
Villa holiday rentals in Rutland
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Top-rated villa rentals in Rutland
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Holiday rentals for every style
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Popular amenities for Rutland villa rentals
Private villa rentals

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

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

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!!!

Sunrise East Glade C8
Great ski in/out location. Cozy place with everything you need.

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.

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!

Sun Castle Resort - Luxury Lakefront Villa
We had a great stay! Location was great with pool and lake access

Stonehouse at Stratton
Overall we had great experience at the house. The inner decorations were cozy and comfortable, and the design was awesome! The host was responsive when the new door lock had some issues. 100% recommend staying at this house!

Modern 4 Bedroom 4 Bath Villa w HotTub/ back trail
Great stay- so nice to be so close to okemo which made skiing really seamless. The house matched the pics perfectly. Kids had a good bunk room and the 3 adult couples all had their own rooms with en suite bathrooms. The hot tub on the upper deck was a nice bonus. Easy in and out, and Nicholas was very easy to communicate with. We had one minor hiccup with the fridge but Nicholas was responsive and accommodating. Thanks for the great weekend away.

100 yrs old 2024! Historic Musician's Villa Bolton
It was spectacular house, beautifully maintained, and restored to its historic beauty. Lake George is beautiful and the village of Bolton Landing is charming. Plenty of room for 11 of us to make meals and have fun together. My only complaint was that it was in the middle of a construction site – with noisy machinery and workers all around the house. Sunday was quiet. However, we tried to focus on the beauty of it – and Kim, the hostess, did everything she could to make us comfortable. I would definitely recommend the house – just check on the status of the construction first.
Villa rentals with a pool

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!!!

Sunrise East Glade C8
Great ski in/out location. Cozy place with everything you need.

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.

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!

Sunrise Timberline I7
Excellent location right on the mountain. Short drive to great food, hikes, and action sports.

Sun Castle Resort - Luxury Lakefront Villa
We had a great stay! Location was great with pool and lake access

Whiffletree base of Killington outdoor pool
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!

Base of Killington with Sports center access
The place is as listed on the photos, We enjoyed our trip in vermont, this is exactly located to the nearby places to visit in killington during fall season. Thanks for the stay.
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