Vacation rentals in Madison

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Top-rated vacation rentals in Madison

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Guest favorite

Apartment in Madison

4.9 out of 5 average rating, 229 reviews

The Studio at Dark Run Retreat

Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*

Jun 7 – 14

R1,553 ZAR per night

Guest favorite

Cottage in Madison

4.91 out of 5 average rating, 138 reviews

Robinson River Roost - Cottage near Shenandoah NP

Enjoy a slice of country life in our rustic 3 BR, 1.5 bath cottage nestled along the Blue Ridge in Madison County. Great for a family or small group. Minutes to scenic hikes at White Oak and Old Rag in Shenandoah National Park, plus wineries, breweries and festivals at Graves Mountain Lodge. Steps away from trout fishing and swimming holes of the peaceful Robinson River, plus Possum's Store across the street. Convenient to Charlottesville, Culpeper, Blue Ridge Pkwy, Luray Caverns, Camp Varsity.

Feb 15 – 22

R2,304 ZAR per night

Guest favorite

Farm stay in Madison

5.0 out of 5 average rating, 201 reviews

Rustic Farmhouse on Farm W/ Mountain & River Views

The retreat at Rooted Land Co. consists of 1 farmhouse and 3 luxury tiny cottages on 350 private acres nestled at the base of the Blue Ridge Mountains with more than 1-mile of Rapidan River frontage. Each home is spaced with privacy in mind and positioned with breathtaking views. Countless outdoor activities including fishing, hiking, and wildlife viewing provide a unique experience during your stay. Rooted Land Co. is located just minutes from wineries, breweries, and Shenandoah National Park.

Oct 25 – Nov 1

R6,933 ZAR per night

Guest favorite

Cottage in Madison

4.98 out of 5 average rating, 125 reviews

Fishback Cottage, Central location

Conveniently located in beautiful countryside of Madison, VA. With easy access to route 29 and centrally located to local breweries, wineries and hiking. Free fast wifi makes it easy for a business trip or for a night of relaxation with Netflix. Local places to visit include Bald Top Brewing Company, Early Mountain Vineyards, Prince Michel Vineyard, Yoder's Country Market, Piedmont Deli, Shenandoah National Park and Graves Mtn Farms. An easy 25-30 minute drive to Charlottesville or Culpeper.

Jul 7 – 14

R3,824 ZAR per night

Guest favorite

Home in Madison

4.96 out of 5 average rating, 344 reviews

Unit A-Mountain Retreat- SAUNA-Hiking-Wineries

Renovated duplex in Madison, VA. Enjoy a peaceful setting, amazing views and convenient to wineries, wedding venues & hiking. New SAUNA! On-site walking trail. Near Early Mtn Vineyards, Prince Michelle Winery, Yoder's Market, Bald Top Brewing & Plow & Hearth. A 30 min drive to Charlottesville, Shenandoah Nat. Park, Culpeper & Orange. Shopping, restaurants, breweries, antiquing, site seeing and more. *RENT ENTIRE HOME* - Inquire for our unit A & B combined rate. Pet (dogs only) $30 per night.

Mar 20 – 27

R3,460 ZAR per night

Guest favorite

Guest suite in Culpeper

4.98 out of 5 average rating, 246 reviews

Spacious property-deluxe amenities; hot tub & more

Enjoy the beauty of nature in our beautiful private 2 room suite. Located in Culpeper County Virginia, you are minutes away from world class dining, wineries, great breweries while only 20 minutes from Shenandoah National Park. Retreat to the deck for an evening soak in the hot tub after a day of exploring the area. This space provides a queen bed, plenty of sitting space, full private bathroom, walk in closet, 50 inch smart TV, WIFI, mini fridge, ice maker, microwave, and coffee maker.

Sep 25 – Oct 2

R1,978 ZAR per night

Guest favorite

Cottage in Orange

4.95 out of 5 average rating, 364 reviews

Private Fenced Yard for Dogs/Horses - 2BR Cottage

2BR Hen and Hound Cottage is located just outside Orange, VA and has a private fenced yard for pets and walk-in access to adjacent James Madison's Montpelier and its many walking trails. In addition, we are minutes away from all of the popular wedding venues in Orange and a short drive to Shenandoah National Park. Our house on Whistle Stop Farm (so named for the train that passes by) is next to the cottage if you need us. Otherwise, the place is yours. Come enjoy some time in country!

Aug 21 – 28

R2,039 ZAR per night

Guest favorite

Cottage in Ruckersville

4.91 out of 5 average rating, 267 reviews

Lake Haven Cottage

Make yourself at home at our peaceful 1-bedroom cottage that has everything you need for your trip to the Blue Ridge Mountains. The cottage comes with heating, AC, Washer+Dryer and DIRECTV. During your stay, you can also enjoy using a convenient private bathroom, kitchen, and living room. Our Airbnb is within driving distance to UVA, the Skyline Drive & Shenandoah National Park, local wineries, craft breweries and much more!

Dec 20 – 27

R1,954 ZAR per night

Guest favorite

Chalet in Brightwood

4.98 out of 5 average rating, 104 reviews

Charming Chalet in Blue Ridge Wine Country

NEW! PICKLEBALL/BASKETBALL COURT PUTT PUTT GOLF Sunset Ridge is in the heart of all you want to do! Newlyweds to families, everyone will love it here! The peace and quiet of the country, or the excitement of exploring new and different places, all await you! Check out our guidebook for local attractions, restaurants, nightlife, and sightseeing. Enjoy the serenity of the country! Follow us: @sunsetridgechalet

Sep 12 – 19

R3,292 ZAR per night

Guest favorite

Guesthouse in Madison

4.97 out of 5 average rating, 229 reviews

Hebron Valley Cottage

Nestled in the scenic Hebron Valley, this 2 bedroom 1 bath cottage is the perfect getaway from busy, city life. The cottage offers panoramic views of the Blue Ridge Mountains, including Old Rag and is located near several wineries, breweries, restaurants, antique shops, hiking trails and historic sites. The cottage is 3 miles from the town of Madison and is convenient to Charlottesville, Culpeper and Orange.

Nov 30 – Dec 7

R3,019 ZAR per night

Superhost

Guest suite in Madison

4.83 out of 5 average rating, 209 reviews

Farmette in Madison - Madison, VA

The Wolftown Farmette has a cozy fireplace, outdoor fire pit, a big front porch, two large bedrooms with two king size beds, a long bath tub and separate shower, all for you to enjoy after a day of hiking or vineyard tours. Come see us in Madison County! We are 3 minutes from Early Mountain Vineyard and 10 minutes from the Shenandoah National Park Graves Mill entrance.

Jul 22 – 29

R1,639 ZAR per night

Superhost

Guesthouse in Syria

4.88 out of 5 average rating, 559 reviews

Cozy 1 room cabin in the mountains.

In the heart of the Shenandoah mountains. 1 mile from White Oak Canyon and Old Rag for amazing hikes. Perfect for the fly fisherman (lots of local streams) or a nice quiet get-away for a couple. Once you park your car you can sit back and just listen to the river flowing in the back yard & enjoy a nice beverage next to the fire pit. The property is a very special place!

Jul 4 – 11

R1,353 ZAR per night