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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 110 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, (63)
"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
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."
The price is AED 459
AED 1,682 total
includes taxes & fees
7 Apr - 8 Apr
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 198
AED 1,009 total
includes taxes & fees
26 Mar - 27 Mar
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.

8.8 out of 10, Excellent, (3)
"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
Fridge, microwave, oven, stovetop

Wade's World Ski Home FirePlace Shuttle Location

2.0 star property
9.6 out of 10, Exceptional, (4)
"Perfectly described and so close the mountain. All you need!"
The price is AED 341
AED 1,282 total
includes taxes & fees
31 Mar - 1 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 "
The price is AED 303
AED 883 total
includes taxes & fees
26 Mar - 27 Mar
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 338
AED 759 total
includes taxes & fees
1 Apr - 2 Apr
Long Trail Suite | 10 Mins to Mountains | A/C
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:
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 7,458 total
includes taxes & fees
26 Mar - 27 Mar
Modern Ski Château - 4 min from Killington Ski mountain lifts
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, (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
Classic Ski getaway in Killington!
Microwave, oven, stovetop, dishwasher

Classic Ski getaway in Killington!

Classic Ski getaway in Killington!
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

8.0 out of 10, Very Good, (3)
"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 915
AED 1,776 total
includes taxes & fees
26 Mar - 27 Mar
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 1,292 total
includes taxes & fees
7 Apr - 8 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 327
AED 1,083 total
includes taxes & fees
7 Apr - 8 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 334
AED 763 total
includes taxes & fees
8 Apr - 9 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
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 Vermont Ski and Snowmobiling House
Interior

Killington Vermont Ski and Snowmobiling House

9.4 out of 10, Exceptional, (42)
"Good utilitarian property for fall leaf touring. Most everything worked ok, great for large family group but definitely not for someone desiring a fully furnished or decorated place. "
Killington Vermont Ski and Snowmobiling House
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, (116)
"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!
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: 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. Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi: Located 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 located in Killington, 9.9 mi/15.9 km away. 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. Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.: It’s located in Killington, 7.8 mi/12.6 km from Pittsfield. Includes free WiFi and Smart TVs.
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.