Apartments in Pittsfield for Rent

Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Pittsfield apartments

Property grounds

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.
$178 nightly
The price is $195
Apr 30 - May 1
Total with taxes and fees
Vermont Double Queen Suite | 10 Mins to Killington
Interior

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.
$145 nightly
The price is $157
May 1 - May 2
Total with taxes and fees
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Property grounds

Vermont Suite | Minutes to Killington | Skiing

Vermont Suite | Minutes to Killington | Skiing
Bridgewater
8.0 out of 10, Very Good, (2 reviews)
"clean, easy to check in and out, convenient location to the GMHA grounds - we stay here every summer! "
United States
Amanda K.
$171 nightly
The price is $187
Apr 30 - May 1
Total with taxes and fees
Vermont Suite | Minutes to Killington | Skiing
Property grounds

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.
$179 nightly
The price is $196
Apr 30 - May 1
Total with taxes and fees
Vermont Suite | 10 Min to Woodstock & Killington
Property grounds

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.
$171 nightly
The price is $187
Apr 30 - May 1
Total with taxes and fees
Vermont Suite | 10 Min to Killington & Woodstock
Fridge, microwave, oven, stovetop

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, (14 reviews)
"Host was very responsive and the home was great! "
United States
Rebecca B.
$241 nightly
The price is $272
May 3 - May 4
Total with taxes and fees
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Indoor pool

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

Clean & bright condo with mountain views & modern kitchen - walk to lifts
Killington
7.0 out of 10, Good, (48 reviews)
"Perfect place for a long weekend"
United States
Patrick D.
$210 nightly
The price is $237
May 2 - May 3
Total with taxes and fees
Clean & bright condo with mountain views & modern kitchen - walk to lifts
Living area

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.
$226 nightly
The price is $253
Apr 30 - May 1
Total with taxes and fees
2 Bedroom apartment in Randolph Village VT
Interior

Scandibearia- Private Suana, Pool, Hot tub

Scandibearia- Private Suana, Pool, Hot tub
Killington
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely loved our stay! The room was everything we needed plus more. Every detail that was put into the room was impeccable, from the cleanliness to all the features being present which cut pointless spending. Our stay was flawless and our hosts went above and beyond to make us feel at home. We will be staying here again in the future for sure! "
United States
Michael H.
Scandibearia- Private Suana, Pool, Hot tub
Golf

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.
$293 nightly
The price is $331
May 3 - May 4
Total with taxes and fees
BearNecessities- Pool, Hot Tub, Gym
Dining

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (7 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
$167 nightly
The price is $186
Apr 30 - May 1
Total with taxes and fees
Cozy Rutland Retreat
Golf

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.
$401 nightly
The price is $441
Apr 30 - May 1
Total with taxes and fees
Bearitime Lodge Pool, Gym, Hot Tub, Close to Resort
Interior

Rabbit Hole- Near Bike park and Golf Pool Hot tub

Rabbit Hole- Near Bike park and Golf Pool Hot tub
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.
Rabbit Hole- Near Bike park and Golf Pool Hot tub
Terrace/patio

Little Bear Landing- Pool, Bike to resort!

Little Bear Landing- Pool, Bike to resort!
Killington
$397 nightly
The price is $437
Apr 30 - May 1
Total with taxes and fees
Little Bear Landing- Pool, Bike to resort!
Interior

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.
$401 nightly
The price is $441
Apr 30 - May 1
Total with taxes and fees
Trails Together! Pool, Hot tub, Sauna, Near Resort
Golf

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.
$253 nightly
The price is $286
May 3 - May 4
Total with taxes and fees
LilBear- AC, Pool, Sauna, Hot Tub, Near Resort
Indoor pool

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)
"Communication was excellent and the condo was extremely clean."
United States
Susan L.
$272 nightly
The price is $307
Apr 30 - May 1
Total with taxes and fees
Spacious mountain studio with free WiFi & full kitchen - close to skiing
Fridge, microwave, oven, stovetop

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.
$285 nightly
The price is $321
Apr 30 - May 1
Total with taxes and fees
Centrally located apartment for the skier & outdoor enthusiast
Terrace/patio

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.
$397 nightly
The price is $437
Apr 30 - May 1
Total with taxes and fees
Wade`s World- AC, Pool, Tennis, Bike to Mountain
Smart TV, fireplace

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

BearHug AC, Pool, Hot Tub, Tennis, Close to Resort
Killington
10.0 out of 10, Exceptional, (10 reviews)
"Great experience staying at Bear Hug for a New Year’s ski trip. Hosts Dan and Holly were very responsive and the unit was as advertised. Made great use of he fireplace and close access to slopes. "
United States
Matthew M.
$722 nightly
The price is $791
Apr 30 - May 1
Total with taxes and fees
BearHug AC, Pool, Hot Tub, Tennis, Close to Resort
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

Brandon Inn

Brandon Inn

10/10 Excellent
"Inn staff was extremely helpful and friendly. Everything was clean, and the Inn was charming, with many historical details. The breakfast was good, and our room great for our purposes. The room did not contain a fridge, which was a bit disappointing. We would stay here again."
Susanne 3-night trip
Posted 7 hours ago
Brandon Inn

Find out more about Pittsfield

Pittsfield Apartments information

Number of reviews
145
Accommodation
141 Apartments
Lowest Price
$157
Highest Price
$791

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 44 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: Cozy renovated barn apartment on first floor: Includes free WiFi and private patios. Access to onsite laundry facilities is available on site. Charming King Loft in Downtown Woodstock: Located 17.9 mi/28.8 km away in Woodstock. Free WiFi and Smart TVs are included. Access to onsite laundry facilities is available on site. Doc's Lake house 1st floor, 2 bedroom apartment: It's situated in Salisbury, 16.6 mi/26.8 km away. Includes free WiFi, fireplaces, and Smart TVs. 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.
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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