Villa vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Rutland villa rentals
Private villa rentals
Villa in Rutland
4.25 out of 5 average rating, 4 reviewsPico 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
Villa in Killington
4.75 out of 5 average rating, 4 reviewsTrail Creek 12, Lovely 1 bedroom close to Mountain
Excellent villa for 4 people. The place was perfect for our 4-day ski trip.
Villa in Killington
4.6 out of 5 average rating, 5 reviewsTrail 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
Villa in Killington
5 out of 5 average rating, 3 reviewsSunrise East Glade C8
Great ski in/out location. Cozy place with everything you need.
Villa in Woodstock
4.8 out of 5 average rating, 5 reviewsWoodstock/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.
Villa in Rupert
4.31 out of 5 average rating, 58 reviewsGorgeous Victorian-Style House w/ Hilltop Pool!
This beautiful house was perfect for our family. So much space, fully stocked kitchen, books and art for days. They ground were filled with fun for kids and adults, archery, bacchi, hommocks, vollyball, chickens, and friendly cat my kids became obsessed with. We loved multiple the fire places and the grounds keeper Mario helped bring in enough wood to keep them going. we went for a local hike and general store trip and had so much fun.
Villa in Winhall
4.9 out of 5 average rating, 21 reviewsStonehouse at Stratton
Our second stay here was just as good as the first. The perfect ski house with a huge entry way and entertaining space. Can’t beat the location too! We look forward to going back, Kara and Adoniram are great hosts!
Villa in Killington
4.64 out of 5 average rating, 11 reviewsTrail Creek 70, Fantastic 3 bed close to Mountain
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.
Villa in Ludlow
4.94 out of 5 average rating, 35 reviewsModern 4 Bedroom 4 Bath Villa w HotTub/ back trail
A perfect place to stay near Okemo! The house was modern, clean, and cozy. We had good communication with the host, it was in a convenient location, and it had great amenities. It was an overall pleasant experience and we would highly recommend this house to anyone!
Villa in Bolton
4.94 out of 5 average rating, 64 reviews100 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 in Killington
4.8 out of 5 average rating, 5 reviewsWhiffletree F6 is on the shuttle bus route with a
Great communication, clean condo and very cozy. Will use again.
Villa rentals with a pool
Villa in Killington
4.67 out of 5 average rating, 3 reviewsWhiffletree 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.
Villa in Brownsville
4.82 out of 5 average rating, 22 reviewsVilla 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.
Villa in Woodstock
4.8 out of 5 average rating, 5 reviewsWoodstock/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.
Villa in Killington
4.33 out of 5 average rating, 3 reviewsSunrise Timberline I7
Excellent location right on the mountain. Short drive to great food, hikes, and action sports.
Villa in Rupert
4.31 out of 5 average rating, 58 reviewsGorgeous Victorian-Style House w/ Hilltop Pool!
This beautiful house was perfect for our family. So much space, fully stocked kitchen, books and art for days. They ground were filled with fun for kids and adults, archery, bacchi, hommocks, vollyball, chickens, and friendly cat my kids became obsessed with. We loved multiple the fire places and the grounds keeper Mario helped bring in enough wood to keep them going. we went for a local hike and general store trip and had so much fun.
Villa in Lake George
4.71 out of 5 average rating, 28 reviewsSun Castle Resort - Luxury Lakefront Villa
We had a great stay! Location was great with pool and lake access
Villa in Killington
4.56 out of 5 average rating, 9 reviewsWhiffletree 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!
Villa in Brownsville
4.67 out of 5 average rating, 3 reviewsVermont Villa Near the Trails
Great stay, lots of room. Front desk was super friendly.
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