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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Pittsfield condo rentals

A living room with a sofa, a dining table with chairs, a kitchen area with wooden cabinets, and a bar.

1. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Killington
9.8 out of 10, Exceptional, (14 reviews)
"We had such a great time staying here. It was clean, cozy and so convenient to walk right out the door to the slopes! "
United States
Susanne B.
The price is CA $222
CA $596 total
includes taxes & fees
Oct 4 - Oct 5
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
A modern kitchen with stainless steel appliances, a dining area with a glass table, and a living room with a fireplace.

2. Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
Killington
9.4 out of 10, Exceptional, (6 reviews)
"Everything was as advertised. Host was responsive to questions. Great stay overall."
United States
Riley T.
The price is CA $230
CA $594 total
includes taxes & fees
Oct 5 - Oct 6
Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
An aerial view of a residential area with houses, a swimming pool, and a lake surrounded by forested hills.

3. 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
8.0 out of 10, Very good, (1 review)
Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

4. Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
The price is CA $104
CA $408 total
includes taxes & fees
Oct 4 - Oct 5
Welcoming condo near the slopes with free WiFi and full kitchen
A modern kitchen with a microwave, stove, and red stools. A living area with a fireplace and a TV is visible in the background.

5. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Killington
9.4 out of 10, Exceptional, (12 reviews)
"Quick trip but would stay here again"
United States
John O.
The price is CA $214
CA $584 total
includes taxes & fees
Oct 4 - Oct 5
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
A building with a covered entrance, a snow-covered ground, and a tree in the foreground.

6. Summit View at Pico | Mountain Views, Balcony, Fireplace

Summit View at Pico | Mountain Views, Balcony, Fireplace
Killington
The price is CA $214
CA $571 total
includes taxes & fees
Oct 4 - Oct 5
Summit View at Pico | Mountain Views, Balcony, Fireplace
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

7. 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.
Killington
9.4 out of 10, Exceptional, (8 reviews)
"Beautiful place . My sister was visiting USA/ Vermont for the first time . We went to the Breakfast cafe next door it was amazing . "
United States
Asad B.
The price is CA $231
CA $537 total
includes taxes & fees
Oct 4 - Oct 5
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

8. Swirl Suite Annex: Studio w/ Kitchenette and Workspace. Discounted Ski Rentals.

Swirl Suite Annex: Studio w/ Kitchenette and Workspace. Discounted Ski Rentals.
Killington
10.0 out of 10, Exceptional, (1 review)
"Perfect place to stay, no issues at all!"
United States
rebecca w.
The price is CA $156
CA $429 total
includes taxes & fees
Oct 4 - Oct 5
Swirl Suite Annex: Studio w/ Kitchenette and Workspace. Discounted Ski Rentals.
A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

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

Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Killington
9.6 out of 10, Exceptional, (71 reviews)
"Cozy space close to the mountain. Host was very responsive and check in and check out was easy. "
United States
Spencer P.
The price is CA $188
CA $553 total
includes taxes & fees
Oct 18 - Oct 19
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Aerial view

10. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is CA $323
CA $667 total
includes taxes & fees
Oct 19 - Oct 20
The Suites at Killington Center
An aerial view of a residential area with houses, a swimming pool, and a lake surrounded by forested hills.

11. Renovated Killington Center Studio. Close to Resort. Bus. Discounted Ski Rentals. 523

Renovated Killington Center Studio. Close to Resort. Bus. Discounted Ski Rentals. 523
Killington
7.4 out of 10, Good, (3 reviews)
"Clean room, perfect location close to the mountain, easy acess and good communication with management. "
Canada
Timothy
The price is CA $144
CA $413 total
includes taxes & fees
Oct 4 - Oct 5
Renovated Killington Center Studio. Close to Resort. Bus. Discounted Ski Rentals. 523
A living room with a fireplace, a sofa, a coffee table, and a television.

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

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (47 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is CA $133
CA $534 total
includes taxes & fees
Oct 6 - Oct 7
Resort condo with mountain views, full kitchen, and free WiFi
A modern kitchen with granite countertops, a stainless steel sink, and a dining area with a table and chairs.

13. 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
The Woods
10.0 out of 10, Exceptional, (14 reviews)
"Great place to stay. Responsive host, very clean place. Close to amenities. Would definitely recommend and stay again!"
United States
Darlene D.
The price is CA $327
CA $802 total
includes taxes & fees
Oct 5 - Oct 6
Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
A spacious restaurant with high ceilings, exposed ductwork, and a mix of wooden and metal furniture.

14. Killington resort: Walk to Mountain, Bike, Pool

Killington resort: Walk to Mountain, Bike, Pool
Killington
9.8 out of 10, Exceptional, (33 reviews)
"Excellent location. Clean and easy."
United States
Todd I.
The price is CA $266
CA $631 total
includes taxes & fees
Oct 28 - Oct 29
Killington resort: Walk to Mountain, Bike, Pool
An indoor swimming pool with a hot tub, a second-floor balcony, and a sign indicating a mountain resort.

15. Mountain view condo with fast WiFi plus on-site amenities

Mountain view condo with fast WiFi plus on-site amenities
Killington
The price is CA $149
CA $485 total
includes taxes & fees
Oct 4 - Oct 5
Mountain view condo with fast WiFi plus on-site amenities
A dining area with a round wooden table and four chairs, a sofa, a lamp, and a kitchen with a stove and microwave.

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

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
8.0 out of 10, Very good, (1 review)
The price is CA $149
CA $478 total
includes taxes & fees
Oct 2 - Oct 3
Comfortable mountain gem with pool, mountain views, & indoor parking space
A modern living room with a glass coffee table, a sofa, a TV mounted on the wall, a fireplace, and a blue accent wall.

17. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Killington
9.6 out of 10, Exceptional, (5 reviews)
"The place was clean and easy to get to. "
United States
Sarah Z.
The price is CA $150
CA $421 total
includes taxes & fees
Oct 5 - Oct 6
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
A snow-covered residential area with multi-story buildings, a ski slope in the background, and a clear sky.

18. Cozy condo, electric fireplace, walk-to-lifts, balcony, views, wif

Cozy condo, electric fireplace, walk-to-lifts, balcony, views, wif
Killington
The price is CA $186
CA $523 total
includes taxes & fees
Oct 2 - Oct 3
Cozy condo, electric fireplace, walk-to-lifts, balcony, views, wif
A bed with a quilt, a pillow with 'LET IT SNOW' text, and a wall-mounted lamp.

19. Summit Glow at Mountain Green | 2BR Mountain-View Condo | Sleeps 6

Summit Glow at Mountain Green | 2BR Mountain-View Condo | Sleeps 6
Killington
The price is CA $272
CA $738 total
includes taxes & fees
Oct 4 - Oct 5
Summit Glow at Mountain Green | 2BR Mountain-View Condo | Sleeps 6
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

Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"The place was so clean. The staff was so friendly. The breakfast was delicious!"
David 2-night trip
Posted 3 hours ago
Mountain Meadows Lodge

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
214
Accommodation
614 Condo Rentals
Lowest Price
CA $408
Highest Price
CA $802

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is CA $408 to CA $802 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 9.4. 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 614 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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