Vacation rentals in Hamilton

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Top-rated vacation rentals in Hamilton

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Guest favorite

Cottage in Hamilton

4.94 out of 5 average rating, 308 reviews

*Cottage @ Firefly Cellars* VA Wine Country escape

The Cottage at Firefly Cellars is a private, tranquil escape on the tasting room property. Come enjoy the private pool (in summer months), walk the property with a glass of wine, enjoy views of the neighboring horses, hop to local wineries, or just sit back and enjoy all the cottage has to offer. The cottage is meticulously maintained, beautifully designed, and you will feel at home the moment you walk through the doors. Perfect for a couple, or an individual looking to escape from busy life!

Sep 13 – 20

G$54,981 GYD per night

Guest favorite

Cabin in Lovettsville

4.95 out of 5 average rating, 150 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.

Jul 6 – 13

G$29,602 GYD per night

Guest favorite

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.

Jul 2 – 9

G$32,434 GYD per night

Guest favorite

Farm stay in Round Hill

4.94 out of 5 average rating, 347 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 17 – 24

G$26,972 GYD per night

Guest favorite

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.

Dec 31 – Jan 7

G$27,259 GYD per night

Guest favorite

Guesthouse in Lovettsville

4.94 out of 5 average rating, 119 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.

Aug 20 – 27

G$24,498 GYD per night

Guest favorite

Tiny home in Purcellville

4.98 out of 5 average rating, 130 reviews

King Bed-Tiny Home-Fire Pit-Historic Farm Stay

Escape to our newly renovated tiny cottage nestled in a charming 25-acre farm dating back to the 1700s! Enjoy a tranquil night in our one bedroom haven, boasting a king bed, speedy wifi, kitchen essentials, blackout shades, and a charming fire pit. Ideal for remote work retreats or romantic getaways! Explore nearby wineries, breweries, and scenic trails, and the quaint town of Purcellville, just 10 minutes away. Say hi to our friendly cows and pigs! Book now for an unforgettable stay!

Jul 27 – Aug 3

G$39,237 GYD per night

Guest favorite

Cottage in Leesburg

4.91 out of 5 average rating, 289 reviews

The Cottage at Forest Hills Farm

Beautiful one bedroom, one bath cottage on a picturesque 14 acre farm just outside of downtown Leesburg. Nestled in close to local vineyards, this charming, free-standing cottage is yours and perfect for a weekend getaway or alternative to a hotel. Enjoy the fresh air, beautiful views, and peace and quiet on our little farm. Wander the property and say hello to our donkeys, mule, Long Horn cows, goats, chickens, and 3 cats (and 3 kiddos!). Just 3 miles to downtown Leesburg.

Nov 29 – Dec 6

G$40,194 GYD per night

Guest favorite

Home in Purcellville

4.99 out of 5 average rating, 270 reviews

Whole House -Seven Elms Farm B&B

Come and enjoy peaceful setting of our 1870 farmhouse situated close to historical Town of Purcellville, great for shopping and enjoying a good meal, W&OD trail is nearby for a walk or a jog. Or you can just sit on either one of the two covered porches with a good book and take in natural open spaces and a view of a serene pond. And of course we are located in heart of Loudoun County's wine country, great spots for picnic and tasting of great selection of wines.

Jan 11 – 18

G$42,847 GYD per night

Guest favorite

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!

Oct 4 – 11

G$32,740 GYD per night

Guest favorite

Guesthouse in Hamilton

4.98 out of 5 average rating, 116 reviews

Trailside Chalet (A storybook chalet with hot tub)

The Trailside Chalet is situated on the W and OD Trail, halfway between Leesburg and Purcellville, Va - an ideal base location for visiting wineries, breweries, and the pastoral countryside of Loudoun County. The chalet will put you just steps from the trail for walking/cycling/horseback riding. Relax and enjoy the amenities of one-of-a-kind interior including wood burning fireplace and peaceful surroundings with hot tub. A perfect getaway for a couple or family.

Oct 5 – 12

G$58,887 GYD per night

Guest favorite

Farm stay in Hamilton

4.95 out of 5 average rating, 179 reviews

Historic Farmhouse in Beautiful Western Loudoun

Historic beautifully restored stone house located on beautiful farm property just outside of Leesburg VA. The house is a perfect spot to unwind, relax, and come explore Loudoun County which is filled with wineries, breweries, farm to table restaurants, hiking trails and more! Beautifully decorated space, king size bed, large comfy couch, dining room and kitchen are a few highlights of the space. This is the entire house. Looking forward to your stay!

Jun 22 – 29

G$54,522 GYD per night