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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

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

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

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

10.0 out of 10, Exceptional, (66)
"Thank you so much! We appreciate the late check out on the cold day :)"
Doc's Lake house 1st floor, 2 bedroom apartment
Vermont Retreat
Fridge, microwave, oven, stovetop

Vermont Retreat

9.8 out of 10, Exceptional, (20)
"Everything was wonderful. There was excellent communication, the place was clean and had everything we needed for a weekend away. Ellen really personalizes the experience with special treats upon arrival and tips for places to eat. She even scraped off our jeep when we were heading out. Thank you Ellen! "
Vermont Retreat
Condo near ski resorts with a private balcony & full kitchen
Fridge, microwave, oven, stovetop

Condo near ski resorts with a private balcony & full kitchen

8.6 out of 10, Excellent, (27)
"It was the best place and near all we ask for. the contraction was not quiet."
Condo near ski resorts with a private balcony & full kitchen
Clean & bright condo with mountain views & modern kitchen - walk to lifts
Property grounds

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 AED 217
AED 930 total
includes taxes & fees
17 Apr - 18 Apr
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.
Pool

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
Microwave, oven, stovetop, coffee/tea maker

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
Smart TV, fireplace

Wade's World Ski Home FirePlace Shuttle Location

2.0 star property
9.6 out of 10, Exceptional, (5)
"We took a Spring snowboard up to Killington from Pennsylvania and had the joy of staying at Wades World. Coming off of our 6 hour drive to a home that was exactly as described was a huge relief. The check in process was as smooth as the spring snow we were carving on. The hosts were extremely responsive to my inquiries and very accommodating to my requests. I would absolutely stay here again! "
The price is AED 298
AED 1,216 total
includes taxes & fees
21 Apr - 22 Apr
Wade's World Ski Home FirePlace Shuttle Location
Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.
Aerial view

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 "
Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.
Long Trail Suite | 10 Mins to Mountains | A/C
Aerial view

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

6.0 out of 10, (1)
The price is AED 298
AED 715 total
includes taxes & fees
21 Apr - 22 Apr
Long Trail Suite | 10 Mins to Mountains | A/C
Modern Ski Château - 4 min from Killington Ski mountain lifts
Fridge, oven, stovetop, dishwasher

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 7,475 total
includes taxes & fees
17 Apr - 18 Apr
Modern Ski Château - 4 min from Killington Ski mountain lifts
Green Mountain Access:
Fridge, microwave, oven, dishwasher

Green Mountain Access:

2.0 star property
10.0 out of 10, Exceptional, (3)
"What’s not to say about this place?! From the comfy couches to the cozy beds this the perfect off-mountain stay for anybody hitting Killington Pico or any of the other nearby mountains. Our host Collin was incredibly kind and communicative all of the details perfectly. If you’re lucky enough to snag this spot over a weekend consider yourself lucky! "
Green Mountain Access:
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (8)
"Had everything that is needed and easy to get to."
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
10 Mi to Ski Resort: Mendon Hideaway!
Interior

10 Mi to Ski Resort: Mendon Hideaway!

3.0 star property
10 Mi to Ski Resort: Mendon Hideaway!
Red Clover Inn: Queen Suite near Killington
Exterior

Red Clover Inn: Queen Suite near Killington

8.8 out of 10, Excellent, (3)
"Such a beautiful stay that feels like home. Sitting in front of the fireplace or soaking in the bear claw tub makes for a lovely experience. Close to anything you need and activities. From the moment you pull into the driveway you will fall in love"
Red Clover Inn: Queen Suite near Killington
Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM
Living area

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

8.8 out of 10, Excellent, (5)
"VRBO was perfect for everything we needed. Location was right next to the slopes so had no stress with parking. Had everything we needed amenity wise, Bar, Ski rental shop, Pool/ Hot tub. Would recommend to anyone and plan on renting here again this season"
The price is AED 731
AED 1,532 total
includes taxes & fees
1 May - 2 May
Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM
Centrally located apartment for the skier & outdoor enthusiast
Fridge, microwave, oven, stovetop

Centrally located apartment for the skier & outdoor enthusiast

2.0 star property
The price is AED 485
AED 1,226 total
includes taxes & fees
17 Apr - 18 Apr
Centrally located apartment for the skier & outdoor enthusiast
Spacious mountain studio with free WiFi & full kitchen - close to skiing
Indoor pool

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

6.2 out of 10, (19)
"Room was smaller..not spacious as the add suggested. It was advertized as having a fireplace. There are pictures of the fireplace, with wood stacked next to it. Couldnt use the fireplace per order of the FD or something. Felt a little untoward to have a key in room amenity like that be unavailable and not share it. Building was very nice, amenities were very nice. Pool area was top notch, restaurant was good. Having a ski shop on site was super convenient. Parking was sufficient."
The price is AED 364
AED 1,079 total
includes taxes & fees
17 Apr - 18 Apr
Spacious mountain studio with free WiFi & full kitchen - close to skiing
Ben & Jerry Suite | Minutes to Woodstock | Hiking
Aerial view

Ben & Jerry Suite | Minutes to Woodstock | Hiking

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 AED 275
AED 691 total
includes taxes & fees
29 Apr - 30 Apr
Ben & Jerry Suite | Minutes to Woodstock | Hiking
Easy access to VAST snowmobile trail system and local mountain bike trails
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (17)
"3 excellent days of snowmobiling in Vermont! Each day, we took off on trails right on this property! So convenient! It was nice to have a warm clean place to return to each day. We will definitely return!"
Easy access to VAST snowmobile trail system and local mountain bike trails
Run, ride, hike and swim in Central Vermont
Fridge, microwave, oven, stovetop

Run, ride, hike and swim in Central Vermont

9.8 out of 10, Exceptional, (16)
"The house was very cozy and well lit, the design was neat and I liked it very much. It wasn't a long drive to the ski resorts in the area from the house either. Overall a great experience and I would recommend anyone considering to stay here to take the place!"
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+
Property grounds

Killington area home - 4-seasons & hot tub. Sleeps 13+

9.8 out of 10, Exceptional, (117)
"We stayed at this property for a ski weekend in March. 8 guys fit comfortably and the accommodations were perfect. Property was as advertised and very clean. We enjoyed the hot tub after hitting the slopes which was a great way to finish the day. Owner was very accommodating and quick to reply to any inquiries or questions. 10/10"
Killington area home - 4-seasons & hot tub. Sleeps 13+
Private Killington Area Inn all to Yourself!
Fridge, microwave, oven, stovetop

Private Killington Area Inn all to Yourself!

10.0 out of 10, Exceptional, (38)
"Eric is a perfect host! The inn is perfect, 9 rooms, private bathrooms. The kitchen is awesome, great appliances and big enough for everyone to be in the kitchen at the same time. This was our third year with family staying and celebrating. We will be back!"
Private Killington Area Inn all to Yourself!
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
TV, fireplace, DVD player, books

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

10.0 out of 10, Exceptional, (489)
"The cabin had everything we needed, was comfortable, and quiet. It was clean and the beds were comfortable. We had a nice getaway to celebrate a milestone birthday. Jeff couldn't have been nicer and provided ample information about the area and where to eat, etc. Would highly recommend staying at the cabin if you're looking for a quiet escape from your regular life...even if you already live in rural new england as we do. "
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 42 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 an indoor pool are on site. Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi: 8.2 mi/13.2 km away in Bethel.
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.