Villa holiday rentals in Rutland

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Popular amenities for Rutland villa rentals

Private villa rentals

Superhost
Villa in Rutland
5 out of 5 average rating, 3 reviews

Pico D305 located slope side at Pico.

NickRating, 5 stars37 months ago
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!
Superhost
Villa in Rutland
4.25 out of 5 average rating, 4 reviews

Pico C103 located at the base of Pico Mountain

ErichRating, 5 stars14 months ago
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
Superhost
Villa in Killington
4.8 out of 5 average rating, 5 reviews

Whiffletree F6 is on the shuttle bus route with a

TuckerRating, 5 stars15 months ago
Great communication, clean condo and very cozy. Will use again.
Superhost
Villa in Killington
4.8 out of 5 average rating, 5 reviews

Trail Creek 12, Lovely 1 bedroom close to Mountain

JasonRating, 5 stars2 weeks ago
This is our second time staying in The Trail Creek and condos and I’ll be happily coming back in the future! There’s no better deal near Killington. Can’t beat the location, amenities, and cabin feel!
Superhost
Villa in Killington
4.6 out of 5 average rating, 5 reviews

Trail Creek, Lovely 2 bedroom close to Mountain

StevenRating, 5 stars39 months ago
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.

Villa rentals with a pool

Guest favourite
Villa in Warren
5 out of 5 average rating, 26 reviews

Cozy, Comfy & Sunny renovated Sugarbush condo

DeanneRating, 5 stars1 month ago
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!!!
Superhost
Villa in Killington
4.67 out of 5 average rating, 3 reviews

Whiffletree B8 Great location with shuttle bus to

FrancoiseRating, 5 stars25 months ago
Very close to ski trails, the cleaning crew team did an excellent job, and really easy to work with the Killington team.
Guest favourite
Villa in Brownsville
4.82 out of 5 average rating, 22 reviews

Villa with Pool + Fitness Center Access

JayRating, 5 stars2 months ago
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.
Villa in Woodstock
4.8 out of 5 average rating, 5 reviews

Woodstock/Barnard Chalet 20 min Killington dog ok

AmyRating, 5 stars18 months ago
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.
Villa in Rupert
4.32 out of 5 average rating, 59 reviews

Gorgeous Victorian-Style House w/ Hilltop Pool!

PeterRating, 5 stars2 months ago
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!
Superhost
Villa in Lake George
4.71 out of 5 average rating, 28 reviews

Sun Castle Resort - Luxury Lakefront Villa

JennaRating, 5 stars8 months ago
We had a great stay! Location was great with pool and lake access
Superhost
Villa in Killington
4.56 out of 5 average rating, 9 reviews

Whiffletree C2 has been totally renovated and look

MeganRating, 5 stars15 months ago
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!
Superhost
Villa in Brownsville
4.67 out of 5 average rating, 3 reviews

Vermont Villa Near the Trails

DavidRating, 5 stars49 months ago
Great stay, lots of room. Front desk was super friendly.

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