Best Apartments in Pittsfield for Your Vacation from ￥25,231

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Our top choices for Pittsfield apartments

Cozy Rutland Retreat

Rutland

Dave M.

￥30,307 total

includes taxes & fees

Jun 14 - Jun 15

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Killington

Daniel T.

￥25,231 total

includes taxes & fees

Jun 9 - Jun 10

BearNecessities- Pool, Hot Tub, Gym

Killington

Matthew S.

￥52,998 total

includes taxes & fees

Jun 9 - Jun 10

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

Killington

Rebecca B.

￥43,652 total

includes taxes & fees

Jun 14 - Jun 15

Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country

Killington

￥41,550 total

includes taxes & fees

Jun 10 - Jun 11

BearsLair- Pool, Hot tub, Bike to Mountain!

Killington

"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 "

Steve D.

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

Killington

patrick w.

￥70,395 total

includes taxes & fees

Jun 9 - Jun 10

Robin`s Nest- Pool, Gym, Fireplace, Near the AT

Killington

Leslie D.

￥96,599 total

includes taxes & fees

Jun 9 - Jun 10

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

Wallingford

debbie r.

￥27,918 total

includes taxes & fees

Jun 14 - Jun 15

Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.

Killington

Joe S.

￥41,193 total

includes taxes & fees

Jun 9 - Jun 10

BellaVista-Mountain bike to the trails, Pool, Gym

Killington

Tara M.

￥97,033 total

includes taxes & fees

Jun 9 - Jun 10

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

Killington

Stephanie D.

￥70,395 total

includes taxes & fees

Jun 9 - Jun 10

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

Killington

Amy G.

￥102,996 total

includes taxes & fees

Jun 16 - Jun 17

Paradise! A sweet little slice of paradise in this 1 bedroom apartment.

Leicester

"Our hosts were fabulous and extremely accessible. They left us home made treats and fresh eggs from their chickens. And no, roosters did not wake us up in the morning LOL. The property is absolutely gorgeous. The apartment was immaculate and had everything we needed . We were there just before the pool opening but they were busy getting everything ready and I wish we could go back to enjoy that fabulous space. There is also a massive game room but we were too busy to enjoy that space."

Debra

￥29,280 total

includes taxes & fees

Jun 9 - Jun 10

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

Killington

Michael K.

￥69,974 total

includes taxes & fees

Jun 16 - Jun 17

Pinnacle C16

Killington

Steve

￥73,961 total

includes taxes & fees

Jun 26 - Jun 27

BaseLoj - Pool, Firepit, Bike to Mountain!

Killington

Scott R.

￥96,403 total

includes taxes & fees

Jun 9 - Jun 10

Apres Hideaway- Bike to Mountain, Pool, Hiking!

Killington

￥75,213 total

includes taxes & fees

Jun 21 - Jun 22

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

Killington

Hannah M.

￥25,231 total

includes taxes & fees

Jun 9 - Jun 10

Hilltopper Haus- Pool, hot tub, Private Sauna

The Woods

Maura S.

￥120,955 total

includes taxes & fees

Jun 21 - Jun 22

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Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

8/10 Good

"Staff was excellent and went the extra mile to accommodate."

Lincoln Inn & Gallery

6/10 Okay

"My primary complaint was the morning we checked out. Actually we just dropped the key in the basket. You would think with checkout at 10:00 the proprietor would be around to see us off at 9:30. Instead, he was nowhere to be found. The desk had a phone number to call which I did, and the cordless phone rang at the desk but he did not have it with him so we left with the answering machine going off. I just wanted some ice to keep our stuff cold till our next stop. Instead I stopped at a gas station to get ice. Sometimes the devil is in the details."

Mountain Sports Inn

8/10 Good

"This is the 4th or 5th time I have stayed here but in the past it was only for a night or two. This time we were there for 5 nights. There were good things and bad, I’ll start with the bad. My biggest complaints were space for clothing, temperature, and the bed. There are two little drawers in each nightstand, but otherwise all storage areas are open. I prefer to have my underclothes in drawers. That’s a preference thing, but nice to know in advance. The temperature was fine during the day but once you close the blackout drapes, you lose any ability to cool using the window units. The first two nights it was cool enough outside to open a window and that kept it cooler. The last night I was there I slept in top of the cover and blanket (took off comforter first night and never put back on) most of the night to stay cool. If you like to sleep cool (I prefer 67 or 68 degrees), bring a fan. Or maybe ask if they had one, I literally thought of that the last night I was there so didn’t. The bed was harder than I remember it being any other time we stayed and the pillows were flat and hard. It’s also on a spring frame, so every time you move it creaked. We could have asked for more pillows but made do. I would definitely stay again but if it was a longer stay in warmer weather, I would plan ahead and bring a fan. The breakfast was great and had been added to since we last stayed. Ample parking, good WiFi (went down once, but was quickly restored), nice location and friendly people."

Find out more about Pittsfield

Pittsfield Apartments information

Number of reviews	58
Accommodation	141 Apartments
Lowest Price	￥25,231
Highest Price	￥120,955

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 38 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: 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 in Rutland, 14.2 mi/22.8 km away. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available on site. Lake Bomoseen Bunkhouse: 20.1 mi/32.4 km away in Bomoseen. Amenities include fireplaces. Easy access to VAST snowmobile trail system and local mountain bike trails: Located in Randolph Center, 16.5 mi/26.5 km from Pittsfield. Includes free WiFi, sofa beds, and Smart TVs. 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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Apartments in Pittsfield for Rent

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pittsfield apartments

Cozy Rutland Retreat

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

BearNecessities- Pool, Hot Tub, Gym

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

Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country

BearsLair- Pool, Hot tub, Bike to Mountain!

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

Robin`s Nest- Pool, Gym, Fireplace, Near the AT

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

Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.

BellaVista-Mountain bike to the trails, Pool, Gym

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

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

Paradise! A sweet little slice of paradise in this 1 bedroom apartment.

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

Pinnacle C16

BaseLoj - Pool, Firepit, Bike to Mountain!

Apres Hideaway- Bike to Mountain, Pool, Hiking!

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

Hilltopper Haus- Pool, hot tub, Private Sauna

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

Find out more about Pittsfield

Pittsfield Apartments information

Frequently asked questions

Explore a world of travel with Expedia