Vacation rentals with a pool in Madison Heights

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Top-rated rentals with a pool in Madison Heights

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Guest favorite

Condo in Wintergreen Resort

4.9 out of 5 average rating, 102 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

The mountains are calling and you must go. Well, you don't have to, but we think it's a good idea. Make Tips Up your home while you're away. With slopeside views, a cozy and comfortable ambiance, and close proximity to skiing (only 100 yards from the slopes!) and hiking, this 1B/1BA condo is the perfect getaway for outdoor enthusiasts seeking a mountain escape. Relax at nearby breweries and wineries with unbeatable views, and return to your condo to enjoy the amenities of Wintergreen Resort.

Jun 3 – 10

G$24,958 GYD per night

Guest favorite

Apartment in Lovingston

4.88 out of 5 average rating, 121 reviews

Lovingston Get-Away Lovingston, VA

Guesthouse for ADULTS ONLY and located in Lovingston, VA. There are wineries, breweries, and distilleries. We have the Wintergreen Ski Resort. The Lockn' Festival each August. Crabtree Falls and Humpback Rock for hiking. In Nelson Co., the Blue Ridge Parkway and Skyland Drive began. Nearby we have UVa's Rotunda, Montecillo, Appomattox, DC, Schuyler (the Waltons). Nelson hosts peach and apple festivals each year. The beautiful foliage to be seen in the fall and the snowy mountains in the winter.

Apr 15 – 22

G$23,895 GYD per night

Guest favorite

Condo in Wintergreen Resort

5.0 out of 5 average rating, 166 reviews

Wintergreen: Mountain View for Miles Sunset Vista

Welcome to Sunset Vista Villa! This beautifully appointed, 2 bedroom, 2 bath, first-floor-unit with second story views, is centrally located to all of the amenities the Wintergreen Resort has to offer. It comfortably sleeps five and with its western vistas, sunsets are a thing to behold! Whether you spend your days hiking, skiing or enjoying the wineries and breweries, Sunset Vista Villa will be sure to enhance your stay. Book today & come enjoy the Wintergreen Resort and Blue Ridge Mountains!

Sep 29 – Oct 6

G$37,919 GYD per night

Guest favorite

Condo in Wintergreen Resort

4.91 out of 5 average rating, 179 reviews

A True Mountain Getaway! Ski in/Ski out!

Located steps away from the top of the ski slopes at Wintergreen Resort. No snow? No problem! Enjoy the cool mountain breezes, hiking and climbing trails, mountain lakes with beaches, wineries, breweries and much much more. Restaurants and shopping within walking distance. Our place has a galley kitchen and small refrigerator, a large deck to enjoy a quiet dinner and has been newly decorated. There is a king sized bed and a smaller fold out sofa that could accommodate two small children.

Sep 8 – 15

G$22,278 GYD per night

Guest favorite

Home in Bedford

4.89 out of 5 average rating, 100 reviews

Bedford Getaway

Perfect place for gathering families and friends (12 max, infants to seniors) in large one level house, with onsite activities and many nearby attractions! Take a dip in the gorgeous heated pool or relax those muscles in the Hot Tub, gather the group for a great meal using the outdoor kitchen, make some memories or get competitive in the game room, play in the children's room complete with board games, books, movies, & satellite tv, or lazily enjoy the beautiful sunsets on our 15 acres.

Nov 28 – Dec 5

G$70,656 GYD per night

Superhost

Home in Lynchburg

4.82 out of 5 average rating, 300 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!

Sep 27 – Oct 4

G$14,760 GYD per night

Guest favorite

Condo in Wintergreen Resort

4.95 out of 5 average rating, 201 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.

Aug 1 – 8

G$21,753 GYD per night

Guest favorite

Guesthouse in Amherst

4.87 out of 5 average rating, 159 reviews

Poolhouse Paradise

**Pool closes Monday, September 4th** Relax and enjoy all that central VA has to offer with Winton's newly renovated poolhouse as home base! Play 18 holes, explore the grounds, or cruise around in a golf cart (message us when you book and we’ll send you rental rates) and take in the mountain views. From hiking to apple picking, there's something for everyone year-round! Upstairs you'll find a comfortable space with a spacious living room, two bedrooms, a full bath, and small kitchen.

Sep 8 – 15

G$24,986 GYD per night

Guest favorite

Home in Lovingston

4.95 out of 5 average rating, 176 reviews

Cottage on The Knoll *heated pool open May 17*

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.

Oct 20 – 27

G$64,671 GYD per night

Guest favorite

Apartment in Forest

4.92 out of 5 average rating, 108 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.

Sep 19 – 26

G$24,189 GYD per night

Guest favorite

Apartment in Rockfish

4.99 out of 5 average rating, 159 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 the dog park, and picnic area it’s an ideal location.

Jan 1 – 8

G$33,677 GYD per night

Guest favorite

Townhouse in Wintergreen Resort

4.94 out of 5 average rating, 141 reviews

Fantastic retreat in ideal location, dogs welcome!

Wintergreen Resort is a fantastic, all season destination, with adventures for everyone! We are a pet and kid friendly, 2br/2ba townhome, located in the heart of all the action. Ski check-in, Mountain Inn, restaurants, & the Market stocked with all the essentials located right next to our community. Come hike, golf, play tennis, swim in our private pool or lakes, ski, snowboard, tube, and vineyard, brewery, distillery, or cider hop. We have it all!

Mar 22 – 29

G$23,147 GYD per night