Search and Rent Pittsfield Condos

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Nov 21 - Nov 23
In two weeks
Nov 28 - Nov 30
In one month
Dec 12 - Dec 14
In two months
Jan 9 - Jan 11

Condo Rentals in Pittsfield

Exterior
Killington Ski Resort VT Vacation Condos

Killington Ski Resort VT Vacation Condos

3.5 star property
Killington
$264 nightly
The price is $295
Nov 18 - Nov 19
Total with taxes and fees
Killington Ski Resort VT Vacation Condos
Exterior
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.

2.0 star property
Killington
9.0 out of 10, Wonderful, (2)
"Beautiful condo. Convenient proximity to slopes. Neighbors upstairs were load til 3am partying but not the fault of the owner."
United States
JR M.
$351 nightly
The price is $397
Nov 17 - Nov 18
Total with taxes and fees
Cozy 3-Bedroom Whiffletree Condo in Killington, VT with Ski-In/Shuttle Access. Ski rental deals.
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.

2.5 star property
Killington
10.0 out of 10, Exceptional, (2)
"The place was perfect for our trip, close to the lifts and the bike park. Host kept good communication throughout the trip from beginning to the end. Would definitely recommend if you are headed to Killington for the bike park."
United States
Scott D.
$368 nightly
The price is $416
Nov 17 - Nov 18
Total with taxes and fees
Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.
Terrace/patio
CozyCub- Location, Fireplace, Ski Off/Shuttle On!

CozyCub- Location, Fireplace, Ski Off/Shuttle On!

Killington
10.0 out of 10, Exceptional, (22)
"Great place to stay and close to the mountain!"
United States
Sam S.
$247 nightly
The price is $279
Nov 17 - Nov 18
Total with taxes and fees
CozyCub- Location, Fireplace, Ski Off/Shuttle On!
Condo, 1 Bedroom, Kitchen, Garden View | Terrace/patio
The Suites at Killington Center

The Suites at Killington Center

3.5 star property
Killington
$310 nightly
The price is $341
Nov 17 - Nov 18
Total with taxes and fees
The Suites at Killington Center
Fridge, microwave, dishwasher, coffee/tea maker
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Killington
9.4 out of 10, Exceptional, (63)
"Comfortable condo in convenient location near Ramshead. Access to the newly renovated health spa: indoor pool, sauna and hot tub a real bonus. Great place for a few days skiing."
United States
Anonymous traveler
$215 nightly
The price is $243
Nov 16 - Nov 17
Total with taxes and fees
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Indoor pool, a heated pool
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access

Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access

2.0 star property
The Woods
10.0 out of 10, Exceptional, (3)
"We headed up to Killington for some fun spring skiing with the fam and the place was great - spacious, well appointed, and comfortable. Would definitely stay again."
United States
Ryan T.
$401 nightly
The price is $453
Nov 17 - Nov 18
Total with taxes and fees
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access
Exterior
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities G2A

Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities G2A

Killington
8.8 out of 10, Excellent, (3)
"Great location, just the right size, and comfy beds."
United States
Mike H.
$199 nightly
The price is $225
Nov 16 - Nov 17
Total with taxes and fees
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities G2A
Microwave, oven, stovetop, dishwasher
Killington 2 Story - Escape 2BR/2BA, Sleeps 6, Family & Friends Retreat w/ WiFi

Killington 2 Story - Escape 2BR/2BA, Sleeps 6, Family & Friends Retreat w/ WiFi

2.0 star property
Killington
2.0 out of 10, (1)
$273 nightly
The price is $309
Nov 19 - Nov 20
Total with taxes and fees
Killington 2 Story - Escape 2BR/2BA, Sleeps 6, Family & Friends Retreat w/ WiFi
Exterior
Snow Better Place: Perfect for Two - On Shuttle Route w/ Amenities

Snow Better Place: Perfect for Two - On Shuttle Route w/ Amenities

Killington
7.4 out of 10, Good, (3)
"Great place"
United States
Jason D.
$214 nightly
The price is $242
Nov 16 - Nov 17
Total with taxes and fees
Snow Better Place: Perfect for Two - On Shuttle Route w/ Amenities
Condo, 2 Bedrooms | Sauna
Fall Line Condo D4 2 Bedroom Condo

Fall Line Condo D4 2 Bedroom Condo

3.5 star property
Killington
10.0 out of 10, Exceptional, (1)
"Super condo à proximité de la montagne de ski Killington. "
Canada
catherine
$505 nightly
The price is $561
Nov 14 - Nov 15
Total with taxes and fees
Fall Line Condo D4 2 Bedroom Condo
Exterior
The Cozy Cubbie: Charming Studio in Killington. Pool. Bus. Discounted Ski Rentals.

The Cozy Cubbie: Charming Studio in Killington. Pool. Bus. Discounted Ski Rentals.

Killington
8.6 out of 10, Excellent, (4)
"This was a great spot and perfect for our little get away. The pool was nice and we were close enough to walk to the many of the local hot spots just up the street. We also enjoyed a short waterfall hike a 5 min drive away. The room was clean and comfortable. We also checked out the breakfast place that is on the same property and it was delicious. Only thing that didn't go well is I left a sleep wedge behind but maybe the next people can use it lol. We would definitely come back and enjoy...
United States
Ryan H.
$217 nightly
The price is $245
Nov 17 - Nov 18
Total with taxes and fees
The Cozy Cubbie: Charming Studio in Killington. Pool. Bus. Discounted Ski Rentals.
Interior
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, (4)
"The place was clean and easy to get to. "
United States
Sarah Z.
$215 nightly
The price is $244
Nov 17 - Nov 18
Total with taxes and fees
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Indoor pool, a heated pool
FirBear- Pool, Gym, Hot tub.

FirBear- Pool, Gym, Hot tub.

The Woods
10.0 out of 10, Exceptional, (22)
"Everything was exactly as pictured and the hosts of the property went above and beyond with their hospitality "
United States
John
$360 nightly
The price is $406
Nov 17 - Nov 18
Total with taxes and fees
FirBear- Pool, Gym, Hot tub.
TV, DVD player, books
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

Killington
9.4 out of 10, Exceptional, (9)
"Could use some updates and the cleaning staff needs to be more thorough."
United States
Sarah S.
$235 nightly
The price is $265
Nov 16 - Nov 17
Total with taxes and fees
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Smart TV, fireplace, video games, books
SunBear-Ski on Ski off, Pool, HotTub, Game Room!

SunBear-Ski on Ski off, Pool, HotTub, Game Room!

Killington
10.0 out of 10, Exceptional, (29)
"House was great"
United States
Alex G.
$569 nightly
The price is $643
Nov 17 - Nov 18
Total with taxes and fees
SunBear-Ski on Ski off, Pool, HotTub, Game Room!
Interior
Alpine Oasis Studio at Mountain Green Resort Killington: Shuttle, Pool, Hot Tub, Gym, Deals!

Alpine Oasis Studio at Mountain Green Resort Killington: Shuttle, Pool, Hot Tub, Gym, Deals!

Killington
9.6 out of 10, Exceptional, (5)
"The location was perfect. The unit had everything in it that we needed. We will definitely come back again!"
United States
AMY W.
$258 nightly
The price is $292
Nov 17 - Nov 18
Total with taxes and fees
Alpine Oasis Studio at Mountain Green Resort Killington: Shuttle, Pool, Hot Tub, Gym, Deals!
Interior
Resort condo with balcony & shared seasonal amenities - close to skiing

Resort condo with balcony & shared seasonal amenities - close to skiing

Killington
8.2 out of 10, Very Good, (35)
"Great condo. Clean and easy process location good."
United States
John F.
Resort condo with balcony & shared seasonal amenities - close to skiing
Fridge, microwave, oven, stovetop
YOUR KILLINGTON BASECAMP 3A4: Free shuttle w/Pool & Hot tub

YOUR KILLINGTON BASECAMP 3A4: Free shuttle w/Pool & Hot tub

Killington
9.8 out of 10, Exceptional, (25)
"Stunning location for hiking and biking. Beautiful fall colors on the mountain for our stay."
United States
Joanne M.
$380 nightly
The price is $416
Nov 17 - Nov 18
Total with taxes and fees
YOUR KILLINGTON BASECAMP 3A4: Free shuttle w/Pool & Hot tub
Exterior
Killington Blue Studio: Sleeps 4, Close to Mtn 123

Killington Blue Studio: Sleeps 4, Close to Mtn 123

Killington
9.4 out of 10, Exceptional, (9)
"Great location and clean property"
United States
KEVIN C.
$201 nightly
The price is $227
Nov 14 - Nov 15
Total with taxes and fees
Killington Blue Studio: Sleeps 4, Close to Mtn 123
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

Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"Loved the whole hotel staff was great and very helpful and it was very clean!!!"
Joseph 1-night trip
Posted 1 day ago
Hampton Inn Rutland

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
203
Accommodation
587 Condo Rentals
Lowest Price
$225
Highest Price
$643

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is $225 to $643 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. 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 587 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.
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.

Explore a world of travel with Expedia