Pittsfield Rentals
From $2015 per night (USD)VRBO
Private Killington Area Inn all to Yourself!
- Bedrooms:
- 10
- Bathrooms:
- 9
- Sleeps:
- 24
Rent an entire Inn to yourself (really, the whole place is yours)! Early check in times and late check outs! Check in ...
From $2015 per night (USD)VRBO
From $591 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 $591 per night (USD)VRBO
From $694 per night (USD)VRBO
Hawk Landing: A cozy 3-bedroom retreat perfect for families and pet-friendly getaways.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to Hawk Landing, a charming three-bedroom, two-bathroom home nestled in the scenic mountains of Pittsfield, Vermo ...
From $694 per night (USD)VRBO
From $470 per night (USD)VRBO
Four Season KILLINGTON Getaway!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
8 miles from Killington/Pico mountains, restaurants, nightlife. 1000 SqFt 3 Bedroom, 1.5 Bathroom mountain home, recom ...
From $470 per night (USD)VRBO
From $878 per night (USD)VRBO
Silver Spring Chalet – Spacious 4BR Retreat in Killington Region, Pittsfield, VT, Sleeps 11
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Silver Spring Chalet — Your Ski-Area Hideaway Near Killington & Pico Brought to you by GetAway Welcome to Silver Spring ...
From $878 per night (USD)VRBO
From $407 per night (USD)Expedia
Killington area home - 4-seasons, hot tub and A/C
- Bedrooms:
- 2
- 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 $407 per night (USD)Expedia
From $570 per night (USD)VRBO
15 Minutes to Killington - 2 Living Rooms - Private Mountain Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
—- The Tweed River House -— 15 minutes to Killington, 11 to Pico. On The Tweed River. Ride & Hike In & Out on the Gre ...
From $570 per night (USD)VRBO
From $783 per night (USD)Expedia
Spacious 4BR / 5 Bath Home - Hot Tub / Pool Table / Ample Private Outdoor Space!
- Bedrooms:
- 4
- 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 $783 per night (USD)Expedia
From $2238 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 $2238 per night (USD)VRBO
From $927 per night (USD)Expedia
Mountain Top - Fresh Pond - Killington - Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Offering free parking pass @ Killington resort! This magnificent 10-acre estate (~15 mins away from Killington resort) ...
From $927 per night (USD)Expedia
From $643 per night (USD)VRBO
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
- 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 $643 per night (USD)VRBO
From $1631 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 $1631 per night (USD)VRBO
From $832 per night (USD)VRBO
Ski/MTB/Arcade/Pool Table near Killington/Pico/Sugarbush/Woodstock
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
-> Sleeps 16 comfortably. Game room Arcade and Pool Table -> Home is a side by side duplex(UNIT A and B). You will be re ...
From $832 per night (USD)VRBO
From $716 per night (USD)VRBO
NEW! Serene Architect-Designed Vermont Chalet
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Architect-Designed Chalet in the Green Mountains – A Serene Vermont Escape Welcome to your private mountain retreat n ...
From $716 per night (USD)VRBO
From $790 per night (USD)VRBO
3-bedroom house in lovely Pittsfield close to wedding venues, trails and skiing!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
| Welcome to The Skyeburst House | Reimagined 1970's Mountain Home 15 mins from the Killington K1 Gondola. This is a ...
From $790 per night (USD)VRBO
From $567 per night (USD)Expedia
Lovely home close to hiking & skiing w/WiFi, firepit, balcony, wood stove, & W/D
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
With a warm and welcoming atmosphere and a secluded location close to hiking trails and skiing, this beautiful home is g ...
From $567 per night (USD)Expedia
From $830 per night (USD)VRBO
Tranquil house w/ apartment, mountain views, pond, bbq, patio, wifi
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 9
Welcome to your tranquil mountain retreat in peaceful Pittsfield, VT—a two-story getaway featuring a spacious 4-bedroom, ...
From $830 per night (USD)VRBO
From $501 per night (USD)Expedia
Tranquil retreat with generous deck, fitness area, & amazing views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
This tranquil, two-story home, surrounded by lush green areas and nestled into the peaceful Pittsfield landscape, boasts ...
From $501 per night (USD)Expedia
From $219 per night (USD)VRBO
Tranquil apartment w/ mountain views, pond, patio, a/c, kitchenette
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape to this cozy, one-bedroom, one-bath apartment located on the ground floor with peaceful mountain views, located i ...
From $219 per night (USD)VRBO
From $633 per night (USD)Expedia
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
POWDER RUN: SMART 3BR BASECAMP W/ HOT TUB, AC, EV CHARGER & FLAT PARKING SKIP THE RESORT TRAFFIC. Positioned exactly o ...
From $633 per night (USD)Expedia