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Vacation rentals in Poolesville

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Top-rated vacation rentals in Poolesville

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Cabin in Leesburg

4.94 out of 5 average rating, 322 reviews

100 Acre Wood

🌳100 Acre Wood🌳is the perfect cabin for a quiet spring getaway🌸🌼we are tucked away in the woods🌳Our custom designed cabin is located on a 100 acre property in the ❤️of Loudoun County, in the charming village of Lucketts, known for its BEAUTIFUL WINERIES🍷FAMOUS ANTIQUE SHOPS & FINE DINING & CRAFT BREWERIES🍻Potomac River, C&O Canal, Appalachian & WO&D Trails & Harpers Ferry are a few miles away.Come relax, unwind & enjoy our peaceful woods & wildlife🐾Located approx 1 hour to DC & 1/2 hr to Dulles✈️

Jun 24 – Jul 1

Cabin in Myersville

4.97 out of 5 average rating, 251 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across the foot bridge to serenity along Middle Creek. Nestled between South Mountain State Park & Gambrill State Park, lies a beautiful & relaxed 9-acre private cabin retreat. Amazing place to unwind, de-stress & get away. Let the sound of the creek or rain on the tin porch roof put you to sleep at night. It has all the essentials of home. Enjoy the fire pit on cool evenings or take a dip in the stream on a warm day. The cabin offers a perfect peaceful or romantic setting.

Mar 21 – 28

Cabin in Lovettsville

4.95 out of 5 average rating, 148 reviews

Cabin On The Cliffside

Once you set foot inside this lovely country cabin you will be truly charmed by the aesthetic of the property, the owner newly restored it while keeping as much of the original structure while adding in newer amenities & design. Whether you plan to relax & unwind or explore nearby attractions (wineries, breweries, hiking, restaurants) this cabin will sure to impress. Highlighted features include king size bed, original walls of hand hewn logs, comfortable living space, fire pit, stone patio.

Mar 5 – 12

Farm stay in Leesburg

5.0 out of 5 average rating, 114 reviews

The Loft at Sneaky Fox Farm

We are close to Morven Park, Rose Hill Manor, Downtown Leesburg, White's Ferry Manor Pool is open May-Sept Retreat away to scenic Sneaky Fox Farm, a newly-constructed barn apartment which sits above our working horse farm. We are conveniently located less than 5 minutes from Historic Downtown Leesburg and within minutes to Loudoun’s best wineries and breweries. Our property offers the feeling of abundant open-space all the while being a stone’s throw away from all that Loudoun has to offer.

Feb 4 – 11

Farm stay in Lovettsville

5.0 out of 5 average rating, 135 reviews

'Waterfront' on 1796 Historic Farm

Feel refreshed when you stay in this rustic gem! The Springhouse is nestled in the rolling hills of Northern Virginia’s Wine Country! Originally constructed in the early 1800's, this structure was built over a natural spring and used for refrigeration. The water from the spring maintains a constant cool temperature throughout the year while also filling a pond. The original stone well, channel and stone flooring are all intact for guests to explore and experience how our ancestors lived.

Sep 2 – 9

Guest suite in Leesburg

4.98 out of 5 average rating, 179 reviews

Suite GG ~ Relax & Enjoy

Let this lovely above-garage apartment be your home away from home. Located in Lucketts, VA we are within a short distance to the small artsy town of Leesburg, local wineries, breweries, antique stores, shopping outlets, hiking, biking and canoeing/kayaking on the Potomac River. Our spacious, fully-furnished apartment with private entrance sits above a detached garage and features a private bedroom with an antique queen-size bed, full-service kitchen, living room, bathroom and laundry room.

Oct 31 – Nov 7

Farm stay in Round Hill

4.94 out of 5 average rating, 345 reviews

Come and get your goat on!

Nestled at the base of the Blue Ridge and tucked away in the woods, we offer a quiet and peaceful get away while being convenient to tons. Enjoy the peace of 13-acres of woodlands and pasture. A large private deck provides a plenty sun with pasture and woodlands views with some great star watching at night. Miles of walking, the Appalachian trail, fantastic cycling; historic towns and places; wineries, breweries, and distilleries; Potomac and Shenandoah rivers. All just minutes away.

Aug 11 – 18

Apartment in Gaithersburg

4.94 out of 5 average rating, 131 reviews

Bright, Private Garden Apt Near DC + Free Parking

GORGEOUS 1 BR apartment w/PRIVATE & separate entrance in lovely family neighborhood. ENJOY a clean, spacious space w/queen-size bed, TV/WiFi, relaxing bathroom, modern kitchenette, full laundry room, natural light & HUGE flower and veggie gardens. PERFECT for visiting families, traveling nurses & relocation assignments! FREE parking w/plenty of wonderful shops & restaurants nearby. MINS from highways to DC/Balt/Fredrick (35 min). SHORT 6 min ride to RED Line Metro (Shady Grove) to DC.

Jun 20 – 27

Guesthouse in Lovettsville

4.94 out of 5 average rating, 116 reviews

The Patent House

Built around 1760, our log cabin sits on our 3 acre farmette, in the countryside in view of the foothills that separate VA, WV & MD. It's fully renovated, with a master bedroom (queen), full bath & convertible sofa downstairs (full). The cabin is next door to our house & shares a fence with our pasture where our miniature donkeys live. We have yappy dogs and friendly outdoor cats. we're in the country, so bugs do make their appearance, but they tend to go straight to the window sills.

Jul 9 – 16

Cottage in Woodbine

4.91 out of 5 average rating, 125 reviews

Gate House

Quaint cottage farm house nestled in beautifully rolling countryside setting on an operating horse farm. Fully furnished with all the modern amenities. Easily accessible from I70, and located within 30 to 40 minutes of Frederick, Baltimore, DC and Gettysburg. This property is also situated at the North west trail head to the Patuxentstate park, with tons of access to easy hiking! Pet friendly, we just ask that pets remain on leash when outside of the space or vehicles.

Dec 22 – 29

Tiny home in Purcellville

4.96 out of 5 average rating, 313 reviews

Remote Tiny House in Purcellville

Nestled in the heart of Purcellville is a tiny home with a ton of charm. Less than 5 miles from vineyards, LOCO ale trail breweries, cideries, WO&D bike trail & 20 min to historic Leesburg, the Shenandoah river & Appalachian Trail. Our tiny house is a bit larger w/ 2 bedrooms, full kitchen & bath, family room & cozy front porch. Guests enjoy private parking & plenty of privacy. Enjoy a remote work getaway, (our broadband is about 8-10Mbps) relax & enjoy LOCO living!

Mar 28 – Apr 4

Loft in Purcellville

4.99 out of 5 average rating, 286 reviews

"When Pigs Fly" Airbnb Most Hospitable Host in VA

Located between Middleburg, VA and Purcellville, VA, our loft is just about 15 minutes away from restaurants, wineries, breweries and many local points of interest. You will have views from every window in addition to all of the amenities you will need for a pleasant stay. We welcome your dogs while you visit. The only thing we ask is that you keep them off the couch, pick up their "business" and crate them if they are left alone.

Nov 24 – Dec 1

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Other great vacation rentals in Poolesville

Guesthouse in Boyds

4.87 out of 5 average rating, 69 reviews

Beautiful Contemporary Basement

May 2 – 9

Loft in Germantown

4.96 out of 5 average rating, 52 reviews

Carriage House loft by lake with wood-fired sauna

Jun 4 – 11

Home in Sterling

4.87 out of 5 average rating, 15 reviews

Modern, fun space 20 min from Dulles Airport!

Jun 2 – 9

Home in Boyds

4.92 out of 5 average rating, 26 reviews

Cool walkout basement!

Jan 11 – 18

Guest suite in Barnesville

5.0 out of 5 average rating, 13 reviews

Unparalleled Views - Comus, MD

Oct 17 – 24

Home in Boyds

5.0 out of 5 average rating, 9 reviews

The Honey Acres House

Mar 6 – 13

Farm stay in Leesburg

5.0 out of 5 average rating, 7 reviews

The Stable House

Nov 4 – 11

Condo in Sterling

4.93 out of 5 average rating, 76 reviews

The Loft at Lakeside

Sep 9 – 16

Destinations to explore