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

Search and Rent Pittsfield Condos

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Pittsfield condo rentals

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (25 reviews)
"I enjoy the location "
United States
troy
$185 nightly
The price is $204
Jul 8 - Jul 9
Total with taxes and fees
Mountain Green

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, (46 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
$302 nightly
The price is $342
Jun 30 - Jul 1
Total with taxes and fees
Resort condo with mountain views, full kitchen, and free WiFi

Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
$256 nightly
The price is $290
Jun 30 - Jul 1
Total with taxes and fees
Welcoming condo near the slopes with free WiFi and full kitchen

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
9.2 out of 10, Wonderful, (7 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.
$233 nightly
The price is $263
Jul 1 - Jul 2
Total with taxes and fees
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Four Season Condo: ski, hike, mountain bike & seasonal pool

Four Season Condo: ski, hike, mountain bike & seasonal pool
Warren
$200 nightly
The price is $225
Jul 5 - Jul 6
Total with taxes and fees
Four Season Condo: ski, hike, mountain bike & seasonal pool

Top-floor condo with mountain views & covered parking space

Top-floor condo with mountain views & covered parking space
Killington
9.0 out of 10, Wonderful, (31 reviews)
"Eceptional views, loved the covered parking, ammenities were clean."
United States
Mark A.
$332 nightly
The price is $375
Jun 30 - Jul 1
Total with taxes and fees
Top-floor condo with mountain views & covered parking space

Mountain view condo with fast WiFi plus on-site amenities

Mountain view condo with fast WiFi plus on-site amenities
Killington
$303 nightly
The price is $343
Jun 30 - Jul 1
Total with taxes and fees
Mountain view condo with fast WiFi plus on-site amenities

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)
$212 nightly
The price is $240
Jun 30 - Jul 1
Total with taxes and fees
Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441

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

Cozy condo on ski shuttle route with free WiFi & full ktichen
Killington
$228 nightly
The price is $258
Jul 10 - Jul 11
Total with taxes and fees
Cozy condo on ski shuttle route with free WiFi & full ktichen

Killington resort: Walk to Mountain, Biking & Pool

Killington resort: Walk to Mountain, Biking & Pool
Killington
9.8 out of 10, Exceptional, (32 reviews)
"Excellent VRBO. Perfect location to the mountain. Condo was modern and clean and very comfortable. Would go back again!! "
United States
Sheri L.
$316 nightly
The price is $346
Jun 30 - Jul 1
Total with taxes and fees
Killington resort: Walk to Mountain, Biking & Pool

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

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
$238 nightly
The price is $269
Jul 7 - Jul 8
Total with taxes and fees
Comfortable mountain gem with pool, mountain views, & indoor parking space

Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.4 out of 10, Exceptional, (63 reviews)
"Good place. Hosts were in touch and the hot tub was great. "
United States
Bethany S.
$479 nightly
The price is $542
Jul 1 - Jul 2
Total with taxes and fees
Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

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

Cozy condo, electric fireplace, walk-to-lifts, balcony, views, wif
Killington
$332 nightly
The price is $375
Jun 30 - Jul 1
Total with taxes and fees
Cozy condo, electric fireplace, walk-to-lifts, balcony, views, wif

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.
$285 nightly
The price is $322
Jul 5 - Jul 6
Total with taxes and fees
Killington condo 5 min to killington resort

FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym

FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym
The Woods
10.0 out of 10, Exceptional, (24 reviews)
"Loved the pool, sauna, and steam room. Really nice place, everything we needed. "
United States
Lisa N.
$350 nightly
The price is $395
Jun 30 - Jul 1
Total with taxes and fees
FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"convenient to okemo"
United States
marcus l.
$618 nightly
The price is $692
Jul 15 - Jul 16
Total with taxes and fees
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.

Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.
Killington
9.6 out of 10, Exceptional, (4 reviews)
"We had a special ski weekend with friends. "
United States
Adam C.
$470 nightly
The price is $531
Jul 1 - Jul 2
Total with taxes and fees
Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.

CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis

CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
Killington
9.8 out of 10, Exceptional, (26 reviews)
"Great trip!"
United States
casey d.
$243 nightly
The price is $274
Jul 26 - Jul 27
Total with taxes and fees
CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis

SunBear- AC, Pool, Game Room, Fireplace, Hiking!

SunBear- AC, Pool, Game Room, Fireplace, Hiking!
Killington
9.8 out of 10, Exceptional, (31 reviews)
"Clean and perfect"
United States
Cyle D.
$503 nightly
The price is $569
Jun 30 - Jul 1
Total with taxes and fees
SunBear- AC, Pool, Game Room, Fireplace, Hiking!

Snowcub- AC, Pool, Hot tub, Tennis, Grill!

Snowcub- AC, Pool, Hot tub, Tennis, Grill!
The Woods
10.0 out of 10, Exceptional, (25 reviews)
"We loved our stay at Snowcub! The condo is beautiful, welcoming and our hosts had excellent communication. We were comfortable and enjoyed the nice amenities- including a pool and hot tub! We would love to stay here again! We loved it! "
United States
Maura A.
$376 nightly
The price is $424
Jul 5 - Jul 6
Total with taxes and fees
Snowcub- AC, Pool, Hot tub, Tennis, Grill!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pittsfield Hotel Reviews

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
318
Accommodation
618 Condo Rentals
Lowest Price
$204
Highest Price
$692

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is $204 to $692 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 9.5. 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 618 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.

Explore a world of travel with Expedia