Search Vacation Homes in Rutland

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Rutland vacation homes

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is AED 364
AED 889 total
includes taxes & fees
24 May - 25 May
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Rutland
10.0 out of 10, Exceptional, (4 reviews)
"House was clean, organized and spacious. Great location as well, close to grocery, gas and restaurants. Host answered questions quickly. "
United States
Dominic C.
The price is AED 701
AED 1,604 total
includes taxes & fees
27 May - 28 May
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.6 out of 10, Exceptional, (4 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AED 978
AED 2,170 total
includes taxes & fees
25 May - 26 May
large ski ranch hot tub close to killington pets ok

Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
The price is AED 1,377
AED 2,703 total
includes taxes & fees
3 Jun - 4 Jun
Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
The price is AED 496
AED 1,220 total
includes taxes & fees
25 May - 26 May
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

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

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
The price is AED 496
AED 1,220 total
includes taxes & fees
25 May - 26 May
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

CozyDen - AC, Grill, Bike to Mountain, Porch!

CozyDen - AC, Grill, Bike to Mountain, Porch!
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is AED 463
AED 1,000 total
includes taxes & fees
22 May - 23 May
CozyDen - AC, Grill, Bike to Mountain, Porch!

The Tower House | Hot Tub | Firepit | Dog-Friendly

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is AED 661
AED 2,403 total
includes taxes & fees
26 May - 27 May
The Tower House | Hot Tub | Firepit | Dog-Friendly

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (41 reviews)
"We had a wondetful time! Thank you! The hosts were so accommodating and the place is the perfect winter wonderland getaway. "
United States
Gabriele K.
The price is AED 496
AED 1,748 total
includes taxes & fees
4 Jun - 5 Jun
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Large Killington Area Home | Sleeps 7 | Game Room

Large Killington Area Home | Sleeps 7 | Game Room
Bridgewater
9.6 out of 10, Exceptional, (7 reviews)
"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."
United States
Owen C.
The price is AED 698
AED 2,053 total
includes taxes & fees
26 May - 27 May
Large Killington Area Home | Sleeps 7 | Game Room

Feel the real VT! Lakes, hikes, a foodies delight!

Feel the real VT! Lakes, hikes, a foodies delight!
Proctor
10.0 out of 10, Exceptional, (1 review)
"Clean and comfortable home. Plenty of space for our family! Great quiet neighborhood made it easy to relax on our trip."
United States
Rebecca
The price is AED 766
AED 2,246 total
includes taxes & fees
17 Jun - 18 Jun
Feel the real VT! Lakes, hikes, a foodies delight!

New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (16 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is AED 985
AED 2,196 total
includes taxes & fees
22 May - 23 May
New Ludlow Village Home with Stunning Okemo Mountain View

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
Breakaway House by Killington Vacation Rentals

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Killington
10.0 out of 10, Exceptional, (19 reviews)
"A very pleasant stay at this place. Nice furnishings, everything clean, the hot tub was utilized. Would recommend this to any group or family seeking nearby cozy accommodations near the slopes. "
United States
Tom W.
The price is AED 929
AED 2,432 total
includes taxes & fees
25 May - 26 May
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!

Pastoral, dog-friendly home surrounded by lush woodland with free WiFi & firepit

Pastoral, dog-friendly home surrounded by lush woodland with free WiFi & firepit
Castleton
9.0 out of 10, Wonderful, (12 reviews)
"Very nice property, beautiful time of year to visit Vermont. Colors were wonderful."
United States
Teresa V.
Pastoral, dog-friendly home surrounded by lush woodland with free WiFi & firepit

Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm

Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm
Woodstock
The price is AED 1,098
AED 2,523 total
includes taxes & fees
28 May - 29 May
Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is AED 682
AED 2,832 total
includes taxes & fees
25 May - 26 May
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
Fair Haven
8.8 out of 10, Excellent, (27 reviews)
"Clean home. Easy to find and conveniently located to shops, stores and restaurants. "
United States
Antony C.
The price is AED 826
AED 1,037 total
includes taxes & fees
25 May - 26 May
Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

BearRight- AC, Pool, Hot Tub, Grill, FirePit

BearRight- AC, Pool, Hot Tub, Grill, FirePit
Killington
9.8 out of 10, Exceptional, (12 reviews)
"Excellent stay, very accommodating hosts. Well organized"
United States
Brian S.
The price is AED 1,429
AED 2,971 total
includes taxes & fees
25 May - 26 May
BearRight- AC, Pool, Hot Tub, Grill, FirePit

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
The Woods
10.0 out of 10, Exceptional, (7 reviews)
"Location/proximity to Killington is awesome! A few minutes drive from the parkland lot at Ramshead. The community kept the roads and parking lots plowed well. Communication from the host was excellent. The condo was very comfortable for our family of 3 (2 adults and 4 yr old) and exactly as described. Great spot to relax after our days skiing! We would definitely come back!"
United States
Elizabeth C.
The price is AED 1,099
AED 2,347 total
includes taxes & fees
28 May - 29 May
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Rutland Hotel Reviews