come for a weekend retreat or week-long vacation! Our cozy home offers plenty of privacy and space to explore, with all of the modern comforts you need. **Pool/tennis access. Message us for details on day passes!**

4.88 out of 5 average rating, 115 reviews

Five Oaks Cabin at The Woods Resort

Get away without going far at our cozy, colorful, family-friendly cabin. Watch the sunset over the woods from the deck, stargaze by the A-frame window, or play ping-pong in our games room. Do some work in our office space overlooking the trees. Enjoy golf, pools, the spa, hiking and fishing, or explore the beautiful countryside of rural West Virginia. Best of all, our cabin is less than two-hours drive from D.C. and Baltimore, so you can feel like you're far away without a long drive.

4.85 out of 5 average rating, 197 reviews

Stylish Retreat w Fireplace, Games & Pool Access

Experience a peaceful getaway at The Woods Resort. With an outdoor screened porch, a fire pit and a wood burning fireplace, you can comfortably enjoy this retreat in any season! Access to two outdoor pools, an indoor pool with hot tub, tennis and pickleball courts, a gym, and 36 holes of golf. Enjoy the indoors and outdoors in any season! The highlights: - Wood burning fireplace - Screened Porch with seating for the group - WiFi for streaming movies & remote work - Resort Amenities

4.93 out of 5 average rating, 29 reviews

Home in Big Pool

Whitetail Meadows Guest House

Come enjoy the country lifestyle at Whitetail Meadows Guest House. No matter what the season, Whitetail Meadows Guest House offers a location embedded in the casual country lifestyle of fishing, hiking, biking, boating and a variety of winter sports. We aim to make your stay with us as pleasant as possible, so please feel free to reach out if there is anything we can do to improve your current or future stay. *See Property Information for Package Details on Larger Day Gatherings*

4.88 out of 5 average rating, 225 reviews

Deer Crossing at The Woods

This WV cabin is a perfect mixture of rustic charm and and modern convenience — a great option for families or friends looking for a place to get away. Nestled in the Appalachian Mountains, it is less than a 2-hr drive from DC and Baltimore (2.5 hrs from Pittsburgh)—close enough to get there quickly, but far enough to feel like a whole different world. Enjoy a massage at the spa, play golf, go for a hike, or just fire up the hot tub, chill out, and relax!

5 out of 5 average rating, 31 reviews

Acorn Moon, round 1977 cabin-pools and pickleball!

Experience this unique, authentic 1977 round cabin with amazing views from the curved wall of windows. Work from home with fast internet or unplug and simply relax in peaceful awe of the view. Located in The Woods resort, with 2 beautiful outdoor pools (open in the summer), pickleball, tennis & golf! Only 25 minutes from Berkeley Springs with its famous hot springs, art center, and shops. Hiking, biking, river floats, horseback riding all nearby.

4.93 out of 5 average rating, 110 reviews

The Cabin on the Run

We have a generator! Never be without power during your vacation. Come spend the winter by the woodstove! Take a trip to The Woods in Wild, Wonderful West Virginia. Cabin on the Run is named after the beautiful run running behind the property with a babbling soundscape that can be heard from the expansive deck. Cabin on the Run provides all modern amenities so that you only need to bring clothes and food for a trip away.

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Popular amenities for Berkeley County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.8 out of 5 average rating, 20 reviews

Home in Clearville

Barnswallow Ranch, 3 BDR Home w private pool

SadraRating, 5 stars9 months ago

We had a unforgettable weekend at Kathryn's home with good friends! The pool, the barn, the privacy and the surroundings were spectacular! I already recommended the home to mu family because it does feel like home 🏡

4.87 out of 5 average rating, 83 reviews

Home in Big Pool

4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acr

KristinRating, 5 stars1 month ago

Gorgeous private property, surrounded by nature. Welcoming home with wonderful amenities. Instantly aware a great deal of thought was put into all aspects of this home, providing a seamless transition to vacation mode. Host was very communicative and helpful. Would highly recommend.

4.88 out of 5 average rating, 204 reviews

Home in Harpers Ferry

The Historic Booth House at the Harpers Ferry KOA

JimRating, 5 stars1 month ago

The house was great. clean, lots of towels, loved the hot tub. There are two things I would point out. The steps to the upstairs are very hard for people with mobility issues but there are four bedrooms on first floor. There are two single steps on the first floor.

4.97 out of 5 average rating, 195 reviews

Home in Harpers Ferry

Harpers Ferry Farmhouse, Heated Year Round Pool

WendyRating, 5 stars1 week ago

Everyone enjoyed our stay here ! S’mores by the firepit, family games around the huge kitchen table and mornings rocking on the front porch rockers . We wished we could stay longer !!!

4.92 out of 5 average rating, 24 reviews

Home in Purcellville

Buckskin Manor - Historic, Pool, 66 Acre Vineyard

DeborahRating, 5 stars1 month ago

I would recommend this home greatly. We were on a girls weekend. We enjoyed the home the surroundings and the peacefulness. It’s in a beautiful setting close to many great restaurants and wineries. The beds were comfortable and the homeless clean. Should we ever find ourselves that way again we’ve already decided we would stay here.

4.76 out of 5 average rating, 269 reviews

Home in Strasburg

Cedar Creek Wayside Castle

TraceyRating, 5 stars1 week 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.

5 out of 5 average rating, 90 reviews

Home in Knoxville

An Escape Bordering National Park land 1 mi to C&O

BethRating, 5 stars1 week ago

Nicole's home is beautiful. Everyone felt comfortable, and at home. Nicole was quick to respond to my many questions, and was eager to make sure all went smoothly. Clear instructions were presented for everything in the house. Thanks for an enjoyable stay.

4.83 out of 5 average rating, 78 reviews

Home in Mercersburg

SKI YA LATER Whitetail

ColeRating, 5 stars2 months ago

Awesome hosts. So responsive and place was sweet. Would recommend to anyone.

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Condo rentals with a pool

5 out of 5 average rating, 20 reviews

SlopeSide

JenniferRating, 5 stars3 months ago

I almost don't want to write a positive review because I'd like this condo to be available only to me. It was perfect! The place is comfortable and had everything we needed for our 2 night stay. Easy ski in/out access, and perfect for a family that has some that stay on the slopes a little longer than others. We just hope this place will be available again when we visit next.

4.93 out of 5 average rating, 15 reviews

Rockwell Suite #104 at the Inns of Whitetail

JosephRating, 5 stars3 months ago

Very nice spot right off the mountain. Pretty short walk from the top of the green hills. Great if you have your equipment already! Living space was big enough to relax after the slopes. Comfortable bed and big tv.

Condo in Paw Paw

4.22 out of 5 average rating, 9 reviews

Avalon Resort Paw Paw WV Condo

MadisonRating, 5 stars9 months ago

We loved staying in this condo! It was very clean and had everything we needed for our weekend stay. Will definitely be recommending this place to others.

4.82 out of 5 average rating, 65 reviews

Ski🎿 & hike from front steps—Mountainside getaway

MarkRating, 5 stars3 months ago

I think this is the best slope side ski condo at Whitetail. The slopes are right outside the door and the place is cute, clean, and comfortable. We will be going back!

4.56 out of 5 average rating, 34 reviews

The Music Room at Ski Whitetail!

KendraRating, 5 stars3 months ago

This studio apartment-room was a great stay! It was the closest building to the top of the Double lift, 8-10 minutes from line to the apt door. Everything was as described for me, sans a guitar and a table or two. The wifi was fine for work, not great for gaming on my pc, though. Overall, my pet and I enjoyed every second of our 2+ weeks, on and off the slopes (just me), and look forward to staying again. Thanks!

4.91 out of 5 average rating, 46 reviews

Whitetail Resort Ski-in/Ski-out slope side condo.

KayleeRating, 5 stars3 months ago

This air bnb was perfect for a weekend getaway to Whitetail resort. The unit is steps away from the slopes, and Renee was not only responsive and extremely helpful, but able to accommodate schedule changes to make our trip happen.