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Compare Apartments in Pittsfield with updated reviews, rates, and availability.

Doc's Lake house 1st floor, 2 bedroom apartment
10.0 out of 10, Exceptional, (55)
"We really enjoyed staying at this cozy, well-equipped lake house. Everything was available to make the stay an enjoyable one. The driveway entrance and property were cleared for our arrival following a significant snowstorm. Communicating with the owner was a pleasure, with every a phone call or text message answered. Who would’ve thought seeing the solar eclipse of 2024 would be so easy and exciting! It was the owner and accommodations that made it all possible for planning the trip. We truly...
Doc's Lake house 1st floor, 2 bedroom apartment
Cozy Studio for 4 - Walk to Mountain w/ Balcony
9.0 out of 10, Wonderful, (13)
"Very nice place."
The price is SAR 315
SAR 726 total
includes taxes & fees
30 Jun - 1 Jul
Cozy Studio for 4 - Walk to Mountain w/ Balcony
Easy access to VAST snowmobile trail system and local mountain bike trails
10.0 out of 10, Exceptional, (10)
"Well kept and well managed. Just what I hoped for and I would recommend it, but that's with mixed feelings because I want it to be available next year (want it to remain my secret, oh well). Like most of rural VT no cell service, but wi-fi calling worked for me in this flat. Great coffee and sandwich place 1.3 mi north, outside seating."
Easy access to VAST snowmobile trail system and local mountain bike trails
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Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily
10.0 out of 10, Exceptional, (9)
"This location is so very close to the skyship gondola, which is the bottom most lift. It’s actually a great spot because you can do the peak to creek run (the great eastern) as a day ender and basically end up walking distance from the home! Overall, the place was big enough to fit all 6 of us very comfortably with plenty of space to get ready and move about. The kitchen was well equipped with all the cookware you can imagine and some. Also, not to mention the HOT TUB!! There were 2, but we only...
Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
9.0 out of 10, Wonderful, (4)
"My husband and I had a very comfortable stay. This was a place like home and I was very comfortable. The hot tub was amazing And a plus to the apartment. Having the space outside on the deck To relax was very nice, relaxing in the apartment was all worth my stay. The bathroom floors which were heated were remarkable. One of my favorite parts of staying here was driving up the long Mountainous driveway On the edge. The hot tub was a pleasure however it needs more privacy around it to block...
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
MapleCastle
MapleCastle
Modern Ski Château - 4 min from Killington Ski mountain lifts
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay- it was perfect for our family of 4. Easy access to Killington and Pico and the pool was a great bonus for the kids!"
Modern Ski Château - 4 min from Killington Ski mountain lifts
Killington Condo w/ Spa ~ 3 Miles to Ski Resort!
3.5 star property
Killington Condo w/ Spa ~ 3 Miles to Ski Resort!
Perfect Getaway minutes to Killington & Woodstock
Perfect Getaway minutes to Killington & Woodstock
LilBear - Pool, Shuttle, Hot Tub, Gym
LilBear - Pool, Shuttle, Hot Tub, Gym
Condo near ski resorts with a private balcony & full kitchen
8.8 out of 10, Excellent, (23)
"Convenient location close to slopes with a shuttle bus too. 4:00 is a late check in and ours was delayed slightly while cleaning crew finished. It did meet our needs and was comfortable."
The price is SAR 330
SAR 1,514 total
includes taxes & fees
27 Jun - 28 Jun
Condo near ski resorts with a private balcony & full kitchen
Lovely Apartment within Walking Distance to Slopes - Year-Round Outdoor Activities
9.0 out of 10, Wonderful, (17)
"We had a great time staying slopeside. It is a short walk down the road to get to Sundowner. We weren't first chair but we almost were. The house itself was clean and tidy. Had everything one would need and even had a coffee maker and Keurig. We will be planning to stay here again if we have the chance."
Lovely Apartment within Walking Distance to Slopes - Year-Round Outdoor Activities
Spacious mountain studio with free WiFi & full kitchen - close to skiing
6.0 out of 10, (17)
"Communication was excellent and service was great."
Spacious mountain studio with free WiFi & full kitchen - close to skiing
Clean & bright condo with mountain views & modern kitchen - walk to lifts
7.4 out of 10, Good, (43)
"Quick trip to and from Killington mt"
Clean & bright condo with mountain views & modern kitchen - walk to lifts
2 Bedroom apartment in Randolph Village VT
7.0 out of 10, Good, (2)
"I enjoyed my stay, it was quite comfy and village center is right nearby."
2 Bedroom apartment in Randolph Village VT
Ben & Jerry Themed Suite | 10 Min to Killington
9.6 out of 10, Exceptional, (4)
"Older building on the outside and yard. But rooms were remodeled and very nice. No contact with any staff except by text and emails. They give you a code for the doors. A little different."
Ben & Jerry Themed Suite | 10 Min to Killington
Run, ride, hike and swim in Central Vermont
9.8 out of 10, Exceptional, (8)
"Everything was excellent. Thank you John."
Run, ride, hike and swim in Central Vermont
Bearfoot - Shuttle or Walk to Ski, Pool, Hot Tub
10.0 out of 10, Exceptional, (3)
"Clean place and close to mountain. Host was responsive. We enjoyed our stay, thank you !!"
Bearfoot - Shuttle or Walk to Ski, Pool, Hot Tub
BearQuad - Ski-Off, Shuttle-On, Renovated in 2023
10.0 out of 10, Exceptional, (1)
"Dan and Holly were great"
BearQuad - Ski-Off, Shuttle-On, Renovated in 2023
Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle
10.0 out of 10, Exceptional, (4)
"The accommodations were excellent. All of our needs at the condo were not only met but exceeded. The hosts answered all of our questions in a kind and helpful way. We would highly recommend staying there."
Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle
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See all available properties in Pittsfield
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

Killington area home - 4-seasons & hot tub. Sleeps 12+
9.8 out of 10, Exceptional, (109)
"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+
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (451)
"The cabin is beautiful and very cozy. I would definitely stay again in the future. Maxis is a great place to eat breakfast. If your planning to cook yourself make sure to get meat and anything else you want on the way as everything is at least 20 minutes or more drive."
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (200)
"Such a beautiful spot - perfect for a much needed weekend of peace and quiet."
Cozy Loft for two with Hot Tub
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.

Frequently asked questions

What's it like to stay at an apartment in Pittsfield?
You’ll find plenty of places to stay in Pittsfield with 31 accommodations. Though there aren’t many apartments, we can help you locate similar accommodations. When you search on Expedia, you can filter by amenities you might find in an apartment such as a kitchen. Even filter by similar properties such as vacation homes, condos, or guest houses.
Why would you choose an apartment over a traditional hotel room?
An apartment is often more spacious than a traditional hotel room and includes a kitchen, so you can have some home-cooked meals. Apartments are ideal for families who want the conveniences of home, and also for solo travelers who want to stay in a quieter area.
What can I expect from the weather in Pittsfield?
Though weather is just one factor, it can really affect your travel plans, especially when you’re planning an extended stay in Pittsfield. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and April, with each month seeing an average of 10 inches of snowfall.
What should I see and do in Pittsfield?
While exploring the area, visit family-friendly sights like Killington Adventure Center, or get outside and enjoy nature at Silver Lake State Park. Appalachian Trail Adventures and Green Mountain National Golf Course are a couple of places you’ll find in the larger area.
What's the best way to get to and around Pittsfield?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 18.1 mi (29.2 km) from the city center. Otherwise, you can search for flights to Lebanon, NH (LEB-Lebanon Municipal), which is 27.2 mi (43.7 km) away. If you’d like to explore around the area, you may want to rent a car for your trip.

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