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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 483 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (19)
"Great Location! Very short drive to Skyeship Gondola. Property was well equipped for all our needs."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

8.0 out of 10, Very Good, (2)
" short stay "
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Living area flooded with natural light.

BruinsDen - Ski On Ski Off (Home Stretch Trail)

10.0 out of 10, Exceptional, (11)
"Wonderful home! Excellent layout for family bonding. Hot tub was great. Skiing equipment storage area was Lu fantastic. Easy ski-in ski-out!!! Communication with host was excellent!! Beds were comfy! Would highly recommend! "
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

9.6 out of 10, Exceptional, (25)
"If you're looking for the perfect getaway near Killington, look no further than this incredible rental home! From the moment we stepped inside, we were blown away by how spacious and welcoming the property felt. It easily accommodated our large group, with plenty of room for everyone to relax and enjoy themselves.The home has such a cozy, homey atmosphere that made it hard to leave! We spent our evenings gathered around the real fireplace, which added so much warmth and charm to the experience....
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
Killington, Vermont Ski House w/ Hot Tub and Sauna
I Our snow country home welcomes you!

Killington, Vermont Ski House w/ Hot Tub and Sauna

9.4 out of 10, Exceptional, (84)
"The perfect home to come back to after a day of skiing with a sauna and hot tub to lounge in. So spacious and close to the mountain!"
Killington, Vermont Ski House w/ Hot Tub and Sauna
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill
Mountain Views from the minute you drive in to the house

6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill

10.0 out of 10, Exceptional, (23)
"Had a wonderful stay! Was cozy, clean, with a well stocked kitchen. Highly recommend. Evan was a lovely host. "
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill
Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn

Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn

10.0 out of 10, Exceptional, (1)
"Was an amazing location with tons to do. Clean property and cozy!"
Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

8.6 out of 10, Excellent, (22)
"Basic ski house, in cool spot. 10 mins from bear mtn. Would definitely stay here again. "
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!
Welcome to your Ideal Killington Escape!

Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!

10.0 out of 10, Exceptional, (16)
"We had two families stay at the home the first week of April during Spring Break so we could do a couple of days of skiing. The house was wonderful. It had so many beds, which made it great for the 6 kids and then separate bedrooms for the two couples, which was great. We enjoyed making a fire in the fireplace at the end of the day as we played board games with the family..we especially enjoyed playing LCR (Left Center Right). Kristin's communication was incredible. She was always so quick to...
Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!
NEW! Modern Log Cabin with Skiing & Work-Friendly Setup
"Tree","Architecture","Building","Outdoors","Shelter"

NEW! Modern Log Cabin with Skiing & Work-Friendly Setup

10.0 out of 10, Exceptional, (1)
"We went skiing with another family at Sugarbush. Location was great. House was cozy and comfortable"
NEW! Modern Log Cabin with Skiing & Work-Friendly Setup
New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b
Exterior

New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b

10.0 out of 10, Exceptional, (44)
"We had a spectacular stay! Ed was great. He was super helpful and a great host. His house was exactly what we needed. The pictures truly don’t do it justice. Plenty of room, high end finishes, charming decorations and breathtaking views of the mountain. Highly recommend this home!!!"
New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b
Perfect Ski in Ski Out House with Fireplace & Hot Tub!!
Ski on ski off on Great Eastern Trail!!!

Perfect Ski in Ski Out House with Fireplace & Hot Tub!!

10.0 out of 10, Exceptional, (80)
"Great cabin for a family ski trip. Right on the trail with easy access. Property is clean, well stocked and maintained. Would definitely come back and stay here."
Perfect Ski in Ski Out House with Fireplace & Hot Tub!!
Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views
Exterior

Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views

9.2 out of 10, Wonderful, (19)
"I loved the size and layout of this house. So many rooms and beds with lots of open communal space so we could all sleep comfortably but also all hang out in one room when we wanted to. The drive to Killington to ski everyday was so quick and easy and lots of food options around in both directions!"
Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views
Off Grid Glamping Shed with River Access
Property grounds

Off Grid Glamping Shed with River Access

2.0 star property
The price is SAR 244
SAR 378 total
includes taxes & fees
20 Feb - 21 Feb
Off Grid Glamping Shed with River Access
Cozy private country setting - 15 miles from Woodstock
Perfect 4 season get away

Cozy private country setting - 15 miles from Woodstock

10.0 out of 10, Exceptional, (25)
"Stayed with my family for a long weekend and skied nearby. 4 of us total with two teenagers. House was immaculate and comfortable. Would definitely stay here again!"
Cozy private country setting - 15 miles from Woodstock
Roundabout Ridge
Dining

Roundabout Ridge

9.2 out of 10, Wonderful, (21)
"The property was advertised. The outdoor stairs and driveway felt a little dangerous after the snow Killington has had recently but management sent some to clean the stairs and the driveway after we made them aware. The home has a lot of character but could use some upgrades. Otherwise, we had a good time and look forward to coming back again. "
Roundabout Ridge
Top of the Hill Modern Retreat
Front of House

Top of the Hill Modern Retreat

10.0 out of 10, Exceptional, (1)
"I love this place! New and spacious. The kitchen has everything you need for the stay. My wife loves cooking in there. The only complaint is the water pressure is too weak. It is definite worth for families who love to cook."
The price is SAR 819
SAR 2,505 total
includes taxes & fees
23 Feb - 24 Feb
Top of the Hill Modern Retreat
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Interior

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

10.0 out of 10, Exceptional, (67)
"Highly recommend. House is beautiful. Plenty to do. "
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
The Brandon Inn - Fourth Floor Queen Room
Point of interest

The Brandon Inn - Fourth Floor Queen Room

8.4 out of 10, Very Good, (5)
"Clean, great location…restaurants, quaint interesting little shops… rent a vehicle and go hiking explore etc"
The price is SAR 544
SAR 704 total
includes taxes & fees
20 Feb - 21 Feb
The Brandon Inn - Fourth Floor Queen Room
Resort townhome with on-site pool, hot tub & easy ski access

Resort townhome with on-site pool, hot tub & easy ski access

9.0 out of 10, Wonderful, (66)
"This is our third stay in Killington VT and every time we have stayed in the Woods development. It is quiet and relaxing but close to everything we need. The fall colors are also wonderful. The home we stayed in was a bit dated but was clean, secure, and very comfortable for our week-long stay. It had modern amenities, a fully equipped kitchen, and was more than enough space for two people. The sauna and whirlpool tub were also great. Communication with the host (Vacasa) was very good, and we...
Resort townhome with on-site pool, hot tub & easy ski access
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Pittsfield

Cozy Loft for two with Hot Tub & Mtn Views
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (230)
"Great stay in the mountains. Listing is exactly as advertised. Jeff was great "
Cozy Loft for two with Hot Tub & Mtn Views
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

8.4 out of 10, Very Good, (27)
"It’s a great location, and the unit is well updated, but being able to lock it while you’re away skiing the whole day is pretty important. When I reached out to the property manager about this, and also a disgusting towel left near the toilet on arrival, the response was basically oh no! That’s awful! We’ve told someone.. aaaand nothing ever happened about either thing. These issues weren’t insurmountable, but doing nothing at all about them just left a terrible impression."
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.