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.

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Private room in Windsor

4.89 out of 5 average rating, 37 reviews

Private Wing of largest Colonial Mansion in US

ClaireRating, 5 stars2 months ago

This was such an incredible place to stay! The whole mansion is absolutely stunning, the surroundings and views are beautiful. However, what made this stay truly special was the incredible kindness and hospitality of the host. This was a wonderful experience and we are all looking forward to our next stay!

Guest favourite

Villa in Bolton

4.94 out of 5 average rating, 64 reviews

100 yrs old 2024! Historic Musician's Villa Bolton

Mary JoRating, 5 stars6 months ago

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 Rupert

4.32 out of 5 average rating, 59 reviews

Gorgeous Victorian-Style House w/ Hilltop Pool!

PeterRating, 5 stars3 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!

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.

Superhost

Villa in Lake George

4.75 out of 5 average rating, 52 reviews

Stumble Abode - 3

GigiRating, 5 stars6 months ago

We visited Stumble Abode over a long weekend. The beautiful cottage was clean and cozy. It was perfect for two adults and two small children. Parking was easy and close by. It had all the amenities we needed and more. We hope to visit again soon, and definitely recommend others to stay there!

Superhost

Villa in Killington

4.56 out of 5 average rating, 9 reviews

Whiffletree base of Killington outdoor pool

MeganRating, 5 stars16 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!

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What guests are saying

Pico D305 located slope side at Pico quiet area

5 out of 5 average rating, 3 reviews38 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!

Villa in Rutland

What guests are saying

Villa with Pool + Fitness Center Access

4.82 out of 5 average rating, 22 reviews2 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 Brownsville

What guests are saying

Whiffletree base of Killington outdoor pool

4.56 out of 5 average rating, 9 reviews16 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!

Villa in Killington

What guests are saying

Modern 4 Bedroom 4 Bath Villa w HotTub/ back trail

4.95 out of 5 average rating, 42 reviews1 month ago

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.

Villa in Ludlow

What guests are saying

100 yrs old 2024! Historic Musician's Villa Bolton

4.94 out of 5 average rating, 64 reviews6 months ago

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 Bolton

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Popular amenities for Rutland villa rentals

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Private villa rentals

Superhost

Villa in Rutland

4.25 out of 5 average rating, 4 reviews

Pico C103 located at the base of Pico Mountain

ErichRating, 5 stars15 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

4.6 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.

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Luxury villa rentals

Superhost

Villa in Killington

5 out of 5 average rating, 3 reviews

Sunrise East Glade C8

KimRating, 5 stars14 months ago

Great ski in/out location. Cozy place with everything you need.

Superhost

Villa in Killington

2.67 out of 5 average rating, 3 reviews

Whiffletree base of Killington outdoor pool

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Villa rentals with a pool

Superhost

Villa in Killington

5 out of 5 average rating, 3 reviews

Sunrise East Glade C8

KimRating, 5 stars14 months ago

Great ski in/out location. Cozy place with everything you need.

Superhost

Villa in Killington

4.67 out of 5 average rating, 3 reviews

Whiffletree B8 Great location with shuttle bus to

FrancoiseRating, 5 stars26 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.

Superhost

Villa in Killington

4.33 out of 5 average rating, 3 reviews

Sunrise Timberline I7

ZackRating, 5 stars43 months ago

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

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 base of Killington outdoor pool

MeganRating, 5 stars16 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 Killington

4.64 out of 5 average rating, 11 reviews

Base of Killington with Sports center access

RakeshRating, 5 stars30 months ago

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.

Superhost

Villa in Brownsville

4.67 out of 5 average rating, 3 reviews

Vermont Villa Near the Trails

DavidRating, 5 stars50 months ago