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Compare 476 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Valley View Retreat is a tastefully decorated home.

10.0 out of 10, Exceptional, (1)
Valley View Retreat is a tastefully decorated home.

Walk to Pickle Barrel & Jax. Hot tub & Views

2.0 star property
10.0 out of 10, Exceptional, (1)
"This is the 2nd time we’ve stayed in this beautiful home and it was just as we remembered. Comfortable bedrooms, deck/yard/hot tub amazing, proximity to so many restaurants as well as the mountain. Everything was clearly communicated throughout our stay and the hosts were incredibly responsive and available for anything we could need. Would highly recommend!"
Walk to Pickle Barrel & Jax. Hot tub & Views

Killington, Vermont Ski House w/ Hot Tub and Sauna

9.4 out of 10, Exceptional, (82)
"Perfect house. This is our second time there and we had a wonderful experience."
Killington, Vermont Ski House w/ Hot Tub and Sauna

BruinsDen - Ski On Ski Off (Home Stretch Trail)

10.0 out of 10, Exceptional, (11)
"Amazing. So clean. Room for everyone to spread out and enjoy their time."
The price is SAR 3,170
SAR 5,413 total
includes taxes & fees
2 Feb - 3 Feb
BruinsDen - Ski On Ski Off (Home Stretch Trail)

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

9.8 out of 10, Exceptional, (18)
"Gorgeous property with everything that we needed! It was relaxing and comfortable for everyone. The kids had a blast! The property management team was great with communication and offered early check in and late check out. Would absolutely stay here again!"
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

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

8.8 out of 10, Excellent, (20)
"Very peaceful & relaxing. "
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

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

10.0 out of 10, Exceptional, (64)
"This house was perfect for our group of twelve. We were three families with kids ranging in ages from 6-14yrs old. There was enough space for everyone to relax after a day of skiing. The kitchen was very well stocked and had everything we needed. The ski hill is only a 5 mins drive. We would definitely stay here again"
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

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!

Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests

9.2 out of 10, Wonderful, (29)
"Beautiful property! The lovely home is clean and convenient to skiing/ restaurants/ shopping.Very quiet neighborhood and so relaxing. The hot tub was well maintained and easily assessable.The property actually has 6 rather than 5 bedrooms. Most bathrooms are very small. I would definitely consider renting it again."
Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests

A Cozy Mountain Retreat in Killington Welcome to Birch Beauty

8.0 out of 10, Very Good, (1)
A Cozy Mountain Retreat in Killington Welcome to Birch Beauty

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

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

Ski-in/out sunrise condo with pool & hot tub - great ski retreat

8.8 out of 10, Excellent, (79)
"Property was nice and location was great even for an of season stay. Lots of fun close by like the killington adventure center & visiting small toes like Woodstock & ludlow. Also hiking close by!! We were a bit disappointed that the indoor pool & hot tub were closed until the peak winter season so may mention that in the listing. We loved having the fire place & sauna inside unit. "
Ski-in/out sunrise condo with pool & hot tub - great ski retreat

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, (40)
"The owner was extremely easy to work with and even more responsive. The house has an AMAZING view Killington. Very clean and once you get the cast iron stove to temp it worked really well to heat the house. The sauna, and foosball table worked well. The hotub was easy to use, it fits 3 full size adults with no issue. The kitchen fridge had plenty of condiments, dressing and sauces. A really nice treat was that the beverage fridge was stocked with prev renters' drinks as well we added to it for...
New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b

Mountain Top - Fresh Pond - Killington - Hot Tub

9.8 out of 10, Exceptional, (6)
"This property was exactly as advertised. Plenty of space for everyone to hangout and have privacy when needed. It is a quick 20 minute drive to Killington. We would definitely rent it again!"
Mountain Top - Fresh Pond - Killington - Hot Tub

Secluded dog-friendly home amongst the trees with sauna, Wii, & 2 scenic decks

9.8 out of 10, Exceptional, (10)
"We loved every aspect of the house. It was just as pictured and we would totally come back again. We were sad we had booked it for only a weekend."
Secluded dog-friendly home amongst the trees with sauna, Wii, & 2 scenic decks

Recently updated home with shared hot tub, pool, and easy ski access

8.4 out of 10, Very Good, (40)
"Overall the stay was very good. The unit was the right size and configuration for our family of three. Great location on the Killington Road. A previous guest didn't clean the pots and pans at all, the glassware was also suspect, so we decided to eat out for most meals but there were many closeby options. We LOVED the pool and spa: it would be helpful to provide information about operating hours in the unit. "
Recently updated home with shared hot tub, pool, and easy ski access

BearRight - Fire Place, Hot tub, on shuttle line

9.2 out of 10, Wonderful, (5)
"Location was perfect to the mountain, easy to find and very comfortable! Hosts were responsive leading up to the visit and super helpful!"
BearRight - Fire Place, Hot tub, on shuttle line

Killington Getaway In Private Community

8.8 out of 10, Excellent, (19)
"Perfect for a ski trip. "
Killington Getaway In Private Community

Killington ski house

9.6 out of 10, Exceptional, (32)
"Great place, great location, great response and communication with the host, Dean. Very much appreciated. "
Killington ski house

Ski-On Ski-Off at Pico Mtn Premier Slopeside House Rental.

10.0 out of 10, Exceptional, (2)
"Dewey’s house was perfect for us! He was super responsive and checked in with us making sure we had everything we needed for our long weekend! He treated us like family staying in his house and we didn’t even meet him! Super nice would stay again! Would recommend to anyone staying at pico! Ski on ski off house was perfect for our growing family. My husband loves to ski but we have two babies (19 months and 3 months) so it was perfect for him to ski and the come back for a lunch break and say hi...
Ski-On Ski-Off at Pico Mtn Premier Slopeside House Rental.
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

Killington area home - 4-seasons & hot tub. Sleeps 12+

9.8 out of 10, Exceptional, (114)
"Had a great stay in the perfect ski house "
Killington area home - 4-seasons & hot tub. Sleeps 12+

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (224)
"We had the best time at Jeff’s perfect cozy ‘little loft’! It exceeded expectations! We especially enjoyed the hot tub after long days of skiing!"
Cozy Loft for two with Hot Tub

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
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.