Search Vacation Homes in Rutland

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 726 Vacation Homes in Rutland with updated reviews, rates, and availability.

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (92)
"We had a great winter weekend! The accommodations were just what we needed, perfect location and the coffee bar was amazing! We cant wait to come back again!"
Beautifully renovated with fireplace and coffee bar

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (201)
"Beautiful cozy cottage, but the road is a little loud. The creek and backyard are gorgeous."
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (19)
"Great Location! Very short drive to Skyeship Gondola. Property was well equipped for all our needs."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

9.8 out of 10, Exceptional, (89)
"Everything about this property was perfect for our family of 6! Location, charm and cleanliness, perfection! "
The price is AED 856
AED 1,664 total
includes taxes & fees
4 Feb - 5 Feb
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo

9.8 out of 10, Exceptional, (38)
"The property is recently renovated so everything is relatively new and in good condition. The unique design choice of using cedar for the walls, floors and ceiling was a bit off putting initially but we got used to it. There was a small issue with the hot tub, but the host responded very quickly and the issue was resolved the next day. Will definitely consider staying here for the next Okemo ski vacation."
Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo

Cozy Vermont House Near Killington and Woodstock. Discounted lift tickets!

8.0 out of 10, Very Good, (1)
" short stay "
Cozy Vermont House Near Killington and Woodstock. Discounted lift tickets!

Modern Farm House…minutes to Okemo; 2 King beds!

9.4 out of 10, Exceptional, (9)
"It is the perfect house for two families to stay in for a ski weekend. There are plenty of arcade and board games to entertain the teens. We will be back!"
Modern Farm House…minutes to Okemo; 2 King beds!

BruinsDen - Ski On Ski Off (Home Stretch Trail)

10.0 out of 10, Exceptional, (11)
"Wonderful home! Excellent layout for family bonding. Hot tub was great. Skiing equipment storage area was Lu fantastic. Easy ski-in ski-out!!! Communication with host was excellent!! Beds were comfy! Would highly recommend! "
The price is AED 3,161
AED 6,307 total
includes taxes & fees
2 Feb - 3 Feb
BruinsDen - Ski On Ski Off (Home Stretch Trail)

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

9.6 out of 10, Exceptional, (36)
"The home is as described with plenty of space for my family of 5. The kitchen was well stocked, and the bathrooms were clean. Plenty of towels and the beds were firm with clean sheets. The views of Lake Rescue were beautiful. The driveway was snow-covered, but with a 4WD, you should have no issue. The 'commute' to Okemo was easy - 8min max. The house seems to have been empty, so a musty smell permeated the home for the first day until the air circulated a few times. Not a big deal. The gas...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Townhome with patio & on-site pool, hot tub, sauna & tennis access

10.0 out of 10, Exceptional, (2)
"Wonderful comfortable place Very clean. We had a great stay the space was perfect for two small families skiing"
Townhome with patio & on-site pool, hot tub, sauna & tennis access

Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

9.8 out of 10, Exceptional, (48)
"We went up in December to Ski Okemo. This is a great house and has all amenities including an awesome fireplace and large eating area. Great location for two of three families to go away together and enjoy VT!"
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

9.6 out of 10, Exceptional, (25)
"If you're looking for the perfect getaway near Killington, look no further than this incredible rental home! From the moment we stepped inside, we were blown away by how spacious and welcoming the property felt. It easily accommodated our large group, with plenty of room for everyone to relax and enjoy themselves.The home has such a cozy, homey atmosphere that made it hard to leave! We spent our evenings gathered around the real fireplace, which added so much warmth and charm to the experience....
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

Killington, Vermont Ski House w/ Hot Tub and Sauna

9.4 out of 10, Exceptional, (84)
"The perfect home to come back to after a day of skiing with a sauna and hot tub to lounge in. So spacious and close to the mountain!"
Killington, Vermont Ski House w/ Hot Tub and Sauna

6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill

10.0 out of 10, Exceptional, (22)
"Our family stayed at Evan's home because we were attending a wedding (conveniently up the road) at Mountain Top Resort. The home gushes with Vermont charm! It was beautifully and thoughtfully decorated which made our stay so cozy. Evan thought of everything- from exact GPS directions, to helpful notes around the home to help his guests be comfortable! Evan was very helpful at every stage of our stay! We would absolutely 100% recommend staying at Evan's beautiful home!"
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill

Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn

Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

8.8 out of 10, Excellent, (21)
"Basic ski house, in cool spot. 10 mins from bear mtn. Would definitely stay here again. "
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!

10.0 out of 10, Exceptional, (16)
"We had two families stay at the home the first week of April during Spring Break so we could do a couple of days of skiing. The house was wonderful. It had so many beds, which made it great for the 6 kids and then separate bedrooms for the two couples, which was great. We enjoyed making a fire in the fireplace at the end of the day as we played board games with the family..we especially enjoyed playing LCR (Left Center Right). Kristin's communication was incredible. She was always so quick to...
Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!

Stunning 4 bed Timber Frame Ski Retreat on 6 acres

10.0 out of 10, Exceptional, (2)
"Great property for a ski trip up to the mountains!"
Stunning 4 bed Timber Frame Ski Retreat on 6 acres

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (155)
"Enjoyed our stay. 5 minute drive to Jackson gore base made it nice to go back and forth with kids. Ursula was very attentive and did her best to make sure everything was in good order. "
Idyllic Lakefront House Suited Two Families

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.2 out of 10, Very Good, (34)
"All in all it was a great trip. The place was very cute and as described. The upstairs bedrooms are not for light sleepers as the walls only go so far up so they are not really divided. I had read this in other reveiws but honestly for us it wasn't a problem. We went as a family group and it was kind of nice to be able to lay in bed and talk to the others in the room next to you. When we got there the hot tub was so hot that we were not able to get in. Maybe a problem with the thermostat but...
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Rutland
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Rutland

MODERN SPACIOUS 2-bedroom apartment

2.0 star property
3.2 out of 10, (5)
"This was very spacious. I think you could have a nice sized group here comfortably. 4-6. The area around the property is a bit run down. Thr property owner did not send instructions to enter prior to arrival, but responded quickly and we were inside within 10 min. The wifi password would not work, so we used cell and downloaded movies nearby to watch on Kindle. The main bedroom was large with a couch or maybe a futon. There was a stove, full fridge, washer and dryer, microwave. I did not see a...
The price is AED 437
AED 913 total
includes taxes & fees
2 Feb - 3 Feb
MODERN SPACIOUS 2-bedroom apartment

Stunning Wedding & Retreat Venue (19 bedrooms)

10.0 out of 10, Exceptional, (2)
"Our corporate group had an incredibly fun stay at Red Clover for a recent ski retreat. The property is impeccably maintained, staff are all very friendly and hospitable, and were communicative before and during our stay. The Red Clover team welcomed our group with open arms (and fresh baked cookies to boot!). It was the perfect setup for our group of ~25, and we appreciated the variety of sleeping rooms, and the number of rooms available. We also loved the dining area and the fact that it could...
Stunning Wedding & Retreat Venue (19 bedrooms)

Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

9.8 out of 10, Exceptional, (63)
"Everything was great! Very clean & cozy. Perfect spot for a ski trip!"
The price is AED 533
AED 1,148 total
includes taxes & fees
11 Feb - 12 Feb
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.