Search Vacation Homes in Pittsfield

Compare 471 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

TV, fireplace, DVD player, music library
The Queens Croft v2 - Luxury Killington Ski Home. Newer. Better. Ski-ier.
10.0 out of 10, Exceptional, (7)
"See you again next year ! Thank you"
The price is $272
$1,038 total
includes taxes & fees
May 27 - May 28
The Queens Croft v2 - Luxury Killington Ski Home. Newer. Better. Ski-ier.
View from property
Quechee Mountain Home w/Jacuzzi, Sunroom, and Private Gym
10.0 out of 10, Exceptional, (3)
"We really enjoyed the location of the home and spent a few days skiing at Killington nearby. The host was communicative and proactive when a cleaning crew was still on site after check in time. The property was clean and the hot tub was a welcoming after a long day on the mountain!"
Quechee Mountain Home w/Jacuzzi, Sunroom, and Private Gym
Fridge, microwave, stovetop, dishwasher
Upscale VT Getaway by Slopes, Lakes & Trails!
9.4 out of 10, Exceptional, (13)
"8 people. Good home layout for people to be together and separate at the same time"
Upscale VT Getaway by Slopes, Lakes & Trails!
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TV, fireplace, DVD player
Rustic home with a private hot tub, fireplace, cable, & washer/dryer
9.6 out of 10, Exceptional, (46)
"Great house! Small issue with getting into the place with the keybox, but was quickly resolved. We had a great time, it was so comfy, great place to come home after a long day of skiing, exploring, etc. Lots of room to spread out with the family and nighttime hot tub soaks in the cold air were so refreshing!"
Rustic home with a private hot tub, fireplace, cable, & washer/dryer
Property grounds
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
9.2 out of 10, Wonderful, (13)
"Great little cabin - really enjoyed our stay"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Fridge, microwave, oven, stovetop
Ski-in/out sunrise condo with pool & hot tub - great ski retreat
9.0 out of 10, Wonderful, (69)
"Easy entry, lots of firewood for the fireplace. Very spacious."
Ski-in/out sunrise condo with pool & hot tub - great ski retreat
Indoor pool
Resort townhome with on-site pool, hot tub & easy ski access
9.0 out of 10, Wonderful, (63)
"We were very impressed with the overall layout of the unit. Nice living room. Bedrooms were just as advertised. the hot tub in the master bedroom was perfect. for us skiers Killington resort was just up the road. Here are a couple of negatives that we encountered. 1) The dishwasher had a note on it that said "Please do not use the dishwasher it is not draining" then under this the previous tenant wrote "this sign was here when we arrived. Have to wash dishes by hand". Really come on Vacasa get...
Resort townhome with on-site pool, hot tub & easy ski access
Exterior
location! location! 5 BR with Hot Tub & Firepit!
9.4 out of 10, Exceptional, (9)
"A great place for the dads and Sons ski/board trip. The place had plenty of space and was very clean. Super close to the base Lodges. Highly recommend"
location! location! 5 BR with Hot Tub & Firepit!
Property grounds
Lake Bomoseen Luxury Waterfront, Family Friendly Getaway!
10.0 out of 10, Exceptional, (8)
"Fabulous - even better than expected."
Lake Bomoseen Luxury Waterfront, Family Friendly Getaway!
Property grounds
Beautiful home located in the Mad River Valley
9.8 out of 10, Exceptional, (32)
"This home was a perfect place to stay with out of town family. The home was just as described and had everything we needed for the weekend . Very quiet and comfortable."
Beautiful home located in the Mad River Valley
A heated pool
Luxe Plymouth Chalet w/ Indoor Pool & 3 Decks!
9.6 out of 10, Exceptional, (9)
"Listing details were accurate and house was very impressive upon arrival. Would love to stay at this property again! The onsite contact (Tanya) was very helpful with questions too."
Luxe Plymouth Chalet w/ Indoor Pool & 3 Decks!
Fridge, microwave, oven, stovetop
BruinsDen - Ski On Ski Off (Home Stretch Trail)
9.8 out of 10, Exceptional, (7)
"We loved our stay. There were plenty of beds and bathrooms for our family. The kitchen was the most well stocked kitchen ever. Better than being at home even! Really loved the porch area for storing ski gear. The hot tub felt great. Loved all the windows. So much light and great view. The only small draw back was it’s not a true ski in ski out. The trail is close but you do need to walk a bit to get to it. Overall we had a great visit and would stay here again!"
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Exterior
BearRight - Great Location! AC and Fire Pit
10.0 out of 10, Exceptional, (2)
"Location was perfect to the mountain, easy to find and very comfortable! Hosts were responsive leading up to the visit and super helpful!"
BearRight - Great Location! AC and Fire Pit
TV, fireplace, DVD player, table tennis
Sweet chalet with private hot tub, firepit, game room & minibar
9.6 out of 10, Exceptional, (32)
"All good lots of fun"
Sweet chalet with private hot tub, firepit, game room & minibar
TV, fireplace, books, stereo
Beechwood - 4 Bedrooms and 3 Baths, sleeps 10
10.0 out of 10, Exceptional, (1)
"We loved our stay here. Only 18 minutes from killington. The house was clean and cozy. I’d definitely book again."
Beechwood - 4 Bedrooms and 3 Baths, sleeps 10
Interior
Post & Beam Home Ideal for families or Groups
9.8 out of 10, Exceptional, (114)
"A wonderful home, abundant firewood, very clear instructions, TV worked great. Highly recommended."
Post & Beam Home Ideal for families or Groups
Property grounds
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
9.2 out of 10, Wonderful, (58)
"Bob’s bungalow was a perfect homebase for our ski trip. It had all the necessities we needed for cooking sleeping, and just plain hanging out after a long day of skiing."
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
Exterior
Spectacular 4 Bed Killington Home
9.8 out of 10, Exceptional, (99)
"Was a great place to stay. Location was awesome and house was clean. Would definitely stay again."
Spectacular 4 Bed Killington Home
Outdoor dining
Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views
9.0 out of 10, Wonderful, (16)
"Irina was a lovely host and her house was a great spot."
Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views
Outdoor dining
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola
9.8 out of 10, Exceptional, (13)
"Lovely stay w lots of common space, nearby to okemo"
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola
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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.

Other property types in Pittsfield

Property grounds
Killington area home - 4-seasons & hot tub. Sleeps 12+
9.8 out of 10, Exceptional, (108)
"My family and I have been renting ski homes for many years. David’s home was, by far, the cleanest property we have ever stayed at. My mother-in-law would have been impressed with the cleanliness of this home. The house was perfectly appointed and was perfect from the time we walked in until the time we left. Thank you David! We are looking forward to next year."
Killington area home - 4-seasons & hot tub. Sleeps 12+
Exterior
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (194)
"Cabin was so wonderful, fire place was lovely right next to the hot tub. Host was great with communication. Very pleasant stay. Cozy, quiet, clean cabin."
Cozy Loft for two with Hot Tub
Interior
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (447)
"Clean and quiet cabin. Perfect for a getaway."
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
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.

Pittsfield Vacation Homes information

Number of reviews
431
Accommodation
471 Vacation Homes
Lowest Price
$272
Highest Price
$272

Recent reviews of Pittsfield hotels
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