Rutland holiday rentals
We found 1,914 holiday rentals — enter your dates for availability
If you are looking to stay near Rutland, VT (RUT-Rutland Southern Vermont Regional), scroll through and discover holiday rentals to choose your home away from home. Whether you're staying in a holiday rental with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Rutland, VT (RUT-Rutland Southern Vermont Regional)
Showing deals for:24 Oct - 31 Oct
Image gallery for Luxury Ski Chalet - Okemo Killington
1010 out of 10 rating
Exceptional
(9 reviews)
Luxury Ski Chalet - Okemo Killington
Ludlow, VT
8% off
Price is AU$6,810
AU$6,810
AU$973 per night
includes taxes & fees
Image gallery for Country house minutes from Killington and Okemo
1010 out of 10 rating
Exceptional
(6 reviews)
Country house minutes from Killington and Okemo
Plymouth, VT
8% off
Price is AU$12,803
AU$12,803
AU$1,829 per night
includes taxes & fees
Image gallery for Spacious And Beautiful Luxury Home In Killington
1010 out of 10 rating
Exceptional
(21 reviews)
Spacious And Beautiful Luxury Home In Killington
Killington, VT
7% off
Price is AU$4,020
AU$4,020
AU$574 per night
includes taxes & fees
Image gallery for Killington area entire Inn to yourself! 14bd/15bth
7.87.8 out of 10 rating
Good
(6 reviews)
Killington area entire Inn to yourself! 14bd/15bth
Pittsfield, VT
8% off
Price is AU$18,931
AU$18,931
AU$2,704 per night
includes taxes & fees
Image gallery for Okemo&Killington Retreat 90acre Private Mountain Getaway! Breathtaking View!
1010 out of 10 rating
Exceptional
(15 reviews)
Okemo&Killington Retreat 90acre Private Mountain Getaway! Breathtaking View!
Shrewsbury, VT
8% off
Price is AU$10,256
AU$10,256
AU$1,465 per night
includes taxes & fees
Image gallery for Spacious 6BR - 5BA Ski Home on Pico Mountain - Minutes to Killington Mountain
9.89.8 out of 10 rating
Exceptional
(48 reviews)
Spacious 6BR - 5BA Ski Home on Pico Mountain - Minutes to Killington Mountain
Killington, VT
8% off
Price is AU$7,805
AU$7,805
AU$1,115 per night
includes taxes & fees
Image gallery for Killington, Right Side of Duplex, Outside HotTub, Charming, Cozy, Clean
9.89.8 out of 10 rating
Exceptional
(33 reviews)
Killington, Right Side of Duplex, Outside HotTub, Charming, Cozy, Clean
Bridgewater Corners, VT
8% off
Price is AU$5,263
AU$5,263
AU$752 per night
includes taxes & fees
Image gallery for Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking
Ludlow, VT
8% off
Price is AU$8,302
AU$8,302
AU$1,186 per night
includes taxes & fees
Image gallery for Spacious 5-bedroom w/ huge yard. Rural getaway!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Spacious 5-bedroom w/ huge yard. Rural getaway!
Granville, NY
8% off
Price is AU$6,030
AU$6,030
AU$861 per night
includes taxes & fees
Image gallery for Get away from the crowd. 400 private acres. Vermont's fresh air. Sleeps 2-14.
8.28.2 out of 10 rating
Very good
(17 reviews)
Get away from the crowd. 400 private acres. Vermont's fresh air. Sleeps 2-14.
Wells, VT
12% off
Price is AU$5,942
AU$5,942
AU$849 per night
includes taxes & fees
Image gallery for Four Season KILLINGTON Getaway!
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Four Season KILLINGTON Getaway!
Pittsfield, VT
19% off
Price is AU$2,140
AU$2,140
AU$306 per night
includes taxes & fees
Image gallery for Cozy 2 bedroom minutes from Okemo base lodge - Inquire about seasonal rental
9.29.2 out of 10 rating
Wonderful
(29 reviews)
Cozy 2 bedroom minutes from Okemo base lodge - Inquire about seasonal rental
Ludlow, VT
7% off
Price is AU$1,918
AU$1,918
AU$274 per night
includes taxes & fees
Image gallery for Rustic Retreat Cozy and Pet friendly Log Cabin in the Woods.
9.09.0 out of 10 rating
Wonderful
(44 reviews)
Rustic Retreat Cozy and Pet friendly Log Cabin in the Woods.
Wells, VT
12% off
Price is AU$2,826
AU$2,826
AU$404 per night
includes taxes & fees
Image gallery for Beautifully appointed lake-view cottage with dock access
1010 out of 10 rating
Exceptional
(37 reviews)
Beautifully appointed lake-view cottage with dock access
Bomoseen, VT
8% off
Price is AU$2,771
AU$2,771
AU$396 per night
includes taxes & fees
Image gallery for Classic 1920s Farmhouse Beautifully Restored, Idyllic Setting with EV charging
1010 out of 10 rating
Exceptional
(23 reviews)
Classic 1920s Farmhouse Beautifully Restored, Idyllic Setting with EV charging
Poultney, VT
18% off
Price is AU$2,768
AU$2,768
AU$395 per night
includes taxes & fees
Image gallery for 5 bedroom, 4 bath OKEMO Ski and LAKE Home with A/C
1010 out of 10 rating
Exceptional
(18 reviews)
5 bedroom, 4 bath OKEMO Ski and LAKE Home with A/C
Ludlow, VT
8% off
Price is AU$12,279
AU$12,279
AU$1,754 per night
includes taxes & fees
Image gallery for Private House with Fantastic Views off Home Stretch Trail
1010 out of 10 rating
Exceptional
(48 reviews)
Private House with Fantastic Views off Home Stretch Trail
Killington, VT
8% off
Price is AU$10,501
AU$10,501
AU$1,500 per night
includes taxes & fees
Image gallery for Okemo 6 Bedroom Chalet.
9.49.4 out of 10 rating
Exceptional
(23 reviews)
Okemo 6 Bedroom Chalet.
Ludlow, VT
12% off
Price is AU$7,834
AU$7,834
AU$1,119 per night
includes taxes & fees
Image gallery for 3 bedroom Cottage at Waters Edge with Spectacular view of water and mountains
1010 out of 10 rating
Exceptional
(6 reviews)
3 bedroom Cottage at Waters Edge with Spectacular view of water and mountains
Poultney, VT
8% off
Price is AU$3,198
AU$3,198
AU$457 per night
includes taxes & fees
Image gallery for Relaxing mountain setting w/private hot tub, 5 minutes to Okemo. Pet friendly!
8.68.6 out of 10 rating
Excellent
(7 reviews)
Relaxing mountain setting w/private hot tub, 5 minutes to Okemo. Pet friendly!
Ludlow, VT
8% off
Price is AU$3,583
AU$3,583
AU$512 per night
includes taxes & fees
Image gallery for Ludlow Vermont Ski House
1010 out of 10 rating
Exceptional
(48 reviews)
Ludlow Vermont Ski House
Ludlow, VT
8% off
Price is AU$12,437
AU$12,437
AU$1,777 per night
includes taxes & fees
Image gallery for Winterplace Condo Steps away from slopes
1010 out of 10 rating
Exceptional
(5 reviews)
Winterplace Condo Steps away from slopes
Ludlow, VT
8% off
Price is AU$10,194
AU$10,194
AU$1,456 per night
includes taxes & fees
Image gallery for Killington area home - 4-seasons & hot tub. Sleeps 13+
9.89.8 out of 10 rating
Exceptional
(118 reviews)
Killington area home - 4-seasons & hot tub. Sleeps 13+
Pittsfield, VT
11% off
Price is AU$3,342
AU$3,342
AU$477 per night
includes taxes & fees
Image gallery for Artisan Ski House for Groups! Killington + Okemo in Minutes. Walk to Long Trail
1010 out of 10 rating
Exceptional
(63 reviews)
Artisan Ski House for Groups! Killington + Okemo in Minutes. Walk to Long Trail
Bridgewater Corners, VT
5% off
Price is AU$10,026
AU$10,026
AU$1,432 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Rutland
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Sleeps 2 · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
51 reviews(51 reviews)
Dramatic Design & Landscape 3500 Sq Ft. Farmhouse W/Jacuzzi&Swim Pond&CentralAC!
Sleeps 28 · 7 bedrooms · 3+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
102 reviews(102 reviews)
Cedarbrook Hotel Room 2 Doubles 119
Sleeps 4 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
7 reviews(7 reviews)
Deluxe one bedroom suite located on first floor with outdoor heated pool 11921
Sleeps 6 · 2 bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 208
Sleeps 4 · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Idyllic Lakefront House Suited Two Families
Sleeps 10 · 3 bedrooms · 2+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
159 reviews(159 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value