Stockbridge Rentals
From $1528 per night (USD)VRBO
Private Killington Area Inn all to Yourself!
- Bedrooms:
- 11
- Bathrooms:
- 9
- Sleeps:
- 23
Rent an entire Inn to yourself (really, the whole place is yours)! Complete with a private bathroom with shower for each ...
From $1528 per night (USD)VRBO
From $1625 per night (USD)VRBO
Killington Big House: Largest Vacation Rental in Killington
- Bedrooms:
- 12
- Bathrooms:
- 13
- Sleeps:
- 30
Killington Big House is a large luxury vacation rental house renovated and fully upgraded, located in Killington, Vermon ...
From $1625 per night (USD)VRBO
From $460 per night (USD)VRBO
Private Post & Beam Home Ideal for Family or Group Gatherings
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 10
This lovely 3,000 sq. ft. Post & Beam home is situated on a private 5 acre homestead in Killington, VT. The open floor ...
From $460 per night (USD)VRBO
From $308 per night (USD)VRBO
\"The Crooked House\" with A\/C and sauna on private wooded lot near Killington
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to the beautiful mountains of Vermont. Our four-season house (now with air conditioning in each bedroom and the l ...
From $308 per night (USD)VRBO
From $392 per night (USD)VRBO
Killington Area Escape w\/ Deck, Views & Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy the incredible beauty of the Green Mountains in all 4 seasons at this versatile 3-bedroom, 2-bath Stockbridge vaca ...
From $392 per night (USD)VRBO
From $412 per night (USD)Expedia
Winter Brook newly renovated
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Winter Brook has been totally renovated. There is a wonderful new kitchen, wood floors, luxurious bathrooms and new fur ...
From $412 per night (USD)Expedia
From $523 per night (USD)VRBO
\"Whispering Pines\" Ski House in the heart of the Green Mountains
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Fantastic 5BR ski house located in private neighborhood in prime location in the heart of the Green Mountains. Enjoy tru ...
From $523 per night (USD)VRBO
From $441 per night (USD)Expedia
Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This cozy ski Chalet home sleeps up to 12 people- an unbeatable choice for a ski trip with friends or family for a memor ...
From $441 per night (USD)Expedia
From $468 per night (USD)VRBO
Pittsfield Chalet Beautiful home in charming Pittsfield Vermont only a few miles from Killington.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Pittsfield, Vermont is like something out of a greeting card with true old school Vermont charm, only 15 minutes from th ...
From $468 per night (USD)VRBO
From $7345 per night (USD)VRBO
37 BR Country Farm House Perfect Venue for Vermont Wedding, Retreat Reunion
- Bedrooms:
- 34
- Bathrooms:
- 37
- Sleeps:
- 74
The Knot's Best of Wedding 2018, 2019 & 2020 Winner! From casual to elegant, we can help build your dream wedding and h ...
From $7345 per night (USD)VRBO
From $819 per night (USD)VRBO
Bear-Foot Lodge Killington, Private! Sauna\/Gameroom. Perfect for Large Groups!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Come enjoy the stunning scenery of Vermont's countryside while you relax in this gorgeous 5,000 sq ft. lodge. This year- ...
From $819 per night (USD)VRBO
From $168 per night (USD)Expedia
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a secluded mountainside retreat. Perfect for a getaway for two and room enough for 4 it is located on eleven pri ...
From $168 per night (USD)Expedia
From $388 per night (USD)VRBO
Killington ski house
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Recently remodeled and tastefully decorated lower level duplex located a short distance from Killington ski area (a twel ...
From $388 per night (USD)VRBO
From $440 per night (USD)VRBO
MapleDreams - Cozy Ski Chalet w\/Hot Tub on Wooded Lot
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Escape the hustle and bustle of city living to the beautiful mountains of Vermont. Our home is nestled in a private wood ...
From $440 per night (USD)VRBO
From $625 per night (USD)VRBO
Newly Renovated Killington House, Private, hot Tub, two Sided Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Open floor plan, two sided fireplace leading to glass walled great room. 10 minutes to the Mountain, hot tub with heate ...
From $625 per night (USD)VRBO
From $13334 per night (USD)VRBO
37 BR Farmhouse: Ideal for Retreats, Reunions, Weddings, Killington skiing
- Bedrooms:
- 34
- Bathrooms:
- 37
- Sleeps:
- 92
Just miles from Killington Ski Resort and overlooking the fairway of Vermont’s top-rated golf course, our up-style count ...
From $13334 per night (USD)VRBO
From $522 per night (USD)VRBO
Silver Spring Chalet – Spacious 4BR Retreat in Killington Region, Pittsfield, VT, Sleeps 11
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
"Your Next Adventure Awaits: Epic Skiing, Thrilling Hikes, and Soothing Hot Tub Bliss! Don't Wait—Book Your Getaway Toda ...
From $522 per night (USD)VRBO
From $1592 per night (USD)Expedia
New Listing - Luxury log home with stunning views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Situated on 31 acres this gorgeous 5 bedroom/4.5 bathroom, custom-built log home offers amazing views of the Green Mount ...
From $1592 per night (USD)Expedia
From $2928 per night (USD)VRBO
Spectacular Mountain Views, 6 Bedroom, 4 Bath with Fireplace, Hot Tub & Elevator
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
6 Bedroom 4 Bath Sleeps 12 This spectacular mountainside home designed by Architect Robert Carl Williams reflects an at ...
From $2928 per night (USD)VRBO
From $168 per night (USD)Expedia
Killington Vermont Ski and Snowmobiling House
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
This peaceful home is far enough from the commercial Killington Access Road and its crowds, yet not completely isolated. ...
From $168 per night (USD)Expedia
From $550 per night (USD)VRBO
'The Mill Stream House' Lux Rustic Home on River w\/JACUZZI & fireplace
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 16
The Mill Stream House, Killington 2.9 miles to access road UPDATED RIVER FRONT HOME with STONE FIREPLACE & CATHEDRAL CE ...
From $550 per night (USD)VRBO
From $459 per night (USD)Expedia
Private Mountain Home w Hot Tub, Sauna, Shuffleboard, etc!
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 10
This luxury home with scenic mountain views was designed for a relaxing getaway for a ski trip or summer adventure. Loca ...
From $459 per night (USD)Expedia
From $872 per night (USD)VRBO
Game Room + Hot Tub - 7BR updated home
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 16
Escape to the serene beauty of Killington, Vermont, and experience the ultimate vacation in our stunning 7-bedroom vacat ...
From $872 per night (USD)VRBO
From $511 per night (USD)Expedia
Gnome Home Mountain Ski Chalet w\/Sauna Killington
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Chalet perched on a mountain in the heart of Green Mountains. Enjoy true mountain living all year long with 3 ski areas ...
From $511 per night (USD)Expedia
From $337 per night (USD)VRBO
Killington Skiers\/Snowmobilers\/MountainBikers Dream with Outdoor Jacuzzi + Wi-Fi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Recently updated, tastefully decorated upper level duplex located only seven miles to the Killington Access Road. This c ...
From $337 per night (USD)VRBO
From $461 per night (USD)VRBO
Cozy A-Frame close to skiing and on VAST Trails
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Newly remodeled and expanded A-Frame in Stockbridge, VT. Four bedrooms that sleeps 12 comfortably. Wood burning fireplac ...
From $461 per night (USD)VRBO
From $323 per night (USD)VRBO
Killington area home - 4-seasons & hot tub. Sleeps 13+
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Set on a private road in the forested hills just north of Pittsfield, our house welcomes you - in all seasons. Right in ...
From $323 per night (USD)VRBO
From $365 per night (USD)VRBO
Private Mountain Sanctuary | 15 Min to Killington
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
*Winter Stays* Must have 4WD vehicle with snow tires or snow chains. We want you to make it safely up the mountain for t ...
From $365 per night (USD)VRBO
From $660 per night (USD)VRBO
Beautiful Green Mountain views near Killington
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Vermont getaway. Located in pretty Timber Hawk Development, this is a private location with incredible mountain/valley, ...
From $660 per night (USD)VRBO
From $192 per night (USD)Expedia
Cozy Killington Retreat ~ 5 Mi to Ski Resort
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Ski aficionados and outdoor adventurers — look no further than this lower-level Killington apartment for your next winte ...
From $192 per night (USD)Expedia
From $431 per night (USD)VRBO
Vermont Retreat - 8 Mi to Killington Ski Area
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Whether the sun is shining or the snow is falling, you’ll find an endless amount of outdoor activities in Killington. Th ...
From $431 per night (USD)VRBO
From $1040 per night (USD)VRBO
Amazing Views on Music Mountain
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 15
Create unforgettable memories at "The Views at Music Mountain". This brand new architecturally stunning modern Log and T ...
From $1040 per night (USD)VRBO
From $523 per night (USD)VRBO
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Rzeka Cottage! Enjoy a stylish experience at this riverfront home in the Green Mountains. Centrally located n ...
From $523 per night (USD)VRBO
From $638 per night (USD)VRBO
Direct Ride or Hike In & Out to GMT Trails - Hiking - Swimming - VAST
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
—- The Tweed River House -— 15 minutes to Killington, 11 to Pico. On The Tweed River. Ride In & Out from your door to ...
From $638 per night (USD)VRBO
From $1694 per night (USD)VRBO
Hot tub, fireplace, Game Room, 20 min drive to Killington
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Enjoy tranquility and the sounds of nature when you stay in our cozy, modern A-frame. Situated in a quiet area only 20 m ...
From $1694 per night (USD)VRBO
Click For PricingExpedia
Large house with fireplace, hot tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Large house suitable for 2-3 families close to Killington (10min to town and 15min to lifts!). The house has 5 bedrooms ...
Click For PricingExpedia
From $699 per night (USD)VRBO
Spacious 4BR \/ 5 Bath Home - Hot Tub \/ Pool Table \/ Ample Private Outdoor Space!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Nestled in the heart of the Green Mountains, this spacious and welcoming home is conveniently located just off Vermont's ...
From $699 per night (USD)VRBO
From $1664 per night (USD)VRBO
Killington area entire Inn to yourself! 14bd\/15bth
- Bedrooms:
- 15
- Bathrooms:
- 14
- Sleeps:
- 30
Please don’t waste your valuable time comparing the Swiss Farm Inn to other venues that host group guests (up to 30 peop ...
From $1664 per night (USD)VRBO
From $885 per night (USD)VRBO
Swiss Farm Inn - Killington Area -Sleeps 12
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 11
Welcome to the charming Swiss Farm Inn, perfectly situated between Killington and Sugarbush, just a short 10-minute driv ...
From $885 per night (USD)VRBO
From $1254 per night (USD)VRBO
Swiss Farm Inn - Killington Area - Sleeps 15
- Bedrooms:
- 10
- Bathrooms:
- 10
- Sleeps:
- 16
Welcome to the charming Swiss Farm Inn, perfectly situated between Killington and Sugarbush, just a short 10-minute driv ...
From $1254 per night (USD)VRBO
From $637 per night (USD)VRBO
The Maple Leaf - Three-bedroom with indoor hot tub ski house, sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
"Cozy 3-Bedroom Escape with Indoor Hot Tub, Fireplace, Near Golf & Skiing!" Nestled in a picturesque setting, The Maple ...
From $637 per night (USD)VRBO
From $523 per night (USD)Expedia
Winding Way Chalet: Large Family Ski Home with Amazing Amenities! Hot Tub.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Winding Way Chalet: Your Ultimate Killington Retreat Nestled amidst the rolling landscapes of Killington, Ve ...
From $523 per night (USD)Expedia
From $317 per night (USD)VRBO
Romantic Cozy Mountain Retreat near Killington
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This architect-designed, contemporary mountain chalet features all the classic element of the Robert Carl Williams aesth ...
From $317 per night (USD)VRBO
From $2446 per night (USD)VRBO
The Cobble House, Exceptional Country House Sleeps 10\/Near Killington, Woodstock
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Above the White River in the foothills of the Green Mountains, The Cobble House is a restored country retreat – a 19th C ...
From $2446 per night (USD)VRBO
From $356 per night (USD)VRBO
The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to this stunning 4-bedroom, 2-bathroom Cape nestled on 2.4 private acres with panoramic mountain views and the so ...
From $356 per night (USD)VRBO
Click For PricingExpedia
Experience the charm of Peak Hill Home, a cozy 3-BR retreat cloe to Killington
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
QUIET, WOODED PROPERTY ON KILLINGTON BORDER, minutes from slopes! Peak Hill is a newly rebuilt ski home on the border o ...
Click For PricingExpedia
From $599 per night (USD)VRBO
The Perfect Modern Killington Getaway Vacation\n\n
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your perfect Killington retreat! Nestled in a prime location, our home offers the ideal getaway for relaxatio ...
From $599 per night (USD)VRBO
From $531 per night (USD)Expedia
Cozy Killington Cabin-Style Home\n\n
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect Killington retreat! Nestled in a prime location, our home offers the ideal getaway for relaxatio ...
From $531 per night (USD)Expedia
From $1160 per night (USD)VRBO
Mountain Bliss: Spacious Retreat Near Killington, 5 Br, 3 Ba Hot tub Sleeps 15
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Escape to Our Enchanting Cabin in Rochester, Vermont – Just 9 miles from Killington Ski Resort Capacity: 15 Guests · 5 B ...
From $1160 per night (USD)VRBO
From $951 per night (USD)VRBO
Charming 3-bedroom house with WiFi, Hot tub, fitness room in Killington
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Unwind in Killington at this wonderful house. With 3 cozy bedrooms featuring a mix of queen, full, and twin beds, guests ...
From $951 per night (USD)VRBO
From $588 per night (USD)VRBO
FiddleHead Lane-Near Killington, Fireplace, Grill
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Fiddlehead Lane! Escape to this inviting mountain home nestled in the beautiful hills of Pittsfield, VT. Fid ...
From $588 per night (USD)VRBO
From $727 per night (USD)Expedia
Window Seat to the Peaks: 4BR\/3BA Retreat with Stunning Mountain Views, Near Killington Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled on 5.26 private acres just a mile from Green Mountain National Golf Course and 10 minutes from Killington Resort ...
From $727 per night (USD)Expedia
From $190 per night (USD)VRBO
Swiss Farm Inn - RM11 \"Snowshed\" 2 Double Beds
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Rent a room at the Swiss Farm Inn in Pittsfield, Vermont! Nestled between Killington and Sugarbush, this charming old fa ...
From $190 per night (USD)VRBO
From $190 per night (USD)VRBO
Swiss Farm Inn - RM12 \"Pipe Dream\" 2 Double Beds
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Rent a room at the Swiss Farm Inn in Pittsfield, Vermont! Nestled between Killington and Sugarbush, this charming old fa ...
From $190 per night (USD)VRBO
From $190 per night (USD)VRBO
Swiss Farm Inn - RM13 \"Outer Limits\" 2 Double Beds
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Rent a room at the Swiss Farm Inn in Pittsfield, Vermont! Nestled between Killington and Sugarbush, this charming old fa ...
From $190 per night (USD)VRBO
From $190 per night (USD)VRBO
Swiss Farm Inn - RM8 \"Superstar\" Queen Bed & Twin Bed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Rent a room at the Swiss Farm Inn in Pittsfield, Vermont! Nestled between Killington and Sugarbush, this charming old fa ...
From $190 per night (USD)VRBO
From $190 per night (USD)VRBO
Swiss Farm Inn - RM7 \"Great Eastern\" Queen Bed & Twin Bed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Rent a room at the Swiss Farm Inn in Pittsfield, Vermont! Nestled between Killington and Sugarbush, this charming old fa ...
From $190 per night (USD)VRBO
From $140 per night (USD)VRBO
Swiss Farm Inn - RM9 \"Solitude\" 1 Queen Bed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Rent a room at the Swiss Farm Inn in Pittsfield, Vermont! Nestled between Killington and Sugarbush, this charming old fa ...
From $140 per night (USD)VRBO
From $190 per night (USD)VRBO
Swiss Farm Inn - RM10 \"Ovation\" 2 Double Beds
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Rent a room at the Swiss Farm Inn in Pittsfield, Vermont! Nestled between Killington and Sugarbush, this charming old fa ...
From $190 per night (USD)VRBO
From $658 per night (USD)VRBO
NEW! Large 5-bedroom family-friendly home with WiFi and office
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to De Berg ("The Mountain" in Dutch), your perfect four-season mountain retreat in Pittsfield, Vermont! This spa ...
From $658 per night (USD)VRBO
From $510 per night (USD)VRBO
Ski\/MTB Home with Mountain Views near Killington\/Woodstock\/Green Mountain Trails
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
UNIT A side. Escape to this spacious(2250 sq ft), newly renovated mountain retreat, perfectly located near Killington, P ...
From $510 per night (USD)VRBO
From $308 per night (USD)Expedia
Cozy log cabin close to recreation, dog-friendly, balcony, BBQ, w\/d, TVs, kayaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Cabin at Fort Defiance Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $308 per night (USD)Expedia
From $472 per night (USD)VRBO
Ski\/MTB Home with Mountain Views near Killington\/Woodstock\/Green Mountain Trails
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
UNIT B side. Escape to this spacious(2250 sq ft), newly renovated mountain retreat, perfectly located near Killington, P ...
From $472 per night (USD)VRBO
From $718 per night (USD)Expedia
Ski\/MTB Sleeps 20 home w\/ mountain views near Killington\/Woodstock. Rent 2 units
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 20
Sleeps 20 people comfortably. Property is a side by side duplex(UNIT A and B). You will be renting the entire property b ...
From $718 per night (USD)Expedia
From $947 per night (USD)VRBO
150 acres of serenity in a stunning, 6 bedroom Vermont estate
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
To the people who have seen it, Light Hill is considered one of the most beautiful properties in the Barnard area. With ...
From $947 per night (USD)VRBO
From $277 per night (USD)Expedia
1920s \"Golden Age\" Cabin w\/ Breathtaking Views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a ...
From $277 per night (USD)Expedia
From $279 per night (USD)VRBO
1950s \"Retro\" Cabin in Vermont w\/ Breathtaking Views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a ...
From $279 per night (USD)VRBO
From $776 per night (USD)VRBO
NEW! Large 5-bedroom family-friendly home with WiFi and office
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
Located in Pittsfield, VT this house is perfect for families or large groups. With 5 bedrooms including 3 full beds, 3 q ...
From $776 per night (USD)VRBO