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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Pittsfield condo rentals

Studio | Exterior

Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo

Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo
2.0 star property
Killington
Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo
Exterior

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
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful studio, clean, safe and extremely convenient if you’re going to local shops, restaurants or killington to ski! Easy to check in and out and the staff was very friendly, accessible and accommodating! Would recommend:)"
United States
Maggie M.
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Exterior

The Cozy Cubbie: Charming Studio in Killington. Pool. Bus. Discounted Ski Rentals.

The Cozy Cubbie: Charming Studio in Killington. Pool. Bus. Discounted Ski Rentals.
Killington
8.8 out of 10, Excellent, (5 reviews)
"We did a quick ski getaway, great place, and close to the mountain!"
United States
Al Z.
$489 nightly
The price is $552
Feb 19 - Feb 20
Total with taxes and fees
The Cozy Cubbie: Charming Studio in Killington. Pool. Bus. Discounted Ski Rentals.
Terrace/patio

CozyCub- Location, Fireplace, Ski Off/Shuttle On!

CozyCub- Location, Fireplace, Ski Off/Shuttle On!
Killington
10.0 out of 10, Exceptional, (24 reviews)
"Really enjoyed our time there. It's a simple and straightforward apartment. Easy to get to, and a really nice location."
United States
Matthew G.
$313 nightly
The price is $353
Mar 4 - Mar 5
Total with taxes and fees
CozyCub- Location, Fireplace, Ski Off/Shuttle On!
Exterior

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
9.2 out of 10, Wonderful, (13 reviews)
"Great property, as advertised."
United States
Chris A.
$291 nightly
The price is $329
Mar 10 - Mar 11
Total with taxes and fees
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Exterior detail

Paging Dr. Powder Condo with Mountain Views on Shuttle Route

Paging Dr. Powder Condo with Mountain Views on Shuttle Route
Killington
7.4 out of 10, Good, (3 reviews)
"Great pool, hot tub, shuttle service."
United States
Patricia H.
$497 nightly
The price is $561
Feb 22 - Feb 23
Total with taxes and fees
Paging Dr. Powder Condo with Mountain Views on Shuttle Route
Dining

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
10.0 out of 10, Exceptional, (3 reviews)
"This was our second time at this property because it’s clean and a great location. "
United States
Kristan K.
$481 nightly
The price is $543
Feb 16 - Feb 17
Total with taxes and fees
The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
Indoor pool

Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
7.4 out of 10, Good, (31 reviews)
"beds were comfortable"
United States
Juan T.
$290 nightly
The price is $328
Mar 2 - Mar 3
Total with taxes and fees
Welcoming condo near the slopes with free WiFi and full kitchen
TV

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Killington
9.6 out of 10, Exceptional, (67 reviews)
"Condo well equipped- hosts very responsive-pool area great! "
United States
gail m.
$295 nightly
The price is $333
Feb 22 - Feb 23
Total with taxes and fees
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Outdoor spa tub

Stonefire Chalet at Topridge | 4BR Luxury Ski-In/Ski-Out Retreat, Sleeps 8

Stonefire Chalet at Topridge | 4BR Luxury Ski-In/Ski-Out Retreat, Sleeps 8
Killington
10.0 out of 10, Exceptional, (1 review)
"We had a great few days here! The house was immaculate and lots of lovely, unexpected touches like coffee pods, spices in the cupboard and games. We had 8 and everyone was comfortable. The downstairs area was great for the kids to have some time on their own. Terrific place!"
United States
Kristin S.
$3,023 nightly
The price is $3,416
Feb 15 - Feb 16
Total with taxes and fees
Stonefire Chalet at Topridge | 4BR Luxury Ski-In/Ski-Out Retreat, Sleeps 8
Exterior

Fall Line Condos by Killington VR - Studios

Fall Line Condos by Killington VR - Studios
2.0 star property
Killington
7.0 out of 10, Good, (2 reviews)
"Yes by a shuttle very easy"
United States
Philip
$507 nightly
The price is $558
Feb 17 - Feb 18
Total with taxes and fees
Fall Line Condos by Killington VR - Studios
Property grounds

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, (35 reviews)
"Great stay!"
United States
Bryann F.
$289 nightly
The price is $327
Mar 2 - Mar 3
Total with taxes and fees
Comfortable mountain gem with pool, mountain views, & indoor parking space
Living area

Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (9 reviews)
"We loved staying here. It was comfortable, had everything we needed. 100% would stay here again!"
United States
Vanessa O.
$338 nightly
The price is $382
Mar 4 - Mar 5
Total with taxes and fees
Killington condo 5 min to killington resort
TV, fireplace, books

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 reviews)
"Great place. Met our needs. "
United States
Sean K.
$264 nightly
The price is $298
Mar 11 - Mar 12
Total with taxes and fees
Cozy condo on ski shuttle route with free WiFi & full ktichen
Interior

Trail Creek 41 | Condo in Killington near lifts/hiking with pool & rec room

Trail Creek 41 | Condo in Killington near lifts/hiking with pool & rec room
Killington
9.0 out of 10, Wonderful, (18 reviews)
"Had a great time in a lovely property between town and the resort. "
United States
Alan S.
$441 nightly
The price is $498
Mar 9 - Mar 10
Total with taxes and fees
Trail Creek 41 | Condo in Killington near lifts/hiking with pool & rec room
Aerial view

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
$517 nightly
The price is $568
Feb 22 - Feb 23
Total with taxes and fees
The Suites at Killington Center
Indoor pool, a heated pool

Alpine Oasis Studio at Mountain Green Resort Killington: Shuttle, Pool, Hot Tub, Gym, Deals!

Alpine Oasis Studio at Mountain Green Resort Killington: Shuttle, Pool, Hot Tub, Gym, Deals!
Killington
9.0 out of 10, Wonderful, (8 reviews)
"My friends and I enjoyed it solid spot for a skiing weekend"
United States
Matt M.
Alpine Oasis Studio at Mountain Green Resort Killington: Shuttle, Pool, Hot Tub, Gym, Deals!
1 bedroom, desk, iron/ironing board, travel crib

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
$445 nightly
The price is $503
Feb 17 - Feb 18
Total with taxes and fees
Charming Killington Center Studio Condo on the Bus Route. Discounted Ski Rentals. Pool.
Dining

YOUR KILLINGTON BASECAMP 3A4: Free shuttle w/Pool & Hot tub

YOUR KILLINGTON BASECAMP 3A4: Free shuttle w/Pool & Hot tub
Killington
9.8 out of 10, Exceptional, (29 reviews)
"Good location, nice host"
United States
Li Z.
$541 nightly
The price is $592
Mar 10 - Mar 11
Total with taxes and fees
YOUR KILLINGTON BASECAMP 3A4: Free shuttle w/Pool & Hot tub
Exterior

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

Cozy condo, dog-friendly, electric fireplace, walk-to-lifts, balcony, views, wif
Killington
8.0 out of 10, Very Good, (2 reviews)
"Excellent location with in easy walking distance to the slopes. "
United States
RAYMOND P.
$341 nightly
The price is $386
Mar 2 - Mar 3
Total with taxes and fees
Cozy condo, dog-friendly, electric fireplace, walk-to-lifts, balcony, views, wif
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 Sports Inn

Mountain Sports Inn

10/10 Excellent
"Great time...Great service"
Michael 1-night trip
Posted 3 days ago
Mountain Sports Inn

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
195
Accommodation
633 Condo Rentals
Lowest Price
$298
Highest Price
$3,416

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is $298 to $3,416 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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