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Compare 91 Apartments in Pittsfield with updated reviews, rates, and availability.

Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM
Miscellaneous

Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM

The price is SAR 935
SAR 1,816 total
includes taxes & fees
22 Jan - 23 January 2025
Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM
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
MODERN SPACIOUS 2-bedroom apartment
Interior

MODERN SPACIOUS 2-bedroom apartment

2.0 star property
4.0 out of 10, (3)
"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 934 total
includes taxes & fees
14 Jan - 15 January 2025
MODERN SPACIOUS 2-bedroom apartment
Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily
Exterior

Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily

9.2 out of 10, Wonderful, (15)
"Great price, location, and property owner. "
Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily
BearPaw- Shuttle to slopes, pool, hot tub, sauna

BearPaw- Shuttle to slopes, pool, hot tub, sauna

The price is SAR 1,188
SAR 2,515 total
includes taxes & fees
7 Jan - 8 January 2025
BearPaw- Shuttle to slopes, pool, hot tub, sauna
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 466
SAR 1,295 total
includes taxes & fees
2 Jan - 3 January 2025
Spacious mountain studio with free WiFi & full kitchen - close to skiing
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
Cozy renovated barn apartment on first floor
Exterior

Cozy renovated barn apartment on first floor

9.2 out of 10, Wonderful, (7)
"Beautiful setting and lovely stay!"
Cozy renovated barn apartment on first floor
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 1,590
SAR 3,334 total
includes taxes & fees
8 Jan - 9 January 2025
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, (7)
"We enjoyed our stay! Stephen was very nice just a message away if we needed anything. "
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 7,718 total
includes taxes & fees
28 Dec - 29 Dec
Modern Ski Château - 4 min from Killington Ski mountain lifts
SnowDen - Ski on and off at Pico, Fireplace
Enjoy the spacious king-size bed with a lovely outdoor view and the gentle breeze of the ceiling fan.

SnowDen - Ski on and off at Pico, Fireplace

The price is SAR 1,768
SAR 3,532 total
includes taxes & fees
2 Jan - 3 January 2025
SnowDen - Ski on and off at Pico, Fireplace
Pinnacle C16
Aerial view

Pinnacle C16

3.0 star property
8.0 out of 10, Very Good, (2)
Pinnacle C16
Wade's World Ski Home FirePlace Shuttle Location

Wade's World Ski Home FirePlace Shuttle Location

2.0 star property
10.0 out of 10, Exceptional, (1)
"This space was perfect for my wife and I as we explored Vermont. Its relative proximity to Woodstock made it an ideal stay for a few days while enjoyed everything the area had to offer. The owner’s instructions for check-in and check-out were simple and clear. It was very clean and orderly, but homely and comfortable."
The price is SAR 620
SAR 1,653 total
includes taxes & fees
7 Jan - 8 January 2025
Wade's World Ski Home FirePlace Shuttle Location
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 469
SAR 761 total
includes taxes & fees
7 Jan - 8 January 2025
Doc's Lake house 1st floor, 2 bedroom apartment
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 623
SAR 1,939 total
includes taxes & fees
2 Jan - 3 January 2025
Condo near ski resorts with a private balcony & full kitchen
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
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"
The price is SAR 657
SAR 1,627 total
includes taxes & fees
26 Jan - 27 January 2025
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 413
SAR 859 total
includes taxes & fees
15 Jan - 16 January 2025
Minutes to Woodstock | Hiking | Ben & Jerry Suite
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, (114)
"Had a great stay in the perfect ski house "
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, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Loft for two with Hot Tub
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (223)
"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
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 40 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?
Here are some of the more popular apartments in the area: Vermont Retreat: Situated in Bridgewater, 15.9 mi/25.6 km from the heart of Pittsfield. Includes free WiFi and Smart TVs. Doc’s Lake house 1st floor, 2 bedroom apartment: Located 16.6 mi/26.8 km away in Salisbury. Free WiFi, fireplaces, and Smart TVs are included. Spacious mountain studio with free WiFi & full kitchen - close to skiing: Located 9.9 mi/15.9 km away in Killington. Separate dining areas and sofa beds are included. A fitness center and an indoor pool are on site.
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. Pico Mountain at Killington Ski Resort and Pico Peak 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.