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

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Pittsfield condo rentals

Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (28 reviews)
"The property is under major construction which was not disclosed when booking. The management fee was almost as much as the room rate, clearer description at time of booking would be appreciated."
United States
Keith
The price is €205
includes taxes & fees
30 Jul - 31 Jul
Mountain Green
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 €298
includes taxes & fees
25 Aug - 26 Aug
Killington condo 5 min to killington resort
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)
The price is €215
includes taxes & fees
29 Jul - 30 Jul
Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
Dining

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
9.4 out of 10, Exceptional, (8 reviews)
"Fantastic place to stay, beds were great. It was wonderful having two full baths. Would definitely recommend this gem again!"
United States
Dawn B.
The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
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, (47 reviews)
"Condo had everything we wanted—comfortable beds, TVs in every room, 2 bathrooms, a balcony-the views are amazing of Killington! We stayed on really hot days but somehow the condo stayed cool (and had fans if needed). Outdoor pool is around the back, and the kids had a blast. It’s so close to Killington resort, too. I received a text from the management co when we arrived which was great, in case we needed anything! We’d go definitely stay again, would like to come back during ski season. The gym...
United States
Corinna
The price is €302
includes taxes & fees
30 Jul - 31 Jul
Resort condo with mountain views, full kitchen, and free WiFi
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, (13 reviews)
"A wonderful up to date property a short walk to the lifts! Would definitely stay here again."
United States
Mike B.
Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
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 location. Clean and easy."
United States
Todd I.
The price is €292
includes taxes & fees
29 Jul - 30 Jul
Killington resort: Walk to Mountain, Biking & Pool
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 €617
includes taxes & fees
27 Jul - 28 Jul
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
TV

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

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
Comfortable mountain gem with pool, mountain views, & indoor parking space
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.
Killington
10.0 out of 10, Exceptional, (12 reviews)
"Great Location"
United States
Brian B.
Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.
Smart TV, fireplace

93 Glazebrook Rd, Unit E2: 2BR/1.5BA Condo. Wood fireplace. Close to Mountain!

93 Glazebrook Rd, Unit E2: 2BR/1.5BA Condo. Wood fireplace. Close to Mountain!
Killington
10.0 out of 10, Exceptional, (3 reviews)
"Great location. Comfortable condo with everything you would need for a ski trip. "
United States
Steven W.
93 Glazebrook Rd, Unit E2: 2BR/1.5BA Condo. Wood fireplace. Close to Mountain!
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 €245
includes taxes & fees
30 Jul - 31 Jul
CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
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
Welcoming condo near the slopes with free WiFi and full kitchen
Desk, free WiFi, bed sheets

Stylish Studio for 4 with EV Charger, Pool & Shuttle Access

Stylish Studio for 4 with EV Charger, Pool & Shuttle Access
Killington
Stylish Studio for 4 with EV Charger, Pool & Shuttle Access
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 €334
includes taxes & fees
27 Jul - 28 Jul
Top-floor condo with mountain views & covered 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
Indoor pool

Mountain view condo with fast WiFi plus on-site amenities

Mountain view condo with fast WiFi plus on-site amenities
Killington
Mountain view condo with fast WiFi plus on-site amenities
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 €453
includes taxes & fees
29 Jul - 30 Jul
Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.
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.
FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym
Property grounds

Cozy 3-Bedroom Whiffletree Condo in Killington, VT with Ski-In/Shuttle Access. Ski rental deals.

Cozy 3-Bedroom Whiffletree Condo in Killington, VT with Ski-In/Shuttle Access. Ski rental deals.
Killington
9.2 out of 10, Wonderful, (5 reviews)
"Everything was as advertised. Th condo was clean, comfortable and had plenty of room. Super convenient to the slopes and yes… it’s a legitimate ski-in property. The host is very responsive and helpful. I look forward to staying at Whiffletree again. "
United States
Aaron J.
Cozy 3-Bedroom Whiffletree Condo in Killington, VT with Ski-In/Shuttle Access. Ski rental deals.
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

Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"The hotel supplied everything we needed. Plenty of toiletries and towels in the room. Bed and pillows were comfortable. The continental breakfast had plenty of items to choose from. Pool was clean and well maintained. The gym was spotless and had enough cardio and free weights."
Michael 2-night trip
Posted 2 hours ago
Hampton Inn Rutland

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
28
Accommodation
621 Condo Rentals
Lowest Price
€205
Highest Price
€205

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is €205 to €205 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 7.2. 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 621 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.