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Compare 171 Apartments in Pittsfield with updated reviews, rates, and availability.

Condo near ski resorts with a private balcony & full kitchen

Condo near ski resorts with a private balcony & full kitchen

8.8 out of 10, Excellent, (25)
"Excellent location, condo in great condition. "
The price is SAR 481
SAR 1,767 total
includes taxes & fees
2 Dec - 3 Dec
Condo near ski resorts with a private balcony & full kitchen
BearHug - HotTub Fireplace shuttle on ski home
Master suite, featuring a spacious king bed, ample closet space, en suite bathroom, and a cozy bonus of a chair that converts to a single bed.

BearHug - HotTub Fireplace shuttle on ski home

10.0 out of 10, Exceptional, (4)
"Exactly as advertised. Immaculate. Great communication. Comfy bed!"
The price is SAR 742
SAR 2,253 total
includes taxes & fees
1 Dec - 2 Dec
BearHug - HotTub Fireplace shuttle on ski home
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
Living area

2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House

9.0 out of 10, Wonderful, (6)
"We had a great stay here. Thank you!"
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
Modern Ski Château - 4 min from Killington Ski mountain lifts
Private kitchen

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!"
The price is SAR 5,077
SAR 7,719 total
includes taxes & fees
28 Nov - 29 Nov
Modern Ski Château - 4 min from Killington Ski mountain lifts
Killington Condo w/ Spa ~ 3 Miles to Ski Resort!
Living area

Killington Condo w/ Spa ~ 3 Miles to Ski Resort!

3.0 star property
Killington Condo w/ Spa ~ 3 Miles to Ski Resort!
Pinnacle C16
Exterior

Pinnacle C16

3.0 star property
8.0 out of 10, Very Good, (2)
Pinnacle C16
LilBear - Pool, Shuttle, Hot Tub, Gym

LilBear - Pool, Shuttle, Hot Tub, Gym

The price is SAR 406
SAR 1,138 total
includes taxes & fees
18 Dec - 19 Dec
LilBear - Pool, Shuttle, Hot Tub, Gym
MODERN SPACIOUS 2-bedroom apartment
Interior

MODERN SPACIOUS 2-bedroom apartment

2.0 star property
5.0 out of 10, (2)
"This was very spacious. I think you could have a nice sized group here comfortably. 4-6. The area around the property is a bit run down. Thr property owner did not send instructions to enter prior to arrival, but responded quickly and we were inside within 10 min. The wifi password would not work, so we used cell and downloaded movies nearby to watch on Kindle. The main bedroom was large with a couch or maybe a futon. There was a stove, full fridge, washer and dryer, microwave. I did not see a...
The price is SAR 447
SAR 929 total
includes taxes & fees
30 Nov - 1 Dec
MODERN SPACIOUS 2-bedroom apartment
Doc's Lake house 1st floor, 2 bedroom apartment
Welcome to Doc’s Lake House

Doc's Lake house 1st floor, 2 bedroom apartment

10.0 out of 10, Exceptional, (60)
"Beautiful area… had everything we needed! Loved the quiet."
The price is SAR 619
SAR 959 total
includes taxes & fees
3 Dec - 4 Dec
Doc's Lake house 1st floor, 2 bedroom apartment
Lovely Apartment within Walking Distance to Slopes - Year-Round Outdoor Activities

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

Spacious mountain studio with free WiFi & full kitchen - close to skiing

6.0 out of 10, (18)
"Communication was excellent and service was great."
The price is SAR 383
SAR 1,190 total
includes taxes & fees
2 Dec - 3 Dec
Spacious mountain studio with free WiFi & full kitchen - close to skiing
Easy access to VAST snowmobile trail system and local mountain bike trails
Snow and ski sports

Easy access to VAST snowmobile trail system and local mountain bike trails

10.0 out of 10, Exceptional, (16)
"Our stay lasted three nights and four days. The accommodations were great, lots of room, and very comfortable. The upstairs barn apartment was cozy, quiet (nobody was in the downstairs apt), and well-situated for our itinerary. We visited 6 waterfalls, 23 covered bridges, and 4 other points of interest. We would have seen some more, but it rained a good part of one day and we skipped a few."
Easy access to VAST snowmobile trail system and local mountain bike trails
Clean & bright condo with mountain views & modern kitchen - walk to lifts

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
Minutes to Woodstock | Hiking | Ben & Jerry Suite
Queen sized bed, extra blankets, Roku TV and plenty of locally inspired charm.

Minutes to Woodstock | Hiking | Ben & Jerry Suite

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."
The price is SAR 323
SAR 745 total
includes taxes & fees
2 Dec - 3 Dec
Minutes to Woodstock | Hiking | Ben & Jerry Suite
Run, ride, hike and swim in Central Vermont
Exterior

Run, ride, hike and swim in Central Vermont

9.8 out of 10, Exceptional, (14)
"This was a nice quiet place to stay! I was in the area for a class and needed a place to stay. It was clean and comfy"
Run, ride, hike and swim in Central Vermont
Bearfoot - Shuttle or Walk to Ski, Pool, Hot Tub
Sink into elegance with our luxurious leather couch.

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, fire place
Stretch Out and Relax: Long Couch, Endless Comfort!

BearQuad - Ski-Off, Shuttle-On, fire place

10.0 out of 10, Exceptional, (1)
"Dan and Holly were great"
BearQuad - Ski-Off, Shuttle-On, fire place
Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle
Experience seamless connection, where the open kitchen design allows for easy interaction between the dining room and living room.

Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle

10.0 out of 10, Exceptional, (6)
"We stayed for five nights at the end of August. We loved it. The condo was very clean and just as described. It was quiet and peaceful. Great communication from/with the owner. We would definitely stay there again."
The price is SAR 389
SAR 1,119 total
includes taxes & fees
8 Dec - 9 Dec
Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle
Vermont Retreat
Private kitchen

Vermont Retreat

9.8 out of 10, Exceptional, (17)
"Cozy and everything you could need. Really nice kitchen set up and excellent appliances. After a week on the road, the washer & dryer were a welcome refresh of clothing. It's a few minutes west of Woodstock down a country road, so secluded. Takes dogs - wish we had one!"
Vermont Retreat
Mountain side condo with easy ski and trail access - fitness center & grill area

Mountain side condo with easy ski and trail access - fitness center & grill area

8.6 out of 10, Excellent, (7)
"Great location and perfect condo for our group of five adults."
Mountain side condo with easy ski and trail access - fitness center & grill area
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+
Here's the main living area - dining is up on the left

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

9.8 out of 10, Exceptional, (113)
"We stayed for a small bachelor party and had a great time! Everyone had room and there was plenty to do."
Killington area home - 4-seasons & hot tub. Sleeps 12+
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, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
"The cabin was peaceful and everything was provided, plus some!" Stacy S

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (473)
"The cabin was amazing, the design and decor is perfect and the space is perfect. The hot tub and fire pit were so lovely in the evening, and the movie theatre was also excellent for watching TV and films. Jeff was an excellent host, super friendly and helpful and the area was lovely and quiet, very peaceful. Thanks again! "
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.

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 34 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's the best apartment for a stay in Pittsfield?
Listed below are some of the favorite apartments in the area to choose from: Condo near ski resorts with a private balcony & full kitchen: Located in Killington, 9.9 mi/15.9 km away. Includes fireplaces and sofa beds. A fitness center and an indoor pool are on site. Doc’s Lake house 1st floor, 2 bedroom apartment: 16.6 mi/26.8 km away in Salisbury. Free WiFi, fireplaces, and Smart TVs are included.
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 December, 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 Green Mountain National Forest. Appalachian Trail Adventures and Pico Mountain at Killington Ski Resort 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.