Search Pittsfield Condo Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Pittsfield condo rentals

Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (25 reviews)
"I enjoy the location "
United States
troy
The price is €177
includes taxes & fees
8 Jun - 9 Jun
Mountain Green
Property grounds

Trailside Village #5: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #5: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.6 out of 10, Exceptional, (25 reviews)
"It was in great conditioning with a functioning fireplace and hot tub. "
United States
Clare B.
The price is €484
includes taxes & fees
8 Jun - 9 Jun
Trailside Village #5: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Terrace/patio

CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis

CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
Killington
10.0 out of 10, Exceptional, (25 reviews)
"Great trip!"
United States
casey d.
The price is €236
includes taxes & fees
14 Jun - 15 Jun
CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
Interior

SunBear- AC, Pool, Game Room, Fireplace, Hiking!

SunBear- AC, Pool, Game Room, Fireplace, Hiking!
Killington
9.8 out of 10, Exceptional, (31 reviews)
"Clean and perfect"
United States
Cyle D.
The price is €487
includes taxes & fees
8 Jun - 9 Jun
SunBear- AC, Pool, Game Room, Fireplace, Hiking!
Smart TV, fireplace

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, (12 reviews)
"A wonderful up to date property a short walk to the lifts! Would definitely stay here again."
United States
Mike B.
The price is €273
includes taxes & fees
9 Jun - 10 Jun
Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
Exterior detail

Sunrise Timberline I7 Quaint 2 bedroom Sunrise Timberline I7 Ski to/from. Pets welcome

Sunrise Timberline I7 Quaint 2 bedroom Sunrise Timberline I7 Ski to/from. Pets welcome
Killington
10.0 out of 10, Exceptional, (8 reviews)
"The condo had everything we needed for a great ski vacation! We loved the ski in/ski out location to the Sunrise lift."
United States
Gary A.
The price is €570
includes taxes & fees
26 Jun - 27 Jun
Sunrise Timberline I7 Quaint 2 bedroom Sunrise Timberline I7 Ski to/from. Pets welcome
Shower, hair dryer, towels

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
9.0 out of 10, Wonderful, (6 reviews)
"Clean studio and very close to both Killington and Pico. Also very close to restaurants and bars. The kitchenette was a little small and had no range but otherwise this was a great place to stay for 2 ppl. Would stay here again."
United States
Karl F.
The price is €230
includes taxes & fees
10 Jun - 11 Jun
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Dining

Killington resort: Walk to Mountain, Biking & Pool

Killington resort: Walk to Mountain, Biking & Pool
Killington
9.6 out of 10, Exceptional, (33 reviews)
"Excellent VRBO. Perfect location to the mountain. Condo was modern and clean and very comfortable. Would go back again!! "
United States
Sheri L.
The price is €299
includes taxes & fees
7 Jun - 8 Jun
Killington resort: Walk to Mountain, Biking & Pool
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)
"Great location!!"
United States
Nicholas C.
The price is €292
includes taxes & fees
7 Jul - 8 Jul
Killington condo 5 min to killington resort
Apartment (Trail Creek 05) | Interior

Trail Creek 05

Trail Creek 05
3.5 star property
Killington
10.0 out of 10, Exceptional, (2 reviews)
"I ended up getting changed to another property trail creek 80. I wish I could give 10 stars! This place is amazing! Clean quiet spacious and so much more. I want to already book this same place for next years Spartan race!! Thank you for having an amazing property "
United States
Kimberly
The price is €352
includes taxes & fees
26 Jun - 27 Jun
Trail Creek 05
Interior

Trail Creek 11 on a ski home trail. Next to Golf course

Trail Creek 11 on a ski home trail. Next to Golf course
Killington
9.2 out of 10, Wonderful, (10 reviews)
"We had a nice stay!"
United States
Jana
The price is €407
includes taxes & fees
26 Jun - 27 Jun
Trail Creek 11 on a ski home trail. Next to Golf course
Interior

Pinnacle D05 Condo | Pool, Hot Tub | Golf Nearby

Pinnacle D05 Condo | Pool, Hot Tub | Golf Nearby
Killington
9.6 out of 10, Exceptional, (4 reviews)
"Great stay!"
United States
Jooho S.
The price is €403
includes taxes & fees
26 Jun - 27 Jun
Pinnacle D05 Condo | Pool, Hot Tub | Golf Nearby
Property grounds

Whiffletree C2 has been totally renovated and is on the Shuttle Bus Route with a ski trail back to the property. Summer Outdoor pool. Near Golf Course

Whiffletree C2 has been totally renovated and is on the Shuttle Bus Route with a ski trail back to the property. Summer Outdoor pool. Near Golf Course
Killington
9.0 out of 10, Wonderful, (39 reviews)
"Excellent location. The unit met all expectations. Warm and comfortable with everything we n the needed "
United States
Ron S.
The price is €432
includes taxes & fees
27 Jun - 28 Jun
Whiffletree C2 has been totally renovated and is on the Shuttle Bus Route with a ski trail back to the property. Summer Outdoor pool. Near Golf Course
Exterior

Modern comfort with ski home access. With AC and pool during summer season. Near Golf Course

Modern comfort with ski home access. With AC and pool during summer season. Near Golf Course
Killington
7.6 out of 10, Good, (5 reviews)
"Great stay. A few minor issues were resolved very fast."
United States
Michael F.
Modern comfort with ski home access. With AC and pool during summer season. Near Golf Course
Property grounds

Whiffletree G1 Close to adventure center for a great day of family fun. Get picked up by the shuttle bus and ski home at the end of the day or for lunch Summer Outdoor pool. Near Golf Course

Whiffletree G1 Close to adventure center for a great day of family fun. Get picked up by the shuttle bus and ski home at the end of the day or for lunch Summer Outdoor pool. Near Golf Course
Killington
8.4 out of 10, Very good, (22 reviews)
"Great spot, close to the mountain"
Canada
t a.
The price is €419
includes taxes & fees
26 Jun - 27 Jun
Whiffletree G1 Close to adventure center for a great day of family fun. Get picked up by the shuttle bus and ski home at the end of the day or for lunch Summer Outdoor pool. Near Golf Course
Fridge, microwave, oven, stovetop

Cozy condo on ski shuttle route with free WiFi & full ktichen

Cozy condo on ski shuttle route with free WiFi & full ktichen
Killington
The price is €219
includes taxes & fees
21 Jun - 22 Jun
Cozy condo on ski shuttle route with free WiFi & full ktichen
Outdoor dining

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 €338
includes taxes & fees
11 Jun - 12 Jun
FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym
Interior

Sunrise East Glade C8 Ski to From Best Sports Center in Killington Indoor Pool Gym Spacious Sunrise condo

Sunrise East Glade C8 Ski to From Best Sports Center in Killington Indoor Pool Gym Spacious Sunrise condo
Killington
9.6 out of 10, Exceptional, (18 reviews)
"Cozy house and great location for ski in ski out. Owners were very responsive. "
United States
Jason L.
Sunrise East Glade C8 Ski to From Best Sports Center in Killington Indoor Pool Gym Spacious Sunrise condo
Indoor pool, a heated pool

Trail Creek: 1 BR with Loft. Ski Home Trail. Bus. Hot Tub. Pool. #64

Trail Creek: 1 BR with Loft. Ski Home Trail. Bus. Hot Tub. Pool. #64
Killington
6.0 out of 10, (1 review)
"it was okay a bit misrepresented"
Canada
Ian P.
Trail Creek: 1 BR with Loft. Ski Home Trail. Bus. Hot Tub. Pool. #64
Interior

Trail Creek 52 located on ski home trail Next to Golf course

Trail Creek 52 located on ski home trail Next to Golf course
Killington
9.6 out of 10, Exceptional, (5 reviews)
"Easy parking, great fireplace, solid location, all the basic amenities needed for a fun winter trip with my son. Thank you!"
United States
Glenn D.
Trail Creek 52 located on ski home trail Next to Golf course
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

10/10 Excellent
"Great stay. Beautiful location"
Brian 2-night trip
Posted 1 hour ago
On The River Inn

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
5
Accommodation
623 Condo Rentals
Lowest Price
€177
Highest Price
€532

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is €177 to €532 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 5.8. 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 623 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.