Pittsfield Rentals
From $1587 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 $1587 per night (USD)VRBO
From $1649 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 $1649 per night (USD)VRBO
From $613 per night (USD)VRBO
Post & Beam Home Ideal for families or Groups
- 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 $613 per night (USD)VRBO
From $444 per night (USD)Expedia
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 $444 per night (USD)Expedia
From $672 per night (USD)VRBO
Beautiful Killington VT Ski & Mountain Bike 5 Season House
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Location: Killington, Vermont, USA (Pittsfield - 8 miles to Killington slopes) Accommodations: House, 5 Bedrooms + livi ...
From $672 per night (USD)VRBO
From $568 per night (USD)Expedia
Winter Brook newly renovated
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Winter Brook has been totally renovated. There is a wonderful new kitchen, wood floors, luxurious bathrooms and new fur ...
From $568 per night (USD)Expedia
From $411 per night (USD)VRBO
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Bob's Bungalow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $411 per night (USD)VRBO
From $1080 per night (USD)VRBO
5 BR 3.5 Bath Killington Home with Hot Tub, Huge Dining Table, K1 Parking pass
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
95 Rock offers a unique Killington vacation experience. It's hard to say which season is best suited for this secluded ...
From $1080 per night (USD)VRBO
From $230 per night (USD)VRBO
Wintergreen 106 - Cozy and peaceful condo, conveniently located between Killington and Pittsfield
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Very quiet, pleasant one level condo with high ceilings and wood stove. This one-bedroom property offers 1 bathroom, 1 b ...
From $230 per night (USD)VRBO
From $766 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 $766 per night (USD)Expedia
From $444 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 $444 per night (USD)VRBO
From $1057 per night (USD)Expedia
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 $1057 per night (USD)Expedia
From $454 per night (USD)VRBO
Perfect secluded cozy getaway pet friendly home Hawk Landing
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our wonderful three-bedroom two-bathroom home is located in the mountains of Pittsfield, Vermont - a postcard Vermont to ...
From $454 per night (USD)VRBO
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Your Vermont Log Cabin Getaway w\/Hot Tub+Firepit-Arrive Early & Stay Late!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy early arrival and a leisurely departure! Our beautiful 2,000 sq ft log home is tucked away in a private community ...
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From $496 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 $496 per night (USD)VRBO
From $670 per night (USD)Expedia
Lovely home close to hiking & skiing w\/WiFi, firepit, balcony, wood stove, & W\/D
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Mountain Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $670 per night (USD)Expedia
From $1177 per night (USD)VRBO
The Ridge Chalet, an A-Frame Killington home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
The Ridge Chalet, Killington 3 Bedrooms plus 2 Bonus Rooms. NEWLY BUILT SOPHISTICATED A-FRAME STYLE HOME WITH CATHEDRAL ...
From $1177 per night (USD)VRBO
From $655 per night (USD)VRBO
Quintessential Vermont Cabin - 4 fireplaces, hot tub, and fire pit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Currier Cabin is a home that offers quintessential Vermont living with both privacy and convenience. Property is located ...
From $655 per night (USD)VRBO
From $640 per night (USD)VRBO
Family & dog-friendly house in Killington
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Big open plan house, lots of light. Great for skiing, hiking, golf, or just taking it easy. Plenty of space to hangout, ...
From $640 per night (USD)VRBO
From $922 per night (USD)Expedia
Silver Spring Chalet Large 4 bedroom, Pittsfield VT, 20 min to Killington Slopes
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Nestled in the picturesque town of Pittsfield, VT, the Silver Spring Chalet offers a serene mountain retreat perfect for ...
From $922 per night (USD)Expedia
From $1616 per night (USD)VRBO
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 $1616 per night (USD)VRBO
From $2928 per night (USD)Expedia
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)Expedia
From $452 per night (USD)VRBO
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 $452 per night (USD)VRBO
From $896 per night (USD)VRBO
'The Mill Stream House' Lux Rustic Home on River w\/JACUZZI & fireplace
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
The Mill Stream House, Killington 2.9 miles to access road UPDATED RIVER FRONT HOME with STONE FIREPLACE & CATHEDRAL CE ...
From $896 per night (USD)VRBO
From $307 per night (USD)VRBO
NorthPorch Farmhouse
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
This cozy, well cared for and well-appointed 1840’s two-story farmhouse is surrounded by National Forest Service land, a ...
From $307 per night (USD)VRBO
From $1425 per night (USD)Expedia
Secluded Mountain Retreat w Hot Tub, Sauna & Disc Golf!
- 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 $1425 per night (USD)Expedia
From $2121 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 $2121 per night (USD)VRBO
From $549 per night (USD)Expedia
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 $549 per night (USD)Expedia
From $476 per night (USD)VRBO
Contemporary Classic Vermont Ski House with 4 bedrooms - Sleeps 8 in Beds
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Contemporary Vermont Ski House with 4 bedrooms in Pittsfield VT with all the amenities and high tech comforts. Gorgeous ...
From $476 per night (USD)VRBO
From $513 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 $513 per night (USD)VRBO
From $382 per night (USD)VRBO
Killington area home - 4-seasons & hot tub. Sleeps 12+
- 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 $382 per night (USD)VRBO
From $267 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 $267 per night (USD)Expedia
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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 ...
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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 $1758 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 $1758 per night (USD)VRBO
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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 ...
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From $751 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 $751 per night (USD)VRBO
From $438 per night (USD)Expedia
Wonderful condo located near the pool and hot tub Highridge J6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Highridge J6 Condominium Welcome to Highridge J6, a charming one-bedroom, one-bathroom condo perfectly situated at the b ...
From $438 per night (USD)Expedia
From $1658 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 $1658 per night (USD)VRBO
From $1343 per night (USD)Expedia
Mountain Top - Fresh Pond - Killington - Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Offering free parking pass @ Killington resort! This magnificent 10-acre estate (~15 mins away from Killington resort) ...
From $1343 per night (USD)Expedia
From $1169 per night (USD)VRBO
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 $1169 per night (USD)VRBO
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Tranquil dog-friendly retreat with generous deck, fitness area, & amazing views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Hawk 1-A Mountain Vista Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
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From $320 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 $320 per night (USD)VRBO
From $1068 per night (USD)Expedia
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 $1068 per night (USD)Expedia
From $715 per night (USD)VRBO
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 ...
From $715 per night (USD)VRBO
From $1704 per night (USD)Expedia
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 $1704 per night (USD)Expedia
From $953 per night (USD)VRBO
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 $953 per night (USD)VRBO
From $1148 per night (USD)Expedia
This house is a 5 bedroom(s), 2 bathrooms, located in Killington, VT.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Welcome to Rockwell Haus, a newly-renovated 70s-inspired cabin nestled just 14 minutes away from Killington Mountain and ...
From $1148 per night (USD)Expedia
From $1256 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 $1256 per night (USD)VRBO
From $977 per night (USD)Expedia
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 $977 per night (USD)Expedia
From $546 per night (USD)VRBO
FiddleHead Lane-Near Killington, Fireplace, Grill
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Fiddlehead Lane! Escape to this inviting mountain home nestled in the beautiful hills of Pittsfield, VT. Fid ...
From $546 per night (USD)VRBO