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Vacation rentals with a pool in Madison Heights

Find and book unique homes with a pool on Airbnb

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 favourite
An open living area features a stone fireplace with a mounted TV above and large windows that provide a panoramic view of the lake. A round glass dining table is set near the window, complemented by a cozy sofa and armchair, inviting relaxation and gatherings.
Condo in Moneta
4.99 out of 5 average rating, 282 reviews

Fun Lake Getaway with Breathtaking Views

Fantastic getaway on beautiful Smith Mountain Lake! Enjoy stunning views on two sides of this top-floor, corner condo with a wrap-around deck and natural shade. It is perfect for a relaxing break or an adventure! Activities include boating (with guest docks), swimming (indoor and outdoor), pickle ball, working out, and relaxing in the hot tub, steam room or sauna! If you are working remotely, this quiet space includes a desk and high-speed wireless. The individual HVAC unit also has a UV light.

Top guest favourite
A spacious great room is featured, furnished with a comfortable brown leather sofa and accent chairs. Large panoramic windows provide expansive views of the Blue Ridge Mountains, while a dining area with a table for six is positioned nearby. Warm wood flooring enhances the inviting space.
Condo in Wintergreen Resort
4.98 out of 5 average rating, 123 reviews

2 bdrm/2 full bath Best Views of Blue Ridge Mtns.

Best View of the Blue Ridge Mountains! Panoramic window views from the great room, dining area and kitchen. If you want to get a closer look step out on the observation deck to see the beautiful mountains and ski slopes (seasonal). Patio furniture is on the deck to enjoy morning sunrises and evening sunsets. All new stainless steel appliances in kitchen, Freshly painted throughout. 2 bedroom 2 bath Lots of activities to do at the Wintergreen Resort all year long. Year round resort activities.

Top guest favourite
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.
Condo in Moneta
4.98 out of 5 average rating, 115 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.

Top guest favourite
A spacious deck is surrounded by greenery, featuring several black Adirondack chairs arranged around a firepit. The glass railing provides an unobstructed view of the outdoors, enhancing the inviting outdoor space.
Home in Nellysford
4.99 out of 5 average rating, 154 reviews

151Escape | 5☆ Group Fun! Game Room/Bar/Deck/4kTVs

Enjoy mountain adventures with friends & family at this beautiful & newly renovated 5 bedroom mountain house ideally located in Virginia Wine Country at Wintergreen Resort’s Stoney Creek valley area. This amazing home features: - 75” & 55” 4k TVs - Fully equipped, live edge wet bar & bar countertop - Professional Ping Pong table - Deck with views, firepit & grill Just minutes from skiing, golf, hiking, wineries, breweries, apple-picking and other adventures the area offers all year long!

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
4.83 out of 5 average rating, 379 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!

Top guest favourite
A private balcony features wooden railings, with a light dusting of snow on the ledge. Lush pine trees stand prominently in the background, contrasting against a clear blue sky and hints of distant landscape, contributing to a serene outdoor viewing experience.
Condo in Wintergreen Resort
4.97 out of 5 average rating, 156 reviews

2-min drive from slopes, stair-free/free firewood!

Peaceful, recently renovated mountain-top retreat. Relax or work from home. End your day with a hike or spa treatment around the corner—linger with a glass of wine at sunset. It’s all only a 2 minute walk from the front door. Welcome to our mountain home! 2-3 min drive from ski lifts/resort, hiking Free firewood (seasonal) Family games & smart TVs (no cable) for movie night (must sign into your own subscriptions) Smartlock entry Stair-free entry *outdoor HOA pools CLOSED for season

Top guest favourite
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
4.98 out of 5 average rating, 208 reviews

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.

Top guest favourite
A contemporary mountain home is surrounded by snow-covered grounds, with a softly lit entryway visible through the glass doors. Frosted trees frame the exterior, highlighting the inviting warmth inside, contrasting with the winter landscape.
Home in Wintergreen Resort
4.96 out of 5 average rating, 114 reviews

Cliffs Edge- A Contemporary Mountain Home

An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its incredible mountain views! This spacious home, with its cantilevered decks, makes this perfect for any family. The large upstairs loft, adjacent to the upstairs bedrooms, offers movies, games, puzzles, and comfortable seating. Wi-Fi, Netflix, and Samsung Smart hub give plenty of entertainment options. The spacious living area and dining room have abundant seating for all.

Guest favourite
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
4.96 out of 5 average rating, 164 reviews

1 bedroom condo, hiking, breweries, wineries

Enjoy the mountains in the spring & summer enjoy hiking or a swim in the heapool! 1BR 1BA centrally located in Wintergreen 5 minute walk to Wintergreen resort Close to many hiking trails Enjoy the many breweries & wineries in the area Mountaintop Market is across the street 1 Bedroom 1 Bath & New queen sleeper sofa Stocked kitchen, cookware, spices & cooking oils Premium coffee & assorted tea Private furnished patio Wood burning fireplace, all you need for a quiet getaway

Top guest favourite
A table set for two features a bottle of sparkling beverage and two glasses, accompanied by an elegant plate of appetizers. The backdrop showcases expansive mountain views under a bright sky, enhancing the serene atmosphere of the outdoor dining area.
Apartment in Wintergreen Resort
4.97 out of 5 average rating, 106 reviews

Mountain View Nest

From the moment you walk in, this condo offers endless opportunities to relax and retreat. The sweeping mountain views over the back deck provide the ideal setting for a romantic getaway, a girls weekend, or much needed time to recharge. This one bedroom/bathroom unit with a king sized bed, fully stocked kitchen, and artistic decor is located on the third floor of the Ledges. It is the perfect location for those who ski, hike, golf, or taste the flavors from local wineries.

Top guest favourite
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.

Top guest favourite
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
4.97 out of 5 average rating, 115 reviews

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!

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 $69 CAD per night before taxes and fees

  • Verified guest reviews

    Over 310 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

  • Wifi availability

    20 of Madison Heights vacation rentals include wifi 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!