Search and Rent Pittsfield Condos

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Compare 453 Condo Rentals in Pittsfield with updated reviews, rates, and availability.

Fridge, microwave, oven, stovetop
Resort condo with balcony & shared seasonal amenities - close to skiing
9.0 out of 10, Wonderful, (21)
"Great condo. Clean and easy process location good."
The price is $67
$307 total
includes taxes & fees
May 26 - May 27
Resort condo with balcony & shared seasonal amenities - close to skiing
Indoor spa tub
Two-story, walk-to-lift condo with indoor pool, hot tub, sauna, gym & game room
9.4 out of 10, Exceptional, (9)
"Very spacious 2-bedroom 2 -bath condo. Loft with bed and seating area a bonus!"
Two-story, walk-to-lift condo with indoor pool, hot tub, sauna, gym & game room
Indoor pool, outdoor pool
⭐️Ski-On/Ski-Off COZY BEAUTIFUL MOUNTAIN CONDO 2-Bed/2-Bath with Fireplace
10.0 out of 10, Exceptional, (47)
"Jim's condo had everything we needed. Check in was seamless. Communication was great. Location was perfect. Our family had a wonderful time making memories. We'd definitely stay here again. Thank you Jim!"
⭐️Ski-On/Ski-Off COZY BEAUTIFUL MOUNTAIN CONDO 2-Bed/2-Bath with Fireplace
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Indoor pool, a heated pool
Ski-in/ski-out condo with resort amenities and mountain views
10.0 out of 10, Exceptional, (2)
Ski-in/ski-out condo with resort amenities and mountain views
Property grounds
Spacious townhouse located in Killington, close to night life, Colony E28
9.8 out of 10, Exceptional, (12)
"This place was exactly as described ... great location, clean, close to Pico and Killington. Would definitely stay again!"
Spacious townhouse located in Killington, close to night life, Colony E28
Studio | Aerial view
Killington Center Inn & Suites by Killington VR - Studios
3.0 star property
10.0 out of 10, Exceptional, (1)
"We loved our little unit. Everything was clean and very modern. We especially loved the electric fireplace. Would stay here again. "
The price is $99
$341 total
includes taxes & fees
May 26 - May 27
Killington Center Inn & Suites by Killington VR - Studios
Indoor pool, outdoor pool
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
10.0 out of 10, Exceptional, (151)
"Property has a great layout and the location was perfect. Would definitely book again."
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
Indoor pool, a heated pool
All-season resort getaway with pool, tennis, spa, sauna, hot tub, & washer/dryer
9.8 out of 10, Exceptional, (18)
"We loved everything about this place. 4 adults staying (2 couples) and we had plenty of room. We liked the spot to put our skis inside. It’s in a perfect location for skiing at Killington and Pico and close to all the restaurants on Killington road. Beds were comfortable enough. The TV is a smart TV so we were able to login to Netflix/streaming services. We also made use of the fireplace on the cold days! This property is the building directly next to the spa, so we were able to easily walk to...
All-season resort getaway with pool, tennis, spa, sauna, hot tub, & washer/dryer
Interior
Killington Sun Dog Trail ski-on ski-off 2 bedroom 2 bathroom 1st floor condo
10.0 out of 10, Exceptional, (20)
"Very relaxing, awesome week snowboarding out our back door"
Killington Sun Dog Trail ski-on ski-off 2 bedroom 2 bathroom 1st floor condo
Condo, 1 Bedroom | Aerial view
Fall Line Condos by Killington VR - Studios
3.0 star property
6.0 out of 10, (1)
"Positives: nice atmosphere in our room, beautiful location. Clean, except for 2 items underneath the bed. Negatives: indoor pool closed for summer (ad said it was open), office closed all weekend, some outside areas need paint."
The price is $99
$302 total
includes taxes & fees
May 25 - May 26
Fall Line Condos by Killington VR - Studios
Fridge, microwave, oven, stovetop
Enjoy this spectacular 3 bedroom 3 bathroom Condo sleeping 8 Highridge B20
Enjoy this spectacular 3 bedroom 3 bathroom Condo sleeping 8 Highridge B20
Fridge, microwave, oven, stovetop
Secluded home with gas fireplace, patio, pool, athletic courts, & laundry room
8.6 out of 10, Excellent, (8)
"Clean and exactly what we needed for our stay. The sliding glass door to the parking lot made coming and going really easy."
Secluded home with gas fireplace, patio, pool, athletic courts, & laundry room
Property grounds
Comfortable mountain gem with pool, mountain views, & indoor parking space
8.6 out of 10, Excellent, (17)
"The unit and building are showing their age, but everything is clean and the location is great. The kids enjoyed the brand new pool, sauna, and hot tub"
The price is $56
$303 total
includes taxes & fees
May 26 - May 27
Comfortable mountain gem with pool, mountain views, & indoor parking space
Exterior
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
9.4 out of 10, Exceptional, (56)
"We came into town to see our friend play a two night show at Pickle Barrel. The place was perfect. Check in info was thorough and easy. Kim was great. She was responsive to communications and very accommodating. Would definitely stay here or one of her other properties again!"
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
Aerial view
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
10.0 out of 10, Exceptional, (7)
"We loved the condo. We stayed for a school break, family of three and it was just what we needed to unplug from our busy life. Easy to get everywhere. We will definitely rent it again on our next trip."
The price is $138
$344 total
includes taxes & fees
May 25 - May 26
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
Indoor spa tub
Trail Creek 33 | Condo in Killington
9.8 out of 10, Exceptional, (12)
"Wonderful location located just south of the slopes. A bit of a walk to the lift but doable and fantastic trail to ski home. Very clean, loft area was a great addition. Very nice to have complimentary shampoo/conditioner/soap and dishwasher and laundry detergent. Everything we need for baking/meals. Lots of extra pillows!"
Trail Creek 33 | Condo in Killington
Pool | Indoor pool
Charming, dog-friendly home with a private sauna, full kitchen, & furnished deck
9.6 out of 10, Exceptional, (53)
"Everything was great, good location close to Killington and the house had everything we needed!"
Charming, dog-friendly home with a private sauna, full kitchen, & furnished deck
Exterior
Location! Location! 1BR/1BA Steps to Mountain. 3E3
9.4 out of 10, Exceptional, (12)
"Location was great and the accommodations were perfect. The listing was a bit inaccurate in that the fireplace doesn’t work, the on site restaurant wasn’t open, no ability to get coffee or snacks, and parking was far from the unit."
The price is $94
$300 total
includes taxes & fees
May 26 - May 27
Location! Location! 1BR/1BA Steps to Mountain. 3E3
Fridge, microwave, oven, stovetop
PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views
8.4 out of 10, Very Good, (7)
"Great location and the host was right on the money anytime I had a problem with question I was able to email them and they got right back to me. That’s the way to do it."
PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views
Fridge, microwave, oven, stovetop
Ski-in/out condo with pool, hot tub, sauna & fast WiFi
8.2 out of 10, Very Good, (17)
"Stayed here with the family for 5 nights for midweek skiing. Have stayed in Sunrise before so we know we like the area. This unit gave us what we needed. Shame the fire wasn't working, but not the end of the world. The keypad door lock was great instead of needing a key. Would prefer regular toilet seats instead of squishy ones. They also don't stay up so have to be held. My teens would have liked the lock on the kids bathroom to work (it locked the handle, but the door could just be pushed...
Ski-in/out condo with pool, hot tub, sauna & fast WiFi
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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.

Other property types in Pittsfield

Property grounds
Killington area home - 4-seasons & hot tub. Sleeps 12+
9.8 out of 10, Exceptional, (108)
"My family and I have been renting ski homes for many years. David’s home was, by far, the cleanest property we have ever stayed at. My mother-in-law would have been impressed with the cleanliness of this home. The house was perfectly appointed and was perfect from the time we walked in until the time we left. Thank you David! We are looking forward to next year."
Killington area home - 4-seasons & hot tub. Sleeps 12+
Exterior
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (194)
"Cabin was so wonderful, fire place was lovely right next to the hot tub. Host was great with communication. Very pleasant stay. Cozy, quiet, clean cabin."
Cozy Loft for two with Hot Tub
Interior
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (447)
"Clean and quiet cabin. Perfect for a getaway."
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.

Pittsfield Condo Rentals information

Number of reviews
360
Accommodation
453 Condo Rentals
Lowest Price
$56
Highest Price
$138

Frequently asked questions

How much do condos in Pittsfield cost?
Condos in Pittsfield range from $56 to $138 per night. These stays offer loads of room for the entire squad at a price that won’t stretch the budget. This price was 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?
Select from multiple condos in Pittsfield with a total average guest review rating of 9.1. Pico Village Resort - Getaway comes highly recommended if you’re traveling with the family or just require some extra space. This 3.5-star stay also offers a swimming pool and a fireplace. Killington Center Suite: Perfect For Families In 3br is another guest fave. It has a 3.5-star rating and amenities such as designer toiletries and mountain views.
How many condos are there in Pittsfield?
Pick from 453 condos in Pittsfield. Whether you’re taking a trip with the family or planning a getaway with your buddies, Expedia will help you find the best space for your crew.
Are there any family-friendly condos in Pittsfield?
You bet there are! Reserve a room at Slopeside Pico 3 Bedroom Condo — a reliable 3-star option just a short drive from downtown Pittsfield. This family-friendly condo includes convenient amenities such as a fridge and fitness facilities. After checking in and chilling out together in your home away from home, it’s time to head out and visit some of the local sights. Pico Mountain at Killington Ski Resort and Pico Peak are some of the best family-friendly attractions in Pittsfield.
Why book your condo in Pittsfield with Expedia?
Booking a condo in Pittsfield is as simple as clicking on your travel dates and picking an option that satisfies your needs. After something luxurious or low cost, or a property that also comes with a laundry and kitchen? Use Expedia’s search filters to further narrow your search results and find your perfect match.
How can I find cheap condos in Pittsfield?
With Expedia’s helpful filter tool, sourcing cheap condos in Pittsfield couldn’t be easier. To find properties that are easy on your bank balance, refine your search by star rating, amenities and budget.
What is there to do in Pittsfield near my condo?
There are plenty of fun things to put on your itinerary in Pittsfield. Discover attractions like Pico Mountain at Killington Ski Resort, Gifford Woods State Park and Fire Tower. Green Mountain National Golf Course, Lefferts Pond and Pico Pond also lure many visitors.

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