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Places to stay near James Monroe's Highland

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Top-rated holiday rentals near James Monroe's Highland

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Guest favourite
An open-concept living space is featured, showcasing a cozy seating area with a light grey armchair and a small side table. A dining table with black chairs is visible in the background, along with dark cabinetry and decorative items on display.
Home in Charlottesville

Rooftop*Mountains*Lake/Near Monticello/DT/Wineries

Spacious modern house with a brand new rooftop deck overlooking Carter Mountain and Monticello. Two spacious primary bedroom suits (one on each floor) with attached decks, plus additional two bedrooms and a full bathroom on the 2nd floor. Located in a quiet neighborhood. Backs up to a lake for beautiful views from each level and tranquil environment. Convenient location - minutes away from Monticello (2 mi/4 min), downtown (2.5 mi/6 min), UVA (3 mi/9 min), wineries (3.5 mi/5 min+) & breweries.

FamilyValueWalkability

4.99 out of 5 average rating, 136 reviews
Guest favourite
A cozy living area features a dark grey sofa adorned with patterned throw pillows. A glass coffee table sits in front, placed on a decorative rug. Natural light filters through bamboo shades on the windows, illuminating the space subtly.
Flat in Charlottesville

Heart of Belmont ~ 15 min walk downtown, free park

Stay here! In the cutest house in Charlottesville's most beloved neighborhood. You'll be in the heart of Belmont, just steps from some of the best restaurants in Cville, and a few blocks from the historic Downtown Mall - restaurants, shops, coffee, yoga, and music venues. 10 min walk ~ downtown mall 5 min ~ Rivanna River - trail and tubing/kayaking/SUP 5-10 min ~ UVA 5-15 min ~ Monticello/Monticello Trail 15-30 min ~ MANY popular wineries, breweries, and hiking in the Blue Ridge Mountains

ValueFamilyAir conditioning

4.94 out of 5 average rating, 145 reviews
Top guest favourite
A charming farmhouse is set on a spacious green lawn, surrounded by trees. Featuring a welcoming front porch with railings, the house displays multiple peaked roofs and large windows, inviting natural light. The grounds offer ample space for outdoor activities.
Home in Charlottesville

Thomas Jefferson Pkwy - Gateway to Monticello

Farmhouse on 14 acres offers closest proximity to Monticello (4 minutes away). Jefferson Vineyard (1 min), Ash Lawn (3 min), Carter's Mountain & Michie Tavern (5 min), Downtown Open-Air Mall (14 min). Relax with a cold drink on the front porch or enjoy views of the mountains and pond from the back deck. There is plenty of space to breathe here. Full kitchen & laundry. Feel free to snack on whatever we have. Great views & country feeling but close to everything. Relax & make yourself at home!

ValueFamilyLaundry

5.0 out of 5 average rating, 208 reviews
Top guest favourite
The image features a charming two-story home surrounded by lush greenery and flowering trees. A circular driveway leads to the entrance, with manicured lawns enhancing the exterior. The backdrop includes rolling hills and bright blue skies, creating a serene and inviting setting.
Home in North Garden

Lux Country Retreat minutes from Charlottesville!

Located just off route 29 this private luxury retreat with surrounding 2 acre fenced yard is one mile from Pippin Hill Farm & Vineyard and only 15 minutes from UVA/Charlottesville. You will find this home spacious, bright and airy, perfect for entertaining groups or families. The house is completely equipped with everything you may need to host the perfect getaway! Nearby attractions: Pippin Hill, Albemarle Ciderworks, Ragged Branch Distillery, Potter's Craft Cider and Charlottesville!

FamilyLocationLayout

4.97 out of 5 average rating, 402 reviews
Guest favourite
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.
Cottage in Charlottesville

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.

LocationFamilyWalkability

4.91 out of 5 average rating, 460 reviews
Top guest favourite
A single-story home with light blue siding is set against a clear sky. A vibrant door adds a pop of color to the entrance, which is framed by landscaped flower beds. A paved walkway leads up from the driveway, inviting visitors towards the front entrance.
Home in Charlottesville

3BR / Pets Welcome / Fenced Yard / Fiber Internet

Sitting atop the neighborhood, Monticello mountain can be seen from our Ridgetop home. Convenient to all parts of Charlottesville, including Downtown, UVA, and Hospitals. Local parks offer swimming, boating, & are all walkable. The fenced yard allows for a safe space for dogs and the private patio is perfect for relaxing. The home offers an open design in the kitchen, living & dining room. Bath has a modern tile with a jacuzzi tub. Fast TING fiber internet. Big Green Egg grill

FamilyLocationOutdoor spaces

4.97 out of 5 average rating, 164 reviews
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

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.

ValueFamilyLayout

4.98 out of 5 average rating, 166 reviews
Top guest favourite
Treehouse in Stanardsville

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 highly recommended.

ValueFamilyAmenities

4.98 out of 5 average rating, 139 reviews
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

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).

ValueFamilyView

4.98 out of 5 average rating, 638 reviews
Top guest favourite
A spacious Great Room showcases exposed beam ceilings and a brick fireplace. Comfortable seating surrounds a coffee table adorned with decorative items and plants. A dining area, visible in the background, features a long table with chairs, and natural light filters in through large windows.
Guest suite in Charlottesville

Spacious home with vintage character

3 BR shabby chic home sleeps 6 at base price. (Up to 9 at $30/night per extra guest). We've divided our enormous old house just outside of Charlottesville into two completely self-contained solar powered homes. EV charging available at no extra charge. 12 min to downtown, 15 min to Monticello or UVA. Convenient to the region's best wineries and right off one of the most beautiful scenic byways in Virginia. Sunny walkout deck with grill.

FamilyLocationTV

4.94 out of 5 average rating, 744 reviews
Top guest favourite
Guest suite in Keswick

Cozy Wine Country Escape | Near Clifton Inn

Tucked in Keswick, Virginia, this renovated 2-bedroom, 850 sq/ft suite is your perfect wine country escape. Two queen bedrooms, full kitchen, living room, and private entrance — all your own. Less than a quarter mile from Clifton Inn, minutes from Keswick Hall, and surrounded by award-winning wineries. Downtown Charlottesville is 15 min away, Monticello just 7. When the day winds down, find your spot in the hammock under the trees.

FamilyValueParks

5.0 out of 5 average rating, 131 reviews
Top guest favourite
A whimsical logo features a pink outline of a cottage, complete with a sloped roof and large front windows, evoking a charming and inviting atmosphere. The text 'Pink Cottage @ Locust Grange' is displayed prominently, emphasizing the location in Charlottesville, Virginia.
Cottage in Charlottesville

pink cottage @ locust grange

A dog lover’s paradise fenced in and safe for your beloved dogs. Located near the University of Virginia,Scott Stadium and all the other sport arenas.Short distance to UVA hospital and 2 miles from downtown Charlottesville. Walking distance to several restaurants and hiking trails. Ample parking right outside cottage.

FamilyValueComfort

4.93 out of 5 average rating, 233 reviews

Popular amenities for holiday rentals near James Monroe's Highland

KitchenWifiPoolFree parking on premisesAir conditioning

Other top sights near James Monroe's Highland

Carter Mountain Orchard

290 locals recommend

James Monroe's Highland

169 locals recommend

Jefferson Vineyards

121 locals recommend

Horton Vineyards

70 locals recommend

Eastwood Farm and Winery

44 locals recommend

Downtown Mall

360 locals recommend

Apartment rentals with wifi

Superhost
A sunlit sunroom features large panoramic windows offering views of the outdoors. Comfortable seating is arranged with two wicker sofas and a daybed, accented by vibrant cushions and a decorative blanket. A coffee table sits in the center on a striped area rug.
Apartment in North Downtown

Luxurious Posh Downtown Condo

ValueFamilySleep quality

4.9 out of 5 average rating, 196 reviews
Top guest favourite
A bright bedroom features a spacious bed flanked by two bedside tables with lamps. A framed cityscape artwork adorns the wall above the bed. Dark curtains frame the window, and a patterned rug covers the hardwood floor, creating a cozy yet modern ambiance.
Apartment in North Downtown

The Townie 3 BD/2BA Historic Downtown Building

ValueLocationWalkability

4.92 out of 5 average rating, 212 reviews
Superhost
Apartment in Charlottesville

Pet-Friendly in Belmont near UVA & Downtown - #311

LocationWalkabilityNearby

5.0 out of 5 average rating, 5 reviews
Superhost
An outdoor pool is showcased under a clear blue sky, surrounded by sun loungers and blue umbrellas. The water appears inviting, with gentle ripples reflecting the sunlight. Lush greenery is visible in the background, contributing to the serene setting.
Apartment in Gordonsville

Beautiful 2BD condo in an equestrian themed resort

FamilyLocationNearby

5.0 out of 5 average rating, 4 reviews
Guest favourite
A three-bedroom cabin is surrounded by tall trees, featuring a wooden exterior that blends with the natural environment. A set of stairs leads to a welcoming front porch, while a paved path guides visitors through the well-maintained landscape.
Apartment in Gordonsville

Shenandoah 3BR Cabin on Lovely Resort w/amenities

FamilyLocationHospitality

5.0 out of 5 average rating, 8 reviews
Superhost
An outdoor pool area is surrounded by lush trees displaying autumn colors. Multiple swimming pools are visible, complemented by an arrangement of sun loungers. A stone patio connects the pools, along with potted plants enhancing the natural scenery.
Apartment in Gordonsville

Shenandoah Crossing 2 Bedroom Cabin

LocationIndoor spacesCheck-in

4.75 out of 5 average rating, 4 reviews
Superhost
A wooden deck area is surrounded by lush trees, featuring two cozy yurts with distinct lattice windows. Soft lighting highlights the structure, creating a serene evening ambiance. Chairs are positioned on the deck, inviting relaxation while enjoying the natural surroundings.
Apartment in Gordonsville

Shenandoah Crossing - 2 Bd Yurt

Superhost
A spacious outdoor recreation area is featured, showcasing multiple pools surrounded by lounge chairs. Lush trees in autumn colors create a scenic backdrop, while umbrellas provide shade throughout the area. Pathways weave between the pools and seating, enhancing accessibility for guests.
Apartment in Gordonsville

Shenandoah Crossing 2 bed 1 bath Yurt Christmas!

LocationIndoor spaces

Family-friendly house rentals

Top guest favourite
A charming cottage with a peaked roof features a welcoming red door. Surrounding gardens with colorful flowers and lush greenery enhance the entryway, while a gravel path leads to the entrance. Trees provide a natural backdrop, contributing to the serene setting.
Home in Keswick

Charming Cottage at Golden Hill

ValueFamilyQuiet

4.99 out of 5 average rating, 924 reviews
Top guest favourite
Home in Charlottesville

10 Vineyards Within 10 Mi, EV charger & Mini Goats

FamilyLocationWalkability

4.97 out of 5 average rating, 144 reviews
Guest favourite
An inviting heated saltwater pool is surrounded by lounge chairs and a small table, set against a backdrop of lush greenery and trees. The calm water reflects the overcast sky, creating a serene outdoor space for relaxation.
Home in Charlottesville

Ivy Retreat | Heated Saltwater Pool & Hot Tub

FamilyValueLayout

4.91 out of 5 average rating, 152 reviews
Guest favourite
A panoramic view reveals rolling hills and a vibrant landscape adorned with autumn foliage. Lush green fields stretch towards the horizon, bordered by trees displaying a spectrum of fall colors under a clear blue sky.
Home in Charlottesville

Scenic Private Farm House Great for Large Groups

ValueFamilyBathroom

4.95 out of 5 average rating, 146 reviews
Top guest favourite
The exterior of a two-story colonial-style house is visible, showcasing a well-maintained front yard with mature greenery. A gravel driveway leads to a covered parking area. Bright blue skies and scattered clouds frame the scene, highlighting the peaceful, natural surroundings.
Home in Charlottesville

Wakefield Ct | Private Parking spots | Fast WiFi

FamilyLocationIndoor spaces

4.97 out of 5 average rating, 195 reviews
Top guest favourite
The exterior showcases a modern home nestled among trees, complemented by a serene koi pond. A wooden deck extends from the house, providing outdoor seating. Natural stone and gravel enhance the landscaping, while sunlight filters through the leaves, creating a calm atmosphere.
Home in Charlottesville

Charlottesville home - hot tub, fire pit & pond

LocationValueParks

4.99 out of 5 average rating, 100 reviews
Top guest favourite
A newly constructed house presents a modern facade with blue siding and white trim. A covered porch offers seating, surrounded by manicured shrubbery and flowers. The driveway leads to a spacious garage, while lush green grass enhances the inviting exterior setting.
Home in Charlottesville

Luxury Home *Steps* from UVA, the Corner, Wineries

ValueLocationAmenities

4.97 out of 5 average rating, 173 reviews
Top guest favourite
The kitchen features white cabinetry with glass-front doors and a herringbone backsplash. A farmhouse sink sits below a window, complemented by modern appliances, including a gas stove and a stainless-steel dishwasher. Natural light streams in, highlighting the spacious countertop area.
Home in Charlottesville

Cavalier Cottage-3 BR/Bath, Calm Amid UVA Grounds

FamilyLocationBack garden

5.0 out of 5 average rating, 215 reviews

Apartment rentals with air conditioning

Top guest favourite
A bright living area features a striped sofa adorned with green and gold cushions. A wooden coffee table sits in the center, complemented by a soft armchair nearby. Natural light filters through two windows, casting a warm glow on the decor, including framed artwork and a large flat-screen TV.
Flat in Charlottesville

Belmont BnB ~ 2BR/1BA ~ Comfort & Convenience

LocationValueLong stay

4.98 out of 5 average rating, 282 reviews
Guest favourite
An open-plan living space is featured, showcasing comfortable seating arrangements, including a beige sofa and dark chairs. A coffee table is positioned centrally, with a TV unit nearby. Light walls and warm lighting create an inviting atmosphere, complemented by a patterned area rug.
Flat in North Downtown

*Private Apartment in Downtown Cville*

FamilyValueWalkability

4.84 out of 5 average rating, 677 reviews
Guest favourite
The living area features a brick fireplace with a framed artwork above. Two green chairs with soft white cushions are positioned nearby, while a gray sofa with an orange accent pillow provides seating. A decorative rug lies on hardwood flooring, complementing the neutral walls.
Flat in Charlottesville

BELMONT DESIGNER APARTMENT- CVILLE CHARM

LocationValueSleep quality

4.9 out of 5 average rating, 730 reviews
Top guest favourite
A modern living area features a gray couch adorned with red accent pillows. A colorful abstract wall art hangs above a white media console, which holds a television. The kitchen area is visible in the background, complemented by red bar stools and wooden cabinets.
Flat in Charlottesville

Modern Belmont home - steps from Downtown Mall!

LocationValueIndoor spaces

4.91 out of 5 average rating, 894 reviews
Guest favourite
A welcoming living room features two sofas, one in cream and another in blue, adorned with colorful throw blankets. A central coffee table is positioned on a vibrant area rug, and a decorative mirror is mounted on the wall. A potted plant adds a touch of greenery to the space.
Flat in Charlottesville

Private 2-Bdrm Apartment 1 mile from Downtown Mall

LocationFamilyCleanliness

4.92 out of 5 average rating, 683 reviews
Top guest favourite
Flat in North Downtown

Boho Vibe: Walkable, Quiet, Historic Downtown

LocationValueAmenities

4.91 out of 5 average rating, 424 reviews
Top guest favourite
Flat in Crozet

The Barn at Haden near Wineries and C'ville

LocationValueBathroom

4.99 out of 5 average rating, 563 reviews
Guest favourite
The image depicts a brick building with a green upper facade and large windows. A wraparound balcony lines the second floor, providing access to outdoor space. The ground floor showcases Maya Restaurant with a large window and an awning, while a traffic light and pedestrian signal are visible at the intersection.
Flat in Charlottesville

Main Street Downtown Balcony Apartment

FamilyLocationLayout

4.91 out of 5 average rating, 405 reviews

Other great holiday rentals near James Monroe's Highland

Guest favourite
A charming brick cottage features a sloped metal roof and white-trimmed front door, framed by vibrant greenery and flowering bushes. A grassy area leads to the entrance, creating a welcoming exterior. Soft clouds drift above, adding to the serene outdoor setting.
Guest house in Charlottesville

The Cottage at Eastwood Farm and Winery

ValueLocationParks

4.89 out of 5 average rating, 172 reviews
Guest favourite
A beautiful farm landscape is displayed, featuring lush green fields bordered by white fencing. Rolling hills extend into the distance under a bright blue sky, with scattered clouds overhead. Several buildings are set amidst the greenery, contributing to the tranquil rural atmosphere.
Farm stay in Charlottesville

Cowboy cottage-hot tub on farm close to everything

ValueFamilyIndoor spaces

4.94 out of 5 average rating, 102 reviews
Top guest favourite
The exterior of the converted barn and silo is softly illuminated by string lights at dusk. A serene pond, framed by smooth stones, reflects the warm glow of light. The porch invites relaxation with its spacious seating and rustic charm, creating a peaceful outdoor setting.
Barn in Louisa

Unique OASIS - Silo Barn - Swim Pond- 5 Miles Trai

LocationFamilyHiking

4.99 out of 5 average rating, 148 reviews
Top guest favourite
Cabin in Charlottesville

Ivy Rose Cottage nestled b/t Cville & Vineyards

FamilyLocationGetting around

4.96 out of 5 average rating, 141 reviews
Top guest favourite
A cozy sleeping area is highlighted by a queen size bed with a floral-patterned quilt. Natural light filters through the large windows, framed by white trim, offering views of lush greenery. A television is positioned on a wooden stand, with decorative plants and artwork adorning the walls.
Serviced apartment in Charlottesville

Sunny private studio, walk to the University

LocationValueHeating

4.98 out of 5 average rating, 392 reviews
Superhost
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.
Cottage in Crozet

Idyllic Cottage Retreat

FamilyValueHospitality

4.89 out of 5 average rating, 269 reviews
Top guest favourite
A welcoming cottage entrance features a covered porch with a white railing, surrounded by lush greenery and colorful flowers. A stone pathway leads to the door, inviting guests into a serene outdoor space with various plantings.
Cottage in Charlottesville

Cottage in the Country (close to UVA!)

FamilyLocationAmenities

5.0 out of 5 average rating, 207 reviews
Top guest favourite
A bright dining space is showcased, featuring a white table surrounded by wooden chairs. Natural light filters through large windows, highlighting the modern decor. A stylish pendant light hangs above the table, complemented by a decorative centerpiece of fresh flowers.
Guest house in Charlottesville

Luxury tiny house 3 min from UVA

ValueFamilySleep quality

5.0 out of 5 average rating, 208 reviews