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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 June - 7 June
In three months
3 July - 5 July
In four months
31 July - 2 Aug

Our top choices for Pittsfield condo rentals

TV

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"The Nest at Hawk Ledges was a perfect summer getaway. The home provides comfort in a tranquil setting while being close enough to many summer adventures. We enjoyed relaxing in the bright, open home after taking many day trips to explore the area. What a gem!"
United States
Ben N.
The price is AU$992
includes taxes & fees
18 Apr - 19 Apr
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Aerial view

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is AU$527
includes taxes & fees
9 Apr - 10 Apr
The Suites at Killington Center
Dining

Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Killington
9.4 out of 10, Exceptional, (11 reviews)
"Loved every aspect of our stay. The condo looked amazing and everything was extremely clean. Would of extended our stay but another person already had it booked."
United States
Amy
The price is AU$503
includes taxes & fees
9 Apr - 10 Apr
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Exterior

Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.4 out of 10, Exceptional, (58 reviews)
"Wonderful location…"
United States
David C.
The price is AU$822
includes taxes & fees
8 Apr - 9 Apr
Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Living area

Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (9 reviews)
"We loved staying here. It was comfortable, had everything we needed. 100% would stay here again!"
United States
Vanessa O.
The price is AU$556
includes taxes & fees
13 Apr - 14 Apr
Killington condo 5 min to killington resort
Exterior

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Killington
9.0 out of 10, Wonderful, (15 reviews)
"Great property, as advertised."
United States
Chris A.
The price is AU$358
includes taxes & fees
9 Apr - 10 Apr
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Smart TV, fireplace

Ski, Hike, Relax - 2BR Killington Condo with Balcony, Pools, Hot Tubs and Free Shuttle

Ski, Hike, Relax - 2BR Killington Condo with Balcony, Pools, Hot Tubs and Free Shuttle
Killington
8.4 out of 10, Very good, (7 reviews)
"Great location by the mountain! Walking distance to Killington Distillery. Nice balcony overlooking woods."
United States
James G.
The price is AU$649
includes taxes & fees
8 Apr - 9 Apr
Ski, Hike, Relax - 2BR Killington Condo with Balcony, Pools, Hot Tubs and Free Shuttle
Indoor pool

Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
7.4 out of 10, Good, (32 reviews)
"Great location."
United States
Dustin S.
The price is AU$420
includes taxes & fees
8 Apr - 9 Apr
Welcoming condo near the slopes with free WiFi and full kitchen
Exterior

The Cozy Cubbie: Charming Studio in Killington. Pool. Bus. Discounted Ski Rentals.

The Cozy Cubbie: Charming Studio in Killington. Pool. Bus. Discounted Ski Rentals.
Killington
9.0 out of 10, Wonderful, (6 reviews)
"We did a quick ski getaway, great place, and close to the mountain!"
United States
Al Z.
The Cozy Cubbie: Charming Studio in Killington. Pool. Bus. Discounted Ski Rentals.
Dining

The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.

The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
Killington
9.8 out of 10, Exceptional, (6 reviews)
"This was our second time at this property because it’s clean and a great location. "
United States
Kristan K.
The price is AU$536
includes taxes & fees
8 Apr - 9 Apr
The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
Indoor pool, a heated pool

Behnke Family Retreat: Mountain View 1BR/1BA Condo at Mountain Green Resort. Ski Shuttle

Behnke Family Retreat: Mountain View 1BR/1BA Condo at Mountain Green Resort. Ski Shuttle
Killington
8.6 out of 10, Excellent, (4 reviews)
"It was clean there was enough beds. Extra blankets were great. The pool and the hot tub were great for the kids."
United States
Dave B.
The price is AU$551
includes taxes & fees
8 Apr - 9 Apr
Behnke Family Retreat: Mountain View 1BR/1BA Condo at Mountain Green Resort. Ski Shuttle
Exterior

Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441

Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
Killington
8.0 out of 10, Very good, (1 review)
Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
Property grounds

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

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
8.4 out of 10, Very good, (36 reviews)
"Great stay!"
United States
Bryann F.
The price is AU$404
includes taxes & fees
13 Apr - 14 Apr
Comfortable mountain gem with pool, mountain views, & indoor parking space
Interior

Trail Creek 41 | Condo in Killington near lifts/hiking with pool & rec room

Trail Creek 41 | Condo in Killington near lifts/hiking with pool & rec room
Killington
9.2 out of 10, Wonderful, (19 reviews)
"Had a great time in a lovely property between town and the resort. "
United States
Alan S.
The price is AU$591
includes taxes & fees
9 Apr - 10 Apr
Trail Creek 41 | Condo in Killington near lifts/hiking with pool & rec room
Exterior

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Killington
8.8 out of 10, Excellent, (5 reviews)
"8 mins drive from ski lodge"
United States
YUXIANG
The price is AU$367
includes taxes & fees
8 Apr - 9 Apr
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Indoor pool

Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (46 reviews)
"Very close to Killington and in the shuttle route."
United States
Craig C.
The price is AU$504
includes taxes & fees
13 Apr - 14 Apr
Resort condo with mountain views, full kitchen, and free WiFi
Interior

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

The Mountain Green Nook with Views, Shuttle Bus, Pools, Hot Tub and Ski Rental Deals
Killington
9.4 out of 10, Exceptional, (8 reviews)
"The room was cute and clean and great to stay in for our vacation!"
United States
Audrey H.
The price is AU$495
includes taxes & fees
8 Apr - 9 Apr
The Mountain Green Nook with Views, Shuttle Bus, Pools, Hot Tub and Ski Rental Deals
Exterior

Renovated Killington Center Studio. Close to Resort. Bus. Discounted Ski Rentals. 523

Renovated Killington Center Studio. Close to Resort. Bus. Discounted Ski Rentals. 523
Killington
7.4 out of 10, Good, (3 reviews)
"Clean room, perfect location close to the mountain, easy acess and good communication with management. "
Canada
Timothy
The price is AU$390
includes taxes & fees
8 Apr - 9 Apr
Renovated Killington Center Studio. Close to Resort. Bus. Discounted Ski Rentals. 523
Dining

Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool

Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool
Killington
10.0 out of 10, Exceptional, (36 reviews)
"Ski in ski out when the sun lift is operational."
United States
Vinayak G.
Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool
Property grounds

Cozy 3-Bedroom Whiffletree Condo in Killington, VT with Ski-In/Shuttle Access. Ski rental deals.

Cozy 3-Bedroom Whiffletree Condo in Killington, VT with Ski-In/Shuttle Access. Ski rental deals.
Killington
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful condo. Convenient proximity to slopes. Neighbors upstairs were load til 3am partying but not the fault of the owner."
United States
JR M.
The price is AU$782
includes taxes & fees
8 Apr - 9 Apr
Cozy 3-Bedroom Whiffletree Condo in Killington, VT with Ski-In/Shuttle Access. Ski rental deals.
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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Top Pittsfield Hotel Reviews

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

10/10 Excellent
"Front desk was helpful and pleasant"
Chester 2-night trip
Posted 11 hours ago
Best Western Inn & Suites Rutland-Killington

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
304
Accommodation
633 Condo Rentals
Lowest Price
AU$358
Highest Price
AU$992

Frequently asked questions

How much do condos in Pittsfield cost?
Condos in Pittsfield range from AU$358 to AU$992 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.
How many condos are there in Pittsfield?
Pick from 633 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.
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.