Holiday rentals with a pool in Madison Heights

A sandy beach area is bordered by calm waters. Shade is provided by tiki umbrellas, while a volleyball net is visible in the soft sand. Kayaks are placed on the shore, and green lawns extend in the background, leading to a serene lakeside view.

4.98 out of 5 average rating, 118 reviews

Tranquility Cove Condo at Smith Mountain Lake

—We Welcome You— Visit and experience the ultimate respite while enjoying amazing water and mountain views, sunrises, and sunsets. This ground level condo is perfectly situated in Bernard's Landing Resort on beautiful Smith Mountain Lake! This bright, stylish & thoughtfully appointed space welcomes you to a full kitchen, spacious bdrm w/king bed, walk-in shower, and a queen sleep sofa. Amenities include restaurant & bar, tennis, pickle ball, gym, sauna, hot tub, three pools and a sandy beach.

4.82 out of 5 average rating, 387 reviews

The kitchen area features light blue walls and modern black cabinetry. A spacious countertop is accompanied by two bar stools and stainless steel appliances. Natural light filters in through a window, creating striped shadows across the floor, enhancing the open feel of the space.

Home in Lynchburg

Lynchburg Midtown Lofts Garage Conversion

Formally a garage, this property has been transformed into a trendy two bedroom home! Located on premises at The Midtown Lofts, you can enjoy all of the amenities the property has to offer. Pool, fitness center, beach volley ball court, fire pit and the private movie theater. Pool is seasonal. The large windows allow all of the natural light you want! Two full-size beds. There is also a work space for those of you who are traveling for business, but please try to have some fun as well!

4.89 out of 5 average rating, 152 reviews

A wooden deck is elevated and features a vibrant red umbrella. Surrounding the deck are leafy green plants and a small seating area with pink chairs. A lattice design is present under the deck, adding texture to the space.

Apartment in Lovingston

Lovingston Get-Away Lovingston, VA

Guesthouse for ADULTS ONLY/ NO kids/pets located in Lovingston, VA. There are wineries, breweries, and distilleries. We have the Wintergreen Ski Resort. The Music Festival in October. Crabtree Falls and Humpback Rock for hiking. In Nelson Co., the Blue Ridge Parkway and Skyland Drive began. Nearby is UVa's Rotunda, Monticello, Appomattox, DC, Schuyler (the Waltons). Nelson hosts peach and apple festivals each year. The beautiful foliage to be seen in the fall and winter snowy mountains.

The exterior of a two-story cabin houses warm wooden accents and large windows. The entrance features a welcoming set of wooden steps leading up to a balcony, surrounded by tall trees, with a concrete pathway leading toward it.

4.94 out of 5 average rating, 247 reviews

Eight Minute Walk to Everything

This one-bedroom, one-bath condo is centrally located. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within an 8 minute walk. It's a one-story, downstairs unit that includes a back porch with just a few steps down to the ground. Perfect for taking the dog outside in the pet-friendly space. Full kitchen and dishes, wood-burning fireplace, balcony, and all towels and linens are provided for your convenience. Sleeps 3.

4.98 out of 5 average rating, 219 reviews

A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.

Apartment in Rockfish

Blue Ridge Bliss - For family & friends to enjoy!

Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from Fire & Frost eatery and the Wintergreen Spa, this is an ideal location.

A breathtaking sunset casts vibrant shades of orange, pink, and purple across the lake's surface. Silhouetted docks extend into the water, framed by distant mountains and a softly illuminated sky, creating a serene lakeside scene.

4.99 out of 5 average rating, 375 reviews

Lake Lover's Paradise

Come to the lake! This spacious one bedroom top floor end unit is uniquely located between Napoli by the Lake restaurant and large outdoor swimming pool. Fantastic views of the lake from the large deck! Sleeps 2 adults and 2 small children under three. The following amenities are provided during your stay (Subject to season and repair): 2 Outdoor Pools Exercise Room Boat & Jet Ski Rental 1 Indoor Pool Hot Tub Courtesy Boat Slips Beach & Boat Launch Area Tennis & Pickleball Courts

4.96 out of 5 average rating, 233 reviews

A private in-ground swimming pool is surrounded by a wooden deck and sun loungers. Shade is provided by a canopy, and lush greenery is visible in the background, highlighting the calming outdoor setting. The pool features a net for recreational activities.

Home in Lovingston

Private Pool Opens April 1 - All Year Hot Tub

Experience the Blue Ridge Mountains and country life of central Virginia and enjoy everything Nelson County has to offer. The Cottage on the Knoll is a comfortable 3br/2bth that’s centrally located in Nelson County, offering the perfect mix of modern comfort and country charm. The Nelson 29 and Nelson 151 craft beverage trails await you, while plenty of hiking, fishing, and mountain views will appease any outdoor recreation lover or nature enthusiast, making it the perfect getaway.

A private furnished patio features a cozy seating area with light-colored cushions on a dark frame sofa. A wooden coffee table sits in front, accented by a woven rug. The surrounding greenery adds a natural backdrop, creating a peaceful setting for relaxation.

4.95 out of 5 average rating, 194 reviews

1 bedroom condo, close to hikes & breweries & pool

Cozy 1BR Wintergreen condo 🌳 🌄 Close to scenic hikes, local breweries and wineries. The resort village, and mountain-top market, just minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax after a day outdoors and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and or cool off in the heated community pool.

4.83 out of 5 average rating, 108 reviews

A cabin entrance is framed by rustic wooden railings and a covered porch. Steps lead up to the door, while a picnic table is positioned nearby. Surrounding trees provide a natural setting, with fallen leaves scattered on the ground.

Farm stay in Moneta

Tiny Cabin in a Country Forest

Far removed from the road and any city noise, our cabins are nestled in-between pastures full of horses and cows, within an easy walk of a healthy creek and fishing pond. Between our breathtaking sunsets and our add-on options (horseback riding, wagon rides, hiking, fishing, a free petting zoo, etc.), there's not much that can beat the value of our facility. You get privacy without isolation, outdoors without "roughing" it, and all within an easy drive of Smith Mountain Lake.

4.92 out of 5 average rating, 131 reviews

A vibrant sunset casts warm hues across the sky, viewed from a covered outdoor area. The scene includes a fenced swimming pool and expansive green fields in the background, indicating a serene outdoor space perfect for relaxation.

Apartment in Forest

Large apartment w private pool / availability.

Beautiful, large 2 bedroom apartment with stunning sunset views. Full kitchen with Keurig Coffee, microwave, oven/stove, toaster, and refrigerator. The large family room has seating for 11 while you watch cable TV. Please NO SMOKING on these premises. Swimming pool MAY be available. The pool is our families, but it often works out that my guests can use it. You must communicate your wishes and we will see it's availability. An outdoor grill is available.

4.97 out of 5 average rating, 115 reviews

Aerial view of the cabin and pool area, surrounded by lush green trees and well-maintained gardens. A rectangular pool is centrally located, flanked by colorful umbrellas alongside sun loungers. The rustic cabin and neighboring structures feature varied roof styles, contributing to the serene country setting.

Farm stay in Hurt

18th Century Cabin Retreat

Come enjoy our 18th century cabin! They don't make them like this anymore. One side built in 1750, the other in 1825. Sit under the giant white oak and enjoy the country air. This is a wonderful retreat to kick back and relax. Enjoy the pool, horseshoes, and fire pit. In the winter months, cozy up by the wood stove or fire place with gas logs. NO PETS!!! Please do not bring your pets. Owners live on site, so if you are in need of anything, please ask!

4.81 out of 5 average rating, 118 reviews

A single-story house with white vinyl siding is surrounded by well-maintained greenery. A front porch features a swing, while large windows invite ample natural light. The muted color palette of the exterior harmonizes with the inviting lawn space, creating a peaceful outdoor setting.

Home in Schuyler

Peaceful Cottage

Wineries, Cideries and Breweries close by. Convenient to Nellysford, Wintergreen and all Charlottesville has to offfer - 3mi Walton’s homestead. Sightseeing, Beer and Wine trail, and Historical Landmarks Very close to the James River Runners tubing and canoeing activities. Old town of Scottsvilles is 9miles away and there is River Rafting company and plently of local eating and a brewery.Pet friendly & fee Type of pet &size requested

Popular amenities for Madison Heights rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area features a stone fireplace as the focal point, framed by large windows that offer views of the surrounding trees. A comfortable sectional sofa is arranged around a coffee table, with a television positioned on a media console to the side.

4.97 out of 5 average rating, 115 reviews

Cozy 5-bedroom home for large gatherings.

4.79 out of 5 average rating, 58 reviews

A refreshing pool surrounded by lush greenery is visible, featuring a stone patio with several sun loungers arranged nearby. Umbrellas provide shade over some seating areas, while pool floats gently rest on the water's surface. The tranquil atmosphere is complemented by the natural surroundings.

Home in Lynchburg

Winton Place | Private Pool +Tennis Court

The exterior of a multi-level home is nestled among trees, with warm lighting illuminating the porch and deck. The spacious deck features a staircase leading down, surrounded by autumn leaves, creating a welcoming atmosphere.

4.89 out of 5 average rating, 154 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

4.92 out of 5 average rating, 12 reviews

Home in Huddleston

Lake Allure Private Dock, Indoor Pool, and Hot Tub

A modern living area features a sleek leather sectional sofa adorned with patterned cushions, accompanied by a wooden coffee table. Large windows offer views of the surrounding trees, while natural light enhances the inviting space. A floor lamp adds illumination next to the sofa.

4.96 out of 5 average rating, 121 reviews

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

A spacious bedroom features a high, wood-beamed ceiling and a large window providing natural light. The bed is dressed in navy bedding with a plaid blanket draped across it. A wooden dresser and lamp complement the rustic decor, and a mounted TV is positioned above.

4.97 out of 5 average rating, 225 reviews

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

4.89 out of 5 average rating, 103 reviews

The bright living area features tall windows allowing natural light to illuminate the space. A fireplace creates a focal point, while comfortable seating is arranged around it. A staircase leads to the upper level, and outdoor views are visible through the glass doors.

Home in Roseland

Wintergreen Resort | Pool, Hike, Hot Tub, Firepit

4.96 out of 5 average rating, 52 reviews

The pool area features a sparkling blue pool surrounded by sun loungers in various colors. A spacious deck provides ample room for relaxation. The background includes a two-story building, and fluffy clouds fill the sky, creating a pleasant atmosphere for outdoor enjoyment.

Home in Lynchburg

Luxury 1BR Condo: OPEN Pool + Prime Location

Condo rentals with a pool

A spacious living area is furnished with a comfortable couch adorned with multiple pillows. A wooden coffee table sits on a textured rug, complemented by a small side table with a plant. Bright light emanates from a floor lamp, while a ceiling fan provides air circulation.

4.89 out of 5 average rating, 129 reviews

Blue Ridge Retreat: Your Cozy Mountain Getaway

A wooden staircase is flanked by trees, leading to a brown wooden building with a triangular roof. Large windows allow natural light to enter, surrounded by a peaceful forested area.

4.78 out of 5 average rating, 105 reviews

Cozy Condo - Sleeps 4

The two-story condo features a warm wood exterior, framed by lush greenery and trees. Wide wooden steps lead to the entrance, giving access to individual balconies that enhance the inviting appearance of the building.

4.96 out of 5 average rating, 350 reviews

Five Minute Walk to Everything!

The entrance features a welcoming door adorned with a decorative fish-themed wreath and two wooden fish wall hangings. Beyond the doorway, a bright kitchen is visible, highlighted by skylights and modern furnishings.

4.92 out of 5 average rating, 177 reviews

Moondance at Bernard’s Landing

A serene outdoor view features rolling hills in the distance under a vibrant sunset sky, blending warm hues of orange and pink. Green grass covers the foreground, accented by a small flower bed with rocks, enhancing the natural beauty of the landscape.

4.97 out of 5 average rating, 129 reviews

Panoramic Views | Sunrise on the Deck | Nelson 151

A modern living area features a cozy sofa facing a stone fireplace. Large glass doors open to reveal expansive lake and mountain views. A dining table is positioned near the window, complemented by natural light and decorative accents throughout the space.

4.95 out of 5 average rating, 153 reviews

Bernard's Landing Bliss! Breathtaking Views

A cozy living area features natural stone accents around a wood-burning fireplace. A small dining table with two chairs is positioned near large windows, allowing ample natural light. Green accent walls enhance the inviting atmosphere, while a comfortable seating area is visible nearby.

4.89 out of 5 average rating, 214 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

The living area features a spacious gray sectional couch with decorative pillows, a low wooden coffee table, and a patterned area rug. A wood-burning fireplace is situated against a white wall adorned with rustic decor. Natural light enters through large windows.

4.94 out of 5 average rating, 263 reviews

Cozy, clean, quiet mountain condo- King bed

Other holiday rentals with a pool

4.94 out of 5 average rating, 71 reviews

A spacious living area features a comfortable sectional sofa centered around a mounted television. Light wood flooring complements the neutral color palette, while large windows allow natural light to fill the room. A dining table with stylish chairs is visible in the background.

Townhouse in Lynchburg

Modern Townhome - 3br 2.5ba - Sleeps 8 - Near LU!

4.97 out of 5 average rating, 32 reviews

A well-appointed bedroom features a spacious bed adorned with a patterned comforter. Two bedside tables with lamps flank the bed, and a wooden dresser provides ample storage. Natural light enters through a window dressed with dark curtains, and the room is completed with neutral wall colors.

Guesthouse in Lynchburg

Spring getaway,2 bedroom, pet friendly guest house

4.98 out of 5 average rating, 47 reviews

Townhouse in Timberlake

Luxury Lynchburg Townhome with Mountain Views

Cabin in Wintergreen Resort

A rustic home is nestled among tall trees, surrounded by a blanket of fresh snow. A spacious outdoor deck is visible, providing a view of the snow-covered landscape. Walkways lined with stones lead to the entrance, creating a serene and inviting atmosphere.

4.84 out of 5 average rating, 100 reviews

'Slippery Slope' Cozy Cabin in Wintergreen Resort

4.99 out of 5 average rating, 83 reviews

A cozy sleeping area is featured with a spacious bed adorned in blue bedding. Nautical decor includes a ship's wheel mounted on the wall, complemented by soft lighting from bedside lamps. A quilted throw and decorative chair add comfort and style to the room.

Apartment in Amherst

The Captain’s Quarters

4.96 out of 5 average rating, 56 reviews

The inviting living area is highlighted by vaulted ceilings and abundant natural light. A plush sofa and two leather armchairs are arranged around a central coffee table on a decorative area rug. A gas fireplace with subtle lighting is positioned against the wall, enhancing the cozy ambiance.

Cabin in Nellysford

Airy farm cabin beneath the mountains

4.93 out of 5 average rating, 89 reviews

The exterior of a two-story townhouse is shown, featuring white siding and blue window shutters. A walkway leads to the entrance, where a star decoration is placed above the door. Surrounding greenery includes shrubs and trees, providing a well-kept appearance.

Townhouse in Lynchburg

Large Comfy Getaway Near Liberty! Your Home Away.

An open living space showcases a modern kitchen island with green cabinetry and white countertops. A cozy seating area includes a gray sofa, and a stone fireplace serves as a focal point. A wall-mounted television is positioned above the fireplace, enhancing the inviting ambiance.