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Places to stay near James Monroe's Highland

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Top-rated vacation rentals near James Monroe's Highland

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Guest favorite
Home in Charlottesville

Newly Built Luxury Home 3min to UVA–Near Downtown

Walk to UVA, Stadium & Downtown! 🚶‍♂️ Our 3-story, 5BR retreat is the ultimate Charlottesville base for fans, families & wine lovers. ✨ Location: 🎓 UVA: 3m drive | 10m walk 🏈 Stadium: 4m drive | 15m walk 🛍️ Downtown: 5m drive | 18m walk 🍷 Wineries: 12-20m drive ✨ Amenities: ☕ Breville Barista: Pro espresso & beans 🎮 Fun: PS5,Foosball,Netflix,Disney+& Hulu 🏋️ Gym: Rowing machine, arm twister & yoga mat 👶 Family: Crib & kid gear 🅿️ FREE 2-car driveway + unlimited street parking! 🎓🏈🍷

FamilyLocationCondition

4.97 out of 5 average rating, 172 reviews
Top guest favorite
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.
Apartment in Charlottesville

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

Welcome to our well-appointed, centrally located 2 BR/1BA apartment! This cozy spot, with comfy queen beds, full kitchen, and cottage garden is a perfect homebase to relax in after a day of exploring. Set out on foot to: • Belmont Park (2 blocks) • Belmont Restaurants (15 min) • The Rivanna Trail (5 min) • The Downtown Mall (20 min) Short drives to Monticello (< 4 mi), grocery stores (1-2 mi), and UVA (2 mi). Your hosts are readily available in the above apartment should you need anything!

ValueLocationLaundry

4.98 out of 5 average rating, 283 reviews
Guest favorite
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.

LocationValueComfort

4.99 out of 5 average rating, 137 reviews
Top guest favorite
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!

LocationFamilyGrill

5.0 out of 5 average rating, 208 reviews
Top guest favorite
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!

FamilyValueAccuracy

4.97 out of 5 average rating, 404 reviews
Guest favorite
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 favorite
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

LocationFamilyWalkability

4.97 out of 5 average rating, 169 reviews
Guest favorite
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.
Guesthouse in Charlottesville

The Cottage at Eastwood Farm and Winery

The Winery Cottage at Eastwood Farm and Winery is located on the historic Woodland estate, built and owned by Jefferson builder, John Dunkum in 1810. Our 78 Cville acres include our family’s winery with indoor (year round) and outdoor (Apr-Nov.) tasting rooms, extensive wooded trails, incredible mountain views and apple orchard. Nestled on the same ridge as Monticello, Carter's Mtn, Jefferson Vineyards, Blenheim and Trump Vineyards. Five minutes to Belmont and Downtown Mall.

ValueFamilyTV

4.89 out of 5 average rating, 172 reviews
Guest favorite
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.

FamilyLocationDecor

4.98 out of 5 average rating, 166 reviews
Top guest favorite
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

Fully-updated, custom home in premier location. Warm hardwoods, lots of light, comfortable sofas & beds, easy check-in -- we strive to make your stay restful and refreshing. Nestled between Scott Stadium & JPJ, O'Hill & the Rotunda, wine country & the downtown mall, you could not be closer to the action yet in a quiet, residential neighborhood. The perfect place for any & all Cville/UVA events, work trips, reunions, weddings, family vacations, college visits, etc.

LocationFamilyIndoor spaces

5.0 out of 5 average rating, 217 reviews
Top guest favorite
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).

ValueFamilyBeach

4.98 out of 5 average rating, 640 reviews
Top guest favorite
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.

FamilyValueIndoor spaces

4.94 out of 5 average rating, 750 reviews

Popular amenities for vacation 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

69 locals recommend

Eastwood Farm and Winery

44 locals recommend

Downtown Mall

360 locals recommend

Condo 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.
Condo in North Downtown

Luxurious Posh Downtown Condo

FamilyLocationOutdoor spaces

4.9 out of 5 average rating, 196 reviews
Top guest favorite
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.
Condo in North Downtown

The Townie 3 BD/2BA Historic Downtown Building

FamilyValueAccuracy

4.92 out of 5 average rating, 214 reviews
Superhost
Condo in Charlottesville

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

LocationComfortView

5.0 out of 5 average rating, 6 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.
Condo in Gordonsville

Beautiful 2BD condo in an equestrian themed resort

FamilyLocationNearby

5.0 out of 5 average rating, 4 reviews
Guest favorite
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.
Condo in Gordonsville

Shenandoah 3BR Cabin on Lovely Resort w/amenities

LocationFamilyCleanliness

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.
Condo in Gordonsville

Shenandoah Crossing 2 Bedroom Cabin

LocationViewDecor

4.75 out of 5 average rating, 4 reviews
Superhost
An expansive outdoor pool area features multiple swimming pools surrounded by lounge chairs and shaded umbrellas. Lush trees in autumnal colors frame the scene, creating a connection with nature. A multi-level building is visible in the background, complementing the inviting atmosphere.
Condo in Gordonsville

2 bedroom Cabin @ Shenandoah resort

DecorAmenitiesPool

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.
Condo in Gordonsville

Shenandoah Crossing - 2 Bd Yurt

Family-friendly house rentals

Top guest favorite
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, 925 reviews
Top guest favorite
Home in Charlottesville

10 Vineyards Within 10 Mi, EV charger & Mini Goats

LocationFamilyQuiet

4.97 out of 5 average rating, 144 reviews
Guest favorite
The exterior of the West Wing showcases a welcoming entrance with a vibrant pink door. Steps lead up to the porch, which is surrounded by lush greenery and potted plants. The house's architecture features a combination of siding and a screened-in area, blending with the mature garden.
Home in Charlottesville

West Wing

FamilyLocationParking

4.91 out of 5 average rating, 326 reviews
Guest favorite
A spacious living room features two green velvet sofas and a yellow tufted couch, complemented by a patterned area rug. Natural light streams in through large windows, while side lamps provide additional illumination. Decorative artwork adorns the walls, enhancing the inviting atmosphere.
Home in North Downtown

The Cherry Tree, downtown estate, 8 parking spaces

LocationFamilyLong stay

4.97 out of 5 average rating, 204 reviews
Top guest favorite
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

ValueLocationAccuracy

4.99 out of 5 average rating, 101 reviews
Top guest favorite
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

FamilyValueIndoor spaces

4.97 out of 5 average rating, 173 reviews
Top guest favorite
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

FamilyValueCleanliness

4.97 out of 5 average rating, 197 reviews
Top guest favorite
A historic two-story estate is visible beyond a cobblestone driveway, framed by lush green trees. In the foreground, a stone statue of a dog holds a basket of fruit, adding charm to the property entrance against a clear blue sky.
Home in Charlottesville

Rivanna Farm Estate North I Pickleball I Pool

FamilyValueSleep quality

4.98 out of 5 average rating, 128 reviews

Apartment rentals with air conditioning

Top guest favorite
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.
Apartment in Charlottesville

Heart of Belmont ~ 15 min walk downtown, free park

FamilyValueComfort

4.95 out of 5 average rating, 148 reviews
Guest favorite
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.
Apartment in Charlottesville

BELMONT DESIGNER APARTMENT- CVILLE CHARM

ValueFamilyWifi

4.9 out of 5 average rating, 732 reviews
Top guest favorite
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.
Apartment in Charlottesville

Modern Belmont home - steps from Downtown Mall!

ValueLocationParking

4.92 out of 5 average rating, 895 reviews
Guest favorite
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.
Apartment in North Downtown

*Private Apartment in Downtown Cville*

LocationValueDecor

4.84 out of 5 average rating, 677 reviews
Guest favorite
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.
Apartment in Charlottesville

Private 2-Bdrm Apartment 1 mile from Downtown Mall

LocationFamilyView

4.92 out of 5 average rating, 688 reviews
Top guest favorite
Apartment in Charlottesville

2 King Beds | 8 Min to UVA | Free Parking

LocationFamilyWalkability

4.97 out of 5 average rating, 476 reviews
Guest favorite
A comfortable living space is highlighted by a bright red sofa adorned with cushions. A wooden coffee table sits on a decorative rug, accompanied by a woven basket. A potted plant adds a touch of greenery, while natural light filters through the window with wooden blinds.
Apartment in Charlottesville

Historic Beauty and Walkable to Everywhere

FamilyValueCheckout

4.94 out of 5 average rating, 250 reviews
Top guest favorite
Apartment in North Downtown

Walkable/Peaceful/Spacious Suite/Downtown/UVA/1 BR

FamilyLocationQuiet

4.92 out of 5 average rating, 122 reviews

Other great vacation rentals near James Monroe's Highland

Top guest favorite
Treehouse in Stanardsville

CloudPointe Retreat

LocationFamilyHot tub

4.98 out of 5 average rating, 140 reviews
Top guest favorite
A charming carriage house is situated among greenery and stone pathways. The light-colored exterior is complemented by a welcoming porch with two chairs, while a blend of trees provides a sense of privacy. A spacious driveway leads into the peaceful surroundings.
Place to stay in Charlottesville

Charlottesville Cottage-2 king beds

ValueFamilyCheckout

4.98 out of 5 average rating, 386 reviews
Guest favorite
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

ValueLocationBathroom

4.94 out of 5 average rating, 102 reviews
Top guest favorite
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.
Apartment in Charlottesville

Sunny private studio, walk to the University

FamilyLocationPets

4.98 out of 5 average rating, 394 reviews
Guest favorite
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

ValueFamilyCleanliness

4.93 out of 5 average rating, 233 reviews
Top guest favorite
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!)

FamilyLocationTV

5.0 out of 5 average rating, 208 reviews
Top guest favorite
A bright yellow door opens to a private outdoor patio, featuring a small bistro table and two chairs. Lush greenery surrounds the space, creating a tranquil environment. Inside, a cozy nook is visible, showcasing soft lighting from a bedside lamp.
Guest suite in Charlottesville

Redbud Garden Suite

LocationValueKitchen

4.98 out of 5 average rating, 347 reviews
Top guest favorite
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

ValueFamilyTV

4.99 out of 5 average rating, 148 reviews