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Vacation rentals with a pool in Rutland County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Rutland County rentals with a pool

House rentals with a pool

Guest favorite
Home in Killington
4.91 out of 5 average rating, 202 reviews

Luxury Condo Tucked in the Heart of Killington

AshleyRating, 5 stars1 week ago
Comfortable and convenient location. Everything we needed was in the kitchen. We had most of our meals in and took advantage of the kitchen. The sleeping accommodations were very comfortable. It is only a short drive to Killington, where my family skied. We would definitely stay there again.
Guest favorite
Home in Killington
4.9 out of 5 average rating, 78 reviews

Golf, Fish, Hike or Bike in Killington!

AgnesRating, 5 stars1 week ago
Had a wonderful weekend at Ashley's place! The condo is located just a few minutes from the K-1 base (and skiable too, but we came late in the season) and had everything we needed. Fireplace and sauna/hot tub (in an adjacent building) was a great bonus. Ashley was incredibly helpful and friendly, I'd love to come back!
Guest favorite
Home in Killington
5 out of 5 average rating, 18 reviews

Ski On/Off Sunrise at Killington

NataliaRating, 5 stars1 month ago
We had a great weekend at Liz's place! The place is super cozy and had everything we needed. It's really spacious and loved all the decorations. They also have a bunch of board games which was fun with the fam. It was really clean and I felt right at home. I'd love to come back in the future! Skiing in an out is totally doable but a little difficult to find your way back if you're not familiar with the sunrise condos. Keep in mind it's not directly on the Sun Dog trail so it was a tad more difficult starting with beginners from there. It ended up better for them to drive to snowshed. Overall would definitely recommend for a large family or bigger group. We had a blast. OH and fantastic DVD collection! Needed to add that in there. 😊
Superhost
Home in Ludlow
5 out of 5 average rating, 5 reviews

Okemo Condo – Ski In/Out

EricaRating, 5 stars2 months ago
Great location - ski in/out! Close to Jackson Gore base and easy ski lift / drive access to Clock Tower base. Condo was perfect for our family of 4 with 2 kiddos, could accommodate more for sure. Well stocked kitchen. We enjoyed the kids board games! Very comfortable all around and good value for typical cost during winter ski season. Would definitely return!
Top guest favorite
Home in Rutland
5 out of 5 average rating, 10 reviews

Entire Home, Near Slopes, Hot Tub, EV Charger

MicahRating, 5 stars1 month 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.
Superhost
Home in Rutland
4.88 out of 5 average rating, 8 reviews

Green Mountain Getaway

HoiRating, 5 stars1 month ago
Excellent place for our group. Definitely would recommend. 10 out of 10
Guest favorite
Home in Ludlow
4.91 out of 5 average rating, 98 reviews

Walk to Okemo Ski Lift - Private Classic VT Ski Ch

MeredithRating, 5 stars1 month 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.
Top guest favorite
Home in Killington
5 out of 5 average rating, 19 reviews

Trailside Vacation

MatthewRating, 5 stars1 month 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!

Condo rentals with a pool

Superhost
Condo in Killington
4.94 out of 5 average rating, 171 reviews

Renovated unit, prime location! Shuttle on/Ski off

KristenRating, 5 stars1 month ago
This was our second time staying at Caitlyn’s condo in Killington, we chose it again for a reason !! The vibe of the condo is super relaxing, the decor is thoughtful and cool. The fire place makes coming back after a day on the slopes so cozy! We love coming to Killington and this condo is so close to the snowshed lot, it’s perfect!
Guest favorite
Condo in Killington
4.95 out of 5 average rating, 20 reviews

Northlands at Trail Creek

ClintRating, 5 stars1 month ago
Super wonderful spot that is walkable to lifts and then able to ski home at the end of the day. There's a great sauna , hot tub and pool right around the corner from the condo. All super convenient. Will be back next year.
Top guest favorite
Condo in Killington
4.86 out of 5 average rating, 84 reviews

Mountain Oasis

CynthiaRating, 5 stars1 month ago
Cozy, clean, well appointed condo with great amenities within walking distance of the mountain, wonderful!
Guest favorite
Condo in Killington
4.91 out of 5 average rating, 127 reviews

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

KateRating, 5 stars1 week ago
Very clean and great location. It was about an 8 minute walk to the Ramshead lodge and we ate at two restaurants within a 5 minute walk. The shuttle was also easy and ran frequently. Would recommend!
Guest favorite
Condo in Killington
4.9 out of 5 average rating, 50 reviews

Killington Mnt Escape Ski/Golf/Bike/Hike/Pool

MichaelRating, 5 stars1 week ago
It was a pleasure staying at Shirley's place for our last trip to Killington this season. The place was nice and clean, the kitchen had everything we needed to cook our meals, and the amenities in the building were great!
Guest favorite
Condo in Killington
4.84 out of 5 average rating, 174 reviews

Skier's Retreat 2bed/1.5 bath condo w/ Amenities

BenRating, 5 stars3 weeks ago
This condo has a great location, and the unit itself is extremely pleasant. If you're going to Killington I highly recommend it
Superhost
Condo in Killington
4.82 out of 5 average rating, 257 reviews

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

ZacharyRating, 5 stars1 month 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.
Superhost
Condo in Killington
4.89 out of 5 average rating, 102 reviews

Updated large condo across from AT and skiing

MikeRating, 5 stars1 month ago
Condo was perfect location for ski getaway only 10 mins to Killington and convenient to other resorts in the area. House was clean, well supplied for meal prep and furnishings/bedding were comfortable. No issues and Mike & Amanda were communicative hosts.

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