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Compare 116 Apartments in Pittsfield with updated reviews, rates, and availability.

Condo near ski resorts with a private balcony & full kitchen

8.6 out of 10, Excellent, (27)
"Excellent location, condo in great condition. "
Condo near ski resorts with a private balcony & full kitchen

Vermont Retreat

10.0 out of 10, Exceptional, (21)
"We thoroughly enjoyed our stay. It was the perfect location between events that we were attending. Beautiful location, wonderful house and attentive/ helpful hosts."
Vermont Retreat

Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi

Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi

Cozy renovated barn apartment on first floor

9.4 out of 10, Exceptional, (8)
"Beautiful setting and lovely stay!"
Cozy renovated barn apartment on first floor

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

8.8 out of 10, Excellent, (5)
"Comfortable stay. Great location. Pool n spa was very nice and new."
The price is AED 526
AED 1,270 total
includes taxes & fees
9 Jun - 10 Jun
Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM

10 MI to Killington Resort - Four Season Retreat!

3.0 star property
10 MI to Killington Resort - Four Season Retreat!

Green Mountain Access:

2.0 star property
10.0 out of 10, Exceptional, (3)
"Our stay at "Green Mountain Access" allowed us to enjoy skiing at Killington easily and comfortably."
Green Mountain Access:

Woodstock Suite | 10 Min to Mountains |A/C| Hiking

10.0 out of 10, Exceptional, (5)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
The price is AED 334
AED 755 total
includes taxes & fees
9 Jun - 10 Jun
Woodstock Suite | 10 Min to Mountains |A/C| Hiking

Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.

8.0 out of 10, Very Good, (2)
"Room was great for the 140 price point it normally is, not the 250 price for World Cup weekend. Would stay again though, very convenient. Checkin was super easy and the room was clean, just needs "
The price is AED 287
AED 813 total
includes taxes & fees
9 Jun - 10 Jun
Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.

Red Clover Inn: Queen Suite near Killington

8.8 out of 10, Excellent, (3)
"We stayed there again for the second weekend in a row and again it was charming and comfortable. The community rooms are especially spacious and show off the beautiful grounds outside the large windows. Carol was over the top attentive to our needs. It was a lovely relaxing stay."
Red Clover Inn: Queen Suite near Killington

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 AED 4,966
AED 7,317 total
includes taxes & fees
10 Jun - 11 Jun
Modern Ski Château - 4 min from Killington Ski mountain lifts

Solar-Powered Brandon Studio Cabin w/ Fire Pit

2.0 star property
10.0 out of 10, Exceptional, (2)
"This was a super great escape from the hustle and bustle we are in every day. This was our first time visiting VT and Doug made it very easy with great communication. The cabin is in a great place for exploring and dining. Two dogs (80lb and 30lb) and two people was a little tight, but the layout made it easy to fit all of our stuff. The cabin is well thought out and has all the perks needed. I would highly recommend this location!"
Solar-Powered Brandon Studio Cabin w/ Fire Pit

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

10.0 out of 10, Exceptional, (67)
"Easy drive to Middlebury Snowball, the owner was very communicative and helpful in giving tips and suggestions."
Doc's Lake house 1st floor, 2 bedroom apartment

Centrally located apartment for the skier & outdoor enthusiast

2.0 star property
4.0 out of 10, (1)
"The oven didn’t work and couldn’t get anyone to come turn a breaker back on! "
The price is AED 485
AED 1,256 total
includes taxes & fees
9 Jun - 10 Jun
Centrally located apartment for the skier & outdoor enthusiast

BearHug AC, Pool, Hot Tub, Tennis, Close to Resort

10.0 out of 10, Exceptional, (8)
"Perfect location, short drive to the mountain. Condo was beautifully decorated and clean. Kitchen was stocked with everything you could need. "
The price is AED 814
AED 2,490 total
includes taxes & fees
9 Jun - 10 Jun
BearHug AC, Pool, Hot Tub, Tennis, Close to Resort

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

9.0 out of 10, Wonderful, (18)
"Great price, location, and property owner. "
Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily

BearNecessities- AC, Pool, Hot Tub, Gym, Sauna

10.0 out of 10, Exceptional, (1)
"The unit was right across from Killington with many great amenities. The place was very cozy and perfect for a quick stay before a day of skiing."
The price is AED 278
AED 999 total
includes taxes & fees
12 Jun - 13 Jun
BearNecessities- AC, Pool, Hot Tub, Gym, Sauna

Clean & bright condo with mountain views & modern kitchen - walk to lifts

7.2 out of 10, Good, (44)
"Quick trip to and from Killington mt"
The price is AED 492
AED 1,343 total
includes taxes & fees
30 Jun - 1 Jul
Clean & bright condo with mountain views & modern kitchen - walk to lifts

Moose Tracks Lodge - Pool, Hot Tub, Golf, Sauna

10.0 out of 10, Exceptional, (3)
"Easy access to skiing. Clean and comfortable accommodations. Gym/Hot tub is in a separate building, but still close."
The price is AED 553
AED 1,878 total
includes taxes & fees
2 Jul - 3 Jul
Moose Tracks Lodge - Pool, Hot Tub, Golf, Sauna

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

10.0 out of 10, Exceptional, (18)
"The property is dated but clean; pretty much everything is there for a nice stay. Owner is on property, so if any issues, they are taken care of quickly. "
Easy access to VAST snowmobile trail system and local mountain bike trails
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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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 45 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 more popular apartments in the area to choose from: Condo near ski resorts with a private balcony & full kitchen: Located 9.9 mi/15.9 km away in Killington. Fireplaces and sofa beds are included. A fitness center and onsite laundry facilities are on site. Vermont Retreat: Located in Bridgewater, 15.9 mi/25.6 km away. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available on site. Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi: 8.2 mi/13.2 km away in Bethel. Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM: It’s situated in Killington, 9.9 mi/15.9 km from Pittsfield.
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. Roger Clark Memorial Central Library and Pittsfield Town Hall are other places to visit while you’re in town.
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.