Holiday houses in Rutland

4.81 out of 5 average rating, 133 reviews

Home in Tinmouth

Vermont Lakefront Getaway "The Wild Loon"

WilliamRating, 5 stars2 months ago

The place was perfect for our winter family vacation. The home was as described in a beautiful setting with a great view. If staying in the winter months having a vehicle with at least all wheel drive is helpful, as this is Vermont. The home is out of the way, but easy driving distance to ski and explore the nearby towns.

4.86 out of 5 average rating, 126 reviews

Cabin in Lake George

Spacious Lake George Lodge -Near West & Gore Mnt

LisaRating, 5 stars2 months ago

We had a wonderful time staying at Nathan’s cabin for my birthday weekend. We were so close to the town of Lake George but also had some privacy. Despite being on a small one-lane highway, it still felt like a lovely woodsy retreat and it turned out to be in our benefit because when it snowed, the road was cleared very quickly. The house is cozy and the beds are comfy! We would def recommend staying here!

5 out of 5 average rating, 5 reviews

Cottage in Mendon

The Mendon Cottage: Cozy Home. Killington / Pico

SeanRating, 5 stars2 months ago

The Mendon Cottage is clean, cozy and private. It’s just a 15 minute drive to Killington base, even in a fairly decent snow storm. There are trails behind the property that offered some good hiking for our doggo (they’re made for snowmobiles, but we didn’t spot one during our stay). The property delivers on its main promise: a less pricey alternative to staying at Killington, with very little inconvenience for the ski bums. Unless you simply can’t live without the ability to take the shuttle and ski off the mountain to your rental, you really can’t go wrong with this property. (It snowed our entire stay and the private road and driveway were plowed repeatedly and always navigable.)

5 out of 5 average rating, 39 reviews

Cabin in Lake George

Great location. Walk to Village attractions/beach!

MarinaRating, 5 stars4 months ago

Katrina was a wonderful host! She was responsive and thoughtful with her recommendations. The home was incredibly clean and had everything you could need for your stay and more. We felt very comfortable in the space and were so impressed with how well the space was maintained and that no detail was overlooked to make guests feel at home. The location was great and the lake views were beautiful at night with the holiday lights! Highly recommend Katrina and the cabin!

4.91 out of 5 average rating, 100 reviews

Cabin in Bridgewater

100 Acres Views & Creek near Woodstock/Killington

ChristopherRating, 5 stars1 month ago

Had a great stay with friends at Laura’s place. Laura was friendly flexible and reached out to make sure we didn’t have any issues checking in. Very nice place with a nice Vermont feel. 10-15 minutes from skyeship base. Had a great weekend. Would stay again.

4.96 out of 5 average rating, 225 reviews

Home in Addison

Brthtkng New Premier Lake Champlain Wfrnt Escape!

RobertRating, 5 stars1 week ago

A perfect spot for us and our small pooch. The only challenge was that I had to carry our small dog upstairs, because she couldn’t do the stairs. Wonderful,private location, and Barb dealt with an internet issue very promptly, but also respected our privacy.

Guest suite in Lake George

4.95 out of 5 average rating, 79 reviews

Lake George Perfect Location

StephenRating, 5 stars2 weeks ago

Peter was a great host! His house is in a great location! My wife and I went to Lake George for a long weekend without our kids. It was our first time away from our kids in 5 years and Peter made the experience perfect! Peter was always willing to help. His place is super clean and well maintained! My wife and I are already planning a trip back! Thank you Peter!

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Popular amenities for Rutland holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Rutland's top sights

Roots42 locals recommend

Table 2434 locals recommend

Paramount Theatre, VT33 locals recommend

Pine Hill Park32 locals recommend

Rutland Farmers Market24 locals recommend

Hannaford Supermarket24 locals recommend

Other great holiday rentals in Rutland

5 out of 5 average rating, 12 reviews

Home in Wells

Breathtaking Lakeside Retreat!

BrianRating, 5 stars2 months ago

Second year renting. Great place, definitely would recommend. Hope to return next year. Brooke is a fantastic host. Thank you

4.8 out of 5 average rating, 15 reviews

Cabin in Barnard

Private post & beam log cabin on Macintosh Pond.

NinaRating, 5 stars4 months ago

It was perfect for what we wanted! We were giving Grandma an 80th Hallmark Experience. A lot of what we did was in Woodstock and it was a noce 30 min ride to the town, but for us very convenient. We had a family of 14 and we played games in ythe main living room all together. The downstairs was perfect for our older kids to hang out in!

5 out of 5 average rating, 9 reviews

Home in Bellows falls

Amazing Views, Skiing Nearby and Amenities Galore!

GillianRating, 5 stars2 months ago

We absolutely loved our stay at Barbara’s home! It was spacious enough to accommodate 6 adults and 1 child with no issue. The kitchen is well appointed, allowing us to cook meals throughout our stay. We had a small storm roll through, which dropped 5” of snow overnight (great for our next day on the mountain!), and we were thrilled to see that the driveway and walkway had been cleared prior to 7am. The bedrooms were comfortable and the view from the great room is truly stunning. Would love to stay here again! Thank you, Barbara!

4.86 out of 5 average rating, 35 reviews

Home in Manchester

Your VT Dream House: Fireplace, Pool, Dogs

AtulRating, 5 stars8 months ago

Beautiful area great amenity. Wish there was 1/2 bath downstairs. That was the only inconvenience.

5 out of 5 average rating, 6 reviews

Cabin in Hudson Falls

Cozy Retreat Near LG – Sleeps 8

MaximusRating, 5 stars3 weeks ago

Such a pretty estate!! Loved staying here. Woohoo!!

5 out of 5 average rating, 8 reviews

Home in Chittenden

Modern Retreat next to Mountain Top Inn,Killington

MaddyRating, 5 stars2 months ago

I couldn't recommend this place more! My cousins and I had a great time and Uli is super attentive. The hot tub has a great view of the lake, it was also salt water which I love. The space was extremely cozy and exactly what we needed. We snowboarded pico and killington and it was about a 25-30 minute ride. We will for sure be back! Thank you guys so much!

5 out of 5 average rating, 16 reviews

Home in Plymouth

Luxury Modern Cabin near Okemo & Killington

TariQRating, 5 stars1 month ago

Stephanie was an Incredible host! The listing matched her description and the property looked even better upon checking in. Stephanie maintains this property really well and I couldn’t have felt any more at home. The home was clean and had a perfect cozy feeling to it. In addition, this was really close to the mountain, which made the getaway even better. I enjoyed the privacy and waking up to a nice snow dusting before my trip to the mountain. I highly suggested staying at Stephanie’s property if you’re looking for a quick getaway. I certainly will be looking to book again soon. Thank you Stephanie!