Cottage holiday rentals in Charlottesville

A cozy cottage, named the 'Sugah Shack,' is nestled amidst the rolling hills of the Blue Ridge Mountains. The white exterior contrasts with the vibrant greenery surrounding the property, while the majestic mountains form a picturesque backdrop against a bright, partly cloudy sky.

5 out of 5 average rating, 219 reviews

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

The Carriage House is viewed from the yard, emphasizing its white exterior and green roof. The screened porch is visible, surrounded by natural landscaping, including grasses and bushes. Tall trees form a backdrop, contributing to the tranquil setting.

4.9 out of 5 average rating, 269 reviews

The Carriage House

Spacious 2 bedroom Carriage House in Crozet. Each of 2 bedrooms has a queen bed with a queen sleeper sofa in living room. Enjoy a quiet country setting with convenience to hiking, outdoor activities, wineries & breweries. Relax & unwind on the screened porch, enjoy meals in the full kitchen and convenience of in unit laundry. The Carriage house is the perfect place for a weekend trip or an extended stay in Central Virginia. You'll have the house to yourself with the ease of keypad self check-in.

5 out of 5 average rating, 149 reviews

A charming cottage is nestled among lush green grass and surrounded by trees. Its metal roof and white siding are complemented by well-maintained shrubbery. Dappled sunlight filters through the tree branches, creating a serene outdoor ambiance.

Cottage in Covesville

Historic cottage with stunning mountain views

Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

A charming cottage exterior showcases a green facade with textured wood siding, complemented by a welcoming porch. Outdoor seating is provided by rustic chairs around a fire pit on the lawn. A table nearby offers an inviting spot for dining, set against a backdrop of distant mountains.

4.91 out of 5 average rating, 215 reviews

Idyllic Cottage Retreat

⭐️ Condé Nast Traveler Approved ⭐️ Cozy cottage nestled on a historic 400-acre Blue Ridge Mountain farm abutting Shenandoah National Park. Every space inside this cozy cottage is creatively styled, with tons of perfectly imperfect charm. Outside, a hammock beneath the elm trees, fire pit and grill, all allow for enjoying the splendor of this peaceful enclave. Excellent day-tripping to many of central Virginia's celebrated wineries and breweries, as well as scenic drives and hiking trails.

The cottage is framed by lush greenery and trees, showcasing rustic wooden siding and a steeply pitched roof. Large windows allow natural light to fill the interior. A pair of rocking chairs is situated on the porch, inviting relaxation in a serene outdoor setting.

4.99 out of 5 average rating, 276 reviews

Oasis in the Blue Ridge Rt. 151 Brew Ridge Trail

Welcome to the Glass Hollow Cottage! Come make yourself at home and enjoy the rustic charm of our custom hand-built cottage. A perfect getaway for a couple or friends who want a 1-of a-kind destination. Adventure and R & R await you!!! Enjoy the well stocked kitchen & the bright, clean, cheery ambience.... everything you need to feel at home & then some. Prime location: Just minutes to Rt. 151/Brew Ridge Trail, dozens of popular wineries/breweries, Wintergreen Resort & Shenandoah Nat. Park.

The image showcases a cozy front porch featuring two rocking chairs, perfect for enjoying mountain views. The living area displays a comfortable couch and a stylish coffee table. A private hot tub is visible on the rear deck, complemented by scenic outdoor seating arrangements.

4.97 out of 5 average rating, 153 reviews

Cottage on 151 w/ Hot Tub, Firepit, Mountain Views

Welcome to Towler Cottage, a getaway in the heart of Route 151 in Afton. The cottage is within minutes from the best wineries and breweries, great local trails, and the Blue Ridge Parkway! Relax in the hot tub on the rear deck, or sit out by the fire pit and gaze at the stars. Enjoy great mountain views from the front porch rocking chairs. With one bedroom with a queen bed, plus a pull-out couch in the living room, the cottage is perfect for couples. Located 25 minutes from Charlottesville.

5 out of 5 average rating, 288 reviews

A comfortable seating area is highlighted by a dark sectional sofa adorned with decorative pillows. A wooden coffee table sits at its center, accompanied by a small potted plant. Light enters through two windows, framed by simple blinds, while leafy plants enhance the inviting atmosphere.

Cottage in Woolen Mills

Meade Cottage

Lovely 1940s cottage located in beautiful downtown Charlottesville. Less than 1 mile to the downtown mall, with coffee shops and top Belmont restaurants close by, some within a 5 minute walking distance. The cottage is across the street from Meade Park and the Wednesday farmers market from May to September. Perfect for a romantic couples getaway or a family vacation. The space is ideal for a traveling professional in Charlottesville and needing to be close to the University or the Hospital.

Cottage in Jefferson Park Avenue

The exterior of a charming cottage is featured, showcasing white brick walls and a sloped gray roof. Two dormer windows enhance the appearance, while a welcoming red door serves as a focal point. Well-maintained green grass and manicured shrubs surround the house, creating a friendly environment.

4.91 out of 5 average rating, 443 reviews

Adorable cottage steps from Grounds

A cozy Milton Grigg designed cottage and detached carriage house three minutes walk to the Lawn and ten minutes walk to the Stadium. Nestled in a wooded neighborhood. Perfect for visiting parents, UVA chapel weddings, med student rotations, and football games. NOTE: The cottage sleeps five adults and the carriage house two adults. There is one bathroom in the cottage and one in the carriage house. Please read through all the information in the 'Description' section below before booking.

5 out of 5 average rating, 193 reviews

A view from an open doorway reveals a covered porch with white rocking chairs. A welcome mat lies on the wooden floor, leading to a scenic landscape of rolling hills adorned with autumn foliage. A glimpse of black chairs is visible in the distance.

Cottage in Gordonsville

Merry View Cottage

Our newly renovated farm cottage sits at the edge of a grove of giant hardwoods. Enjoy year round mountain views, including Merry Mountain. Ease into the morning while watching wildlife from a front porch rocker. Visit local wineries, breweries, restaurants, museums, shops, hiking trails or wedding venues. Unwind in the hammock or practice yoga on the back deck. Prepare dinner in our full size kitchen. Then, star gaze around the fire-pit after dark. This peaceful oasis awaits you.

Superhost

A charming cottage exterior is depicted, showcasing a white wooden facade with a blue roof. A patio area is furnished with a table and chairs under a green umbrella, surrounded by landscaped gardens and a pathway. Warm light is visible from the windows, suggesting a welcoming interior.

4.87 out of 5 average rating, 619 reviews

Couples Getaway,heart of RT 151,stunning views

The Cottage is conveniently located along the Brew Ridge Trail. Sit on your patio and watch the sun set over Humpback rock and the Blue Ridge Mountains. Amazing location that’s set right in the middle of all the breweries. Spacious 6 acre farm with Route 151 road frontage. This handsome cottage is the perfect romantic get-a-way. Enjoy WiFi, air con, parking, self check-in and all the amenities you need to feel at home. Picturesque mountain views and beautifully landscaped grounds.

Cottage in Charlottesville

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.

5 out of 5 average rating, 176 reviews

Honey B - Beautiful loft near UVA, Monticello

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.

Cottage in Charlottesville

4.95 out of 5 average rating, 700 reviews

Tranquil Cottage sleeps 5

An adorable home with breathtaking sunsets over the Blue Ridge mountains. We are 4 miles to downtown and minutes to many vineyards, shows and restaurants. Enjoy comfortable beds, the fire pit with Adirondack chairs, big skies filled with stars and animals. Walk our country roads, feed the horses, enjoy the views of the mountains and meadows. Base price is for 2 people, no pets or children under 8 for safety. Stays more than 3 nights will have an added cleaning fee of 20.00

Popular amenities for cottage rentals in Charlottesville

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.79 out of 5 average rating, 306 reviews

A cozy bedroom features a wooden ceiling with warm lighting and a queen-sized bed adorned with a textured blanket. A wooden desk and chair sit nearby, with natural light filtering through the large windows. Complementary furnishings enhance the inviting atmosphere.

Cottage in Stanardsville

Glade Cottage at White Lotus Eco Spa Retreat

A charming cottage is depicted with a steeply pitched roof and a white exterior. Green shutters frame the windows, and flower boxes hold vibrant plants. A wooden gate leads to an inviting entrance, surrounded by manicured grass and a stone wall.

4.98 out of 5 average rating, 53 reviews

Cheerful & Charming Newly Renovated Cottage

An outdoor space features a wooden deck illuminated by string lights, creating a warm ambiance. A vibrant sunset is visible through bare trees, casting hues of orange and pink across the sky. A sign labeled 'Virginia Lovers' is positioned against a decorative wall.

4.97 out of 5 average rating, 62 reviews

Riverfront Tree House- Ski, Hot Tub, 3 Fire Pits

4.88 out of 5 average rating, 191 reviews

An inviting outdoor deck features a luxurious hot tub surrounded by trees, creating a serene retreat. Inside, a vibrant bathroom showcases floral wallpaper and elegant fixtures. A cozy bedroom is highlighted by bright orange walls, while the living area features a comfortable blue couch and greenery.

Cottage in Stanley

Vibrant Cottage | Hot Tub | Pets | Shenandoah NP

A charming cottage exterior features a welcoming front porch with white railings, inviting seating, and decorative plants along the pathway. The light-colored siding is complemented by large windows with sheer curtains, enhancing the serene woodland surroundings.

4.93 out of 5 average rating, 58 reviews

Hillside Hideaway. Quiet.clean.hot tub.family

4.95 out of 5 average rating, 467 reviews

An aerial view captures the guest house and the surrounding property, showcasing a spacious grass area and a 30,000-gallon in-ground pool. The pool area features several blue lounge chairs and is framed by mature trees and landscaped pathways.

Cottage in Madison

THE PERFECT HIKING & WINERY COUNTRY RETREAT

4.84 out of 5 average rating, 167 reviews

The Servants' Cottage, built in 1856, is showcased with a classic white exterior and a metal roof. Surrounded by well-maintained grass and shrubs, it is set against a backdrop of trees and open fields. Natural light casts gentle shadows on the lawn.

Cottage in Gordonsville

Quaint Cottage - Wolftrap Farm (Horse neighbors)

A modern cottage is nestled among vibrant autumn foliage, featuring a gravel pathway leading to the entrance. Large windows illuminate the building, while a covered porch invites relaxation. The surrounding landscape offers a serene green lawn, complemented by trees displaying fall colors.

4.99 out of 5 average rating, 93 reviews

42Private Acres*Hot Tub*National Park*Hiking*WI-FI

Pet-friendly cottage rentals

The cabin features a rustic wooden exterior, complemented by multiple large windows that allow natural light to enter. A small covered porch is accessed by a set of steps, surrounded by a forest of trees with autumn foliage.

4.94 out of 5 average rating, 124 reviews

#1 Mountain Cabin Near Shenandoah National Park

4.89 out of 5 average rating, 211 reviews

A charming single-story house is presented with a light-colored exterior and dark shutters. Rocking chairs are positioned on the front porch, inviting relaxation. A well-maintained lawn surrounds the home, and a backdrop of trees complements the serene setting.

Cottage in Orange

Willie's Place Country Cottage Pets Allowed

A charming green cottage features a covered front porch with seating, inviting visitors to enjoy outdoor moments. The well-maintained yard showcases a mix of grass and stone pathways, with large windows allowing natural light to enhance the inviting exterior.

4.98 out of 5 average rating, 265 reviews

High Street | Walk to Everything Crozet | Pet-Frie

The exterior of a cozy, white house is surrounded by lush greenery. A covered porch is visible, along with colorful outdoor seating. Warm string lights hang above the outdoor area, inviting relaxation and enjoyment of the natural surroundings.

4.88 out of 5 average rating, 486 reviews

GreenHouseNelson

Superhost

The exterior of the cottage features a welcoming porch with two seated chairs and a wooden railing. Lush greenery and trees surround the cottage, complemented by a beige wooden fence that offers privacy. A clear blue sky brightens the scene, enhancing the inviting atmosphere.

Cottage in Waynesboro

4.9 out of 5 average rating, 309 reviews

The Copper Cottage - near the Appalachian Trail

4.96 out of 5 average rating, 474 reviews

A living area features a comfortable gray sofa and armchair, set on a light area rug. A wooden coffee table is centrally located, while a TV sits on a decorative stand. Natural light enters through a window, complemented by soft lighting from a chandelier above.

Cottage in Orange

Private Fenced Yard for Dogs/Horses - 2BR Cottage

Cottage in Charlottesville

4.95 out of 5 average rating, 201 reviews

pink cottage @ locust grange

A charming cottage is nestled among greenery, showcasing a light-colored exterior. The porch features a railing and steps leading to the entrance. Surrounding landscaping includes blooming flowers and shrubs, enhancing the tranquil setting. A gravel driveway provides access to the home.

4.96 out of 5 average rating, 159 reviews

The Cottage at Peavine Hollow Farm-No cleaning fee

Private cottage rentals

4.95 out of 5 average rating, 165 reviews

A light-filled living room features a comfortable sofa adorned with decorative cushions. A coffee table sits in front, and two lamps illuminate the space. Large windows overlook the backyard, allowing natural light to enhance the inviting atmosphere.

Cottage in Palmyra

Bluebird Cottage B: Quiet, Firepit, Patio, Games

4.99 out of 5 average rating, 175 reviews

A well-lit bedroom features a cozy bed adorned with decorative pillows. Two bedside lamps provide soft lighting, while a ceiling fan adds airflow. Natural light enters through a window framed by light curtains, complementing the serene artwork displayed above the bed.

Cottage in Madison

Fishback Cottage, Convenient Central location

4.9 out of 5 average rating, 115 reviews

A white post bearing the address '9114' stands in a green lawn, with a charming white house featuring red shutters and a covered porch visible in the background. A clear sky with scattered clouds is overhead, and trees line the property.

Cottage in Culpeper

The Cottage at Old Salem School

A serene landscape surrounds the cottage, featuring a well-maintained garden with vibrant green shrubs and colorful flowers. A gravel path guides the way to the entrance, while large rocks and a variety of plants enhance the natural beauty of the property.

4.99 out of 5 average rating, 167 reviews

Beautiful, Remodeled Eco Cottage in Afton

4.98 out of 5 average rating, 198 reviews

A modern cottage is enveloped in a blanket of fresh snow, with a red and cream exterior. The front porch features steps leading to the entrance. Surrounding trees and shrubs are covered in white snow, creating a serene winter landscape.

Cottage in Etlan

Amy's Place

4.97 out of 5 average rating, 109 reviews

A spacious grassy area features a well-maintained building with a wooden deck. A wooden fence borders the property, complementing the serene countryside view that includes trees and rolling hills under a blue sky with scattered clouds.

Cottage in Grottoes

Cheerful 3 bedroom cottage on secluded horse farm

4.94 out of 5 average rating, 208 reviews

A serene landscape is captured at dusk, showcasing sweeping fields with hints of frosted ground. Majestic mountains are visible in the distance, highlighted by the warm hues of a vibrant sunset, blending shades of orange and pink against the evening sky.

Cottage in Shenandoah

Cozy Cottage Retreat: SNP, Luray Caverns, River

A single-story house is framed by a large tree, with a fenced front yard featuring green grass. The house displays a mix of windows and a door beneath blue shutters, nestled in a peaceful, open landscape.