Vacation rentals with a pool in Rutland County

4.91 out of 5 average rating, 212 reviews

Luxury Condo Tucked in the Heart of Killington

Welcome to our ❄newly renovated❄ Cozy Condo Located right off the "loop" walking trail on river road. Our end unit condo sits just 5 min from the base of Killington with easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our condo. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in Killington!

4.85 out of 5 average rating, 265 reviews

Comfy ski in/out studio at base of Pico-Killington

Studio at the base of Pico with a balcony. Free shuttle service from my place to Killington, which is 10 minutes away.Brand new sofa bed with a pillow top. Room divider. Lots of TV channels with Xfinity. Luggage cart and elevator for easy access. Fast Wi-Fi. Free ski locker with one key for each guest. There is a laundry room with coin operated machines. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for one day. No daily cleaning service. No parties. Free parking

4.93 out of 5 average rating, 107 reviews

Condo in Mendon

Hotel Chic - Home Comfort -Ski Easy.

HOTEL CHIC - SKI EASY Elegant - Cozy - Spotless Our condo is located minutes from Pico & Killington, 🥾AT&LT, 💍wedding venues, 🚴‍♀️mountain biking, ⛳️golf and many local events. Superhost level comfort welcomes you! OUR ULTRA COZY RETREAT WAITS JUST FOR YOU ⛷️Pico -5 minutes ⛷️Killington -15 minutes 🥾Minutes from LT/AT •Squeaky Clean •Fireplace, TV, WIFI •Seasonal Pool(towels provided) •Private covered porch •Keypad check in •Smoke free/Pet free NOTE: Condo regs allow 2 adults(21yrs)

Guest suite in Killington

4.95 out of 5 average rating, 145 reviews

Cozy, spacious, 3 bedrooms, 4 beds, swimming pool.

Great value! Cozy, clean, SPACIOUS, 3 bedrooms w/4 beds (2 double, 2 twins). You have entire first floor (5 rooms) w/private entrance & private full bath. Sitting area w/ TV & electric fireplace. Dining table. Coffee maker, tea kettle, toaster, microwave, small fridge, sink . Sorry, no stove. Laundry room with washer/dryer. Wi-Fi. Indiv heat. Ideal for 4 singles, 2 couples or families w 1-3 kids. Max 5 people. 5 mi. to Killington Rd restaurants, bars, nightlife, shops. Summer swimming pool.

4.94 out of 5 average rating, 120 reviews

Treehouse in Stockbridge

Romantic Treehouse- Hot tub, A/C, 20 Min to KLT

New treehouse was built by me with my own two hands during the pandemic. The architect styled design is one of a kind with huge windows. Radiant Heat, custom bathroom/kitchen. My grandparents once owned and operated a dairy farm in the area and I want to share this treehouse and surrounding area with my guests. Ski or Ride in only 20 min to Killington and resorts. My treehouse is located on the historic ski highway with Killington-20 min, Pico, Okemo, Sugarbush, Saskadena Six, and Stowe.

4.94 out of 5 average rating, 111 reviews

Glamorous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

Our 2-bedroom, 2.5-bath Airbnb, nestled in Vermont’s Green Mountains, invites you to escape into a haven of year-round adventure. Enjoy breathtaking views of a scenic pond, skiing through pristine slopes, bike along winding trails, or hike amidst the number 1 ranked foliage in the USA. Rejuvenate in the indoor pool and spa, with hot tubs, steam rooms, sauna and gym. Unwind by the cozy fireplace, creating unforgettable memories. Experience the charm and beauty of Killington like never before.

4.9 out of 5 average rating, 908 reviews

Guesthouse in Granville

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.

4.94 out of 5 average rating, 157 reviews

CozyCub - Pool, Hiking, Mountain Biking

Delight in this friendly, fully renovated (2022) modern ski condo next to Killington's popular Snowshed base area, learn-to-ski trails, and golf course. Shuttle-On / Ski-Off to the condo during peak season. The location is prime for accessing everything the area has to offer. Relax for some streaming after a day on the mountain on the 65" TV. Enjoy the Whiffletree condo association's outdoor pool and tennis courts in the summer, settle in by the gas fireplace, or head out to explore.

4.88 out of 5 average rating, 112 reviews

Condo in Mendon

105 Fox Hollow Village Pvt - Red Fox - Unit B-4

105 Fox Hollow Village is located near Pico and Killington ski areas. There are year round outdoor activities including access to trails for skiing/snowboarding, mountain biking, golfing, and hiking. Accommodations include 2 bedrooms, 2 full bathrooms (newly renovated), fully updated kitchen, living room, separate dining area, a mudroom at entrance, backyard access with sliding door, and a common pool area. No smoking/vaping, and no pets are allowed in or around the condo.

4.96 out of 5 average rating, 131 reviews

Dog-Friendly Mtn Escape/AC/Pool/

Experience year-round adventure at Sunrise Village at Killington, just steps from scenic trails and the Sunrise Village Triple Lift (488 ft away). After a day of outdoor fun, unwind by the cozy electric fireplace. Explore nearby hiking, mountain biking, kayaking, and golfing. The indoor sports complex—featuring a pool, hot tub, and gym—is a short walk away. Perfect for outdoor lovers looking to relax and make unforgettable memories!

4.97 out of 5 average rating, 115 reviews

Townhouse in Killington

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!

4.89 out of 5 average rating, 130 reviews

Location + Spa! - Cozy 2BR Condo - Mountain Side

Our cozy two-bedroom condo is just steps from the lifts, spa, ski shops, and restaurants, with a three-minute drive to Killington. Nestled in the Green Mountains, you’ll have access to skiing, hiking, world-class golf, snow tubing, and scenic mountain views. The condo features seasonal amenities including a pool, fitness center, hot tub, sauna, steam room, and more — perfect for both adventure and relaxation!

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Villas

Luxurious estates for the ultimate escape

Houses

A space thats all yours, with room for everyone

Popular amenities for Rutland County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 80 reviews

Golf, Bike, Fish, or Hike!

SooRating, 5 stars1 month ago

Ashley was super friendly and responsive and her place was as described with everything I need and more to make me feel right at home. Would love to stay here again. Thank you so much for letting us stay at your beautiful place!

4.92 out of 5 average rating, 13 reviews

Home in Ludlow

Ski-In/Ski-Out Hike Okemo Mountain Condo

StephanieRating, 5 stars3 weeks ago

Words can’t describe the experience we had this weekend. Linda was the best host we have ever worked with and the place was extraordinary to say the least! Extremely clean, comfortable and well located! Kid friendly and close to downtown! We will highly recommend it to friends and family and if we could leave more stars than a 5-star review we would! Looking forward to booking this place again in the near future! Thank you Linda for your amazing hospitality!

5 out of 5 average rating, 10 reviews

Home in Rutland

Entire Home, Near Slopes, Hot Tub, EV Charger

MicahRating, 5 stars2 months ago

The stay was excellent. The home was beautifully renovated. The rooms were large and very comfortable. Location was perfect for the 8 of us for a ski weekend at Killington. Hope to be back.

4.91 out of 5 average rating, 98 reviews

Home in Ludlow

Walk to Okemo Ski Lift - Private Classic VT Ski Ch

MeredithRating, 5 stars3 months ago

Our family really enjoyed our stay at the trailside chalet! A quick walk up the road to the ski lifts and plenty to keep us entertained after a day of skiing. We really enjoyed the fire place and pool table!! Prescott was a great host, quick to respond to our questions.

5 out of 5 average rating, 19 reviews

Trailside Vacation

MatthewRating, 5 stars2 months ago

We absolutely love our stay! It was exactly as described. Great location, easy ski on and ski off. Very clean and had every amenity you could think of. We felt right at home there. Can’t wait to go back next year!

4.91 out of 5 average rating, 89 reviews

Home in Chittenden

Comfortable, relaxing large country home

EdwardRating, 5 stars3 months ago

Great spot for a week of skiing! Danielle was very helpful and communicative throughout

4.89 out of 5 average rating, 46 reviews

Home in Bridgewater

Luxurious family retreat home in the mountains

DanielleRating, 5 stars10 months ago

Andreas place was gorgeous and looked just like the pictures. The house was clean and organized and the backyard was wonderful to relax in.

4.92 out of 5 average rating, 13 reviews

Luxury Ski & Summer Trail Creek Condo

JamesRating, 5 stars2 months ago

We stayed for over three weeks and had a tremendous time. The condo had everything we needed to accommodate us for our extended stay. We were able to walk to the slopes and ski back. The pool, hot tub, and sauna were all very close to the condo.

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Condo rentals with a pool

4.59 out of 5 average rating, 100 reviews

NEW Killington Studio: Great Location! Comfy. 431

JohnRating, 5 stars4 months ago

Nice cheaper lodging on the access road

4.95 out of 5 average rating, 105 reviews

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

PatriciaRating, 5 stars2 months ago

This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place again!

4.93 out of 5 average rating, 80 reviews

Bike trails open low $ 2 Bedrm min to Mtn & Apres

BrianRating, 5 stars3 months ago

Looks exactly like the photos. It is close to the ski slopes, and spacious for a group of three.

4.92 out of 5 average rating, 12 reviews

Beautifully renovated spacious 2 room 2 BA suite

StevenRating, 5 stars5 months ago

great place to stay Joanne was a great host and responded quickly if I need anything

4.8 out of 5 average rating, 107 reviews

Cozy 3BR/2BA Chalet – Mins to Mtn & Biking Trails

MikeRating, 5 stars3 months ago

Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!

4.82 out of 5 average rating, 257 reviews

Ski, Ride, Walk On/Off Condo On Pico at Killington

ZacharyRating, 5 stars3 months ago

Great location for pico mountain. The ski on ski off was pretty easy to find and nicely located. The location is slightly less ideal for killington, as you need to take a shuttle that has multiple stops. We also ended up on a bigger bus to take us back from Killington and the drop off was on the main road, which was a bit difficult to walk on in our snow gear. Overall, nice apartment and perfect for my group of friends.

4.93 out of 5 average rating, 198 reviews

Newly renovated ski retreat at Killington

YangRating, 5 stars2 months ago

Wayne is super nice, friendly, and responsive. He gave me heads up note on check-in day when the main road (Killington Access Road) was closed due to downed trees&wires. He also helped me confirm the parking spot in late night when I arrived late. The place is cozy and clean. There’s a number of good restaurants and taverns nearby.