
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.

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.

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!

2-min drive to 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

1 bedroom condo, walk to the slopes !
Cozy 1BR Wintergreen condo ⛷️❄️ 5-minute walk to the ski slopes, resort village, and mountain-too market, with snow tubing only minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax by the wood burning fire 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 close access to the village for après-ski.

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.

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.

Lake Escape - Smith Mountain Lake Condo
Located in Bernard's Landing, SML, this ground-floor condo offers everything you need for a quick getaway or a week-long vacation. The condo has recently been re-decorated and offers beautiful lake views, convenient access to boat rentals, one of the best restaurants on SML (Napoli by the Lake), and all the amenities you need. Guests have access to indoor and outdoor pools (outdoor pools open seasonally), sandy beach area, sauna, gym, and tennis and pickle ball courts.

Bernard's Landing Bliss! Breathtaking Views
Come savor the breathtaking lake and mountain views and experience the best of Bernards Landing in this condo! Enjoy the best amenities - high end stainless appliances, big flat screen TVs, keypad door access – and the list goes on! River Rock Tiled Shower and Silestone Counters! Bernard’s Landing offers so much – 2 outdoor/1 indoor pool, hot tub, beach, gym, sauna, boat launch, courtesy dock, tennis, pickle ball, racquetball courts, The Landing Restaurant, and more!

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.

Mountaintop Overlook – Updated 2BR w/ Deck & Views
Breathe in the crisp mountain air, cozy up by the fireplace, and soak in sweeping views of the Blue Ridge Mountains. This clean, comfortable 2-bedroom condo at Wintergreen Resort features two king beds, two full bathrooms, and a sleeper sofa—perfect for up to 6 guests. Enjoy panoramic windows overlooking the mountains,, a fully stocked kitchen, in-unit washer/dryer, central heat/AC, and free parking. The shuttle to the ski lodge is just steps away!

Cozy Condo - Sleeps 4
A wonderful weekend escape no matter the time of year. Condo has been completely renovated in the heart of Wintergreen Resort. Fully equipped condo for guests to come and enjoy the slopes. Within walking distance to the ski lift and all the amenities that the area has to offer. We are the only condo complex that also has a pool it's own pool for condo owners only. **the pool is for the condo complex and is shared with the other units.

Cozy Laurelwood condo - 10 min walk to slopes
This beautiful 1-bedroom, 1-bath Laurelwood condo is perfectly located just a short walk from the pool, market, coffee shop, restaurants, and the Wintergreen Conference Center. Inside, you’ll find a fully equipped kitchen, a cozy wood-burning fireplace (with complimentary firewood), and a spacious king-size bed. Step outside to your private deck and enjoy the peace of the surrounding forest—an ideal retreat for relaxation and comfort.
Popular amenities for Madison Heights rentals with a pool
House rentals with a pool

Cozy 5-bedroom home for large gatherings.

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

Private Pool Opens April 1 - All Year Hot Tub

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

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

Misty Mountain Cabin w/spa

5 min toSki! Mntn View HotTub Pool Table MovieRoom

Peaceful Cottage
Condo rentals with a pool

Cozy getaway with heated floors

The Modern Mountain Condo

Panoramic Peak: Wintergreen Condo with Views

New Construction! 1 Bed/2 Bath, pet friendly

Tips Up: Cozy Slopeside Retreat w/ Fireplace

Ski-in/Ski-out Wintergreen Highlands Condo -Views!

Cozy Comfort with a View - Wintergreen Resort

Relax in Style | 2 KING Beds - *POOL* - PacMan!
Other vacation rentals with a pool

Winton Place | Private Pool +Tennis Court

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

Modern 1-Bed Condo: OPEN POOL with City Access

Luxury Lynchburg Townhome with Mountain Views

The Captain’s Quarters

Large Comfy Getaway Near Liberty! Your Home Away.

Basic Pet Friendly Whole Home w/ Fireplace

Owl Bnb | Walkable to Slopes | Speakeasy Room
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 $68 CAD per night before taxes and fees

Verified guest reviews
Over 350 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!
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- Smith Mountain Lake State Park
- Wintergreen Resort
- Frontier Culture Museum
- Amazement Square
- Blenheim Vineyards
- Liberty Mountain Snowflex Centre
- Cardinal Point Winery
- Devils Backbone Brewing Co Basecamp
- National D-Day Memorial
- Virginia Horse Center
- Taubman Museum of Art
- James River State Park
- Virginia Museum of Transportation
- Natural Bridge State Park
- Appomattox Court House National Historical Park
- Percival's Island Natural Area
- Explore Park
- Mill Mountain Zoo
- Mill Mountain Star




