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

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

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 AED 220
AED 756 total
includes taxes & fees
1 Jul - 2 Jul
Mountain Green
TV, fireplace, DVD player, books

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, (46 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is AED 247
AED 1,255 total
includes taxes & fees
1 Jul - 2 Jul
Resort condo with mountain views, full kitchen, and free WiFi
Indoor pool

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 AED 270
AED 1,064 total
includes taxes & fees
1 Jul - 2 Jul
Welcoming condo near the slopes with free WiFi and full kitchen
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
9.2 out of 10, Wonderful, (7 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.
TV

Four Season Condo: ski, hike, mountain bike & seasonal pool

Four Season Condo: ski, hike, mountain bike & seasonal pool
Warren
The price is AED 351
AED 825 total
includes taxes & fees
5 Jul - 6 Jul
Four Season Condo: ski, hike, mountain bike & seasonal pool
Interior

Top-floor condo with mountain views & covered parking space

Top-floor condo with mountain views & covered parking space
Killington
9.0 out of 10, Wonderful, (31 reviews)
"Eceptional views, loved the covered parking, ammenities were clean."
United States
Mark A.
The price is AED 482
AED 1,378 total
includes taxes & fees
1 Jul - 2 Jul
Top-floor condo with mountain views & covered parking space
Indoor pool

Mountain view condo with fast WiFi plus on-site amenities

Mountain view condo with fast WiFi plus on-site amenities
Killington
The price is AED 386
AED 1,258 total
includes taxes & fees
1 Jul - 2 Jul
Mountain view condo with fast WiFi plus on-site amenities
Exterior

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
TV, fireplace, books

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 AED 247
AED 947 total
includes taxes & fees
10 Jul - 11 Jul
Cozy condo on ski shuttle route with free WiFi & full ktichen
Dining

Killington resort: Walk to Mountain, Biking & Pool

Killington resort: Walk to Mountain, Biking & Pool
Killington
9.8 out of 10, Exceptional, (32 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 AED 432
AED 1,270 total
includes taxes & fees
7 Jul - 8 Jul
Killington resort: Walk to Mountain, Biking & Pool
TV

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

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
The price is AED 204
AED 989 total
includes taxes & fees
7 Jul - 8 Jul
Comfortable mountain gem with pool, mountain views, & indoor parking space
Interior

Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.4 out of 10, Exceptional, (63 reviews)
"Good place. Hosts were in touch and the hot tub was great. "
United States
Bethany S.
Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Exterior

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

Cozy condo, electric fireplace, walk-to-lifts, balcony, views, wif
Killington
Cozy condo, electric fireplace, walk-to-lifts, balcony, views, wif
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 AED 364
AED 1,183 total
includes taxes & fees
5 Jul - 6 Jul
Killington condo 5 min to killington resort
Smart TV, fireplace, video games, books

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 AED 554
AED 1,452 total
includes taxes & fees
1 Jul - 2 Jul
FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym
TV

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"convenient to okemo"
United States
marcus l.
The price is AED 675
AED 2,540 total
includes taxes & fees
15 Jul - 16 Jul
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Smart TV, fireplace

Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.

Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.
Killington
9.6 out of 10, Exceptional, (4 reviews)
"We had a special ski weekend with friends. "
United States
Adam C.
The price is AED 543
AED 1,931 total
includes taxes & fees
1 Jul - 2 Jul
Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.
Terrace/patio

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 AED 447
AED 1,007 total
includes taxes & fees
26 Jul - 27 Jul
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.
SunBear- AC, Pool, Game Room, Fireplace, Hiking!
Dining

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

Snowcub- AC, Pool, Hot tub, Tennis, Grill!
The Woods
10.0 out of 10, Exceptional, (25 reviews)
"We loved our stay at Snowcub! The condo is beautiful, welcoming and our hosts had excellent communication. We were comfortable and enjoyed the nice amenities- including a pool and hot tub! We would love to stay here again! We loved it! "
United States
Maura A.
The price is AED 637
AED 1,559 total
includes taxes & fees
5 Jul - 6 Jul
Snowcub- AC, Pool, Hot tub, Tennis, Grill!
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

Sleep Woodstock Motel

Sleep Woodstock Motel

10/10 Excellent
"The owners were very friendly and I was attracted to the property because of the high ratings it was given. It’s not a property that you would drive by and say, I’d like to stay there. However, they’ve put a lot of thought into it and even provide a fire pit and smores kits in the lobby so you could roast marshmallows if you wanted. The rooms are decorated nicely and the clientele staying on both side of us were very nice couples like ourselves. We got to know them and they felt the same way. I would definitely stay there again and the rates are inexpensive compared to the large chains and other properties. Highly recommend."
Mark 1-night trip
Posted 1 hour ago
Sleep Woodstock Motel

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is AED 756 to AED 2,540 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 618 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.