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Compare 112 Apartments in Pittsfield with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (66)
"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

Vermont Retreat

9.8 out of 10, Exceptional, (20)
"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

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

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 217
AED 934 total
includes taxes & fees
4 May - 5 May
Clean & bright condo with mountain views & modern kitchen - walk to lifts

Pinnacle F21, 3 bedroom 2 bath with shuttle to the slopes every day of the week.

9.0 out of 10, Wonderful, (4)
"The unit was exactly as advertised. Slept 4 adults and 3 children comfortably. Killington is very close and Pico is about a 15 minute ride. Would stay again. Thank you."
Pinnacle F21, 3 bedroom 2 bath with shuttle to the slopes every day of the week.

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

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

Wade's World Ski Home FirePlace Shuttle Location

2.0 star property
9.6 out of 10, Exceptional, (5)
"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 AED 298
AED 1,224 total
includes taxes & fees
5 May - 6 May
Wade's World Ski Home FirePlace Shuttle Location

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
4 May - 5 May
Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.

Long Trail Suite | 10 Mins to Mountains | A/C

6.0 out of 10, (1)
The price is AED 272
AED 679 total
includes taxes & fees
4 May - 5 May
Long Trail Suite | 10 Mins to Mountains | A/C

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
5 May - 6 May
Modern Ski Château - 4 min from Killington Ski mountain lifts

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:

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

9.0 out of 10, Wonderful, (8)
"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

10 MI to Killington Resort - Four Season Retreat!

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

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

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 584
AED 1,341 total
includes taxes & fees
1 Jun - 2 Jun
Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM

Centrally located apartment for the skier & outdoor enthusiast

2.0 star property
The price is AED 485
AED 1,218 total
includes taxes & fees
4 May - 5 May
Centrally located apartment for the skier & outdoor enthusiast

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

6.2 out of 10, (19)
"Communication was excellent and service was great."
The price is AED 364
AED 1,048 total
includes taxes & fees
4 May - 5 May
Spacious mountain studio with free WiFi & full kitchen - close to skiing

Ben & Jerry Suite | Minutes to Woodstock | Hiking

9.6 out of 10, Exceptional, (4)
"Pleasant and convenient. "
The price is AED 272
AED 679 total
includes taxes & fees
4 May - 5 May
Ben & Jerry Suite | Minutes to Woodstock | Hiking

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

10.0 out of 10, Exceptional, (17)
"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

Run, ride, hike and swim in Central Vermont

9.8 out of 10, Exceptional, (16)
"Thank you had a great time would recommend. Very nice accommodation perfect for ski trips to killington"
Run, ride, hike and swim in Central Vermont
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 13+

9.8 out of 10, Exceptional, (117)
"Had a great stay in the perfect ski house "
Killington area home - 4-seasons & hot tub. Sleeps 13+

Private Killington Area Inn all to Yourself!

10.0 out of 10, Exceptional, (38)
"Overall fabulous place to stay. Will be back next year!!"
Private Killington Area Inn all to Yourself!

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"Very nice place only negative was the sauna did not work"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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 43 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?
Below are some of the more popular apartments in the area: Doc’s Lake house 1st floor, 2 bedroom apartment: Situated in Salisbury, 16.6 mi/26.8 km from the heart of Pittsfield. Includes free WiFi, fireplaces, and Smart TVs. Clean & bright condo with mountain views & modern kitchen - walk to lifts: Located in Killington, 9.9 mi/15.9 km away. Includes sofa beds. A fitness center and onsite laundry facilities are on site. Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi: 8.2 mi/13.2 km away in Bethel. Condo near ski resorts with a private balcony & full kitchen: Located in Killington, 9.9 mi/15.9 km from Pittsfield. Includes fireplaces and sofa beds. A fitness center and onsite laundry facilities 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. 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.