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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Pittsfield condo rentals

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 Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
2.0 star property
Killington
10.0 out of 10, Exceptional, (1)
"8 mins drive from ski lodge"
United States
YUXIANG
The price is AED 456
AED 1,169 total
includes taxes & fees
19 Jan - 20 January 2026
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Condo, 4 Bedrooms | Dining
Sunrise Bear Ridge C4 4 Bedroom Condo

Sunrise Bear Ridge C4 4 Bedroom Condo

Sunrise Bear Ridge C4 4 Bedroom Condo
3.0 star property
Killington
Sunrise Bear Ridge C4 4 Bedroom Condo
Interior
Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access

Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access

Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access
2.0 star property
Killington
The price is AED 562
AED 1,440 total
includes taxes & fees
13 Jan - 14 January 2026
Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access
TV, DVD player, books
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

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Killington
9.4 out of 10, Exceptional, (9)
"Great property, as advertised."
United States
Chris A.
The price is AED 488
AED 1,240 total
includes taxes & fees
7 Jan - 8 January 2026
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Condo, 1 Bedroom, Kitchen, Garden View | Terrace/patio
The Suites at Killington Center

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The Suites at Killington Center
Fridge, microwave, dishwasher, coffee/tea maker
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Killington
9.4 out of 10, Exceptional, (64)
"Condo well equipped- hosts very responsive-pool area great! "
United States
gail m.
The price is AED 526
AED 1,150 total
includes taxes & fees
6 Jan - 7 January 2026
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Indoor pool, a heated pool
Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.

Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.

Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.
2.5 star property
Killington
10.0 out of 10, Exceptional, (2)
"Roomy, excellant property. I would rent again, loved it"
United States
Mickey E.
The price is AED 676
AED 1,866 total
includes taxes & fees
13 Jan - 14 January 2026
Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.
Interior
Resort condo with balcony & shared seasonal amenities - close to skiing

Resort condo with balcony & shared seasonal amenities - close to skiing

Resort condo with balcony & shared seasonal amenities - close to skiing
Killington
8.2 out of 10, Very Good, (35)
"Perfect accommodations. Clean, modern, comfortable, plenty of space, walking distance from the entire resort. The queen bed is incredibly comfortable! 10/10!"
United States
Ryan L.
The price is AED 404
AED 1,338 total
includes taxes & fees
26 Jan - 27 January 2026
Resort condo with balcony & shared seasonal amenities - close to skiing
Indoor pool
Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
7.2 out of 10, Good, (30)
"beds were comfortable"
United States
Juan T.
The price is AED 404
AED 1,321 total
includes taxes & fees
4 Jan - 5 January 2026
Welcoming condo near the slopes with free WiFi and full kitchen
Exterior detail
Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals

Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals

Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals
2.0 star property
Killington
Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals
Exterior
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

Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
Killington
9.2 out of 10, Wonderful, (5)
"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.
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
Condo, 1 Bedroom | Exterior
Killington Ski Resort VT Vacation Condos

Killington Ski Resort VT Vacation Condos

Killington Ski Resort VT Vacation Condos
3.5 star property
Killington
Killington Ski Resort VT Vacation Condos
1 bedroom, desk, iron/ironing board, free WiFi
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

Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
Killington
The price is AED 553
AED 1,323 total
includes taxes & fees
12 Jan - 13 January 2026
Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
Terrace/patio
Killington condo 5 min to killington resort

Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (8)
"We loved staying here. It was comfortable, had everything we needed. 100% would stay here again!"
United States
Vanessa O.
The price is AED 612
AED 1,500 total
includes taxes & fees
8 Jan - 9 January 2026
Killington condo 5 min to killington resort
Property grounds
Comfortable mountain gem with pool, mountain views, & indoor parking space

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, (32)
"Great stay!"
United States
Bryann F.
The price is AED 371
AED 1,342 total
includes taxes & fees
12 Jan - 13 January 2026
Comfortable mountain gem with pool, mountain views, & indoor parking space
Indoor pool
Cozy condo on ski shuttle route with free WiFi & full ktichen

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)
"Great place. Met our needs. "
United States
Sean K.
The price is AED 378
AED 1,174 total
includes taxes & fees
11 Jan - 12 January 2026
Cozy condo on ski shuttle route with free WiFi & full ktichen
Fridge, microwave, oven, stovetop
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

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

Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Killington
9.8 out of 10, Exceptional, (61)
"We enjoyed our stay, location was super convenient for dining & skiing. We will consider this property for any future trips. Thank you"
United States
Kyle H.
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Property grounds
Resort condo with mountain views, full kitchen, and free WiFi

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

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.6 out of 10, Excellent, (45)
"Very close to Killington and in the shuttle route."
United States
Craig C.
The price is AED 610
AED 1,853 total
includes taxes & fees
21 Jan - 22 January 2026
Resort condo with mountain views, full kitchen, and free WiFi
Indoor pool, a heated pool
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

Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
3.0 star property
The Woods
9.8 out of 10, Exceptional, (7)
"Very clean and well equipped condo! We enjoyed our stay."
United States
Tanya W.
Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
Indoor pool
Mountain view condo with full kitchen and free WiFi

Mountain view condo with full kitchen and free WiFi

Mountain view condo with full kitchen and free WiFi
Killington
7.8 out of 10, Good, (37)
"Clean, comfortable, full kitchen, fast internet, plenty of parking, great location right by the Killington base lodges. Would definitely stay here again."
United States
Brian B.
The price is AED 522
AED 1,401 total
includes taxes & fees
11 Jan - 12 January 2026
Mountain view condo with full kitchen and free WiFi
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

Brandon Inn

Brandon Inn

10/10 Excellent
"Staff is friendly and courteous. location is only 40 minutes from Killington."
Gene 4-night trip
Posted 1 day ago
Brandon Inn

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is AED 1,150 to AED 1,866 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.
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.