Search Condo Rentals in Pittsfield

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 609 Condo Rentals in Pittsfield with updated reviews, rates, and availability.

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Indoor pool

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

8.4 out of 10, Very Good, (29)
" Convenient location right off Killington Rd. Short drive to ski or restaurants. One bar/restaurant on site- Vermont Craft. Newly renovated studio, clean on arrival. Check-in as described, did not need to contact host during stay. Thorough details provided in pre arrival communications. "
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
Indoor pool, outdoor pool

SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside

10.0 out of 10, Exceptional, (171)
"Great location for ski on/off, updated kitchen and bathrooms, quiet, spacious and comfortable. Plan on coming back."
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
TV, DVD player, books

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

9.2 out of 10, Wonderful, (7)
"This is super clean. It's really close to the lifts. It's basic but it has everything you need."
The price is SAR 375
SAR 1,133 total
includes taxes & fees
7 Apr - 8 Apr
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

3.0 star property
9.8 out of 10, Exceptional, (6)
"Everything was excellent. 3 baths 3 beds. Perfect. Bring coffee filters and hangers."
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
Exterior

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

10.0 out of 10, Exceptional, (2)
"Clean and electronic check in. Great hot tub, pool and hot showers. Room also has a small fridge they don’t mention. Nice to be close to Ramshead lodge. WiFi was 30-10 so good for work connection. Recommend"
The price is SAR 309
SAR 830 total
includes taxes & fees
31 Mar - 1 Apr
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Desk, free WiFi, bed sheets

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

9.0 out of 10, Wonderful, (48)
"We came to Killington for a weekend ski trip. We were able to find the location just fine. I loved that it was tucked away in the corner unit. There was ample parking and the snowy roads in the neighborhood were plowed regularly. We found the bed to be the best part! It was so cozy and comfortable, especially after a long ski day. I was happy to see that the space has been updated. The high ceiling opened up the small space and there was plenty of extra linens. The second best part and what made...
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Newly renovated cozy ski retreat with view of Killington slopes
Spa

Newly renovated cozy ski retreat with view of Killington slopes

9.6 out of 10, Exceptional, (37)
"Waybe is very friendly and helpful. The place would need a bigger update"
The price is SAR 863
SAR 1,687 total
includes taxes & fees
6 Apr - 7 Apr
Newly renovated cozy ski retreat with view of Killington slopes
Ski-In/ski-out condo with views, pool, hot tubs, gym & tennis access
Fridge, microwave, oven, stovetop

Ski-In/ski-out condo with views, pool, hot tubs, gym & tennis access

8.4 out of 10, Very Good, (55)
"Cold first night"
Ski-In/ski-out condo with views, pool, hot tubs, gym & tennis access
Ski condo close to multiple resorts
Fireplace

Ski condo close to multiple resorts

9.8 out of 10, Exceptional, (13)
"Great property for a couple with kids going skiing and or other activities at Killington."
Ski condo close to multiple resorts
Beautiful 2BR/2BA Fall Line Condo w/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G2B
Exterior

Beautiful 2BR/2BA Fall Line Condo w/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G2B

10.0 out of 10, Exceptional, (16)
"Very nice and well thought out condo! Clearly very well loved and taken care of by owners. Our family enjoyed it and would return. "
Beautiful 2BR/2BA Fall Line Condo w/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G2B
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Aerial view

Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

9.2 out of 10, Wonderful, (5)
"We enjoyed our stay clean friendly hospitable located couple minutes from Mountain perfect"
The price is SAR 578
SAR 1,550 total
includes taxes & fees
31 Mar - 1 Apr
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Two-Bedroom Condo with Stunning Views and Prime Location A4
Fridge, microwave, oven, stovetop

Two-Bedroom Condo with Stunning Views and Prime Location A4

9.6 out of 10, Exceptional, (4)
"We were very satisfied with this condo for skiing at Killington. Had a great stay!"
Two-Bedroom Condo with Stunning Views and Prime Location A4
Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
Exterior

Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631

9.0 out of 10, Wonderful, (2)
"The property was very clean and in an excellent location. The host was very responsive when we had questions. Overall it was a great experience."
The price is SAR 314
SAR 907 total
includes taxes & fees
31 Mar - 1 Apr
Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.
Smart TV, fireplace

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

10.0 out of 10, Exceptional, (1)
"We had a special ski weekend with friends. "
The price is SAR 978
SAR 2,551 total
includes taxes & fees
31 Mar - 1 Apr
Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.
Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes
Property grounds

Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

8.6 out of 10, Excellent, (17)
"Thanks for everything "
The price is SAR 431
SAR 1,330 total
includes taxes & fees
7 Apr - 8 Apr
Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes
Killington Condo Penthouse Mountain View Underground parking Pool Hot Tub - 3F10
Interior

Killington Condo Penthouse Mountain View Underground parking Pool Hot Tub - 3F10

9.4 out of 10, Exceptional, (38)
"This is a nice property that was comfortable, quiet and well equipped. Living area might be tight for more than 4 people due to sloped ceilings, top floor end of corridor location made it quiet yet convenient. Nice that it has parking in garage but was very tight space - our 2017 Subaru fit, but so close to car on right that passenger could not enter/exit if another car was parked next to it. Entry wasn't quite smooth - had to spin lock considerably after entering code. Nice entertainment system...
Killington Condo Penthouse Mountain View Underground parking Pool Hot Tub - 3F10
Trail Creek 75 | Condo in Killington
Interior

Trail Creek 75 | Condo in Killington

10.0 out of 10, Exceptional, (12)
"The condo is conveniently located near Killington resort and is well appointed and comfortable.Everything worked well except the dishwasher. While the kitchen had all the utensils we needed, a few spices would be nice."
Trail Creek 75 | Condo in Killington
Amazing Mountain Condo - Right across the street to Killington Resort
Exterior

Amazing Mountain Condo - Right across the street to Killington Resort

9.8 out of 10, Exceptional, (172)
"Overall impression is very good. The condo was very sweet and comfortable! Owner was very responsive and took time to suggest places to eat and things to do when not skiing! We loved the convenience of the property to the mountain, having a bar onsite and a nice workout/pool/spa. "
Amazing Mountain Condo - Right across the street to Killington Resort
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (22)
"We really enjoyed our stay. You must have a 4-wheel drive, but once you're up the windy road it's flat. Easy loading and unloading - no stairs. The one gotcha is with this Vermont bear and compost thing. You need to separate food from general trash which is a hassle loading a bucket in the refrigerator with anything listed on their triple laminated instruction manual. Other than this minor preventive measure to keep nuisance bears out of garbage cans, it's worth the safety precaution....
The price is SAR 540
SAR 2,277 total
includes taxes & fees
7 Apr - 8 Apr
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Trail Creek 31 | Walk-to-lift condo in Killington with pool, hot tub, gym, sauna
Interior

Trail Creek 31 | Walk-to-lift condo in Killington with pool, hot tub, gym, sauna

10.0 out of 10, Exceptional, (11)
"Highly recommend "
Trail Creek 31 | Walk-to-lift condo in Killington with pool, hot tub, gym, sauna
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.
Don't see what you're looking for?
See all available properties in Pittsfield
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Pittsfield

Killington Vermont Ski and Snowmobiling House
Interior

Killington Vermont Ski and Snowmobiling House

9.4 out of 10, Exceptional, (42)
"Was not listed that soaps and toilet paper is not included. Just would’ve preferred that be out in the listing "
Killington Vermont Ski and Snowmobiling House
Killington area home - 4-seasons & hot tub. Sleeps 13+
Property grounds

Killington area home - 4-seasons & hot tub. Sleeps 13+

9.8 out of 10, Exceptional, (116)
"We stayed at this property for a ski weekend in March. 8 guys fit comfortably and the accommodations were perfect. Property was as advertised and very clean. We enjoyed the hot tub after hitting the slopes which was a great way to finish the day. Owner was very accommodating and quick to reply to any inquiries or questions. 10/10"
Killington area home - 4-seasons & hot tub. Sleeps 13+
Private Killington Area Inn all to Yourself!
Fridge, microwave, oven, stovetop

Private Killington Area Inn all to Yourself!

10.0 out of 10, Exceptional, (38)
"Eric is a perfect host! The inn is perfect, 9 rooms, private bathrooms. The kitchen is awesome, great appliances and big enough for everyone to be in the kitchen at the same time. This was our third year with family staying and celebrating. We will be back!"
Private Killington Area Inn all to Yourself!
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.

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is SAR 309 to SAR 978 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?
A traveler favorite is Pico Village Resort - Getaway. Base yourself at this 3.5-star property which comes with ski-in/ski-out facilities and a swimming pool. Silver Spring Chalet - Getaway is another highly rated condo to consider. Spend your break at this popular 3-star option and you’ll have access to amenities like a yard and a fireplace. There are multiple condos in Pittsfield with a total average guest review rating of 9.2.
How many condos are there in Pittsfield?
You can choose from 609 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.