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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

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, (31)
"Property was not cleaned well, had an awful smell and door was ajar when we arrived. "
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 with trail access. The pool, sauna and steam room were great. Very clean and very convenient. Owners were very responsive and helpful."
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)
"Condo was perfect for our weekend ski getaway the bus to the K! lodge runs about every 15 min. to the front door of the building will defiantly stay again"
The price is $233
includes taxes & fees
$206 per night
May 2 - May 3
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)
"Excellent location"
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, (50)
"Great location, great accommodations. Easy in and out, no issues at all!"
The price is $192
includes taxes & fees
$170 per night
Jun 1 - Jun 2
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)
"Amazing place and great location!"
The price is $368
includes taxes & fees
$325 per night
May 21 - May 22
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)
"Unit was very clean and comfortable and conveniently located close to all. "
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

8.8 out of 10, Excellent, (6)
"A buddy and I decided to do a last minute lead-peeping motorcycle weekend. The condo was very clean and comfortable. Perfect for our needs. After riding we were able to easily walk to two terrific restaurants and one excellent ice cream shop. Breakfast at the cafe by the entrance was delicious as well. "
The price is $391
includes taxes & fees
$346 per night
May 4 - May 5
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, (5)
"Overall good. Lower level bath needs a light bulb. Got locked in Christmas Eve but staff was on the spot, jumped over balcony to get in and take lock apart from inside. Broken part was replaced and we were freed."
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)
"For a relatively cheap stay it was worth the price."
The price is $229
includes taxes & fees
$203 per night
May 4 - May 5
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 $618
includes taxes & fees
$547 per night
May 4 - May 5
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)
"Beautiful ski condo, very conveniently located, super clean with a very comfy bed! Had a great stay."
The price is $357
includes taxes & fees
$316 per night
May 2 - May 3
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)
"Enjoyed our stay, great condo Just a little disappointed the hot tub , pool, and suana were under construction and unable to be used."
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)
"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, (174)
"It was cozy, clean, and in the greatest location. "
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)
"Beautiful property. It must have been recently remodeled as every detail was thoughtfully planned. Right down to new hangers in every closet. We thoroughly enjoyed our stay and would love to stay here again when we are back in the area."
The price is $579
includes taxes & fees
$517 per night
May 2 - May 3
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, (12)
"Very clean. Great location. Would definitely stay again. "
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, (117)
"Had a great stay in the perfect ski house "
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)
"Overall fabulous place to stay. Will be back next year!!"
Private Killington Area Inn all to Yourself!
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"Very nice place only negative was the sauna did not work"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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 $192 to $618 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.