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Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Condo Rentals in Pittsfield

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
9.4 out of 10, Exceptional, (10)
"Excellent location"
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub
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, (172)
"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
Killington condo 5 min to killington resort
Terrace/patio

Killington condo 5 min to killington resort

9.2 out of 10, Wonderful, (7)
"Great little getaway! Loved the fireplace! Super warm and cozy, had everything we needed. "
Killington condo 5 min to killington resort
NEW Killington Studio: Great Location! Comfy. 431
Exterior

NEW Killington Studio: Great Location! Comfy. 431

9.6 out of 10, Exceptional, (4)
"Great place to stay!"
$179 nightly
The price is $202
Jun 27 - Jun 28
Total includes taxes and fees
NEW Killington Studio: Great Location! Comfy. 431
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."
$203 nightly
The price is $229
Jun 26 - Jun 27
Total includes taxes and fees
Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
Killington Mountain Ski resort five minutes away
Fridge, microwave, oven, stovetop

Killington Mountain Ski resort five minutes away

9.6 out of 10, Exceptional, (124)
"Good location. Fit a few guys on a ski trip comfortably. Good sized rooms. Good communication with owner. "
$319 nightly
The price is $357
Jul 13 - Jul 14
Total includes taxes and fees
Killington Mountain Ski resort five minutes away
Trail Creek 75 | Condo in Killington
Interior

Trail Creek 75 | Condo in Killington

10.0 out of 10, Exceptional, (14)
"Having six in this place was tight, but we enjoyed our time. "
Trail Creek 75 | Condo in Killington
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-in/shuttle-out condo w/WiFi, fireplace, balcony, & newly renovated kitchen
Interior

Ski-in/shuttle-out condo w/WiFi, fireplace, balcony, & newly renovated kitchen

9.4 out of 10, Exceptional, (22)
"Clean and had everything we needed. Would stay here again!"
Ski-in/shuttle-out condo w/WiFi, fireplace, balcony, & newly renovated kitchen
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)
"Amazing place and great location!"
Newly renovated cozy ski retreat with view of Killington slopes
Experience the ultimate Vermont getaway at our cozy 1BR/1BA ski-in/ski-out condo in Killington
Exterior

Experience the ultimate Vermont getaway at our cozy 1BR/1BA ski-in/ski-out condo in Killington

$464 nightly
The price is $524
Jun 26 - Jun 27
Total includes taxes and fees
Experience the ultimate Vermont getaway at our cozy 1BR/1BA ski-in/ski-out condo in Killington
Pinnacle A23 Oversized Pinnacle with quaint Moose theme, shuttle to the slopes everyday of the week. The outdoor pool, hot tub, and, tennis courts are open during summer only.
Pool

Pinnacle A23 Oversized Pinnacle with quaint Moose theme, shuttle to the slopes everyday of the week. The outdoor pool, hot tub, and, tennis courts are open during summer only.

10.0 out of 10, Exceptional, (4)
"The location was fantastic, right across from the Ramshead lot. The condo was very comfortable for all of us. Will absolutely stay here again!"
Pinnacle A23 Oversized Pinnacle with quaint Moose theme, shuttle to the slopes everyday of the week. The outdoor pool, hot tub, and, tennis courts are open during summer only.
Pinnacle F01 Fully remodeled unit. The property also offers shuttle to the slopes everyday of the week.
Fridge, microwave, stovetop, dishwasher

Pinnacle F01 Fully remodeled unit. The property also offers shuttle to the slopes everyday of the week.

10.0 out of 10, Exceptional, (11)
"Very nice condo. The frequent shuttle to Snowshed is very convenient."
Pinnacle F01 Fully remodeled unit. The property also offers shuttle to the slopes everyday of the week.
Ski-in/ski-out condo with resort amenities and mountain views
Exterior

Ski-in/ski-out condo with resort amenities and mountain views

8.0 out of 10, Very Good, (7)
"Plenty of space for our group!"
Ski-in/ski-out condo with resort amenities and mountain views
Mt Green 2BR/2BA Condo: Close to Resort and Skiing. 3B7
Exterior

Mt Green 2BR/2BA Condo: Close to Resort and Skiing. 3B7

9.0 out of 10, Wonderful, (2)
"Very close to the slopes."
Mt Green 2BR/2BA Condo: Close to Resort and Skiing. 3B7
Charming Two bedroom Townhouse within walking distance to all activities Glazebrook J4
Property grounds

Charming Two bedroom Townhouse within walking distance to all activities Glazebrook J4

9.6 out of 10, Exceptional, (21)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: My family had a magnificent time the rental was amazing! It was clean and spacious. The manager was amazing and so accommodating. We will go back k again very soon!!"
Charming Two bedroom Townhouse within walking distance to all activities Glazebrook J4
Killington Sapphire
Living area

Killington Sapphire

9.2 out of 10, Wonderful, (5)
"Everything we needed to enjoy your family trip!"
Killington Sapphire
BearTrax- Pool, Hot tub, Gym, Sauna, Near Resort
Property grounds

BearTrax- Pool, Hot tub, Gym, Sauna, Near Resort

9.2 out of 10, Wonderful, (5)
"Enjoyed our stay"
$580 nightly
The price is $656
Jul 8 - Jul 9
Total includes taxes and fees
BearTrax- Pool, Hot tub, Gym, Sauna, Near Resort
Mountain Green Resort By Killington VR - 3 Bedrooms
Condo, 3 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

Mountain Green Resort By Killington VR - 3 Bedrooms

3.5 star property
10.0 out of 10, Exceptional, (1)
$543 nightly
The price is $606
Jun 30 - Jul 1
Total includes taxes and fees
Mountain Green Resort By Killington VR - 3 Bedrooms
Mnt Green Resort-Walk to Killington Snowshed-Free shuttle-Pool-Hot tub-Massage
Exterior

Mnt Green Resort-Walk to Killington Snowshed-Free shuttle-Pool-Hot tub-Massage

9.8 out of 10, Exceptional, (25)
"Great host. The condo was in a great location. Very clean and great amenities in the building. I would highly recommend this condo and host. "
$341 nightly
The price is $373
Jun 30 - Jul 1
Total includes taxes and fees
Mnt Green Resort-Walk to Killington Snowshed-Free shuttle-Pool-Hot tub-Massage
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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Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is $202 to $656 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?
There are multiple condos in Pittsfield with a total average guest review rating of 9.3. Pico Village Resort - Getaway comes highly rated if you're with a group or just want some extra space. This 3.5-star stay also has a fireplace and a swimming pool. Silver Spring Chalet - Getaway is another guest favorite. It has a 3-star rating and conveniences such as a furnished patio and a yard.
How many condos are there in Pittsfield?
You can choose from 608 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.