Vacation rentals with a pool in Rutland County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Rutland County

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

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Guest favorite

Condo in Killington

4.97 out of 5 average rating, 144 reviews

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

3 bedroom townhouse with 2 full baths. Third bedroom is an open loft with 2 twin beds. The Woods is a luxury condo development located 3 miles from the lifts at Killington. Pool, gym and spa facilities. New for Winter 2024/25: Killington Cafe & Wine Bar at the The Woods! 6 guests max per law. ONE well-behaved DOG upon approval (NOT 2 DOGS); $90 pet fee per stay. *INCLUDE YOUR PET AS A GUEST AND TELL ME ABOUT YOUR DOG WHEN BOOKING. Sorry, NO CATS. Summer guests, NO A/C in the unit.

Superhost

A dining area is set with a wooden table adorned with plates and glassware, complemented by a stylish chandelier overhead. In the background, a comfortably furnished living area features a sofa and a smart TV, creating a welcoming environment.

Condo in Killington

4.89 out of 5 average rating, 159 reviews

Modern Killington Farmhouse Condo: Close to Resort

Welcome to our condo in picturesque Killington. This 2RM/2BA modern farmhouse-style unit features an open kitchen, stainless appliances, island, dining area, living room w/ smart TV, gas fireplace, sofa bed, queen bed, easy chair & amazing tile shower w/ body jets. The primary bedroom has ensuite bathroom, TV, flexible king bed, AC & washer/dryer. Reclaimed barn board finishes & sliding barn doors add rustic charm. Plus a summer pool! Book now for modern comfort & rustic charm in Killington!

Guest favorite

An elevated view captures a blue pool surrounded by lush greenery. Trees frame the scene, and soft clouds drift above, creating a serene backdrop. A wooden deck leads to the pool, inviting relaxation and enjoyment within this natural setting.

Home in Ticonderoga

4.87 out of 5 average rating, 39 reviews

4 BR/2BA Downtown Ticonderoga

Bring the whole family to this 4BD/ 2BA rental that has your entertainment needs in mind. Equipped with a large back deck, pool, swing set, privacy fence, inflatable hot tub and yard to enjoy! With views of the Lachute River and walking trail in your backyard. Walking distance to Star Trek Original Series Set Tour, local shops and restaurants. A short drive to a gorgeous beach on Lake George. Amazing hiking trails, fishing, boating, rich history and more. You are sure to enjoy your stay!

Superhost

The inviting pool area is surrounded by a sleek railing, offering views of the lush green landscape and the cabin in the background. Sunlight reflects off the clear water, creating a serene ambiance for relaxation.

Cabin in Ludlow

4.73 out of 5 average rating, 11 reviews

Contemporary 4-BR Cabin 5-min to Okemo

Contemporary, newly-renovated cabin perched on a hill overlooking the Green Mountains, 5-minutes to Okemo Base and 2-minutes in to town. Enjoy 4 bedrooms, atrium-style living room, separate dining room, breakfast nook, and basement game room. Grounds include a private pool, expansive yard, and sweeping views. Get the best of the traditional log cabin-feel with modern comfort and contemporary design; renovated in 2023 with AC and updated finishes throughout. Winter reservations: 4x4 required

Guest favorite

The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.

Guesthouse in Granville

4.9 out of 5 average rating, 877 reviews

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Superhost

A spacious room features two queen beds adorned with vibrant patterned comforters. A flat-screen TV is mounted on the wall. A window allows natural light to fill the space, while an air conditioning unit is positioned nearby. A wooden dresser and lamps add functional touches.

Condo in Killington

4.59 out of 5 average rating, 98 reviews

NEW Killington Studio: Great Location! Comfy. 431

Welcome to our Killington studio, perfect for skiing, biking, hiking, antiquing, beer tasting, kayaking, exploring, or simply unwinding. This hotel room-style condo sleeps four in two comfortable queen beds. Enjoy cable/streaming on the large smart TV. Amenities include a mini-fridge, microwave, Keurig & coffee maker. The full bathroom offers a tub & shower. Outside, a heated pool awaits (open June to mid-September). You'll love it! (Note: This unit is hotel-room style without a kitchen.)

Guest favorite

A spacious outdoor saltwater pool is framed by comfortable lounge chairs and red umbrellas, providing shade. The surrounding area features lush greenery, enhancing the relaxing atmosphere. A shaded gazebo with seating is visible, inviting guests to unwind beside the pool.

Condo in Killington

4.94 out of 5 average rating, 109 reviews

Updated Dog-Friendly/Free Shuttle/Across From Lift

Step into comfort and convenience with this beautifully renovated 1BR/1BA condo, nestled in the main Mountain Green building #3. Offering a cozy, dog-friendly environment, it’s perfectly situated across from Snowshed and Ramshead lodges, giving you effortless access to both winter and summer activities. A free shuttle service stops in front of the building during the winter months. The condo boasts modern updates throughout, ensuring a stylish stay. A true getaway for all seasons!

Guest favorite

A cozy living area is furnished with a grey sofa and two patterned chairs. A wooden coffee table sits center stage, complemented by a stone fireplace. A large television is positioned on a wooden media console, while sliding glass doors offer access to an outdoor balcony, revealing greenery.

Condo in Killington

4.93 out of 5 average rating, 193 reviews

Newly renovated ski retreat at Killington

Located at Mountain Green Resort, Building III. Walk to Snowshed Lodge to begin your day of skiing, or take the free shuttle that will pick you up outside the entrance. After your day of skiing ends and you return to the unit, to experience the many amenities that the resort has to offer: indoor pool, eucalyptus steam room, two spas, sauna, fitness center,. You may prefer to stay in the unit and watch skiers come down the mountain. check VRBO.1532508 mention this for a better deal

Guest favorite

Condo in Killington

4.95 out of 5 average rating, 103 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

Ski On-Ski Off!! Beautiful remodeled condo is in the heart of Sunrise at Bear Mountain. The designer kitchen features granite counter tops and top of the line stainless steel appliances. The main focal point in the living room is a massive stacked stone fireplace with a flat screen on the mantel. Recent upgrades include new living room furniture, master bed room furniture & updated tile in both showers. Additionally I own the adjoining unit & if you want more info see below

Guest favorite

An indoor pool area features a large, inviting swimming pool with clear blue water. High ceilings allow natural light to fill the space, while large windows enhance the open feel. Potted plants and wooden accents contribute to a relaxed ambiance.

Condo in Killington

4.96 out of 5 average rating, 137 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

Contactless checkin steps from Killington Skiing/ Mountain Biking/ Adventure Center, refurbished ski-home condo with its own private sauna, hotel-style condo amenities, excellent common area (pool, jacuzzi, showers, etc) in idyllic central Vermont. Travel guide provided after booking! The resort includes an indoor pool, two hot tubs, pool table, treadmills, and is nestled at the base of the mountain with its own ski-home trail (or mountain bike-home in the summer).

Guest favorite

An outdoor salt-water pool is surrounded by a spacious patio featuring lounge chairs and shaded seating areas. A pool house is visible in the background, alongside a red umbrella. Lush greenery borders the area, contributing to a tranquil setting.

Condo in Killington

4.85 out of 5 average rating, 103 reviews

Exceptional Retreat, ski, hike, bike, adventures

This is a 2 bedroom,1 bath condo in building 1. It is on the top floor so you have beautiful views and no noise above you. It is quiet and comfortable. The indoor pool, hot tub, sauna, steam, and spa are open. We are open from Thanksgiving to Easter. The outdoor salt water pool is open from Memorial Day till Labor Day. There is also a key for an outdoor locker for skis. Parking is plentiful and there is an elevator in the building.

Guest favorite

The outdoor area features a swimming pool surrounded by a spacious deck. Colorful flowers in shades of pink bloom in the foreground, while shaded seating and umbrellas provide comfort near the pool. The modern building showcases large windows, allowing natural light to fill the interior.

Townhouse in Killington

4.96 out of 5 average rating, 107 reviews

Beautiful Spacious Condo at Killington Resort

This cozy and spacious Sunrise Mountain Village condo is perfectly situated to nearby mountain sports at Killington Ski Resort. It welcomes up to eight guests for an unforgettable stay in the Green Mountains! Exceptional access to year round outdoor activities, great community amenities, and a comfortable condo to come home to - what more could you ask for? Book Timberline K4 today for a thrilling Vermont getaway!