Pittsfield Rentals
- From $110 per night (USD)
VRBO
Wintergreen 106 - Cozy and peaceful condo, conveniently located between Killington and Pittsfield
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Very quiet, pleasant one level condo with high ceilings and wood stove. This one-bedroom property offers 1 bathroom, 1 b ...
From $110 per night (USD)VRBO
- From $1840 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 $1840 per night (USD)Expedia
- From $193 per night (USD)
VRBO
Killington Vermont Ski and Snowmobiling House
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
This peaceful home is far enough from the commercial Killington Access Road and its crowds, yet not completely isolated. ...
From $193 per night (USD)VRBO
- From $279 per night (USD)
Expedia
Silver Spring Chalet Large 4 bedroom, Pittsfield VT, 20 min to Killington Slopes
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Looking to get away from it all? Well, Silver Spring Chalet is the place you and your guest. This large 4 bedrooms priva ...
From $279 per night (USD)Expedia
- From $918 per night (USD)
VRBO
Game Room + Hot Tub - 7BR updated home
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 16
Summary: Retreat after a long day on the mountain to a spacious home with all of the desired amenities, and then some! ...
From $918 per night (USD)VRBO
- From $710 per night (USD)
VRBO
Mountain Top - Fresh Pond - Killington - Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Offering free parking pass @ Killington resort! This magnificent 10-acre estate (~15 mins away from Killington resort) ...
From $710 per night (USD)VRBO
- From $900 per night (USD)
VRBO
Swiss Farm Inn - Killington Area -Sleeps 12
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 12
Rent an entire Bed & Breakfast in the valley of Vermont! Nestled between Killington and Sugarbush, this old farmhouse tu ...
From $900 per night (USD)VRBO
- From $1040 per night (USD)
VRBO
Swiss Farm Inn - Killington Area - Sleeps 15
- Bedrooms:
- 10
- Bathrooms:
- 10
- Sleeps:
- 15
Rent an entire Bed & Breakfast in the valley of Vermont! Nestled between Killington and Sugarbush, this old farmhouse tu ...
From $1040 per night (USD)VRBO
- From $995 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 $995 per night (USD)VRBO
- From $424 per night (USD)
VRBO
Hillside log home in Pittsfield 7 miles from Killington base and Pico ski areas
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
“The Owl’s Nest” is centrally located in the heart of the Green Mountains in the town of Pittsfield, close to several wo ...
From $424 per night (USD)VRBO
- From $400 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 $400 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Killington area home - 4-seasons & hot tub. Sleeps 12+
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $250 per night (USD)VRBO
- From $280 per night (USD)
VRBO
Four Season KILLINGTON Getaway!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
8 miles from Killington/Pico mountains, restaurants, nightlife. 1000 SqFt 3 Bedroom, 1.5 Bathroom mountain home, recom ...
From $280 per night (USD)VRBO
- From $433 per night (USD)
Expedia
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 $433 per night (USD)Expedia
- From $315 per night (USD)
VRBO
Perfect secluded cozy getaway pet friendly home Hawk Landing
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The wonderful three-bedroom two-bathroom home is located in the mountains of Pittsfield, Vermont - a postcard Vermont to ...
From $315 per night (USD)VRBO
- From $1100 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 $1100 per night (USD)VRBO
- From $423 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 $423 per night (USD)VRBO
- From $528 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 $528 per night (USD)VRBO
- From $1188 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 $1188 per night (USD)VRBO
- From $625 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 $625 per night (USD)VRBO
- From $1500 per night (USD)
VRBO
Swiss Farm Inn - Killington Area - Sleeps up to 30
- Bedrooms:
- 15
- Bathrooms:
- 14
- Sleeps:
- 30
One and Only Swiss Farm Inn is located between Killington and Sugarbush. It only needs around 10 minute drive to Killing ...
From $1500 per night (USD)VRBO
- From $211 per night (USD)
Expedia
Tranquil dog-friendly retreat with generous deck, fitness area, & amazing views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Hawk 1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dat ...
From $211 per night (USD)Expedia
- Click For Pricing
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 ...
Click For PricingVRBO
- From $260 per night (USD)
Expedia
Lovely home close to hiking & skiing w\/WiFi, firepit, balcony, wood stove, & W\/D
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Mountain Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $260 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $410 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 $410 per night (USD)Expedia
- From $340 per night (USD)
VRBO
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 $340 per night (USD)VRBO
- From $650 per night (USD)
Expedia
The Ridge Chalet, an A-Frame Killington home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Ridge Chalet, Killington 3 Bedrooms plus 2 Bonus Rooms. NEWLY BUILT SOPHISTICATED A-FRAME STYLE HOME WITH CATHEDRAL ...
From $650 per night (USD)Expedia
- From $460 per night (USD)
VRBO
Beautiful Log Cabin w\/Hot Tub + Fireplace-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 ...
From $460 per night (USD)VRBO
- From $242 per night (USD)
Expedia
Lori and Dean's Killington Ski House with Wi-Fi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Recently remodeled and tastefully decorated lower level duplex located a short distance from Killington ski area (a twel ...
From $242 per night (USD)Expedia
- From $759 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 $759 per night (USD)VRBO
- From $236 per night (USD)
Expedia
Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
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 $236 per night (USD)Expedia
- From $110 per night (USD)
VRBO
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Bob's Bungalow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $110 per night (USD)VRBO
- From $295 per night (USD)
Expedia
Post & Beam Home Ideal for families or Groups
- Bedrooms:
- 4
- Bathrooms:
- 4
- 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 $295 per night (USD)Expedia
- From $273 per night (USD)
VRBO
Killington Area Escape w\/ Deck & Private Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy the incredible beauty of the Green Mountains in all 4 seasons at this versatile 3-bedroom, 2-bath Stockbridge vaca ...
From $273 per night (USD)VRBO
- From $350 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 $350 per night (USD)Expedia
- From $383 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 $383 per night (USD)VRBO
- From $570 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 $570 per night (USD)VRBO
- From $521 per night (USD)
VRBO
'The Mill Stream House' Luxury 4 BR 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 $521 per night (USD)VRBO
- From $264 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 $264 per night (USD)VRBO
- From $1240 per night (USD)
VRBO
Killington Big House: Largest Vacation Rental in Killington
- Bedrooms:
- 12
- Bathrooms:
- 12
- Sleeps:
- 30
Killington Big House is a large luxury vacation rental house renovated and fully upgraded, located in Killington, Vermon ...
From $1240 per night (USD)VRBO
- From $767 per night (USD)
VRBO
5 BR 3.5 Bath Killington All-Season Home With Pool, Hot Tub, Huge Dining Table
- 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 $767 per night (USD)VRBO
- From $255 per night (USD)
VRBO
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 $255 per night (USD)VRBO
- From $219 per night (USD)
VRBO
Wonderful One bedroom condo located in Highridge J6
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Highridge J6, A wonderful One bedroom condo located in Highridge Condominiums is conveniently located off of East Mounta ...
From $219 per night (USD)VRBO
- From $223 per night (USD)
VRBO
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 $223 per night (USD)VRBO
- From $217 per night (USD)
Expedia
Vermont Retreat - 8 Mi to Killington Ski Area
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $217 per night (USD)Expedia
- From $475 per night (USD)
VRBO
Treehouse-One of a Kind , AC, tubing, fire table, fire pit, 20 min to Killington
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
New Treehouse with architect design and very unique. When you wake up in the morning you will literally wake up in the ...
From $475 per night (USD)VRBO
- From $333 per night (USD)
Expedia
Family & dog-friendly house in Killington
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $333 per night (USD)Expedia
- Click For Pricing
VRBO
Rockwell Haus: 70s Ski Vibes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
Welcome to our Rockwell Haus, a newly-renovated 70s inspired ski cabin nestled just 10 minutes away from the base of Kil ...
Click For PricingVRBO