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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare 484 Condo Rentals in Pittsfield with updated reviews, rates, and availability.

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

9.0 out of 10, Wonderful, (43)
"Great location, great accommodations. Easy in and out, no issues at all!"
The price is SAR 356
SAR 678 total
includes taxes & fees
18 Feb - 19 Feb
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
Interior

SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside

10.0 out of 10, Exceptional, (165)
"The property was great! Well equipped kitchen with plenty of dishes, utensils, and drinkware for our group of 7. Easy to get to/from the main mountain. Nicely configured living room with a huge TV... very clean. Looking forward to going again!"
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

8.4 out of 10, Very Good, (27)
"It’s a great location, and the unit is well updated, but being able to lock it while you’re away skiing the whole day is pretty important. When I reached out to the property manager about this, and also a disgusting towel left near the toilet on arrival, the response was basically oh no! That’s awful! We’ve told someone.. aaaand nothing ever happened about either thing. These issues weren’t insurmountable, but doing nothing at all about them just left a terrible impression."
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
The Forest Fun Suite at Killington Center: 2RM/2BA Condo. Pool. Bus. Discounted Ski Rentals!
Renovated 2-room, 2-bath condo with a fully equipped kitchen, private patio with an electric grill, and access to a heated outdoor pool.

The Forest Fun Suite at Killington Center: 2RM/2BA Condo. Pool. Bus. Discounted Ski Rentals!

10.0 out of 10, Exceptional, (1)
"The place was great, super convenient to both the access road and Killington. I would highly recommend it."
The Forest Fun Suite at Killington Center: 2RM/2BA Condo. Pool. Bus. Discounted Ski Rentals!
Killington Condo Penthouse Mountain View Underground parking Pool Hot Tub - 3F10
Kitchen Table with Balcony behind. See snowcats grooming the trails at night.

Killington Condo Penthouse Mountain View Underground parking Pool Hot Tub - 3F10

9.4 out of 10, Exceptional, (35)
"Apartment was exactly as described. Great place to relax when not skiing. Property manager was prompt in responding to questions."
Killington Condo Penthouse Mountain View Underground parking Pool Hot Tub - 3F10
PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views
Kitchen

PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views

8.4 out of 10, Very Good, (10)
"Great spot. Has everything you need and ski/in ski out right on property "
PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views
The Mountain Green Nook with Views, Shuttle Bus, Pools, Hot Tub and Ski Rental Deals
Mountain Green 2F8 offers you a cozy living space with your private balcony and fireplace.

The Mountain Green Nook with Views, Shuttle Bus, Pools, Hot Tub and Ski Rental Deals

10.0 out of 10, Exceptional, (2)
"Very close to the mountain and just what the description and pictures showed. "
The price is SAR 895
SAR 1,905 total
includes taxes & fees
23 Feb - 24 Feb
The Mountain Green Nook with Views, Shuttle Bus, Pools, Hot Tub and Ski Rental Deals
Ski, Ride,Relax, Read in this Exclusive Luxury, family friendly Vermont getaway
Pool

Ski, Ride,Relax, Read in this Exclusive Luxury, family friendly Vermont getaway

10.0 out of 10, Exceptional, (34)
"Great location, very spacious, lots of beds. Perfect for a long ski weekend away!"
Ski, Ride,Relax, Read in this Exclusive Luxury, family friendly Vermont getaway
Amazing Mountain Condo - Right across the street to Killington Resort
Living area

Amazing Mountain Condo - Right across the street to Killington Resort

9.8 out of 10, Exceptional, (169)
"Perfect spot for a weekend skiing killington! Cozy and clean!"
Amazing Mountain Condo - Right across the street to Killington Resort
New and Modern 1BR Condo at Killington
Living area

New and Modern 1BR Condo at Killington

7.8 out of 10, Good, (6)
"Exterior of property in disrepairCouch aged and sagging towards the middle and worn outBed uncomfortable with dirty comfortermold in bathroom and sinkSmells of old food We left first thing in the morning, as I could not stay another night.Texted the owner and received no reply.I personally would not stay here again. I have pictures of defects."
New and Modern 1BR Condo at Killington
Killington condo 5 min to killington resort
Living area

Killington condo 5 min to killington resort

10.0 out of 10, Exceptional, (4)
"The place was great all around! Thanks for having us and we look forward to coming back!"
The price is SAR 544
SAR 1,416 total
includes taxes & fees
3 Mar - 4 Mar
Killington condo 5 min to killington resort
Comfortable mountain gem with pool, mountain views, & indoor parking space

Comfortable mountain gem with pool, mountain views, & indoor parking space

8.6 out of 10, Excellent, (28)
"I would recommend to friends and family "
Comfortable mountain gem with pool, mountain views, & indoor parking space
Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

8.4 out of 10, Very Good, (15)
"Beautiful ski condo, very conveniently located, super clean with a very comfy bed! Had a great stay."
The price is SAR 683
SAR 1,723 total
includes taxes & fees
16 Mar - 17 Mar
Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes
Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
This cozy studio condo at Killington Center Inn & Suites comes with two queen beds.

Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631

8.0 out of 10, Very Good, (1)
"For a relatively cheap stay it was worth the price."
Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

10.0 out of 10, Exceptional, (1)
"Great location for ski condo, especially for Killington (8-min drive to K1 Lodge). The rooms are comfy and the beds/couches are firm but pliant (no getting eaten by the cushions). The parking lot & nearby roads around this condo center are plowed often, but definitely recommend 4WD/AWD vehicles for ski season as we still slid on the icy coverings on the roads. Kitchen appliances are in good condition."
The price is SAR 2,364
SAR 3,945 total
includes taxes & fees
18 Feb - 19 Feb
Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.
Cozy living room of the Sunrise Timberline ski-in ski-out rental condo in Killington, VT, featuring a large L-shaped sofa, a balcony and a high window showing mountain views, and an exposed-brick wall with a fireplace.

Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.

10.0 out of 10, Exceptional, (1)
"We had a special ski weekend with friends. "
Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.
The Summit Suite at Whiffletree Killington: Shuttle Bus. Pool. Discounted Ski Rentals.

The Summit Suite at Whiffletree Killington: Shuttle Bus. Pool. Discounted Ski Rentals.

10.0 out of 10, Exceptional, (2)
"Perfect spot for a Killington ski weekend. Just two of us, and that was ideal. So close to the mountain, and so well maintained. I highly recommend this rental for our next trip up."
The price is SAR 912
SAR 1,980 total
includes taxes & fees
20 Feb - 21 Feb
The Summit Suite at Whiffletree Killington: Shuttle Bus. Pool. Discounted Ski Rentals.
⭐️Ski-On/Ski-Off COZY BEAUTIFUL MOUNTAIN CONDO 2-Bed/2-Bath with Fireplace
Relax in front of the stacked stone fire place.

⭐️Ski-On/Ski-Off COZY BEAUTIFUL MOUNTAIN CONDO 2-Bed/2-Bath with Fireplace

10.0 out of 10, Exceptional, (51)
"Great condo with SI-SO access to Killington ski resort. Nicely updated and decorated. New appliances. Will definitely rent again!"
⭐️Ski-On/Ski-Off COZY BEAUTIFUL MOUNTAIN CONDO 2-Bed/2-Bath with Fireplace
Ski condo close to multiple resorts
Cozy open livingroom space

Ski condo close to multiple resorts

9.8 out of 10, Exceptional, (9)
"Property was as described and shown in the pictures. It was a great location, very clean. Short drive to stores, restaurants and ski lifts. Mike, the property manager was incredible!! Very responsive, even came and pulled me out of a snow drift when the rental that was supposed to be an AWD (it wasn’t) got stuck. "
Ski condo close to multiple resorts
Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
Cozy studio condo featuring a fully-equipped kitchen with a Keurig machine, a private balcony with mountain views, and an inviting living space with an electric fireplace and smart TV.

Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.

9.4 out of 10, Exceptional, (3)
"Cozy little place close to killington mountain "
Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
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

Cozy Loft for two with Hot Tub
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (230)
"Would definetly go back. Enjoyable, quiet, just an enjoyable stay!"
Cozy Loft for two with Hot Tub
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

9.0 out of 10, Wonderful, (43)
"Great location, great accommodations. Easy in and out, no issues at all!"
The price is SAR 356
SAR 678 total
includes taxes & fees
18 Feb - 19 Feb
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
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?
Condos in Pittsfield range from SAR 356 to SAR 2,364 per night. These properties offer lots of space for the entire squad at a price that’s easy on your wallet. 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?
You can pick from multiple condos in Pittsfield with a total average guest review rating of 9.3. Pico Village Resort - Getaway comes highly recommended if you’ve got the whole crew in tow or just require some extra space. This 3.5-star stay also has ski-in/ski-out facilities and a fireplace. Silver Spring Chalet - Getaway is another popular option. It has a 3-star rating and conveniences such as a yard and a fireplace.
How many condos are there in Pittsfield?
Claim your vacation time and choose from 484 condos in Pittsfield. For an official business trip, a getaway with pals or anything in between, Expedia can help you find the right place in just a click or two.
Why book your condo in Pittsfield with Expedia?
Reserving a condo in Pittsfield is as easy as deciding on your travel dates and selecting a place suited to your needs. On the lookout for something luxurious or affordable, or a stay that also includes a pool? 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 handy filter tool, booking cheap condos in Pittsfield is a piece of cake. To discover accommodations that’ll make your hip pocket happy, narrow down your search by amenities, budget and star rating.