Holiday rentals with a pool in Rutland County

Find and book unique homes with a pool on Airbnb

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Guest favourite
Condo in Killington
4.97 out of 5 average rating, 147 reviews

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

EileenRating, 5 stars4 weeks ago
Nice place for the 6 of us and dog for a long ski weekend in March. Condo was as described. The kitchen was very clean, nothing in fridge. New fridge and new oven. The bathrooms were very clean. The beds were comfortable. The upstairs space a bit tight for 4 adults, but we managed fine. Two of the twin beds are in an open loft area, which didn’t bother us as we were all going to bed at the same time and waking early to go skiing. Just mentioning this in case you were looking for a 3rd bedroom that was fully enclosed. The Spa and Cafe/ Wine Bar were a great addition to our ski weekend activities. The host was wonderful and very responsive. We highly recommend this condo.

Popular amenities for Rutland County rentals with a pool

House rentals with a pool

Guest favourite
Home in Killington
4.91 out of 5 average rating, 200 reviews

Luxury Condo Tucked in the Heart of Killington

KatieRating, 5 starstoday
“Great stay in a cozy home close to the slopes! The place was clean, well-equipped, and exactly as described. Perfect spot for a ski/ snowboard getaway. Wish the fireplace would work. Would definitely come back!”
Guest favourite
Home in Killington
4.89 out of 5 average rating, 75 reviews

Spring Ski - Lift Discounts Available!

JeffRating, 5 stars3 weeks ago
Ashley is a great host and well worth the stay! Beautiful view out the back windows and great fire place made it very relaxing stay.
Superhost
Home in Ludlow
4.67 out of 5 average rating, 6 reviews

Solitude 3BR- Walk to Ski Trail!

JasonRating, 5 stars1 month ago
The accommodations exceeded our expectations. Home was clean and orderly(left it how we found it:)). Perfect for our family trip. Location on the mountain couldn’t have been better.
Superhost
Home in Ludlow
4.94 out of 5 average rating, 33 reviews

Hilltop 9-BR Mountain Retreat 5-min to Okemo

NicoleRating, 5 stars1 month ago
Great communication, even with two days of snow excellent clearance. Definitely recommend 4WD as noted in the listing. Otherwise great place/location for large family gathering! GO BIRDS!
Top Guest favourite
Home in Rutland
5 out of 5 average rating, 10 reviews

Entire Home, Near Slopes, Hot Tub, EV Charger

MicahRating, 5 stars2 weeks 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 stars3 weeks ago
Excellent place for our group. Definitely would recommend. 10 out of 10
Guest favourite
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.
Superhost
Home in Killington
5 out of 5 average rating, 10 reviews

Bear Lodge at Killington - Seconds to Slopes

MarisaRating, 5 stars9 months ago
What an incredible experience at this beautiful, private house that fit our large group beautifully. John was an exceptional host - he made planning easy with frequent communication, generous help with local activities, and thinking about our every need. The house was even better than described with so many amenities and everything you could possibly need. Would absolutely recommend to any group coming to Killington!

Condo rentals with a pool

Superhost
Condo in Killington
4.94 out of 5 average rating, 170 reviews

Renovated unit, prime location! Shuttle on/Ski off

ElizabethRating, 5 stars4 weeks ago
Cute place to stay with great location close to Killington Mtn! (Snowshed/Ramshead bases just a few min away.) Although advertised as "ski off," we used the shuttle since skiing off would require a bit of a walk on a busy road that was too much for our little kids. Beds were very comfortable (even the couch in the living room!). Heat-producing gas fireplace made it very nice and cozy. Well-stocked kitchen. Responsive host.
Superhost
Condo in Ludlow
4.92 out of 5 average rating, 12 reviews

Okemo Mountain Resort 3 BR ski in / ski out condo

KiraRating, 5 stars1 month ago
Ann’s condo was perfect for our ski trip, easy walk to the slopes and access to the pool and hot tub that the kids enjoyed. The kitchen was stocked with everything we needed and there was plenty of space for our group to hang out in the kitchen/dining/ living room.
Top Guest favourite
Condo in Killington
4.86 out of 5 average rating, 84 reviews

Mountain Oasis

CynthiaRating, 5 stars2 weeks ago
Cozy, clean, well appointed condo with great amenities within walking distance of the mountain, wonderful!
Guest favourite
Condo in Killington
4.91 out of 5 average rating, 124 reviews

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

MarkRating, 5 stars3 weeks ago
We had a great multi-day stay and did some spring skiing at Killington. Place was perfect location with an easy shuttle 5 minutes from the Snowshed lifts, and a two minute walk from the main building with the pool and sauna facilities. The condo has everything you need for an easy stay close to the mountain, the abundant parking is adjacent to the building, and the facilities are great for kids. 5/5 will look to stay here again!
Guest favourite
Condo in Killington
4.9 out of 5 average rating, 48 reviews

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

KateRating, 5 stars1 week ago
We had the best stay here! The unit was so well equipped for cooking all our meals, the beds were comfy, and the property amenities were great! Having the pool in the same building was amazing! Shirley was so kind and responsive. The mountain lost power overnight at the end of our stay and she was accommodating with our restrictions for check-out, and even went above and beyond to check the local forecast to alert us to a closed road and alternative travel. I truly hope to come back again!
Guest favourite
Condo in Killington
4.84 out of 5 average rating, 173 reviews

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

JianyangRating, 5 stars2 weeks ago
Very nice place to stay for skiing trips. Cozy and very close to the resort.
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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