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Vacation rentals with a pool in Nelson County

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Top-rated rentals with a pool in Nelson County

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

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Condo in Wintergreen Resort

4.9 out of 5 average rating, 101 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.

May 1 – 8

Condo in Wintergreen Resort

4.96 out of 5 average rating, 236 reviews

Five Minute Walk to Everything!

**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within a 5 minute walk! This is a two-story unit with loft style master bedroom and en suite bath, and first floor bedroom with hall bath. Parking, pool access, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps 5.

Oct 17 – 24

Guesthouse in Afton

5.0 out of 5 average rating, 223 reviews

Mountain Cottage / Pool, heart of 151 Brew Trail

Wake to gorgeous Mountain views and our rolling green meadows bordering the Rockfish River on our family estate. Private attached unit with an inground pool (mid April-mid Sept.) in the Blue Ridge mountains of Nelson County Virginia centered on the 151 Brew Ridge Trail. Much preparation has gone into making your stay beautiful, convenient and comfortable. No need to physically interact if that is your desire. Enjoy swimming, hiking, kayaking, horse back riding, skiing, snowboarding, and more!

Oct 10 – 17

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!

Jul 16 – 23

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.

Jun 28 – Jul 5

Condo in Wintergreen Resort

4.95 out of 5 average rating, 199 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.

Oct 15 – 22

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.

Aug 27 – Sep 3

Home in Lovingston

4.95 out of 5 average rating, 175 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

Condo in Wintergreen Resort

4.99 out of 5 average rating, 175 reviews

Cozy getaway w/ heated floors, dog friendly

Close your eyes and imagine opening the door to a beautifully handcrafted live edge oak breakfast bar with 4 leather bar stools, granite countertops and stainless steel appliances. As you walk into the living room, two plush, comfy leather sofas beckon you to rest & relax in front of the fireplace. Sleeps 3. Comfy wrought iron QUEEN bed for a good night’s rest and a twin pull out in the living room. There is radiant heat flooring throughout our home to pamper your feet.

Aug 5 – 12

Apartment in Rockfish

4.99 out of 5 average rating, 158 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.

Apr 1 – 8

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!

Dec 9 – 16

Condo in Wintergreen Resort

4.94 out of 5 average rating, 225 reviews

Cozy, clean mountain condo- King bed, dog friendly

Everything you need to make your getaway relaxing and convenient has been thought out in this tastefully decorated condo including new King Bed, Queen sofa pullout bed, plush linens, new spacious couch, 55" & 28" Smart TVs, Roku, WiFi, DVD player & movies, fully equipped kitchen, dining area for 4, wood burning fireplace, and private patio. Non-smoking condo. Please provide all guest names and dog info if applicable upon inquiry or booking.

Sep 6 – 13

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Popular amenities for Nelson County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Wintergreen Resort

4.97 out of 5 average rating, 153 reviews

Ski-In/Ski-Out Renovated Chalet on Lower Tyro

Apr 20 – 27

Home in Lovingston

4.85 out of 5 average rating, 280 reviews

Secluded Mountain Cabin w/ Pool, Trails & Winery ❤️

Jan 18 – 25

Home in Afton

4.94 out of 5 average rating, 133 reviews

Farmhouse on Working Vineyard

Oct 22 – 29

Home in Wintergreen Resort

4.87 out of 5 average rating, 119 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

Sep 24 – Oct 1

Home in Lyndhurst

4.97 out of 5 average rating, 99 reviews

Oak Tree Cottage - beautiful farm, mountain views.

Mar 21 – 28

Home in Roseland

4.98 out of 5 average rating, 140 reviews

Dove's Landing at Wintergreen Resort

Oct 15 – 22

Home in Nellysford

4.95 out of 5 average rating, 21 reviews

Mountain Bauhaus | Sleeps 8 | Large Deck

Nov 14 – 21

Home in Wintergreen Resort

4.89 out of 5 average rating, 9 reviews

Walk to Ski! Mntn View+Magnificent Stone Fireplace

May 1 – 8

Condo rentals with a pool

Condo in Wintergreen Resort

4.96 out of 5 average rating, 154 reviews

The Modern Mountain Condo

Aug 24 – 31

Condo in Wintergreen Resort

4.89 out of 5 average rating, 126 reviews

Cozy Comfort with a View - Wintergreen Resort

Sep 11 – 18

Condo in Wintergreen Resort

4.91 out of 5 average rating, 106 reviews

Panoramic Peak: Wintergreen Condo with Views

Dec 7 – 14

Condo in Wintergreen Resort

4.99 out of 5 average rating, 141 reviews

3 BR 3 BA, 2 story condo in Highlands

Jan 9 – 16

Condo in Wintergreen Resort

4.96 out of 5 average rating, 155 reviews

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

Oct 28 – Nov 4

Condo in Wintergreen Resort

4.9 out of 5 average rating, 191 reviews

Light Filled Awe-Inspiring Views from Every Window

Sep 10 – 17

Condo in Wintergreen Resort

4.94 out of 5 average rating, 106 reviews

Cozy 2BR+4 min to slopes+hike+golf course view!

Jul 20 – 27

Condo in Wintergreen Resort

4.91 out of 5 average rating, 145 reviews

Gorgeous Wintergreen Condo – 2-min to Slopes

Jun 30 – Jul 7

Destinations to explore