Holiday rentals in Hollymead

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Top-rated holiday rentals in Hollymead

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A charming cottage with a metal roof features a welcoming front porch, surrounded by greenery. Rocking chairs offer a cozy spot, while stone pathways lead to a landscaped yard. Light spills onto the deck from nearby trees, blending indoor and outdoor spaces harmoniously.
Home in Barboursville
4.92 out of 5 average rating, 306 reviews

Spaniel Hill; cozy hilltop home w privacy & views

Cozy hilltop with Views, deck and hot tub. Cottage furnished with original art and antiques collected by us, the cottage is easy to get to but feels like a world away. Recently renovated main level has three cozy bedrooms and 1.5 baths, sleeps 6, and the garden level suite offers one large king bed and a twin bed with full bath and separate sink area, sleeps 3. Close to UVA, Pantops 250 corridor, theDowntown Mall, Gordonsville and Orange to our north. Over 20 highly rated wineries within 20 m

Top guest favourite
The unique octagonal house is framed by lush greenery, showcasing its distinctive architecture. A spacious deck offers a vantage point for enjoying unobstructed views of the surrounding landscape. Panoramic windows reflect the natural beauty of the Blue Ridge Mountains, inviting light into the living space.
Home in Afton
4.99 out of 5 average rating, 103 reviews

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

Top guest favourite
A modern structure is nestled among tall trees, surrounded by lush greenery. The building features a dark exterior with large windows, allowing natural light to highlight the inviting entrance. Vibrant plants and foliage are visible in the foreground, enhancing the serene landscape.
Guest house in Charlottesville
4.98 out of 5 average rating, 312 reviews

Renew @ Coniferidge.

Constructed in 2017 “ Renew” offers a peaceful, clean and simple space furnished with a comfortable modern mix style. It is situated a short distance from the main home and offers just the privacy you are looking for. This property, located outside beautiful Charlottesville Va. is an easy drive to restaurants, shopping, art, culture, wineries, history, parks and the Uva . Flat Screen Smart TV (use your logins to access your favorite sites ) NO pets - out of consideration of future guests

Top guest favourite
The entrance features double wooden doors that open to a welcoming interior. A 'hello' mat is placed on the threshold, and two stylish chairs are positioned on the balcony above, inviting guests to enjoy the view. Lush plants accentuate both sides of the entrance.
Flat in Somerset
4.99 out of 5 average rating, 217 reviews

Cozy Farm Apt near Cville•wineries, mt. views

Come experience a relaxing getaway on our family’s dairy farm! Set in beautiful Orange County, We are close enough to Charlottesville (25 min) to fulfill all your shopping and eating needs, but have the privacy, calm and tranquility of the country, with beautiful majestic mountain views! This is a wonderful location for exploring all of wine country, unwinding from the hustle of busy life, and then taking in the sunset in this quiet country setting with rolling hills as your backdrop!

Top guest favourite
The dark wooden cabin, framed by lush greenery, sits at a hillside location with panoramic mountain views. A deck extends from the cabin, featuring a hanging basket chair. A warm sunset casts a golden hue across the sky, enhancing the serene atmosphere.
Cabin in Free Union
4.99 out of 5 average rating, 222 reviews

Shenandoah Stargazer with Sauna

Stargazer is the perfect place to get away from it all! The stillness and serenity of being nestled in a bird and wildlife sanctuary is so good for your soul. Watch the sunrise from a hanging basket chair at 2700 feet of elevation, or wait for moonrise and toast spectacular star views! Relax in the sauna after a day filled with hiking and an al fresco meal on the deck. Roast s’mores at the deck fire table or over the side yard fire pit. There's magic in the air at this mountaintop retreat!

Top guest favourite
A charming log cabin with a dark metal roof features a welcoming front porch adorned with potted flowers and decorative pumpkins. The rustic wooden door adds character, while the surrounding grassy area and trees provide a natural setting against a backdrop of distant mountains.
Cabin in Stanardsville
4.99 out of 5 average rating, 259 reviews

Cabin at Rabbit Hollow

Charming log cabin nestled in a glen by the Shenandoah National Park is an ideal retreat for a romantic get-a-way. The first floor contains a beautiful kitchen, dining area, full bathroom featuring a whirlpool tub, and cozy living room with a wood burning fire place. The second level holds the bedroom with a comfortable king size bed and a half bathroom. There are two porches where guests can relax with their morning coffee or evening cocktails while enjoying the wooded and mountain views.

Top guest favourite
A spacious living area displays soft beige sofas paired with dark blue accent tables. Natural light filters through large windows, enhancing the warm, neutral tones of the walls. A glimpse of the kitchen and bedroom can be seen through open doorways, providing a sense of flow.
Home in Charlottesville
4.96 out of 5 average rating, 219 reviews

Woodwind Cottage

Woodwind Cottage is a brand new, beautifully built cottage with living room, bedroom, bath, kitchen and loft. It has charming architectural details and a covered porch for enjoying the view of the woods. The loft has a fold out sofa for an extra guest or private work space. The home has wifi, smart tv for streaming, and a gas fireplace. Enjoy reading in the oversized window seat, rise early to see deer in the yard or, perhaps, a hot air balloon overhead in the spring and fall.

Top guest favourite
A serene patio area features a small round table surrounded by two black chairs. Lush greenery and a pathway visible in the background enhance the tranquil setting, with garden views inviting relaxation.
Cottage in Charlottesville
5 out of 5 average rating, 194 reviews

Honey B - Beautiful small house 9 minutes from UVA

Best of both worlds! In beautiful nature but close to UVA, Monticello and downtown. Honey B (Honey House 2) has a lofty feel with the footprint of a small house. High ceilings and several skylights allow for light and privacy in the quiet neighborhood, Located on the southwest side of Charlottesville, just 7 minutes to Scott Stadium, UVA campus, and restaurants, 10 minutes to historic downtown mall, Thomas Jefferson’s Monticello and central to many major wineries and breweries.

Top guest favourite
A grassy open area is depicted, with a black and white dog lying comfortably on the ground. In the background, several canoes are visible on a trailer, positioned under trees that provide partial shade.
Guest suite in Charlottesville
4.93 out of 5 average rating, 171 reviews

The Brothers Great Room

Your private guest suite is located in Northern Albemarle County Virginia. We cannot allow cats(due to family members with allergies and the extra cleaning required) We are just off of Route 29 with easy access to local venues. The suite is up one flight of stairs. Albemarle County is central to the University of Virginia, Monticello, Montpelier, wineries, craft beer breweries, and wedding venues in the area. Your dogs may run the open areas. Please clean up after your pet.

Guest favourite
A welcoming exterior of a curved house is presented, featuring a light stone pathway leading to a front porch. Two white rocking chairs are positioned in front, with decorative planters filled with greenery on either side. The backdrop consists of lush trees and a blue sky.
Home in Charlottesville
4.97 out of 5 average rating, 153 reviews

Unit 1_Expansive Luxury Suite for up to 4 Persons

Take a journey to Albemarle County and experience historical sites and luxurious accommodations. Sonsak is uniquely situated on the Thomas Jefferson Parkway; nears area's most celebrated landmarks, including Monticello - Home of Thomas Jefferson, directly across Michie Tavern and near Ash Lawn - Home of James Monroe, Carter Mountain Orchard and numerous Vineyards. Embark on a 'Journey Through Hallowed Ground', an unforgettable experience that's packed with history and beauty.

Top guest favourite
Treehouse in Stanardsville
4.97 out of 5 average rating, 105 reviews

CloudPointe Retreat

Rare Appalachian Treehouse Gem! Luxurious, one-of-a-kind retreat for couples. Elevated tiny house among the treetops, private parking, plush bedroom, sleek bathroom, beautiful kitchenette, loveseat, lounge, private double-level decks, fireside lounging (wood provided), gas grill, and patio with a hot tub! Surrounded by nature, with wineries, hikes, restaurants and shopping all nearby. Please come and relax and revel in the beauty of nature! 4WD is recommended.

Top guest favourite
An open living area is highlighted by a light-colored sofa and a wooden coffee table. A spiral staircase leads to an upper loft, while a dining table with wooden chairs sits nearby. Large windows provide ample natural light, illuminating the space.
Home in Charlottesville
4.98 out of 5 average rating, 612 reviews

The Loft at Minor Mill - Private loft apartment.

Our place is a newly constructed barn loft in our 1960's barn. Enjoy beautiful views of the surrounding countryside from large windows and a private balcony. The barn is surrounded by our horse pastures and neighboring fields. Self check in with the key lockbox. This loft is separate from the main house where we live. Private parking and entrance for our guests directly outside of barn loft (this is separate from the main house driveway).

Popular amenities for Hollymead holiday rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Albemarle County
  5. Hollymead