Vacation rentals with a pool in Madison Heights

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Top-rated rentals with a pool in Madison Heights

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
A wooden walkway leads to the entrance of the house, framed by vibrant pink rhododendron flowers. Tall trees provide a natural backdrop, with dappled sunlight filtering through the leaves, creating a serene outdoor setting.
Home in Wintergreen Resort
4.95 out of 5 average rating, 149 reviews

Bear's Mountain Escape

Dog friendly, 3 BR, 2 BA, loft style condo located in the heart of the Wintergreen Resort. Ski check-in, restaurants, the mountaintop market, & The Mountain Inn are all right across the street! 2-story unit with a main floor primary BR & hall bath. Main floor bonus room with single & trundle. The loft contains 2 twin beds and the 2nd full bath. Parking, pool, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps up to six.

Superhost
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
4.82 out of 5 average rating, 387 reviews

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!

Guest favorite
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
4.89 out of 5 average rating, 152 reviews

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.

Top guest favorite
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.
Condo in Wintergreen Resort
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.

Top guest favorite
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
4.96 out of 5 average rating, 233 reviews

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.

Guest favorite
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.
Condo in Wintergreen Resort
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.

Guest favorite
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
4.83 out of 5 average rating, 108 reviews

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.

Top guest favorite
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
4.92 out of 5 average rating, 131 reviews

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.

Guest favorite
Chalet in Lovingston
4.85 out of 5 average rating, 308 reviews

Secluded Mountain Cabin + Trails & Firepit 12 ppl

Escape to a secluded mountain retreat in Lovingston, VA with 3BR + Loft, a spacious living area, and a private pool. Set beside 800 acres of hiking trails, this rustic yet comfortable home offers a Weber grill, fire pit, Sonos sound system, and fast WiFi. Relax by the pool, gather around the fire, or explore nearby wineries, breweries, and Charlottesville. Perfect for families, groups, and nature lovers seeking peace and adventure in the Blue Ridge.

Guest favorite
The open living area features high ceilings and large windows, allowing natural light to enhance the space. A comfortable seating arrangement includes a sofa and two armchairs, while an adjoining kitchen is visible in the background, equipped with modern appliances.
Home in Nellysford
4.9 out of 5 average rating, 116 reviews

Mountain Bauhaus | Sleeps 8 | Amenities | Grill

Welcome to your newly decorated and upgraded home in the Blue Ridge Mountains at Wintergreen Resort! A bright and welcoming feel will let you settle in and relax in no time. This space is perfect for families, groups, couples, and adventurous souls who want to explore the mountains or take in the beautiful mountain scenery. Please be sure the read below for Wintergreen Resort Amenities rules and accessibility during your stay.

Top guest favorite
Apartment in Lynchburg
4.87 out of 5 average rating, 188 reviews

Central location! 2 miles to LU! Downstairs suite

Welcome home to our spacious basement studio.Beautiful 3 story town home in premier Lynchburg community. There is a mini fridge, microwave, Keurig and other amenities to make your stay with us as comfortable as staying in your own home! Located directly off of Hwy 460. Convenient to Liberty University, 2.2 miles, Lynchburg College,4.6 miles, Wards Road restaurants, 2.1 miles and Wards Crossing shops, 2.1 miles.

Guest favorite
A modern kitchen is equipped with stainless steel appliances and a granite countertop. A pop of color is provided by a turquoise kettle and a 'HOME' sign above the cabinets. Soft lighting is cast from overhead fixtures, illuminating the workspace and creating a welcoming feel.
Apartment in Wintergreen Resort
4.94 out of 5 average rating, 112 reviews

Wintergreen Escape | King Bed + Porch Views

Escape to our four-season Wintergreen condo! Enjoy crisp mountain air, scenic hikes, fall foliage, and nearby wineries and breweries. Walk to Discovery Ridge, the spa, and activities! Relax at the seasonal heated pool, play a round of golf, or explore the Blue Ridge Parkway and Shenandoah National Park. Perfect for couples or families, cook a cozy meal or unwind by the fire after a day outdoors!

Popular amenities for Madison Heights rentals with a pool

Quick stats about vacation rentals with a pool in Madison Heights

  • Total vacation rentals

    Explore 20 vacation rentals in Madison Heights

  • Nightly prices starting at

    Madison Heights vacation rentals start at G$10,449 GYD per night before taxes and fees

  • Verified guest reviews

    Over 360 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Madison Heights vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Madison Heights rentals

  • 4.9 Average rating

    Madison Heights stays are highly rated by guests—averaging 4.9 out of 5!