
Holiday rentals in Hamilton
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Top-rated holiday rentals in Hamilton
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*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!

The Hunt Box @ Tally Yo Farm
Residence above 5-stall horse barn. Two bedroom house with 2 bath, Juliette balcony, vaulted ceilings, fully appointed kitchen, laundry. Traditional English equestrian decor, with horse shows & fox hunts close by. Pool open 5/15-10/15. Extra guests $55/night. Pet fee $35 each. Please advise through Airbnb. Lovely antiques, equestrian art & decor, warm rugs. On site also~AirBnb: www.airbnb.com/rooms/826639006057875355?guests=1&adults=1&s=67&unique_share_id=4cdf4b76-3173-498a-9287-5ab54a38b4ee

A Hidden Jewel in Loudoun County, Virginia
This charming 5000 sqft huge single family guest house is located just off of Route 7 in the historic town of Hamilton, VA. Enjoy a cup of coffee on the back deck while relaxing in a country environment. Take a walk in a beautiful rural area with magnificent view over the countryside or Enjoy a bike ride on the former W&OD Railroad, which is sitting just outside the house. Listing is for the two upper floors. Access between the basement and the upper floors is locked and secured at all times.

Hope Flower Farm Winery Cottage
Welcome to Hope Flower Farm & Winery! This charming 3-bedroom, 1-bath cottage is the perfect retreat for those seeking a peaceful getaway in the heart of Loudoun County wine country. The cottage features a kitchen, cozy living room, and a screened-in porch perfect for enjoying your morning coffee or an evening glass of wine. The cowboy cauldron is the perfect spot for roasting marshmallows or enjoying a cozy fire. Come experience the beauty and tranquility of Hope Flower Farm & Winery.

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 donkey, mule, Long Horn cows, goats, chickens, and 3 barn cats (and 3 kiddos!). Just 3 miles to downtown Leesburg.

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.

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.

Cozy Cuddle up on 1700’s Clydesdale Farm
The Hunt Box at Sylvanside Farm is a couples favorite! Cozy bedroom with bay window overlooks the stone barn, Clydesdales field and pond. Full kitchen, full bath and small living room. Enjoy a glass of wine on dock, hike the fields and streams, enjoy the animals, roam the our beautiful 25 acres. Escape the city and relax. Our visitors to date have proclaimed it magical and we hope you agree. In accordance with Airbnb’s policies parties are not permitted.

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!

Tiny House near 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 with private parking. Enjoy a remote work getaway, (our broadband is about 8-10Mbps) relax & enjoy LOCO living!

Wheatland Spring Farm + Brewery Cottage House
The charm of yesterday with the amenities of today. The private cottage house is appointed with a premium queen size bed, 1.5 baths, and a clothes washer and dryer. The full kitchen includes: oven, stove, microwave, full size refrigerator, dishwasher, and cookware. Guests enjoy scenic views of the 30 acre Wheatland Spring property. A romantic getaway or longer term stay. Just a 100 yard walk from our on-farm brewery.

The Cottage at Stone Tower Winery
The Cottage at Stone Tower Winery is a fully renovated, one-bedroom house located only an hour from DC, 30 minutes from Dulles Airport, and 15 minutes from Leesburg. The home is perfectly situated to enjoy a peaceful stay in the country and serves as an ideal location to explore the Northern Virginia wine region and historic Loudoun County.
Popular amenities for Hamilton holiday rentals
Other great holiday rentals in Hamilton

Woodhaven Reserve | Pool + Hot Tub + Views

Wine Country Townhouse

Designer Modern Mountain Escape (w/View & Hot Tub)

Guest-Favorite A-Frame with Hot Tub Harpers Ferry

#2 Cottage in Loudoun Co. (Upper of 2 units)w/Pond

Blue Skies

Romantic Barn Loft | Wine Country & Weddings

Scarlet Springs, Peaceful Farm Stay with Highlands
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- Georgetown University
- Walter E Washington Convention Center
- National Mall
- Nationals Park
- The White House
- District Wharf
- National Museum of Natural History
- Capital One Arena
- Liberty Mountain Resort
- National Museum of African American History and Culture
- Stone Tower Winery
- Arlington National Cemetery
- Howard University
- Washington Monument
- Georgetown Waterfront Park
- National Harbor
- Cunningham Falls State Park
- The Anthem
- Smithsonian American Art Museum
- Great Falls Park
- The Pentagon
- Lincoln Park
- Berkeley Springs State Park
- Library of Congress




