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

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Pittsfield condo rentals

Living area

1. 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.
The price is €336
includes taxes & fees
11 Sept - 12 Sept
Killington condo 5 min to killington resort
Dining

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

3. 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.
Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
Smart TV, fireplace, video games, books

4. 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.
The price is €333
includes taxes & fees
14 Sept - 15 Sept
FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym
Dining

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

Snowcub- AC, Pool, Hot tub, Tennis, Grill!
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.
The price is €336
includes taxes & fees
14 Sept - 15 Sept
Snowcub- AC, Pool, Hot tub, Tennis, Grill!
Aerial view

6. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (29 reviews)
"The property is under major construction which was not disclosed when booking. The management fee was almost as much as the room rate, clearer description at time of booking would be appreciated."
United States
Keith
The price is €200
includes taxes & fees
11 Sept - 12 Sept
Mountain Green
Dining

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

Killington resort: Walk to Mountain, Bike, Pool
Killington
9.8 out of 10, Exceptional, (32 reviews)
"Excellent location. Clean and easy."
United States
Todd I.
The price is €299
includes taxes & fees
14 Sept - 15 Sept
Killington resort: Walk to Mountain, Bike, Pool
Interior

8. The Sunup Suite at Killington: 2RM/2BA Condo w/ Pool. Bus Route. Discounted Ski Rentals!

The Sunup Suite at Killington: 2RM/2BA Condo w/ Pool. Bus Route. Discounted Ski Rentals!
Killington
10.0 out of 10, Exceptional, (1 review)
"We had a fantastic three-night stay at this cozy condo in Killington, perfect for our family of four. The location was ideal, just a short drive to the mountain, making it easy for us to hit the slopes each day. The accommodations were comfortable and well-equipped, providing a wonderful home base for our ski vacation!"
United States
Catherine N.
The Sunup Suite at Killington: 2RM/2BA Condo w/ Pool. Bus Route. Discounted Ski Rentals!
TV, fireplace, DVD player, books

9. 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 €326
includes taxes & fees
11 Sept - 12 Sept
Resort condo with mountain views, full kitchen, and free WiFi
Smart TV, fireplace

10. Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.

Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
Killington
10.0 out of 10, Exceptional, (14 reviews)
"A wonderful up to date property a short walk to the lifts! Would definitely stay here again."
United States
Mike B.
Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
Indoor pool

11. 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 €254
includes taxes & fees
13 Sept - 14 Sept
Welcoming condo near the slopes with free WiFi and full kitchen
Indoor pool

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

Mountain view condo with fast WiFi plus on-site amenities
Killington
The price is €301
includes taxes & fees
13 Sept - 14 Sept
Mountain view condo with fast WiFi plus on-site amenities
TV

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

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
The price is €295
includes taxes & fees
11 Sept - 12 Sept
Comfortable mountain gem with pool, mountain views, & indoor parking space
Terrace/patio

14. 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.
The price is €239
includes taxes & fees
20 Sept - 21 Sept
CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
Exterior

15. 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
8.0 out of 10, Very good, (6 reviews)
"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.
The price is €219
includes taxes & fees
20 Sept - 21 Sept
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
Exterior

16. How to Lose Your Ski Pass in 10 Days with Mountain Views on Shuttle Route A1

How to Lose Your Ski Pass in 10 Days with Mountain Views on Shuttle Route A1
Killington
9.0 out of 10, Wonderful, (10 reviews)
"Just all around great!"
United States
chaim f.
The price is €344
includes taxes & fees
20 Sept - 21 Sept
How to Lose Your Ski Pass in 10 Days with Mountain Views on Shuttle Route A1
Terrace/patio

17. Cozy 1BR/1BA Mt Green Condo with Amenities and Discounted Ski Rentals. Shuttle.

Cozy 1BR/1BA Mt Green Condo with Amenities and Discounted Ski Rentals. Shuttle.
Killington
10.0 out of 10, Exceptional, (2 reviews)
"I would highly recommend a stay at this cozy Mt Green Condo. It was clean, spacious, had everything we needed, and was only a five minute shuttle ride to the mountain. The indoor pool and hot tub in the building were great to come back to after a full day of skiing. Thank you to Dave and the Simple Vacations Rental Team for a great few days away!"
United States
Erin M.
Cozy 1BR/1BA Mt Green Condo with Amenities and Discounted Ski Rentals. Shuttle.
Exterior

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

Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.4 out of 10, Exceptional, (58 reviews)
"Great stay. We really loved the ski in ski out feature. Host was responsive with any issues"
United States
Andrea W.
The price is €499
includes taxes & fees
14 Sept - 15 Sept
Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Interior

19. Walk-to-lift condo w/ balcony, fireplace, pool, hot tub, sauna, gym, gameroom

Walk-to-lift condo w/ balcony, fireplace, pool, hot tub, sauna, gym, gameroom
Killington
10.0 out of 10, Exceptional, (1 review)
"Great renovated unit. Very clean. "
United States
Andrea G.
Walk-to-lift condo w/ balcony, fireplace, pool, hot tub, sauna, gym, gameroom
Exterior

20. Luxury Mountain Suite - Ski/Golf/Hike/Play

Luxury Mountain Suite - Ski/Golf/Hike/Play
Killington
9.8 out of 10, Exceptional, (26 reviews)
"This lodge is thoughtfully put together with great amenities and a great set up. Very close to the mountain. We walked, but you also have the option of taking a shuttle that runs frequently."
United States
George O.
The price is €501
includes taxes & fees
24 Sept - 25 Sept
Luxury Mountain Suite - Ski/Golf/Hike/Play
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
"What a wonderful place to stay!! Everything was top notch. We will definitely be staying here again."
caroline 1-night trip
Posted 2 hours ago
Mountain Meadows Lodge

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
247
Accommodation
621 Condo Rentals
Lowest Price
€200
Highest Price
€501

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is €200 to €501 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 621 condos in Pittsfield. No matter if you're travelling with the kids or organising 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.