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

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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.
$329 nightly
The price is $372
Oct 18 - Oct 19
Total with taxes and fees
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Aerial view

2. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
$376 nightly
The price is $414
Oct 20 - Oct 21
Total with taxes and fees
The Suites at Killington Center
An aerial view of a residential area with houses, roads, and a mountain in the background.

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)
$228 nightly
The price is $257
Oct 18 - Oct 19
Total with taxes and fees
Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
A modern kitchen with stainless steel appliances, a dining area with a glass table, and a living room with a fireplace.

4. 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
9.6 out of 10, Exceptional, (7 reviews)
"Everything was as advertised. Host was responsive to questions. Great stay overall."
United States
Riley T.
$325 nightly
The price is $367
Oct 18 - Oct 19
Total with taxes and fees
Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
A modern living room with a stone fireplace, a flat-screen TV mounted above it, wooden flooring, and a kitchen area in the background.

5. Modern Killington Farmhouse Condo: Close to it all! 412

Modern Killington Farmhouse Condo: Close to it all! 412
Killington
10.0 out of 10, Exceptional, (61 reviews)
"Fantastic spot for hitting mountains as a family. Incredibly clean, convenience, and comfortable. Couldn’t be better! EV charging on site was the icing on the cake "
United States
Tyler L.
$329 nightly
The price is $372
Oct 18 - Oct 19
Total with taxes and fees
Modern Killington Farmhouse Condo: Close to it all! 412
A bedroom with a large bed, a bedside table, a chair, a window, and an air conditioning unit.

6. Charming Killington Center Studio Condo on the Bus Route. Discounted Ski Rentals. Pool.

Charming Killington Center Studio Condo on the Bus Route. Discounted Ski Rentals. Pool.
Killington
$243 nightly
The price is $275
Oct 18 - Oct 19
Total with taxes and fees
Charming Killington Center Studio Condo on the Bus Route. Discounted Ski Rentals. Pool.
A cozy living room with a brick fireplace, two sofas, a coffee table, and a TV mounted on the wall.

7. Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (9 reviews)
"Great location!!"
United States
Nicholas C.
$345 nightly
The price is $390
Oct 18 - Oct 19
Total with taxes and fees
Killington condo 5 min to killington resort
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

8. 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.
$261 nightly
The price is $295
Oct 21 - Oct 22
Total with taxes and fees
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
A modern kitchen with white cabinets, a built-in microwave, and a stainless steel refrigerator.

9. The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.

The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
Killington
9.2 out of 10, Wonderful, (9 reviews)
"Great condo! We enjoyed our stay! "
United States
Frank M.
$329 nightly
The price is $372
Oct 19 - Oct 20
Total with taxes and fees
The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
An aerial view of a residential area with houses, a swimming pool, and a lake surrounded by forested hills.

10. 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
$257 nightly
The price is $291
Oct 18 - Oct 19
Total with taxes and fees
Renovated Killington Center Studio. Close to Resort. Bus. Discounted Ski Rentals. 523
A building with a covered entrance, a snow-covered ground, and a tree in the foreground.

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

Summit View at Pico | Mountain Views, Balcony, Fireplace
Killington
$370 nightly
The price is $418
Oct 18 - Oct 19
Total with taxes and fees
Summit View at Pico | Mountain Views, Balcony, Fireplace
A modern dining room with a glass table, chairs, a fireplace, and a television.

12. SnowCub- Pets Indoor Pool Hot Tub Sauna Fireplace

SnowCub- Pets Indoor Pool Hot Tub Sauna Fireplace
The Woods
10.0 out of 10, Exceptional, (26 reviews)
"We had an excellent time and will definitely stay again. Great home, perfect location, well appointed kitchen and welcomed our pets!"
United States
Lisa A.
$352 nightly
The price is $398
Oct 20 - Oct 21
Total with taxes and fees
SnowCub- Pets Indoor Pool Hot Tub Sauna Fireplace
A modern living room with a fireplace, a television mounted on the wall, and a dining area with chairs and a table.

13. Trailside Loft at Pico | Ski-In/Out Condo w/ Loft + 2BR | Steps to Lift

Trailside Loft at Pico | Ski-In/Out Condo w/ Loft + 2BR | Steps to Lift
Killington
10.0 out of 10, Exceptional, (3 reviews)
"Great midweek ski vacation. Easily walked to the slope to get to the kiosk for our ticket. Kitchen had all that we needed. "
United States
Casey C.
$447 nightly
The price is $505
Oct 19 - Oct 20
Total with taxes and fees
Trailside Loft at Pico | Ski-In/Out Condo w/ Loft + 2BR | Steps to Lift
A living room with a sofa, coffee table, and fireplace. There is a large window and a balcony with outdoor furniture.

14. FirBear- Pool, Gym, Fireplace, Hot tub!

FirBear- Pool, Gym, Fireplace, Hot tub!
The Woods
9.8 out of 10, Exceptional, (25 reviews)
"Loved the pool, sauna, and steam room. Really nice place, everything we needed. "
United States
Lisa N.
$350 nightly
The price is $395
Oct 20 - Oct 21
Total with taxes and fees
FirBear- Pool, Gym, Fireplace, Hot tub!
A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

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

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
$255 nightly
The price is $289
Oct 18 - Oct 19
Total with taxes and fees
Welcoming condo near the slopes with free WiFi and full kitchen
A modern kitchen with granite countertops, a stainless steel sink, and a dining area with a table and chairs.

16. 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.
$418 nightly
The price is $472
Oct 18 - Oct 19
Total with taxes and fees
Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

17. 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)
"This condo is in a great location and offers plenty of space with 2 full bathrooms. It is ground floor with no steps to get in. Beds were comfortable and plenty of towels were provided. We came in summer and the unit does have two AC units in it. The description and photos are accurate, and it was a very pleasant stay."
United States
Mari B.
$344 nightly
The price is $388
Oct 18 - Oct 19
Total with taxes and fees
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
A bedroom with two beds, a dresser, a window with a view of greenery, and a painting on the wall.

18. Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631

Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
Killington
9.0 out of 10, Wonderful, (7 reviews)
"Easy, convenient location. Perfect no frills last minute ski trip. Would stay again. Good communication."
United States
Marcus G.
$221 nightly
The price is $250
Oct 19 - Oct 20
Total with taxes and fees
Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
A modern kitchen with stainless steel appliances, a black countertop, and wooden cabinets.

19. Spacious 2BR/3BA Killington Condo w/ EV Charger, Ski Discounts & Pool

Spacious 2BR/3BA Killington Condo w/ EV Charger, Ski Discounts & Pool
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great location! Check in and check out process was super easy. Loved it!"
United States
Justin P.
$409 nightly
The price is $462
Oct 18 - Oct 19
Total with taxes and fees
Spacious 2BR/3BA Killington Condo w/ EV Charger, Ski Discounts & Pool
An indoor swimming pool with a clear view of the surrounding area, including a seating area and a staircase.

20. Trail Creek: 1 BR with Loft. Ski Home Trail. Bus. Hot Tub. Pool. #64

Trail Creek: 1 BR with Loft. Ski Home Trail. Bus. Hot Tub. Pool. #64
Killington
7.0 out of 10, Good, (2 reviews)
"it was okay a bit misrepresented"
Canada
Ian P.
$352 nightly
The price is $398
Oct 18 - Oct 19
Total with taxes and fees
Trail Creek: 1 BR with Loft. Ski Home Trail. Bus. Hot Tub. Pool. #64
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
"Wonderful place! Very helpful staff"
Blair 2-night trip
Posted 2 hours ago
Mountain Meadows Lodge

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
258
Accommodation
617 Condo Rentals
Lowest Price
$250
Highest Price
$505

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is $250 to $505 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 9.2. 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 617 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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