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Villa holiday rentals in Rutland
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Top-rated villa rentals in Rutland
Guests agree: These villas are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Rutland villa rentals
Private villa rentals
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Pico D305 located slope side at Pico.
This was perfect for my son and I to relax in over a weekend at Pico. Everything was clean, comfortable, and we loved the fireplace as an added touch. Convenience and location were perfect; walk right out the front door and you're skiing with the buzz of the lodge right there - true ski in and out. We will definitely stay here again, for longer next time hopefully!
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Pico C103 located at the base of Pico Mountain
Killington group was very nice and also super helpful even after midnight when our key cards were deactivated.... Make sure to keep the cards away from your phone lol. Overall great place
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Whiffletree F6 is on the shuttle bus route with a
Great communication, clean condo and very cozy. Will use again.
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Trail Creek 12, Lovely 1 bedroom close to Mountain
Excellent villa for 4 people. The place was perfect for our 4-day ski trip.
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Trail Creek, Lovely 2 bedroom close to Mountain
Great stay, able to walk to the mountain and ski off the mountain. Activity center hot tub was great to utilize after a long day on the slopes.
Luxury villa rentals
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Sunrise East Glade C8
Great ski in/out location. Cozy place with everything you need.
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Gorgeous Victorian-Style House w/ Hilltop Pool!
Our stay at the house was amazing! Place is very spacious so our guests were very comfortable! Plenty rooms and beds to sleep in. Kitchen is stocked up. There is everything you need ti make meals. We absolutely loved it!! Our group had people whi ski and hike . Everyone had plenty to do!! Definitely recommend that place! If we ever go back to Vermont we’ll stay there for sure!! Thank you so much for having us!
Villa rentals with a pool
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Cozy, Comfy & Sunny renovated Sugarbush condo
We had a wonderful time and felt right at home!! Her place is SPOTLESS and cozy. Simone’s instructions to get there were perfect. Everything is well labeled (like which switches do what), USB ports on bedroom lamps., binder with check in/check out info. Couch is 10/10 for post-ski nap, beds and linens are super comfortable. Kitchen items look brand new. Shower pressure is also 10/10 There is a shuttle that takes you to the resort with a stop in this neighborhood (5-10 min walk), but uphill so with kids and ski gear we drove to resort each day (2-3 min drive). The houses in the neighborhood are spaced out so you don’t feel like you are right on top of someone but also aren’t completely secluded in the wilderness. We stayed Presidents’ Day weekend and skied Lincoln Peak. The lift lines moved quickly and didn’t feel overly crowded. This rental was priced higher than other rentals we considered, but based on pristine condition and ease of our stay it was worth it!!!
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Whiffletree B8 Great location with shuttle bus to
Very close to ski trails, the cleaning crew team did an excellent job, and really easy to work with the Killington team.
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Villa with Pool + Fitness Center Access
Such a great deal considering the price and amenities. The location was quite a drive from our destination but it was close to other places like Okemo and Woodstock. Beautiful surroundings. A warm full size pool in the winter time is unbeatable. Place was clean when we arrived. The building was quiet and peaceful. No issues with noise nor difficulty with checking in.
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Gatehouse Villa at Blue Water Manor w/pool, lake
We had an excellent experience… best way for our family to spend summer vacation. The home was a perfect fit for all 6 of us in terms of space and layout. We enjoyed the porch, pool , lake and all town had to offer. We will be back. Thank you, Michelle for being an excellent host !!!
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Woodstock/Barnard Chalet 20 min Killington dog ok
Great stay at this location. Owner was friendly and very responsive. This is a large home with a bedroom on the main floor and 4 others upstairs. The kids room we call the Peter Pan room as it is right off of another room with twin beds. So cute! The house has tall ceilings and big rooms with real beds in each one to suit your guests. The home is a very special place where you are minutes to Woodstock but have true privacy and amazing views. A great stay. Will be back soon.
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Sun Castle Resort - Luxury Lakefront Villa
We had a great stay! Location was great with pool and lake access
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Whiffletree C2 has been totally renovated and look
What a great condo in the best location! Unbeatable for the price. The condo was spotless, and had every amenity as described. Plenty of towels, soaps, kitchen necessities. Beds were comfortable! We really felt right at home. And the fire place was so nice! We’d definitely recommend this for a great weekend get away!
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Vermont Villa Near the Trails
Great stay, lots of room. Front desk was super friendly.
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