Holiday rentals with breakfast in Orange County

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Top-rated Holiday Accommodation with Breakfast in Orange County

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Private room in Locust Dale

Shearer Suite - The Inn and Tavern at Meander

This elegant and refined two-room suite is upstairs in the Manor House of our Virginia Wine Country bed and breakfast and opens onto an inviting upstairs porch with magnificent Blue Ridge mountain views. The gracious, private sitting room is decorated in gold, ivory and Chinese reds and features an Oriental rug on the pine floor, a gas fireplace and wingback chairs. The dramatically decorated bedroom has a cherry queen four-poster bed piled with elegant linens and pillows. The private bath offers an over-sized soaking tub with shower. The suite is a tribute to former owners, the Shearer sisters, taste and refinement and has in-room Wi-Fi.

Guest favourite

Home in Mineral

4.95 out of 5 average rating, 19 reviews

Lake Life with all the Views!

Unwind at this tranquil Lake Anna retreat! This 5-bed, 3-bath home welcomes you with stunning sunrises & breathtaking sunsets from your screened-in porch, deck, or dock. The open-concept main level living features panoramic water views in the the cozy living room, sitting area, spacious kitchen with bar & dining area for 10. The lower level offers 2 bedrooms, bath, family room & more. With a game room & dock for boating, fishing or sunbathing, this serene lakeside getaway is your perfect escape!

Top Guest favourite

Guesthouse in Rapidan

4.98 out of 5 average rating, 51 reviews

Romantic & Private Guest Cottage on a Lovely Farm

Nested at the base of Cedar Mountain, the 100 acre Farm at Cedar Mountain's guest cottage is a beautiful mix of mid-century modern and vintage. It's the ideal space for a couple looking for a romantic getaway or for friends wanting to explore the area and relax. Please contact us in advance if you are interested in bringing a pet. PRIOR APPROVAL is required and a pet fee per dog (up to 2) is required. No unattended pets are allowed in the cottage. Please do not allow them on furniture.

Top Guest favourite

Bungalow in Orange

4.99 out of 5 average rating, 437 reviews

Farm Cottage just outside town of Orange.

Charming 1920's cottage on a large farm just outside the town of Orange. Completely renovated and updated. Convenient to vineyards, battlefields, wedding venues and popular tourist destinations. Bucolic setting, very private. Spaces to enjoy the out of doors. Less than 2 miles to in-town wedding venues and Rounton Farm. Less than 4 miles to Inn at Willow Grove. 5 miles to Montpelier. Less than 7 miles to Grelen. 10 miles to Gordonsville. 12 miles to Barboursville. 19 miles to Mineral.

Guest favourite

Private room in Gordonsville

5 out of 5 average rating, 13 reviews

Gorgeous Country living at Chase Cottage Suite

Chase Cottage surrounded by green fields with white fencing, horses, and mountains. If you want a quiet romantic getaway or just a comfortable place to stay while you go vineyard hopping, horse showing, fox hunting, hot air ballooning or UVA events The Suite at Chase Cottage is perfect. Featuring a Queen Bedroom en suite with organic bedding, a luxury living room with a big couch to curl up on to snuggle by the electric fireplace. A private patio to enjoy your favorite beverage.

Top Guest favourite

Home in Madison

4.96 out of 5 average rating, 420 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. 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. Dogs allowed-$30 fee.

Guest favourite

Home in Madison

4.94 out of 5 average rating, 278 reviews

Unit B -Tatum’s Retreat -SAUNA- Hiking-Wineries

Beautifully renovated and cozy home in Madison, VA. Unit B is the bottom level of a duplex offering a peaceful setting, amazing views, close to wineries, wedding venues, hiking. SAUNA! On-site walking trail. Near Early Mtn Vineyards, Prince Michelle, Yoder's Market, Bald Top Brewing & Plow & Hearth. A 30 min drive to Charlottesville, Greene, Shenandoah Nat. Park, Culpeper & Orange, w/ shopping, restaurants, breweries, hiking, antiquing, site seeing & more. Dogs allowed- $30 fee.

Private room in Unionville

5 out of 5 average rating, 35 reviews

Lynn Haven Manor - Hunter's Retreat

Stately Virginia manor home, private landscaped grounds, 60 miles to DC and 55 miles to Richmond. Visit numerous nearby historic sites, such as Montpelier and Monticello. Also nearby are many of Virginia's most celebrated wineries such as Barboursville, Keswick and Merrie Mills, not to mention our fabulous fox hunting country. Enjoy our comfortable bedrooms, and the plenty of private spaces to relax, read or just reflect.

Guest favourite

Private room in Barboursville

4.96 out of 5 average rating, 24 reviews

Private guesthouse with full bath and free parking

Take it easy at this unique and tranquil getaway. Brand new private room, detached from original farmhouse. Private entrance behind garage. Centrally located to many nearby vineyards and breweries, and 25 minutes from Charlottesville. If you are looking for a getaway, you will find rest and relaxation here. Enjoy the abundance of several vineyards and breweries close by, as well as hiking. Come visit Barboursville.

Private room in Orange

Women's Weekend Wellness Retreat

Welcome to a transformative weekend healing retreat designed exclusively for women—a safe, nurturing space where you can relax your nervous system and reconnect with your inner peace. Over the course of this retreat, you’ll experience a unique blend of restorative activities, including playful goat therapy, therapeutic crafts, and empowering affirmations to help renew your soul.

Guest favourite

Home in Mineral

4.94 out of 5 average rating, 17 reviews

6BR Lakefront Lake Anna, Views, Boat Dock, Hot Tub

Brand new luxury listing! The PERFECT house for large families. Breathtaking lake views and 500+ ft of private waterfront property! This 6 bed 4 bath 5,000+ square foot Waterfront home is cozy, meticulously cared for and the greatest spot for your next memorable family vacation. Great for kids, wedding parties, large groups of friends, and fur babies!

Top Guest favourite

Cottage in Madison

4.95 out of 5 average rating, 445 reviews

THE PERFECT HIKING & WINERY COUNTRY RETREAT

Welcome! Our charming 2 bedroom guesthouse is located in the middle of our 23 acre farm. Currently the property is being used for livestock - cattle (and one donkey named Jasper). Please note: The pool will be open the first week in May thru Labor Day Weekend (sometimes longer if weather permits).