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

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Pittsfield apartments

Room

1. 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, (16 reviews)
"Great condo and building. Everything in excellent condition. Convenient location."
United States
Joseph S.
The price is CA $174
CA $377 total
includes taxes & fees
Sep 7 - Sep 8
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Apartment (1 Bedroom)

2. Cozy Hotel Room Style Studio Condo With Pool

Cozy Hotel Room Style Studio Condo With Pool
3.0 star property
Killington
The price is CA $201
CA $381 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Hotel Room Style Studio Condo With Pool
Property grounds

3. CubsCorner - Pool, Sauna, Gym, Close to Mountain!

CubsCorner - Pool, Sauna, Gym, Close to Mountain!
Killington
10.0 out of 10, Exceptional, (6 reviews)
"Great location with access to both Pico and Killington Mountains!"
United States
Olaf G.
The price is CA $318
CA $636 total
includes taxes & fees
Sep 7 - Sep 8
CubsCorner - Pool, Sauna, Gym, Close to Mountain!
Exterior

4. 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 $116
CA $400 total
includes taxes & fees
Sep 10 - Sep 11
Spacious mountain studio with free WiFi & full kitchen - close to skiing
Golf

5. 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 $167
CA $453 total
includes taxes & fees
Sep 8 - Sep 9
BearNecessities- Pool, Hot Tub, Gym
Exterior

6. 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 $155
CA $231 total
includes taxes & fees
Sep 6 - Sep 7
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Exterior

7. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is CA $166
CA $317 total
includes taxes & fees
Sep 10 - Sep 11
Bridgewater Living - Ski VT Suite
Terrace/patio

8. 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 $315
CA $626 total
includes taxes & fees
Sep 6 - Sep 7
Wade`s World- AC, Pool, Tennis, Bike to Mountain
Golf

9. 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 $311
CA $626 total
includes taxes & fees
Sep 7 - Sep 8
Bearitime Lodge Pool, Gym, Hot Tub, Close to Resort
Living area

10. 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, (4 reviews)
"Great location to Pico Mountain, clean, warm and spacious! "
United States
Leslie D.
The price is CA $427
CA $895 total
includes taxes & fees
Sep 15 - Sep 16
Robin`s Nest- Pool, Gym, Fireplace, Near the AT
Dining

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

Trails Together! Pool, Hot tub, Sauna, Near Resort
Killington
10.0 out of 10, Exceptional, (2 reviews)
"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 $320
CA $635 total
includes taxes & fees
Sep 7 - Sep 8
Trails Together! Pool, Hot tub, Sauna, Near Resort
Exterior

12. 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 $406
CA $858 total
includes taxes & fees
Sep 8 - Sep 9
BaseLoj - Pool, Firepit, Bike to Mountain!
Room

13. Charming Killington Studio w/ Pool. Bus Route. Ski Rental Deals! - Killington Center Suites 131

Charming Killington Studio w/ Pool. Bus Route. Ski Rental Deals! - Killington Center Suites 131
Killington
The price is CA $95
CA $336 total
includes taxes & fees
Sep 8 - Sep 9
Charming Killington Studio w/ Pool. Bus Route. Ski Rental Deals! - Killington Center Suites 131
Private kitchen

14. Centrally located apartment for the skier & outdoor enthusiast

Centrally located apartment for the skier & outdoor enthusiast
Rutland
The price is CA $181
CA $462 total
includes taxes & fees
Sep 10 - Sep 11
Centrally located apartment for the skier & outdoor enthusiast
Living area

15. 2-BD short drive to DHMC & Dartmouth College

2-BD short drive to DHMC & Dartmouth College
Sharon
The price is CA $263
CA $426 total
includes taxes & fees
Sep 7 - Sep 8
2-BD short drive to DHMC & Dartmouth College
Living area

16. 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 $321
CA $629 total
includes taxes & fees
Sep 8 - Sep 9
BearsLair- Pool, Hot tub, Bike to Mountain!
Living area

17. Birch Hollow- AC, Pool, Hot tub, Gym, Sauna!

Birch Hollow- AC, Pool, Hot tub, Gym, Sauna!
The Woods
10.0 out of 10, Exceptional, (1 review)
"Perfect spot for a low-key off-season vacation for our family of three. Dan and Holly were exceptionally responsive. Would return. "
United States
Jessica T.
The price is CA $407
CA $863 total
includes taxes & fees
Sep 8 - Sep 9
Birch Hollow- AC, Pool, Hot tub, Gym, Sauna!
Terrace/patio

18. BlueBird Escape- Pool, Near Bike Park and Golf!

BlueBird Escape- Pool, Near Bike Park and Golf!
Killington
The price is CA $429
CA $899 total
includes taxes & fees
Sep 6 - Sep 7
BlueBird Escape- Pool, Near Bike Park and Golf!
Pool

19. 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 $418
CA $838 total
includes taxes & fees
Sep 6 - Sep 7
RabbitHole | AC, Pool, Hot Tub, Near Resort
Property grounds

20. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
The price is CA $166
CA $318 total
includes taxes & fees
Sep 10 - Sep 11
Bridgewater Living - Ben&Jerry Suite
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

On The River Inn

On The River Inn

10/10 Excellent
"Very nice. Breakfast is just an ordinary meal buffet."
Orrin 1-night trip
Posted 1 hour ago
On The River Inn

Find out more about Pittsfield

Pittsfield Apartments information

Number of reviews
49
Accommodation
133 Apartments
Lowest Price
CA $231
Highest Price
CA $899

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?
Below is a favorite apartment in the area to consider: Solar-powered Brandon Studio Cabin: Hiking Access: Located 14 mi/22.6 km away in Brandon. Amenities include private patios. Access to free parking 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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