Search Condo Rentals in Pittsfield

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

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
9.6 out of 10, Exceptional, (9)
"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)
"Property exactly as advertised. Has everything 6-8 people would need for ski-in/out of Killington."
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
Aerial view

NEW Killington Studio: Great Location! Comfy. 431

9.6 out of 10, Exceptional, (4)
"Great place to stay!"
The price is AED 250
AED 738 total
includes taxes & fees
17 Jun - 18 Jun
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."
The price is AED 307
AED 842 total
includes taxes & fees
17 Jun - 18 Jun
Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
Trail Creek 75 | Condo in Killington
Interior

Trail Creek 75 | Condo in Killington

10.0 out of 10, Exceptional, (14)
"Trail creek access made it easy, have to hike back to Snowshed base but that is easy from the home. Also, can walk to Killington Grand for dinner!"
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

The price is AED 740
AED 1,689 total
includes taxes & fees
17 Jun - 18 Jun
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
Indoor pool, a heated pool

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
Aerial view

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

9.0 out of 10, Wonderful, (2)
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
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

8.4 out of 10, Very Good, (18)
"Beautiful ski condo, very conveniently located, super clean with a very comfy bed! Had a great stay."
The price is AED 488
AED 1,387 total
includes taxes & fees
20 Jun - 21 Jun
Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes
Killington Sapphire
Living area

Killington Sapphire

9.2 out of 10, Wonderful, (5)
"Everything we needed to enjoy your family trip!"
Killington Sapphire
Luxury ski resort condo with on-site pool, hot tub, sauna & game room
Interior

Luxury ski resort condo with on-site pool, hot tub, sauna & game room

9.0 out of 10, Wonderful, (26)
"Very comfortable stay & amazing location."
Luxury ski resort condo with on-site pool, hot tub, sauna & game room
BearTrax- Pool, Hot tub, Gym, Sauna, Near Resort
Indoor pool, a heated pool

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

9.2 out of 10, Wonderful, (5)
"Enjoyed our stay"
The price is AED 719
AED 2,415 total
includes taxes & fees
17 Jun - 18 Jun
BearTrax- Pool, Hot tub, Gym, Sauna, Near Resort
Mountain Green Resort*Walk to Killington Snowshed*Free shuttle*Pool*Hot tub*Massage
Exterior

Mountain 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. "
The price is AED 491
AED 1,334 total
includes taxes & fees
17 Jun - 18 Jun
Mountain 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is AED 250 to AED 740 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 9.2. 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 601 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.