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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Pittsfield condo 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)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is £256
includes taxes & fees
16 May - 17 May
Resort condo with mountain views, full kitchen, and free WiFi
Property grounds

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

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
8.6 out of 10, Excellent, (37 reviews)
"Property was just as advertised. Shuttle to the mountain is only a short 2-3 ride. The spa area was amazing. "
United States
Quinten M.
The price is £208
includes taxes & fees
16 May - 17 May
Comfortable mountain gem with pool, mountain views, & indoor parking space
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 £217
includes taxes & fees
16 May - 17 May
Welcoming condo near the slopes with free WiFi and full kitchen
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)
"Great location!!"
United States
Nicholas C.
The price is £229
includes taxes & fees
20 May - 21 May
Killington condo 5 min to killington resort
Dining

Killington Condo: Walk to Mountain, Pool & Hot Tub

Killington Condo: Walk to Mountain, Pool & Hot Tub
Killington
9.8 out of 10, Exceptional, (32 reviews)
"Excellent VRBO. Perfect location to the mountain. Condo was modern and clean and very comfortable. Would go back again!! "
United States
Sheri L.
The price is £256
includes taxes & fees
16 May - 17 May
Killington Condo: Walk to Mountain, Pool & Hot Tub
Exterior

Cozy condo, electric fireplace, walk-to-lifts, balcony, views, wif

Cozy condo, electric fireplace, walk-to-lifts, balcony, views, wif
Killington
7.4 out of 10, Good, (3 reviews)
"Excellent location with in easy walking distance to the slopes. "
United States
RAYMOND P.
The price is £266
includes taxes & fees
16 May - 17 May
Cozy condo, electric fireplace, walk-to-lifts, balcony, views, wif
Indoor pool

Mountain view condo with fast WiFi plus on-site amenities

Mountain view condo with fast WiFi plus on-site amenities
Killington
8.0 out of 10, Very good, (20 reviews)
"close to ski lift within a short walking distance"
United States
Jun W.
The price is £257
includes taxes & fees
17 May - 18 May
Mountain view condo with fast WiFi plus on-site amenities
Interior

SunBear- AC, Pool, Game Room, Fireplace, Hiking!

SunBear- AC, Pool, Game Room, Fireplace, Hiking!
Killington
9.8 out of 10, Exceptional, (31 reviews)
"Clean and perfect"
United States
Cyle D.
The price is £419
includes taxes & fees
16 May - 17 May
SunBear- AC, Pool, Game Room, Fireplace, Hiking!
Outdoor dining

FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym

FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym
The Woods
10.0 out of 10, Exceptional, (24 reviews)
"Great place to stay for an escape to the mountains!"
United States
Kristin G.
The price is £287
includes taxes & fees
18 May - 19 May
FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym
Terrace/patio

CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis

CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
Killington
10.0 out of 10, Exceptional, (25 reviews)
"We loved our stay! Very cozy condo with the cutest welcome gifts/snacks! It was so nice waking up so close to the resort and being first chair each morning "
United States
Brittany G.
The price is £202
includes taxes & fees
17 May - 18 May
CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
TV, DVD player, books

Top-floor condo with mountain views & covered parking space

Top-floor condo with mountain views & covered parking space
Killington
9.0 out of 10, Wonderful, (31 reviews)
"Easy access to the lifts. Nice pool and sauna, We'll be back. "
United States
Andrus P.
The price is £275
includes taxes & fees
16 May - 17 May
Top-floor condo with mountain views & covered parking space
Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (24 reviews)
"I enjoy the location "
United States
troy
The price is £217
includes taxes & fees
2 Jun - 3 Jun
Mountain Green
Smart TV, fireplace, offices

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

BearTrax- Pool, Hot tub, Gym, Sauna, Near Resort
Killington
9.4 out of 10, Exceptional, (8 reviews)
"Enjoyed our stay"
United States
Adam M.
The price is £573
includes taxes & fees
17 May - 18 May
BearTrax- Pool, Hot tub, Gym, Sauna, Near Resort
Dining

Snowcub- AC, Pool, Hot tub, Tennis, Grill!

Snowcub- AC, Pool, Hot tub, Tennis, Grill!
The Woods
10.0 out of 10, Exceptional, (23 reviews)
"We loved our stay at Snowcub! The condo is beautiful, welcoming and our hosts had excellent communication. We were comfortable and enjoyed the nice amenities- including a pool and hot tub! We would love to stay here again! We loved it! "
United States
Maura A.
The price is £289
includes taxes & fees
19 May - 20 May
Snowcub- AC, Pool, Hot tub, Tennis, Grill!
Property grounds

Trail Creek: Ski home to renovated 1st floor, 1br condo. Sleeps 4.

Trail Creek: Ski home to renovated 1st floor, 1br condo. Sleeps 4.
Killington
10.0 out of 10, Exceptional, (83 reviews)
"Family have fun"
United States
Yanyi
The price is £377
includes taxes & fees
17 May - 18 May
Trail Creek: Ski home to renovated 1st floor, 1br condo. Sleeps 4.
Indoor pool

⛷ 1BR Ski-Home Condo. Pool/Hot Tub/Sauna. Short walk 2 lifts, golf, hikes.

⛷ 1BR Ski-Home Condo. Pool/Hot Tub/Sauna. Short walk 2 lifts, golf, hikes.
Killington
10.0 out of 10, Exceptional, (27 reviews)
"I loved this place. I felt at home and loved how clean it was. "
United States
David & Ali H.
The price is £352
includes taxes & fees
17 May - 18 May
⛷ 1BR Ski-Home Condo. Pool/Hot Tub/Sauna. Short walk 2 lifts, golf, hikes.
Interior

Walk-to-lift condo w/ balcony, fireplace, pool, hot tub, sauna, gym, gameroom

Walk-to-lift condo w/ balcony, fireplace, pool, hot tub, sauna, gym, gameroom
Killington
10.0 out of 10, Exceptional, (1 review)
"Great renovated unit. Very clean. "
United States
Andrea G.
The price is £478
includes taxes & fees
16 May - 17 May
Walk-to-lift condo w/ balcony, fireplace, pool, hot tub, sauna, gym, gameroom
Exterior

Four Season Condo: ski, hike, mountain bike & seasonal pool

Four Season Condo: ski, hike, mountain bike & seasonal pool
Warren
The price is £153
includes taxes & fees
16 May - 17 May
Four Season Condo: ski, hike, mountain bike & seasonal pool
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

Courtyard Middlebury

Courtyard Middlebury

10/10 Excellent
"Clean room, helpful staff, good restaurants, onsite guest laundry."
Anne 1-night trip
Posted 1 day ago
Courtyard Middlebury

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
436
Accommodation
621 Condo Rentals
Lowest Price
£153
Highest Price
£573

Frequently asked questions

How much do condos in Pittsfield cost?
The price range for condos in Pittsfield is £153 to £573 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?
Pittsfield offers multiple condos with a total average guest review rating of 9.2. Pico Village Resort - Getaway is a favourite pick here. Guests staying at this 3.5-star condo can access ski-in/ski-out facilities and a swimming pool. Silver Spring Chalet - Getaway is another top pick. This 3-star property offers a fireplace and a furnished patio.
How many condos are there in Pittsfield?
You can choose from 621 condos in Pittsfield. No matter if you're travelling with the kids or organising a weekend break with some friends, Expedia can help you find the perfect space for your entire crew.
Are there any family-friendly condos in Pittsfield?
Settle in at Pico Village Resort - Getaway, a 3.5-star option just a quick drive from town. Amenities here include a swimming pool and a fireplace. Another family-friendly condo is Silver Spring Chalet - Getaway. A fireplace and a yard help make this 3-star property a favourite among guests. After checking in and chilling out together in your cosy new digs, it's time to explore some of the local sights. Pico Mountain at Killington Ski Resort and Gifford Woods State Park are fun family-friendly attractions in Pittsfield.
Why book your condo in Pittsfield with Expedia?
With Expedia, it's easy to find your dream condo in Pittsfield. After a luxury stay? Take advantage of our filters to search for properties that are 5-star rated. If you have a budget in mind, click on how much you'd like to spend and then check out our amazing deals. We'll help you find a suitable stay whatever your style of travel or plans.
How can I find cheap condos in Pittsfield?
Expedia can help you narrow your search for cheap condos in Pittsfield. To discover your special stay in a few clicks, try out the filter tool to refine your search by star rating, budget and amenities.