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Our top choices for Pittsfield apartments

Vermont Suite | 10 Min to Woodstock & Killington

Vermont Suite | 10 Min to Woodstock & Killington
Bridgewater
10.0 out of 10, Exceptional, (5 reviews)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
United States
Rosie L.
The price is CA $109
CA $265 total
includes taxes & fees
May 18 - May 19
Vermont Suite | 10 Min to Woodstock & Killington

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Killington
9.6 out of 10, Exceptional, (18 reviews)
"Would stay again!"
United States
Hannah M.
The price is CA $143
CA $216 total
includes taxes & fees
May 24 - May 25
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

Vermont Double Queen Suite | 10 Mins to Killington

Vermont Double Queen Suite | 10 Mins to Killington
Bridgewater
8.8 out of 10, Excellent, (5 reviews)
"This was perfect for our girls weekend! Great location, spacious & clean. Our host was so responsive & kind- highly recommend staying here when you visit Salem! "
United States
Brianna L.
The price is CA $110
CA $266 total
includes taxes & fees
May 19 - May 20
Vermont Double Queen Suite | 10 Mins to Killington

BearNecessities- Pool, Hot Tub, Gym

BearNecessities- Pool, Hot Tub, Gym
Killington
10.0 out of 10, Exceptional, (3 reviews)
"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."
United States
Matthew S.
The price is CA $166
CA $453 total
includes taxes & fees
May 18 - May 19
BearNecessities- Pool, Hot Tub, Gym

Vermont Suite | 10 Min to Killington & Woodstock

Vermont Suite | 10 Min to Killington & Woodstock
Bridgewater
9.2 out of 10, Wonderful, (7 reviews)
"Overall, a great stay. "
United States
Meghan J.
The price is CA $103
CA $256 total
includes taxes & fees
Jun 2 - Jun 3
Vermont Suite | 10 Min to Killington & Woodstock

2 Bedroom apartment in Randolph Village VT

2 Bedroom apartment in Randolph Village VT
Randolph
7.0 out of 10, Good, (2 reviews)
"I enjoyed my stay, it was quite comfy and village center is right nearby."
United States
Bryan J.
The price is CA $206
CA $351 total
includes taxes & fees
May 18 - May 19
2 Bedroom apartment in Randolph Village VT

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (8 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
The price is CA $105
CA $256 total
includes taxes & fees
May 18 - May 19
Cozy Rutland Retreat

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Killington
10.0 out of 10, Exceptional, (15 reviews)
"Host was very responsive and the home was great! "
United States
Rebecca B.
The price is CA $173
CA $373 total
includes taxes & fees
May 20 - May 21
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Bearitime Lodge Pool, Gym, Hot Tub, Close to Resort

Bearitime Lodge Pool, Gym, Hot Tub, Close to Resort
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Overall, property was excellent. Only issue was no ac. A fan was provided but air was not moving in the little apartment. It was also unusually hot when were there. Location was excellent for all the hiking we had planned :-)"
United States
Kim C.
The price is CA $297
CA $605 total
includes taxes & fees
May 18 - May 19
Bearitime Lodge Pool, Gym, Hot Tub, Close to Resort

Rabbit Hole | Bike Park, Hot Tub, Pool, AC

Rabbit Hole | Bike Park, Hot Tub, Pool, AC
Killington
10.0 out of 10, Exceptional, (2 reviews)
"Our hosts were super communicative. The check in process was smooth. The condo was clean and well appointed. Beds good. Our hosts even gave us some local coffee and maple syrup as a welcome gift (along with a few other things). Definitely recommend "
United States
Amy G.
The price is CA $395
CA $854 total
includes taxes & fees
May 18 - May 19
Rabbit Hole | Bike Park, Hot Tub, Pool, AC

Trails Together! Pool, Hot tub, Sauna, Near Resort

Trails Together! Pool, Hot tub, Sauna, Near Resort
Killington
10.0 out of 10, Exceptional, (1 review)
"Our stay was great. The condo was spacious with plenty of storage space. Everything we needed was there. The hosts were quickly responsive to questions. The welcome treats were such a nice touch."
United States
Stephanie D.
The price is CA $297
CA $605 total
includes taxes & fees
May 18 - May 19
Trails Together! Pool, Hot tub, Sauna, Near Resort

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

Spacious mountain studio with free WiFi & full kitchen - close to skiing
Killington
6.4 out of 10, (21 reviews)
"Very close to the mountain"
United States
Rachel H.
The price is CA $136
CA $420 total
includes taxes & fees
May 18 - May 19
Spacious mountain studio with free WiFi & full kitchen - close to skiing

Centrally located apartment for the skier & outdoor enthusiast

Centrally located apartment for the skier & outdoor enthusiast
Rutland
7.0 out of 10, Good, (2 reviews)
"We had to head up to killington early and we found this place to crash before our rental was open. The place was great. It was clean and the check in and check out process was very easy. Beds were comfortable. "
United States
tyler m.
The price is CA $182
CA $442 total
includes taxes & fees
May 18 - May 19
Centrally located apartment for the skier & outdoor enthusiast

LilBear- AC, Pool, Sauna, Hot Tub, Near Resort

LilBear- AC, Pool, Sauna, Hot Tub, Near Resort
Killington
10.0 out of 10, Exceptional, (7 reviews)
"Great location and comfortable condo."
United States
Timothy R.
The price is CA $173
CA $392 total
includes taxes & fees
May 18 - May 19
LilBear- AC, Pool, Sauna, Hot Tub, Near Resort

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

Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM
Killington
7.8 out of 10, Good, (6 reviews)
"Comfortable stay. Great location. Pool n spa was very nice and new."
United States
Jerry G.
The price is CA $197
CA $476 total
includes taxes & fees
May 31 - Jun 1
Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM

Little Bear Landing- Pool, Bike to resort!

Little Bear Landing- Pool, Bike to resort!
Killington
The price is CA $291
CA $597 total
includes taxes & fees
May 18 - May 19
Little Bear Landing- Pool, Bike to resort!

Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.

Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Wallingford
10.0 out of 10, Exceptional, (1 review)
"Great stay as always. "
United States
debbie r.
The price is CA $118
CA $239 total
includes taxes & fees
May 18 - May 19
Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.

Wade`s World- AC, Pool, Tennis, Bike to Mountain

Wade`s World- AC, Pool, Tennis, Bike to Mountain
Killington
9.6 out of 10, Exceptional, (7 reviews)
"Perfectly described and so close the mountain. All you need!"
United States
Dana E.
The price is CA $291
CA $597 total
includes taxes & fees
May 18 - May 19
Wade`s World- AC, Pool, Tennis, Bike to Mountain

BearsLair- Pool, Hot tub, Bike to Mountain!

BearsLair- Pool, Hot tub, Bike to Mountain!
Killington
10.0 out of 10, Exceptional, (1 review)
"The Host is amazing, they responded quickly to any questions or concerns we had then to our surprise they left us some gifts from Vermont to enjoy during our stay. The unit was immaculate and is extremely easy and close to get to the slopes and when we were done skiing the hot tub and pool were a great way to reflect on the day. The condo complex has a pro shop for rental equipment as well as a bar/restaurant on site. This place is 5 star "
United States
Steve D.
The price is CA $291
CA $597 total
includes taxes & fees
May 19 - May 20
BearsLair- Pool, Hot tub, Bike to Mountain!

BlueBird Escape- Pool, Near Bike Park and Golf!

BlueBird Escape- Pool, Near Bike Park and Golf!
Killington
The price is CA $395
CA $854 total
includes taxes & fees
May 18 - May 19
BlueBird Escape- Pool, Near Bike Park and Golf!
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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Top Pittsfield Hotel Reviews

Find out more about Pittsfield

Pittsfield Apartments information

Number of reviews
93
Accommodation
141 Apartments
Lowest Price
CA $216
Highest Price
CA $854

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?
Here are some of the more popular apartments in the area: Charming King Loft in Downtown Woodstock: Located in Woodstock, 17.9 mi/28.8 km from the heart of Pittsfield. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available on site. Cozy Rutland Retreat: Located 14.2 mi/22.8 km away in Rutland. Free WiFi and Smart TVs are included. Access to onsite laundry facilities is available on site. Yurt in Middlebury, Vermont: It's located in Middlebury, 20.4 mi/32.8 km away. Doc's Lake house 1st floor, 2 bedroom apartment: 16.6 mi/26.8 km away in Salisbury. Free WiFi, fireplaces, and Smart TVs are included.
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.

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