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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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.
The price is €338
includes taxes & fees
28 Oct - 29 Oct
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
A modern kitchen with stainless steel appliances, a dining area with a glass table, and a living room with a fireplace.

2. 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.
Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

3. 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, (10 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.
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
A modern kitchen with a microwave, stove, and red stools. A living area with a fireplace and a TV is visible in the background.

4. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Killington
9.4 out of 10, Exceptional, (12 reviews)
"Quick trip but would stay here again"
United States
John O.
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
A modern kitchen with white cabinets, a built-in microwave, and a stainless steel refrigerator.

5. 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, (10 reviews)
"Perfect clean space, very comfortable and great location for the week. We were not big fans of the mattress toppers, they kept sliding off, but that is a personal preference matter. Staff communication was 10 out of 10. Highly recommend."
United States
Lisa
The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. 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.

6. 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.
The price is €327
includes taxes & fees
28 Oct - 29 Oct
Modern Killington Farmhouse Condo: Close to it all! 412
An aerial view of a residential area with houses, a swimming pool, and a lake surrounded by forested hills.

7. 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)
Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
Pass snacks across the counter without leaving the conversation in the main room.

8. 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.
Trailside Loft at Pico | Ski-In/Out Condo w/ Loft + 2BR | Steps to Lift
A cozy living room with a fireplace, a television mounted above it, and a large window offering a view of a snowy landscape.

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

Summit View at Pico | Mountain Views, Balcony, Fireplace
Killington
6.0 out of 10, (1 review)
"We arrived to our booked condo only to find that the place had not been cleaned from the prior renter. It was late, after 9:00 at night. I notified the company and sent pictures. They expeditiously provided us with new accommodations that were not only clean but better. So, I can’t comment on this property much only to say there was a lapse in cleaning and preparing for our booked arrival. What I can say is that management handled the situation appropriately in a timely fashion."
United States
Darlene D.
Summit View at Pico | Mountain Views, Balcony, Fireplace
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
Renovated Killington Center Studio. Close to Resort. Bus. Discounted Ski Rentals. 523
A kitchen with granite countertops, stainless steel faucets, and a rustic chandelier.

11. Forest Hearth at The Woods | 2BR Garden Condo with Pool & Spa | Sleeps 6

Forest Hearth at The Woods | 2BR Garden Condo with Pool & Spa | Sleeps 6
The Woods
10.0 out of 10, Exceptional, (1 review)
"All went extremely well and the condo was even better than expected. Probably one of our best experiences in a while. Would definitely stay here again!"
United States
Dew
Forest Hearth at The Woods | 2BR Garden Condo with Pool & Spa | Sleeps 6
A modern living room with a fireplace, a sofa, a dining area, and a kitchen counter with a sink.

12. Ski-in/Ski-out at Pico | 3BR for 8, Fireplace, Balcony & Killington Shuttle

Ski-in/Ski-out at Pico | 3BR for 8, Fireplace, Balcony & Killington Shuttle
Killington
Ski-in/Ski-out at Pico | 3BR for 8, Fireplace, Balcony & Killington Shuttle
A hotel room with two beds, a desk, a chair, a dresser, a TV, and a window with blinds.

13. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is €420
includes taxes & fees
8 Nov - 9 Nov
The Suites at Killington Center
A modern living room with a glass coffee table, a sofa, a TV mounted on the wall, a fireplace, and a blue accent wall.

14. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Killington
9.6 out of 10, Exceptional, (5 reviews)
"Great room!"
United States
Carla M.
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
A bedroom with a large bed, a bedside table, a chair, a window, and an air conditioning unit.

15. 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
Charming Killington Center Studio Condo on the Bus Route. Discounted Ski Rentals. Pool.
A modern interior with a kitchen, dining area, and living room. A wooden staircase leads to the upper floor.

16. Cedarwood Retreat: 3BR Killington Condo w/ Spa, Pool, Fireplace & Private Jacuzzi Tub

Cedarwood Retreat: 3BR Killington Condo w/ Spa, Pool, Fireplace & Private Jacuzzi Tub
The Woods
10.0 out of 10, Exceptional, (4 reviews)
"The property was nice, very quiet this time of year. The pool and hot tub building was nice.we had a great stay."
United States
Terry R.
Cedarwood Retreat: 3BR Killington Condo w/ Spa, Pool, Fireplace & Private Jacuzzi Tub
A bedroom with two beds, a dresser, a window with a view of greenery, and a painting on the wall.

17. 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.
Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

18. Mountain Green ground-floor condo with private yard off the patio

Mountain Green ground-floor condo with private yard off the patio
Killington
The price is €262
includes taxes & fees
31 Oct - 1 Nov
Mountain Green ground-floor condo with private yard off the patio
A living room with a sofa, coffee table, and fireplace. There is a large window and a balcony with outdoor furniture.

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

FirBear- Pool, Gym, Fireplace, Hot tub!
The Woods
9.8 out of 10, Exceptional, (25 reviews)
"Great place to stay for an escape to the mountains!"
United States
Kristin G.
The price is €346
includes taxes & fees
28 Oct - 29 Oct
FirBear- Pool, Gym, Fireplace, Hot tub!
A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

20. 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, (72 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.
The price is €615
includes taxes & fees
26 Nov - 27 Nov
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
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
"Extremely good B&B. Great breakfast. Very friendly and helpful staff/managers. Beautiful area and site location."
Wm Lynn 3-night trip
Posted 2 hours ago
Mountain Meadows Lodge

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
228
Accommodation
614 Condo Rentals
Lowest Price
€228
Highest Price
€512

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is €228 to €512 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 9.1. 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 614 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.