Holiday rentals with a pool in Augusta County

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Top-rated rentals with a pool in Augusta County

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

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Top guest favourite

Apartment in Wintergreen Resort

Extremely private, 2-min drive to skiing/hiking

Extremely private, 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 pool CLOSED for season

ValueFamilyPool

4.97 out of 5 average rating, 183 reviews

Top guest favourite

A spacious bedroom features a high, wood-beamed ceiling and a large window providing natural light. The bed is dressed in navy bedding with a plaid blanket draped across it. A wooden dresser and lamp complement the rustic decor, and a mounted TV is positioned above.

Home in Wintergreen Resort

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

Completely renovated, 3 BR/2BA chalet, located on Lower Tyro slope, just below Tequila. Rustic decor, fully stocked kitchen, high end appliances, granite counters. Open floor plan, walls of windows, mtn views. Beautiful stone fireplace, ample comfortable seating. 2 main floor Masters, each w/King bed, TV, luxurious bedding. Loft is a dedicated kids space: 2 sets of bunks, daybed w/trundle, TV & PS4. Gas grill, 6 person hot tub. Perfect ski home to host 2 Families, or a romantic couple's getaway.

LocationFamilySkiing

4.97 out of 5 average rating, 238 reviews

Top guest favourite

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

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.

FamilyLocationGetting around

4.95 out of 5 average rating, 170 reviews

Top guest favourite

A spacious living area is highlighted by large floor-to-ceiling windows, offering views of the surrounding trees. A comfortable gray sofa and a round glass coffee table are present, along with a wooden dining table that seats six. An electric fireplace adds warmth to the space.

Villa in Wintergreen Resort

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

We had to create a new listing for this property. Previous listing had 70+ reviews with a 4.8 Star rating. Same great host and same great house, just a new listing. Screenshots of old listing in additional photos. Stay at this luxurious 4-bedroom, 3-full bath vacation rental home for 10 in Wintergreen, within minutes of top-notch golf courses, skiing / snow boarding at the Mountain Inn, and dozens of hiking trails . In addition to the unbeatable location, the property offers a private hot tub!

LocationValueAccuracy

4.96 out of 5 average rating, 151 reviews

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

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!

LocationValuePets

4.99 out of 5 average rating, 173 reviews

Top guest favourite

A scenic view of rolling hills is captured at sunset, with soft hues of orange, pink, and purple coloring the sky. In the foreground, a glass of clear liquid rests on a wooden railing, enhancing the tranquil atmosphere.

Apartment in Wintergreen Resort

3 BR 3 BA, 2 story condo in Highlands

Newly renovated condo! You can't beat the view from up here. Top floor/vaulted ceilings, next to the Highlands Lift. Just steps from the expert slopes and on the Wintergreen shuttle route. Enjoy hiking, skiing, snowboarding, tubing, outdoor pool time or a local brewery. This condo has 2 master's with king beds, 1 bunk bed (twin over full), a single twin bed and a pull out twin sleeper sofa. The king beds have new high quality mattresses and luxury bedding and a 60" HDTV in living room

FamilyLocationAccess

4.99 out of 5 average rating, 185 reviews

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.

Flat in Rockfish

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.

LocationValueLayout

4.98 out of 5 average rating, 233 reviews

Top guest favourite

Home in Wintergreen Resort

Cliffs Edge - It’s Pumpkin Spice Time!

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.

LocationFamilyWalkability

4.97 out of 5 average rating, 130 reviews

Superhost

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.

Apartment in Wintergreen Resort

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.

FamilyValueGetting around

4.92 out of 5 average rating, 216 reviews

Top guest favourite

A hot tub bubbles invitingly on a concrete pad in a spacious yard. Surrounding the tub is a well-maintained green lawn, with majestic mountains visible in the background. White Adirondack chairs are positioned nearby for relaxing moments outdoors.

Home in Nellysford

Spacious retreat: Game Room, Hot Tub & Fire Pit

Gather family & friends for a memorable getaway at The Myrtle at Wintergreen. This spacious golf-course retreat combines luxury, comfort and exceptional amenities minutes from Nelson 151 wineries, breweries, hiking, golf and Wintergreen Resort. 💦 Hot tub 🎱 Game room with pool, ping pong, foosball & air hockey 🛏️ Sleeps 10 with 2 Kings, 1 Queen & 2 Full (each with TV) 🔥 Screened porch, fire pit, BBQ ⚡ EV charger 🏊 Community pool, tennis & pickleball 🚗 40 minutes to Charlott

FamilyLocationParks

5.0 out of 5 average rating, 113 reviews

Top guest favourite

A rustic cabin is nestled among greenery, featuring a wooden deck with rockers. A metal roof and timber exterior give it a charming country feel. The landscape showcases gentle rolling hills and is framed by trees, with a gravel area in the foreground.

Cabin in Sugar Grove

Ebenezer Cabin - Hot Tub - Private - BBQ - Views

Disconnect, reset & recharge in this countryside cabin escape with hot tub & bird watching. ★ "Clean, stylish, private, and authentic cabin experience." ☞ Backyard w/ fire pit + wood ☞ Front porch w/ rocking chairs ☞ Patio w/ BBQ Grill + propane ☞ Fully equipped + stocked kitchen ☞ Parking → driveway (4 cars) ☞ Books + board games ☞ La-Z-Boy loveseat ☞ 250 Mbps wifi 20 mins → DT Franklin (cafes, dining, shopping) 48 mins → Nelson Rocks 30 mins → Reddish Knob (360 view)

LocationValueNearby

4.98 out of 5 average rating, 334 reviews

Top guest favourite

Double doors framed by potted plants and embellished with decorative wreaths welcome guests into the home. The brick exterior and pathway provide a warm entryway, hinting at the charm within.

Guest suite in Penn Laird

On Cottonwood Pond

A beautiful country setting just minutes from Harrisonburg and JMU, winter snow sports (skiing/tubing/ice skating) at Massanutten Resort, Shenandoah National Park, hiking, other local universities and countless Shenandoah Valley attractions! You won't want to miss the new features in this home with a full kitchen, updated fixtures, plush accommodations and thoughtful touches throughout. Enjoy a quaint getaway in this meticulously designed home away from home!

ValueFamilySolo travel

5.0 out of 5 average rating, 177 reviews