Vacation rentals with a pool in Berkeley County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Berkeley County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Cabin in Hedgesville

4.96 out of 5 average rating, 51 reviews

Serene Woods Escape-HOT TUB,Pets,Fire Pit+Pool/Gym

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!

Apr 26 – May 3

G$53,964 GYD per night

Guest favorite

Cabin in Hedgesville

4.93 out of 5 average rating, 101 reviews

NEW! Boutique-Chic w/fireplace @ The Woods

A cool, retro, dog-friendly, Mid-Century modern A-frame cabin in a woodsy, secluded setting near DC and Baltimore! 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. Free firewood. Basic supplies provided. Hike + golf + swim + ski+ fish + spa + shopping + breweries + farm markets nearby.

Aug 12 – 19

G$38,901 GYD per night

Guest favorite

Cabin in Hedgesville

5.0 out of 5 average rating, 54 reviews

Orion’s Getaway~Large deck+Gameroom+Firepit

Get away and play at this spacious cabin. Sip your morning coffee on the large deck as the sun rises through the trees. By day, swim, explore nearby hiking trails, play tennis or golf at The Woods facilities, or lounge while the kids play in the fenced yard. As the sun sets, dine outdoors on the picnic table, or indoors on the large dining room table. At night, retire to the detached game shed for a nightcap or gather around the fire while you cherish the serenity and search the sky for Orion.

Oct 9 – 16

G$91,226 GYD per night

Guest favorite

Cabin in Hedgesville

4.94 out of 5 average rating, 200 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.

Feb 12 – 19

G$61,201 GYD per night

Guest favorite

Cabin in Hedgesville

4.93 out of 5 average rating, 70 reviews

Rustic Retreat

Come & enjoy this Rustic Retreat nestled serenely within The Woods community! Relax on the screened-in porch or on the spacious deck with beautiful views. A majestic oak growing through the deck gives a tree house feel. The Woods community offers numerous amenities, including indoor & outdoor pools, indoor hot tub, tennis, racket ball, two golf clubs & a restaurant. The surrounding Sleepy Creek Wildlife Area, 22,000 acres, offers trails to explore the varied wildlife and beautiful flora.

Jul 23 – 30

G$31,711 GYD per night

Guest favorite

Cabin in Hedgesville

4.96 out of 5 average rating, 80 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.

Oct 27 – Nov 3

G$42,404 GYD per night

Guest favorite

Cabin in Hedgesville

5.0 out of 5 average rating, 30 reviews

Grateful Moments Cozy Cabin in the Woods Resort!

The Grateful Moments Cabin has been a long time member and a 5 Star listing on both Airbnb and VRBO for over 3 years. The new listing aims to provide an even better experience for guests, with improved features and amenities. Guests will enjoy the picturesque views and the tranquility of the surrounding area. Whether you're exploring the resort grounds or venturing out to nearby attractions, there are ample opportunities to connect with nature and experience the beauty of the region.

Oct 24 – 31

G$75,488 GYD per night

Guest favorite

Cabin in Hedgesville

4.92 out of 5 average rating, 76 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, cuddle up by the fireplace, 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.

Oct 11 – 18

G$32,692 GYD per night

Guest favorite

Cabin in Hedgesville

4.93 out of 5 average rating, 119 reviews

Hot Tub, Dog Friendly Boho Cabin in The Woods

Unwind at this secluded A-frame cabin in The Woods. Feel transported into the trees as you enjoy coffee on the screened-in porch, grill on the deck, relax in the hot tub, or simply look out the expansive windows. Furry friends will feel at home with a custom-built 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.

Aug 27 – Sep 3

G$66,083 GYD per night

Guest favorite

Cabin in Hedgesville

4.93 out of 5 average rating, 136 reviews

Stylish Retreat with Pool Access and Fire Pit

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! With an additional fee you can enjoy access to two outdoor pools, an indoor pool with hot tub, tennis and pickle ball courts, a gym, and 36 holes of golf. Close to the Sleepy Creek WMA, public river access, Berkeley Springs and tons of hiking - enjoy the indoors or outdoors in any season.

Feb 25 – Mar 4

G$29,357 GYD per night

Superhost

Cabin in Hedgesville

4.9 out of 5 average rating, 214 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!

Aug 29 – Sep 5

G$58,710 GYD per night

Guest favorite

Cabin in Hedgesville

5.0 out of 5 average rating, 8 reviews

T&A Getaway near Berkeley Springs WV

Come visit T&A Getaway near Berkeley Springs, West Virginia! SuperHost owners Tony & Amy recently renovated this cabin to be stylish and glamorous, yet comfortable and cozy. The result is truly special. The cabin is on acre in a private resort community with full guest access to its many amenities. Less than two-hours from Washington DC, T&A Getaway is perfect for a fun weekend excursion, work-from-home alternative, or just a change of scenery.

Mar 13 – 20

G$59,915 GYD per night