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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

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

9.4 out of 10, Exceptional, (8)
"This is super clean. It's really close to the lifts. It's basic but it has everything you need."
The price is AED 257
AED 974 total
includes taxes & fees
13 Apr - 14 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, (7)
"The location of this unit was ideal for people who like to vacation without having to drive. We literally skied to The Sunrise Cafe for dinner the first night. All of our outdoor adventures started right from our door with excellent access to trails. The Community center had a great hot tub and free equipment to use. We would definitely go back. "
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"
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, (49)
"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, (38)
"When I arrived at the place, it was very clean and looked recently renovated. The bed was a tempurpedic, so it was extremely comfortable and all the furniture was conveniently placed. I liked the table right by the door and the nice little island in the kitchen area. The instructions for everything were simple and my stay was effortless. Thank again Wayne!"
The price is AED 845
AED 1,652 total
includes taxes & fees
1 May - 2 May
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, (56)
"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"
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 AED 307
AED 888 total
includes taxes & fees
11 Apr - 12 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.

9.0 out of 10, Wonderful, (2)
"We had a special ski weekend with friends. "
The price is AED 958
AED 2,497 total
includes taxes & fees
11 Apr - 12 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 AED 422
AED 1,314 total
includes taxes & fees
11 Apr - 12 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, (39)
"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, (13)
"Having six in this place was tight, but we enjoyed our time. "
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, (174)
"Condo was as advertised and would stay there again for easy access and convenience to Ramshead, Snowden & K-1 Lodge locations!Restaurant, skier store and all amenities are on site within the building! "
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, (23)
"convenient to okemo"
The price is AED 529
AED 2,225 total
includes taxes & fees
11 Apr - 12 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.
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Other property types in Pittsfield

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!
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
TV, fireplace, DVD player, books

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (487)
"Took a ride up for a nice little retreat and for my wife’s bday, such a treat! Jeff even stopped by with some wine as a gift, since I had mentioned it when booking. The space is super cozy and functional, and the hot tub was great way to relax at the end of the day. The gas fireplace gets things nice and warm, too! It had been a while since I personally visited this area of Vermont, super beautiful and remote, but still not too long of a drive to several areas of interest. Looking forward to...
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
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 AED 257 to AED 958 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 9.3.
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.