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

Search Condos Rentals in Pittsfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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 £319
includes taxes & fees
4 Oct - 5 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
9.4 out of 10, Exceptional, (6 reviews)
"Everything was as advertised. Host was responsive to questions. Great stay overall."
United States
Riley T.
The price is £317
includes taxes & fees
5 Oct - 6 Oct
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 lake surrounded by forested hills.

3. 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)
The price is £224
includes taxes & fees
5 Oct - 6 Oct
Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

4. 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 £222
includes taxes & fees
4 Oct - 5 Oct
Welcoming condo near the slopes with free WiFi and full kitchen
A modern kitchen with a microwave, stove, and red stools. A living area with a fireplace and a TV is visible in the background.

5. 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.
The price is £300
includes taxes & fees
4 Oct - 5 Oct
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
A cozy living room with a brick fireplace, two sofas, a coffee table, and a TV mounted on the wall.

6. 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 £291
includes taxes & fees
15 Oct - 16 Oct
Killington condo 5 min to killington resort
A building with a covered entrance, a snow-covered ground, and a tree in the foreground.

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

Summit View at Pico | Mountain Views, Balcony, Fireplace
Killington
The price is £308
includes taxes & fees
4 Oct - 5 Oct
Summit View at Pico | Mountain Views, Balcony, Fireplace
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

8. 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, (8 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.
The price is £285
includes taxes & fees
5 Oct - 6 Oct
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

9. Swirl Suite Annex: Studio w/ Kitchenette and Workspace. Discounted Ski Rentals.

Swirl Suite Annex: Studio w/ Kitchenette and Workspace. Discounted Ski Rentals.
Killington
10.0 out of 10, Exceptional, (1 review)
"Perfect place to stay, no issues at all!"
United States
rebecca w.
The price is £227
includes taxes & fees
5 Oct - 6 Oct
Swirl Suite Annex: Studio w/ Kitchenette and Workspace. Discounted Ski Rentals.
A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

10. 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, (71 reviews)
"Cozy space close to the mountain. Host was very responsive and check in and check out was easy. "
United States
Spencer P.
The price is £288
includes taxes & fees
25 Oct - 26 Oct
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Aerial view

11. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is £354
includes taxes & fees
19 Oct - 20 Oct
The Suites at Killington Center
An aerial view of a residential area with houses, a swimming pool, and a lake surrounded by forested hills.

12. 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
The price is £225
includes taxes & fees
4 Oct - 5 Oct
Renovated Killington Center Studio. Close to Resort. Bus. Discounted Ski Rentals. 523
A living room with a fireplace, a sofa, a coffee table, and a television.

13. 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 £284
includes taxes & fees
6 Oct - 7 Oct
Resort condo with mountain views, full kitchen, and free WiFi
A modern kitchen with granite countertops, a stainless steel sink, and a dining area with a table and chairs.

14. 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
The Woods
10.0 out of 10, Exceptional, (14 reviews)
"Great place to stay. Responsive host, very clean place. Close to amenities. Would definitely recommend and stay again!"
United States
Darlene D.
The price is £429
includes taxes & fees
5 Oct - 6 Oct
Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
A spacious restaurant with high ceilings, exposed ductwork, and a mix of wooden and metal furniture.

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

Killington resort: Walk to Mountain, Bike, Pool
Killington
9.8 out of 10, Exceptional, (33 reviews)
"Excellent location. Clean and easy."
United States
Todd I.
The price is £316
includes taxes & fees
27 Oct - 28 Oct
Killington resort: Walk to Mountain, Bike, Pool
An indoor swimming pool with a hot tub, a second-floor balcony, and a sign indicating a mountain resort.

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

Mountain view condo with fast WiFi plus on-site amenities
Killington
The price is £263
includes taxes & fees
4 Oct - 5 Oct
Mountain view condo with fast WiFi plus on-site amenities
A dining area with a round wooden table and four chairs, a sofa, a lamp, and a kitchen with a stove and microwave.

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

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
8.0 out of 10, Very good, (1 review)
The price is £263
includes taxes & fees
2 Oct - 3 Oct
Comfortable mountain gem with pool, mountain views, & indoor parking space
A modern living room with a glass coffee table, a sofa, a TV mounted on the wall, a fireplace, and a blue accent wall.

18. 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)
"The place was clean and easy to get to. "
United States
Sarah Z.
The price is £226
includes taxes & fees
5 Oct - 6 Oct
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
A snow-covered residential area with multi-story buildings, a ski slope in the background, and a clear sky.

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

Cozy condo, electric fireplace, walk-to-lifts, balcony, views, wif
Killington
The price is £287
includes taxes & fees
2 Oct - 3 Oct
Cozy condo, electric fireplace, walk-to-lifts, balcony, views, wif
A bed with a quilt, a pillow with 'LET IT SNOW' text, and a wall-mounted lamp.

20. Summit Glow at Mountain Green | 2BR Mountain-View Condo | Sleeps 6

Summit Glow at Mountain Green | 2BR Mountain-View Condo | Sleeps 6
Killington
The price is £395
includes taxes & fees
4 Oct - 5 Oct
Summit Glow at Mountain Green | 2BR Mountain-View Condo | Sleeps 6
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

On The River Inn

On The River Inn

8/10 Good
"We had a river view suite. Trouble was you couldn’t see the river. There was to much undergrowth and trees, so you couldn’t tell there was a river there. The view from our balcony was beautiful, out onto the large lawn and a small pond. The TVs are old, so you couldn’t stream. Make sure you tell the front desk or put out your door hanger or you won’t get your room refreshed. The bar seemed open only during dinner hours. During our stay, one night the chief was “out” and they only served burgers. Breakfast was around $18, we never went down. Our room was large and bathroom adequate. It’s a 10 minute drive to town. It’a satisfactory hotel, but not worth the price."
Loxley 3-night trip
Posted 2 hours ago
On The River Inn

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
223
Accommodation
608 Condo Rentals
Lowest Price
£222
Highest Price
£429

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is £222 to £429 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 9.4. Pico Village Resort - Getaway is a favourite pick here. Guests staying at this 3.5-star condo can access ski-in/ski-out facilities and a swimming pool. Silver Spring Chalet - Getaway is another top pick. This 3-star property offers a fireplace and a furnished patio.
How many condos are there in Pittsfield?
You can choose from 608 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?
Settle in at Pico Village Resort - Getaway, a 3.5-star option just a quick drive from town. Amenities here include a swimming pool and a fireplace. Another family-friendly condo is Silver Spring Chalet - Getaway. A fireplace and a yard help make this 3-star property a favourite among guests. After checking in and chilling out together in your cosy new digs, it's time to explore some of the local sights. Pico Mountain at Killington Ski Resort and Gifford Woods State Park are fun family-friendly attractions in Pittsfield.
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.