search location
Travel Dates:
Reset Dates
828 Rentals In Rutland Area
United States
Vermont
Rutland Area
Filters
Sub Areas
Killington
(119)
Mendon
(21)
Pittsfield
(3)
Chittenden
(2)
Sudbury
(1)
Rutland
(1)
Pittsford
(1)
Mount Tabor
(1)
Lake Hortonia
(1)
Hubbardton
(1)
Brandon
(1)
Benson
(1)
Guests
Guests
1
2
3
4
5
6
7
8+
Price
Per Night:
Amenities
Pool
Internet
Washer
Fishing
FirePlace
Wheelchair Access
Non Smoking
Yard
TV
Balcony
Patio
Parking
AC
Microwave
No Pets
Jacuzzi
Pet Allowed
Dishwasher
Kitchen
Sauna
Crib
Smoking Allowed
Grill
Luxury Meets Rustic: Trail Creek 2Bed/2Bath+Loft - Sleeps 6 (On Ski Home Trail)
2
2.0
6
Killington Vermont Condo
From $1619 per night
(USD)
Top of Hadley Peak, panoramic views, 4,500 sq. ft house
4
3.0
13
Killington Vermont Private vacation home
From $1420 per night
(USD)
Modern Barn home near 5 Ski Areas
5
2.0
10
Sudbury Vermont Private vacation home
From $701 per night
(USD)
Killington 2 Bdrm Condo on Access Rd. w/ Health Spa and Pool
2
2.0
6
Killington Vermont Condo
From $258 per night
(USD)
Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts
4
3.0
7
west rutland Vermont Private vacation home
From $512 per night
(USD)
Snowberry Hill, 5 bedroom, Private Luxury Ski Home on Killington Mtn, sleeps 12
5
3.0
12
Killington Vermont Private vacation home
From $1294 per night
(USD)
\" SUMMER/FALL 2026\"...THE WOODS RESORT & SPA\"- SPACIOUS TOWNHOME-Not A Condo--
2
2.0
6
Killington Vermont Private vacation home
From $388 per night
(USD)
Private Mountain View minutes to Hiking, biking, golfing, skiing, snowboarding
3
2.0
6
Killington Vermont Private vacation home
From $812 per night
(USD)
Luxe Trailside! Bike + Ski On/Off. Closest unit to hot tub, lift, hotel & trail!
2
2.0
6
Killington Vermont Condo
From $265 per night
(USD)
Central Ski home with Hot Tub, sauna, walk to restaurants, and ski shops
4
2.0
8
Killington Vermont Chalet
From $1516 per night
(USD)
Ski-on Ski-Off Killington 2 BR Condo at Sunrise, with Pool, Hot Tub and Gym
2
2.0
6
Killington Vermont Condo
From $241 per night
(USD)
Killington Condo Penthouse Mountain View Underground parking Pool Hot Tub - 3F10
2
2.0
6
Killington Vermont Condo
From $367 per night
(USD)
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tubs, Sauna -
2
2.0
6
Killington Vermont Condo
From $452 per night
(USD)
Visit- StayinVermont.org - Village Victorian Classic - Pet Friendly
3
2.0
10
Wallingford Vermont Private vacation home
From $143 per night
(USD)
Cabin at Killington Left: 4BR with Wood Stove, Deck and Hot Tub
4
2.0
10
Killington Vermont Cabin
From $540 per night
(USD)
Orwell Cabin on Sunrise Lake w/ Private Dock & BBQ
4
2.0
10
Orwell Vermont Cabin
From $767 per night
(USD)
Killington Getaway In Private Community
2
1.0
6
Killington Vermont Private vacation home
From $323 per night
(USD)
All Season Three Level Log Vacation Home On 21 Acres Between Okemo & Killington!
4
2.0
14
Mt Holly Vermont Cabin
From $432 per night
(USD)
Cozy Killington Mountain View Condo
3
2.0
8
Killington Vermont Condo
From $362 per night
(USD)
Luxury Resort Condo Across From Killington Ski Slope - AAA Rated
2
1.0
4
Killington Vermont Condo
From $432 per night
(USD)
Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
3
2.0
12
Fair Haven Vermont Private vacation home
From $361 per night
(USD)
Private and Artistic cabin, Pet friendly, no cleaning fee
2
4.0
7
West Pawlet Vermont Cabin
From $265 per night
(USD)
Cozy & Private Killington Ski House - Hot Tub - 4 Min to Resort - 4BR/3BA
4
3.0
12
Killington Vermont Private vacation home
From $619 per night
(USD)
Guest Cabin-- a Mountain Get-Away for Relaxation... or Romance
1
1.0
2
Belmont Vermont Cabin
From $241 per night
(USD)
Experience the ultimate mountain getaway at Highridge B4,
2
2.0
6
Killington Vermont Condo
From $413 per night
(USD)
Private Killington Area Inn all to Yourself!
9
10.0
24
Pittsfield Vermont Private vacation home
From $2015 per night
(USD)
The Slopes Strike Back 1BR w/ Mountain Views. Hot Tub, Sauna, Pool
1
1.0
4
Killington Vermont Condo
From $372 per night
(USD)
Trail Creek hot tub/sauna/pool totally renovated king bed+2twins 1.5 bath
1
1.0
4
Killington Vermont Condo
From $613 per night
(USD)
Charming cottage located on peaceful Lake Bomoseen
2
1.0
4
Hubbardton Vermont Cottage
From $234 per night
(USD)
Custom 3-br Log Home: Perch Pond
3
2.0
6
Benson Vermont Cabin
From $345 per night
(USD)
Splendid Green Mountain Retreat with Views & Pond
4
3.0
8
MIddletown Springs Vermont Private vacation home
From $472 per night
(USD)
Modern Killington Farmhouse Condo: Close to it all! 412
1
2.0
6
Killington Vermont Condo
From $220 per night
(USD)
Killington Condo with 3 Flat Screen TVs, pool & tennis !
2
1.0
8
Killington Vermont Condo
From $237 per night
(USD)
Updated Ski-In, Ski-Out at Pico Mountain.
1
1.0
4
Killington Vermont Condo
From $255 per night
(USD)
Killington Big House: Largest Vacation Rental in Killington
12
11.0
30
killington Vermont Private vacation home
From $1796 per night
(USD)
Private Post & Beam Home Ideal for Family or Group Gatherings
4
3.0
10
Killington Vermont Private vacation home
From $623 per night
(USD)
Killington Mountain Ski resort five minutes away
2
1.0
10
Mendon Vermont Condo
Click For Pricing
Elegant Killington Condo with True Ski-on/Ski-Off January-March
3
4.0
8
Killington Vermont Condo
From $1251 per night
(USD)
Ground floor entry with ski in/out access to Pico & FREE shuttle to Killington
1
1.0
4
Killington Vermont Condo
From $484 per night
(USD)
Great View/Full Serv. Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b
3
2.0
12
Killington Vermont Private vacation home
From $770 per night
(USD)
Tastefully decorated Condo, pool, hot tub, sports center - Highridge C8
2
2.0
6
Killington Vermont Condo
From $360 per night
(USD)
Pico Mountain Resort Ski Chalet, Ski-on/Ski-Off, 4BR/2BA
4
2.0
8
Killington Vermont Private vacation home
From $658 per night
(USD)
The mountains are calling! Renovated 2 Bdrm 3 Bath 4 queen beds close to all
2
3.0
9
Killington Vermont Condo
From $542 per night
(USD)
Killington Sun Dog Trail ski-on ski-off 2 bedroom 2 bathroom 1st floor condo
2
2.0
6
Killington Vermont Condo
From $1046 per night
(USD)
Spacious, tastefully decorated 3 bedroom condo w/sports center - Highridge A18
3
3.0
8
Killington Vermont Condo
From $435 per night
(USD)
Skiers! Fox Hollow 2BR/2BA Condo. Across from Pico, Minutes to Killington
2
2.0
6
Mendon Vermont Condo
From $283 per night
(USD)
Ski in/ski out at Pico Mountain Resort
2
2.0
6
Pico / Killington Vermont Condo
From $477 per night
(USD)
Beautifully Renovated Trail Creek #50 3BR/2BA Loft Condo. Close to slopes. AC.
3
2.0
6
Killington Vermont Condo
From $390 per night
(USD)
Cozy Chalet 5mins from Okemo, SAUNA JACUZZI HOT TUB
4
3.0
9
Mount Holly Vermont Private vacation home
From $788 per night
(USD)
Luxury Ski House on Killington Mtn, 2 beds & Den w/ 3 en-suite baths, hot tub
2
3.0
6
Killington Vermont Private vacation home
From $584 per night
(USD)
Newer One bedroom cottage at water's edge on Lake St. Catherine with kayaks
1
1.0
2
Poultney Vermont Cottage
From $320 per night
(USD)
Comfortable Ski House w/ Outdoor Hot Tub, fireplace, game room & EV charger.
3
3.0
8
Killington Vermont Private vacation home
From $855 per night
(USD)
Beautiful Killington Mountain Views - 2.1 miles to New Killington Base Lodge
4
1.0
10
Killington Vermont Private vacation home
From $1017 per night
(USD)
SunBear- AC, Pool, Game Room, Fireplace, Hiking!
4
2.0
8
Killington Vermont Condo
From $569 per night
(USD)
Beautiful 2BR/2BA Fall Line Condo w/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G2B
2
2.0
6
Killington Vermont Condo
From $366 per night
(USD)
Okemo Ski Getaway in Mount Holly/Ludlow VT Under 5 miles to the slopes.
3
2.0
8
Mt Holly Vermont Private vacation home
From $337 per night
(USD)
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!
5
2.0
12
killington Vermont Private vacation home
From $461 per night
(USD)
Cortina Mountain Chalet - Outdoor Hot Tub - Close to Pico and Killington Mountains
3
3.0
8
Mendon Vermont Private vacation home
From $434 per night
(USD)
Lakefront Cottage w/Breathtaking Views! Hiking.PaddleBoat.Doc.Fishing.WiFi
2
1.0
4
Wells Vermont Cottage
From $421 per night
(USD)
Rustic Cabin Minutes From Okemo - Views of Lake Ninevah, Nestled In Mt. Holly
2
1.0
7
Mount Holly Vermont Cabin
From $271 per night
(USD)
Mountain Retreat: 4 Bedroom / 2 Bath, Ski In, Bus Out - Sleeps 10
4
2.0
10
Killington Vermont Condo
From $575 per night
(USD)
Trail Creek Top Two Floor End Unit 2 Full Bath 2 Queen Beds plus a sleeper sofa
1
2.0
4
Killington Vermont Condo
From $596 per night
(USD)
Waterfront Ponds, Beautiful , 51 Acre Property Retreat
4
3.0
7
Brandon Vermont Private vacation home
From $406 per night
(USD)
Hideaway Chalet-Sleeps 24 Perfect location 2min to ski slopes HOT TUB
8
5.0
24
Killington Vermont Private vacation home
From $1407 per night
(USD)
Trail Creek 3 bed 2.5 bath Sauna/Jet Tub/pool/hot tub ski home on shuttle
3
3.0
8
Killington Vermont Condo
From $715 per night
(USD)
Secluded Lake St. Catherine Lakefront - 2 Homes for a perfect Family Getaway;
4
2.0
10
Poultney Vermont Private vacation home
From $777 per night
(USD)
Royalbear-AC, Hot Tub, Grill, FirePit, Gameroom
6
3.0
14
Killington Vermont Private vacation home
From $957 per night
(USD)
Ski On/off Lovely Home In Sunrise Village With Pool, Sauna, Jacuzzi
3
4.0
10
Killington Vermont Private vacation home
From $1503 per night
(USD)
Charming Converted Horse Barn
4
1.0
6
Lake Bomoseen Vermont Private vacation home
From $273 per night
(USD)
True ski in/out condo at The Lodges - Trailside Luxury w/ pool & hot tub access
3
3.0
8
Killington Vermont Condo
From $1467 per night
(USD)
Killington Chalet - Great Space and Location!
6
4.0
16
Killington Vermont Chalet
From $498 per night
(USD)
3 bedroom Cottage at Waters Edge with Spectacular view of water and mountains
3
1.0
7
Poultney Vermont Cottage
From $345 per night
(USD)
Spacious Townhouse on the Killington Access Road
3
3.0
8
Killington Vermont Private vacation home
From $839 per night
(USD)
Killington Area Private Home, 3 Bd, 2 BR
3
2.0
11
Chittenden Vermont Private vacation home
From $512 per night
(USD)
Immaculate Cottage in Belmont Mt Holly: Ski Okemo, Killington, VAST,lakes, golf
2
1.0
6
Belmont Vermont Private vacation home
From $650 per night
(USD)
Hemlock Ridge 2B: Charming two floor condo in the heart of Killington. Perfect!
3
2.0
8
Killington Vermont Condo
From $353 per night
(USD)
Left Duplex Home Directly Across From Pico Mountain, Close to Killington.
3
2.0
8
Killington Vermont Private vacation home
From $582 per night
(USD)
Two Cottages at Waters Edge with Spectacular View of Water and Mountains
5
2.0
11
Poultney Vermont Cottage
From $579 per night
(USD)
Visit- Stayinvermont.org - Fiber-optic one gigabit per second. Dog Friendly
3
2.0
9
Wallingford Vermont Private vacation home
From $160 per night
(USD)
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
2
2.0
6
Killington Vermont Cabin
Click For Pricing
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
1
2.0
6
Killington Vermont Condo
From $215 per night
(USD)
Vermont Lakefront Paradise
5
3.0
10
Tinmouth Vermont Lodge
From $699 per night
(USD)
Two bedroom home on Northwest shore of Beautiful Lake St. Catherine with kayaks
2
1.0
4
Poultney Vermont Private vacation home
From $312 per night
(USD)
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
6
3.0
10
Killington Vermont Private vacation home
From $480 per night
(USD)
Wyldwood Lodge, on the lakeshore with views of the water & Green Mountains of VT
4
1.0
8
Wells Vermont Cabin
From $403 per night
(USD)
Two Double Bed Standard Hotel Room with outdoor heated pool 101
1
1.0
4
Killington Vermont Hotel
From $141 per night
(USD)
Deluxe Two Bedroom Suite on the 1st floor with outdoor heated pool 10304
2
2.0
8
Killington Vermont Hotel
From $278 per night
(USD)
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
1
1.0
4
Killington Vermont Apartment
From $167 per night
(USD)
Stunning Mountain Retreat!
3
2.0
5
East Dorset Vermont Cabin
From $803 per night
(USD)
2400sq.ft of relaxation. Only 7-10 Miles from Killington and Pico
4
3.0
9
Rutland Vermont Private vacation home
From $633 per night
(USD)
Two Double bed Standard Hotel room 217
1
1.0
4
Killington Vermont Hotel
From $141 per night
(USD)
Spectacular opportunity to enjoy the finest property in Killington Summit
7
4.0
14
Killington Vermont Private vacation home
From $1457 per night
(USD)
Deluxe Two Bedroom Suite on the 1st floor outdoor heated pool 10708
2
2.0
8
Killington Vermont Hotel
From $278 per night
(USD)
106 One bedroom Queen Suite on the 1st floor w/ outdoor heated pool
2
1.0
4
Killington Vermont Hotel
From $167 per night
(USD)
Stunning Vermont Cabin w/ Private Lake Access
5
2.0
8
Poultney Vermont Cabin
From $2000 per night
(USD)
Premier ski/in/out Killington/Sunrise townhome 3BDR/Sleep6 spa/gym/holiday rates
3
2.0
6
Killington Vermont Private vacation home
From $914 per night
(USD)
Spacious And Beautiful Luxury Home In Killington
4
4.0
8
Killington Vermont Private vacation home
From $655 per night
(USD)
Beautiful Killington VT Ski & Mountain Bike 5 Season House
5
2.0
12
Pittsfield Vermont Private vacation home
From $591 per night
(USD)
Hot tub, pool table, wet bar, shuffleboard, whole house generator
7
3.0
20
Mt. Holly Vermont Lodge
From $704 per night
(USD)
Trail Creek Upper unit 2Br/2Bath King/Twins + Queen + loft on ski home trail
2
2.0
6
Killington Vermont Condo
From $707 per night
(USD)
Load More Results
