Search Condo Rentals in Pittsfield

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

  • 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

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

Condo Rentals in Pittsfield

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.
The price is AED 451
AED 1,528 total
includes taxes & fees
17 Nov - 18 Nov
Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.
Condo, 1 Bedroom, Kitchen, Garden View | Terrace/patio
The Suites at Killington Center

The Suites at Killington Center

3.5 star property
Killington
The price is AED 403
AED 1,251 total
includes taxes & fees
17 Nov - 18 Nov
The Suites at Killington Center
Exterior
Killington Ski Resort VT Vacation Condos

Killington Ski Resort VT Vacation Condos

3.5 star property
Killington
The price is AED 437
AED 1,083 total
includes taxes & fees
18 Nov - 19 Nov
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.
The price is AED 396
AED 1,458 total
includes taxes & fees
17 Nov - 18 Nov
Cozy 3-Bedroom Whiffletree Condo in Killington, VT with Ski-In/Shuttle Access. Ski rental deals.
Exterior
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

Killington
9.2 out of 10, Wonderful, (5)
"I don’t think I’ve ever had such wonderful service checking in and caring for our needs. Amazing response time and outstanding stay. Thank you."
United States
Margaret L.
The price is AED 287
AED 860 total
includes taxes & fees
16 Nov - 17 Nov
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
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.
The price is AED 298
AED 1,025 total
includes taxes & fees
17 Nov - 18 Nov
CozyCub- Location, Fireplace, Ski Off/Shuttle On!
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.
The price is AED 263
AED 828 total
includes taxes & fees
16 Nov - 17 Nov
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities G2A
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
The price is AED 327
AED 893 total
includes taxes & fees
16 Nov - 17 Nov
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
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.
The price is AED 307
AED 888 total
includes taxes & fees
16 Nov - 17 Nov
Snow Better Place: Perfect for Two - On Shuttle Route w/ Amenities
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.
The price is AED 294
AED 974 total
includes taxes & fees
17 Nov - 18 Nov
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
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.
The price is AED 513
AED 1,663 total
includes taxes & fees
17 Nov - 18 Nov
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access
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.
The price is AED 250
AED 834 total
includes taxes & fees
15 Nov - 16 Nov
Killington Blue Studio: Sleeps 4, Close to Mtn 123
Condo, 2 Bedrooms | Dining
The Woods by Killington Vacation Rentals - 2 Bedrooms

The Woods by Killington Vacation Rentals - 2 Bedrooms

3.0 star property
The Woods
10.0 out of 10, Exceptional, (2)
"The condo had everything we needed for a comfortable and enjoyable stay. The pool and hot tub area were great additions. We would definitely stay again."
United States
Paul
The price is AED 719
AED 2,316 total
includes taxes & fees
15 Nov - 16 Nov
The Woods by Killington Vacation Rentals - 2 Bedrooms
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.
The price is AED 279
AED 894 total
includes taxes & fees
17 Nov - 18 Nov
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Fridge, microwave, oven, stovetop
⛷ 1BR Ski-Home Condo. Pool/Hot Tub/Sauna. Short walk 2 lifts, golf, hikes.

⛷ 1BR Ski-Home Condo. Pool/Hot Tub/Sauna. Short walk 2 lifts, golf, hikes.

Killington
10.0 out of 10, Exceptional, (21)
"Excellent location "
United States
Colin G.
The price is AED 493
AED 1,113 total
includes taxes & fees
16 Nov - 17 Nov
⛷ 1BR Ski-Home Condo. Pool/Hot Tub/Sauna. Short walk 2 lifts, golf, hikes.
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.
The price is AED 335
AED 1,073 total
includes taxes & fees
17 Nov - 18 Nov
Alpine Oasis Studio at Mountain Green Resort Killington: Shuttle, Pool, Hot Tub, Gym, Deals!
Exterior
Sunrise West Glade: 3BR, 3BA Ski In/Ski Out Condo

Sunrise West Glade: 3BR, 3BA Ski In/Ski Out Condo

Killington
9.4 out of 10, Exceptional, (16)
"Perfect ski in ski out location. Unit is as represented. Issue on check in when we arrived it was uncleaned and we spent first hour of occupancy with the cleaning crew. Also was ongoing leak in master bedroom from roof which saturated the carpet. This was obviously of long standing duration and rather disgusting. "
United States
jon d.
The price is AED 606
AED 2,111 total
includes taxes & fees
17 Nov - 18 Nov
Sunrise West Glade: 3BR, 3BA Ski In/Ski Out Condo
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
The price is AED 389
AED 1,444 total
includes taxes & fees
18 Nov - 19 Nov
FirBear- Pool, Gym, Hot tub.
Exterior
Cozy 2 BR Ski On Ski Off Condo in Killington's Sunrise Mountain Village. Pool. Hot Tub.

Cozy 2 BR Ski On Ski Off Condo in Killington's Sunrise Mountain Village. Pool. Hot Tub.

2.0 star property
Killington
9.4 out of 10, Exceptional, (3)
"Absolutely perfect spot. Kids and parents loved it. Everything you’re looking for in an on mountain condo. Pool and hot tub are a short drive away but we still used it. "
United States
nicholas d.
The price is AED 711
AED 1,977 total
includes taxes & fees
17 Nov - 18 Nov
Cozy 2 BR Ski On Ski Off Condo in Killington's Sunrise Mountain Village. Pool. Hot Tub.
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.
The price is AED 638
AED 1,526 total
includes taxes & fees
17 Nov - 18 Nov
YOUR KILLINGTON BASECAMP 3A4: Free shuttle w/Pool & Hot tub
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 3 days ago
Hampton Inn Rutland

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is AED 828 to AED 2,316 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 9.6. 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.
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.