Search and Rent Pittsfield Condos

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Our top choices for Pittsfield condo rentals

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
2.0 star property
Killington
10.0 out of 10, Exceptional, (1)
"8 mins drive from ski lodge"
United States
YUXIANG
$282 nightly
The price is $318
Jan 19 - Jan 20, 2026
Total with taxes and fees
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Sunrise Bear Ridge C4 4 Bedroom Condo

Sunrise Bear Ridge C4 4 Bedroom Condo
3.0 star property
Killington
Sunrise Bear Ridge C4 4 Bedroom Condo

Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access

Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access
2.0 star property
Killington
$337 nightly
The price is $381
Jan 13 - Jan 14, 2026
Total with taxes and fees
Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Killington
9.4 out of 10, Exceptional, (9)
"Great property, as advertised."
United States
Chris A.
$299 nightly
The price is $338
Jan 7 - Jan 8, 2026
Total with taxes and fees
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
$406 nightly
The price is $447
Jan 14 - Jan 15, 2026
Total with taxes and fees
The Suites at Killington Center

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Killington
9.4 out of 10, Exceptional, (64)
"Condo well equipped- hosts very responsive-pool area great! "
United States
gail m.
$277 nightly
The price is $313
Jan 4 - Jan 5, 2026
Total with taxes and fees
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.

Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.
2.5 star property
Killington
10.0 out of 10, Exceptional, (2)
"Roomy, excellant property. I would rent again, loved it"
United States
Mickey E.
$506 nightly
The price is $571
Jan 13 - Jan 14, 2026
Total with taxes and fees
Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.

Resort condo with balcony & shared seasonal amenities - close to skiing

Resort condo with balcony & shared seasonal amenities - close to skiing
Killington
8.2 out of 10, Very Good, (35)
"Perfect accommodations. Clean, modern, comfortable, plenty of space, walking distance from the entire resort. The queen bed is incredibly comfortable! 10/10!"
United States
Ryan L.
$323 nightly
The price is $365
Jan 26 - Jan 27, 2026
Total with taxes and fees
Resort condo with balcony & shared seasonal amenities - close to skiing

Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
7.2 out of 10, Good, (30)
"beds were comfortable"
United States
Juan T.
$325 nightly
The price is $367
Jan 7 - Jan 8, 2026
Total with taxes and fees
Welcoming condo near the slopes with free WiFi and full kitchen

Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals

Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals
2.0 star property
Killington
$357 nightly
The price is $403
Jan 12 - Jan 13, 2026
Total with taxes and fees
Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals

Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
Killington
9.2 out of 10, Wonderful, (5)
"I don’t think I’ve ever had such wonderful service checking in and caring for our needs. Amazing response time and outstanding stay. Thank you."
United States
Margaret L.
$338 nightly
The price is $382
Dec 31 - Jan 1, 2026
Total with taxes and fees
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

Killington Ski Resort VT Vacation Condos

Killington Ski Resort VT Vacation Condos
3.5 star property
Killington
$377 nightly
The price is $423
Jan 21 - Jan 22, 2026
Total with taxes and fees
Killington Ski Resort VT Vacation Condos

Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441

Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
Killington
$297 nightly
The price is $335
Jan 12 - Jan 13, 2026
Total with taxes and fees
Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441

Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (8)
"We loved staying here. It was comfortable, had everything we needed. 100% would stay here again!"
United States
Vanessa O.
$341 nightly
The price is $385
Jan 19 - Jan 20, 2026
Total with taxes and fees
Killington condo 5 min to killington resort

Comfortable mountain gem with pool, mountain views, & indoor parking space

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
8.4 out of 10, Very Good, (32)
"Great stay!"
United States
Bryann F.
$338 nightly
The price is $382
Jan 12 - Jan 13, 2026
Total with taxes and fees
Comfortable mountain gem with pool, mountain views, & indoor parking space

Cozy condo on ski shuttle route with free WiFi & full ktichen

Cozy condo on ski shuttle route with free WiFi & full ktichen
Killington
8.4 out of 10, Very Good, (38)
"Great place. Met our needs. "
United States
Sean K.
$283 nightly
The price is $320
Jan 11 - Jan 12, 2026
Total with taxes and fees
Cozy condo on ski shuttle route with free WiFi & full ktichen

Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Killington
9.8 out of 10, Exceptional, (61)
"We enjoyed our stay, location was super convenient for dining & skiing. We will consider this property for any future trips. Thank you"
United States
Kyle H.
$333 nightly
The price is $377
Jan 14 - Jan 15, 2026
Total with taxes and fees
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.6 out of 10, Excellent, (45)
"Very close to Killington and in the shuttle route."
United States
Craig C.
$446 nightly
The price is $504
Jan 21 - Jan 22, 2026
Total with taxes and fees
Resort condo with mountain views, full kitchen, and free WiFi

Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5

Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
3.0 star property
The Woods
9.8 out of 10, Exceptional, (7)
"Very clean and well equipped condo! We enjoyed our stay."
United States
Tanya W.
$405 nightly
The price is $458
Jan 5 - Jan 6, 2026
Total with taxes and fees
Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5

Mountain view condo with full kitchen and free WiFi

Mountain view condo with full kitchen and free WiFi
Killington
7.8 out of 10, Good, (37)
"Clean, comfortable, full kitchen, fast internet, plenty of parking, great location right by the Killington base lodges. Would definitely stay here again."
United States
Brian B.
$336 nightly
The price is $379
Jan 11 - Jan 12, 2026
Total with taxes and fees
Mountain view condo with full kitchen and free WiFi
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 Condo Rentals information

Number of reviews
219
Accommodation
633 Condo Rentals
Lowest Price
$313
Highest Price
$571

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is $313 to $571 per night. No matter your budget, you'll find someplace that suits your needs — as well as your entire squad! These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best condos in Pittsfield?
Pittsfield offers multiple condos with a total average guest review rating of 8.8. Silver Spring Chalet - Getaway is one highly recommended option. Guests staying at this 3-star condo will enjoy amenities such as a furnished patio and a fireplace. Slopeside Pico 3 Bedroom Condo is another popular choice. This 3-star property offers a swimming pool and ski-in/ski-out facilities.
How many condos are there in Pittsfield?
You can choose from 633 condos in Pittsfield. No matter if you're traveling with the kids or organizing a weekend break with some friends, Expedia can help you find the perfect space for your entire crew.
Are there any family-friendly condos in Pittsfield?
Put your feet up at Silver Spring Chalet - Getaway, a 3-star option not far from town. Conveniences here include a furnished patio and a fireplace. Another family-friendly condo is Slopeside Pico 3 Bedroom Condo. Ski-in/ski-out facilities and a swimming pool help make this 3-star escape a hit with guests. Once you've checked in and unpacked your suitcase, there are loads of family-friendly attractions to explore in and around Pittsfield. Pico Mountain at Killington Ski Resort and Gifford Woods State Park guarantee fun for all ages.
Why book your condo in Pittsfield with Expedia?
With Expedia, it's easy to find your dream condo in Pittsfield. After a luxury stay? Take advantage of our filters to search for properties that are 5-star rated. If you have a budget in mind, click on how much you'd like to spend and then check out our amazing deals. We'll help you find a suitable stay whatever your style of travel or plans.
How can I find cheap condos in Pittsfield?
Expedia can help you narrow your search for cheap condos in Pittsfield. To discover your special stay in a few clicks, try out the filter tool to refine your search by star rating, budget and amenities.

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