A lake surrounded by autumn-colored trees and a rocky shoreline.

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Pittsfield apartments

Coffee/tea maker, fridge, microwave, oven

Centrally located apartment for the skier & outdoor enthusiast

Centrally located apartment for the skier & outdoor enthusiast
Rutland
The price is CA $184
CA $461 total
includes taxes & fees
Jul 22 - Jul 23
Centrally located apartment for the skier & outdoor enthusiast
1 bedroom, desk, iron/ironing board, travel crib

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 $177
CA $381 total
includes taxes & fees
Jul 19 - Jul 20
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Dining

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (12 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is CA $128
CA $287 total
includes taxes & fees
Aug 12 - Aug 13
Cozy Rutland Retreat
Coffee/tea maker, fridge, microwave, oven

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, (2 reviews)
"Great stay as always. "
United States
debbie r.
The price is CA $120
CA $245 total
includes taxes & fees
Jul 22 - Jul 23
Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
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.
The price is CA $169
CA $463 total
includes taxes & fees
Jul 19 - Jul 20
BearNecessities- Pool, Hot Tub, Gym
Exterior

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

Spacious mountain studio with free WiFi & full kitchen - close to skiing
Killington
The price is CA $131
CA $430 total
includes taxes & fees
Jul 20 - Jul 21
Spacious mountain studio with free WiFi & full kitchen - close to skiing
Smart TV, fireplace

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

Robin`s Nest- Pool, Gym, Fireplace, Near the AT
Killington
10.0 out of 10, Exceptional, (3 reviews)
"Great location to Pico Mountain, clean, warm and spacious! "
United States
Leslie D.
The price is CA $380
CA $841 total
includes taxes & fees
Jul 19 - Jul 20
Robin`s Nest- Pool, Gym, Fireplace, Near the AT
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.
The price is CA $146
CA $221 total
includes taxes & fees
Jul 23 - Jul 24
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Interior

RabbitHole | AC, Pool, Hot Tub, Near Resort

RabbitHole | AC, Pool, Hot Tub, Near Resort
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 $403
CA $867 total
includes taxes & fees
Jul 21 - Jul 22
RabbitHole | AC, Pool, Hot Tub, Near Resort
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)
"Gorgeous little spot. Slept for comfortably had a fantastic vacation weekend. Great snow first class owners. Perfect for a ski weekend."
United States
Michael K.
The price is CA $297
CA $613 total
includes taxes & fees
Jul 20 - Jul 21
Wade`s World- AC, Pool, Tennis, Bike to Mountain
Dining

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 $303
CA $620 total
includes taxes & fees
Jul 20 - Jul 21
Trails Together! Pool, Hot tub, Sauna, Near Resort
Smart TV, books

Sunny Alpine Suite • Walk to Lake • Private Deck • Yard and Gardens w/Fire Pit

Sunny Alpine Suite • Walk to Lake • Private Deck • Yard and Gardens w/Fire Pit
East Warren
10.0 out of 10, Exceptional, (1 review)
"This was a beautiful VRBO clean, cozy and so well equipped. "
United States
Laura H.
The price is CA $204
CA $423 total
includes taxes & fees
Jul 29 - Jul 30
Sunny Alpine Suite • Walk to Lake • Private Deck • Yard and Gardens w/Fire Pit
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)
"Everything we needed. "
United States
patrick w.
The price is CA $303
CA $620 total
includes taxes & fees
Jul 20 - Jul 21
Bearitime Lodge Pool, Gym, Hot Tub, Close to Resort
TV, fireplace

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 $297
CA $613 total
includes taxes & fees
Jul 28 - Jul 29
BearsLair- Pool, Hot tub, Bike to Mountain!
Terrace/patio

Apres Hideaway- Bike to Mountain, Pool, Hiking!

Apres Hideaway- Bike to Mountain, Pool, Hiking!
Killington
The price is CA $296
CA $608 total
includes taxes & fees
Jul 19 - Jul 20
Apres Hideaway- Bike to Mountain, Pool, Hiking!
Golf

BaseLoj - Pool, Firepit, Bike to Mountain!

BaseLoj - Pool, Firepit, Bike to Mountain!
Killington
10.0 out of 10, Exceptional, (5 reviews)
"Great location, everything we needed for our vacation was there, and really easy access to the multiple base lodges. Skiing conditions were excellent. "
United States
Scott R.
The price is CA $378
CA $835 total
includes taxes & fees
Jul 21 - Jul 22
BaseLoj - Pool, Firepit, Bike to Mountain!
Pool

Hilltopper Haus- Pool, hot tub, Private Sauna

Hilltopper Haus- Pool, hot tub, Private Sauna
The Woods
9.0 out of 10, Wonderful, (2 reviews)
"We thoroughly enjoyed our stay and especially enjoyed the spa after a day of skiing. Open floor plan is terrific and the additional 3 bedrooms allowed privacy. "
United States
Maura S.
The price is CA $498
CA $1,075 total
includes taxes & fees
Jul 22 - Jul 23
Hilltopper Haus- Pool, hot tub, Private Sauna
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, (11 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.
The price is CA $515
CA $1,111 total
includes taxes & fees
Jul 20 - Jul 21
BearHug AC, Pool, Hot Tub, Tennis, Close to Resort
Exterior

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Killington
8.8 out of 10, Excellent, (8 reviews)
"Great room, plenty of amenities, close to restaurants and mountains"
United States
Daniel T.
The price is CA $146
CA $221 total
includes taxes & fees
Jul 29 - Jul 30
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Terrace/patio

BlueBird Escape- Pool, Near Bike Park and Golf!

BlueBird Escape- Pool, Near Bike Park and Golf!
Killington
The price is CA $453
CA $940 total
includes taxes & fees
Jul 18 - Jul 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

Brandon Inn

Brandon Inn

10/10 Excellent
"The property was excellent. Very old inn well maintained, looks almost new. I'd recommend it to all. There is an elevator but is operated by the staff. Old style manual controller."
allen 1-night trip
Posted 4 hours ago
Brandon Inn

Find out more about Pittsfield

Pittsfield Apartments information

Number of reviews
65
Accommodation
134 Apartments
Lowest Price
CA $221
Highest Price
CA $1,111

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: 20.4 mi/32.8 km away in Middlebury. Lake Bomoseen Bunkhouse: It's located in Bomoseen, 20.1 mi/32.4 km from Pittsfield. Includes fireplaces.
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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