Pittsfield Condo Rentals from CA $117

Q: Are there any family-friendly condos in Pittsfield?

Put your feet up at Silver Spring Chalet - Getaway , a 3-star option not far from town. Conveniences here include a furnished patio and a fireplace. Another family-friendly condo is Slopeside Pico 3 Bedroom Condo . Ski-in/ski-out facilities and a swimming pool help make this 3-star escape a hit with guests. Once you've checked in and unpacked your suitcase, there are loads of family-friendly attractions to explore in and around Pittsfield. Pico Mountain at Killington Ski Resort and Gifford Woods State Park guarantee fun for all ages.

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Our top choices for Pittsfield condo rentals

A multi-story building with a snow-covered roof and a parking area in front.

1. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Killington

Susanne B.

CA $546 total

includes taxes & fees

Nov 16 - Nov 17

Wide steps and a handrail lead into the water from the deck.

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

Killington

Asad B.

CA $467 total

includes taxes & fees

Nov 16 - Nov 17

Entry steps lead into the shared outdoor pool, with loungers around the deck for a break when the pool is open.

3. Charming Killington Center Studio Condo on the Bus Route. Discounted Ski Rentals. Pool.

Killington

CA $486 total

includes taxes & fees

Nov 16 - Nov 17

Spend time swimming or sitting by the shared outdoor pool when it is open.

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

Killington

The community pool has entry steps and handrails, with seating around the deck.

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

Killington

Marcus G.

CA $466 total

includes taxes & fees

Nov 16 - Nov 17

A modern kitchen with a central island, stainless steel appliances, and blue bar stools.

6. Modern Killington Farmhouse Condo: Close to it all! 412

Killington

Tyler L.

CA $647 total

includes taxes & fees

Nov 16 - Nov 17

Take a break beneath an umbrella at the shared pool during its operating season.

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

Killington

Timothy

CA $500 total

includes taxes & fees

Nov 16 - Nov 17

A residential building with a sign indicating a charging station for electric vehicles.

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

Killington

Lisa

CA $691 total

includes taxes & fees

Nov 16 - Nov 17

A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted above the fireplace.

9. Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5

The Woods

Keaton S.

CA $825 total

includes taxes & fees

Nov 16 - Nov 17

A rectangular swimming pool with clear blue water, surrounded by white lounge chairs and umbrellas, and a white fence.

10. The Suites at Killington Center

Killington

CA $671 total

includes taxes & fees

Nov 22 - Nov 23

Pass snacks across the counter without leaving the conversation in the main room.

11. Trailside Loft at Pico | Ski-In/Out Condo w/ Loft + 2BR | Steps to Lift

Killington

Casey C.

CA $984 total

includes taxes & fees

Nov 16 - Nov 17

A multi-story hotel with a snow-covered parking area and trees in front.

12. Summit View at Pico | Mountain Views, Balcony, Fireplace

Killington

"We arrived to our booked condo only to find that the place had not been cleaned from the prior renter. It was late, after 9:00 at night. I notified the company and sent pictures. They expeditiously provided us with new accommodations that were not only clean but better. So, I can’t comment on this property much only to say there was a lapse in cleaning and preparing for our booked arrival. What I can say is that management handled the situation appropriately in a timely fashion."

Darlene D.

CA $649 total

includes taxes & fees

Nov 16 - Nov 17

Take a swim or choose a lounger beside the shared outdoor pool when it is open.

13. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Killington

Carla M.

CA $486 total

includes taxes & fees

Nov 16 - Nov 17

A dining area with a wooden table and chairs, a kitchen in the background, and a forest mural on the wall.

14. FirBear- Pool, Gym, Fireplace, Hot tub!

The Woods

Kristin G.

CA $551 total

includes taxes & fees

Nov 16 - Nov 17

A rectangular swimming pool with a metal ladder, surrounded by white and brown lounge chairs, and a white fence.

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

Killington

Kristen O.

CA $675 total

includes taxes & fees

Nov 16 - Nov 17

A rectangular swimming pool with a covered seating area and a small building, surrounded by trees with autumn foliage.

16. Mountain Green ground-floor condo with private yard off the patio

Killington

CA $419 total

includes taxes & fees

Nov 17 - Nov 18

An indoor swimming pool with a hot tub, surrounded by a forest-themed mural, and a metal ladder for access.

17. SnowCub- Pets Indoor Pool Hot Tub Sauna Fireplace

The Woods

Brittany R.

CA $556 total

includes taxes & fees

Nov 16 - Nov 17

A modern kitchen with stainless steel appliances, a dining area with a wooden table, and a cozy seating area with a fireplace.

18. The Sunup Suite at Killington: 2RM/2BA Condo w/ Pool. Bus Route. Discounted Ski Rentals!

Killington

Catherine N.

CA $720 total

includes taxes & fees

Nov 16 - Nov 17

A modern kitchen with a large island, wooden cabinets, and a red stool. There is a dining area with a wooden table and chairs, and a red telephone booth.

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

Killington

John O.

CA $734 total

includes taxes & fees

Nov 16 - Nov 17

A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

20. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Killington

Michael S.

CA $706 total

includes taxes & fees

Nov 22 - Nov 23

View all properties

Learn more about Pittsfield

Nestled in Vermont's Green Mountains, Pittsfield offers excellent hiking on the Long Trail and thrilling mountain biking at Green Mountain Trails. Riverside picnics along the Tweed River provide peaceful breaks between seasonal activities at nearby Killington Resort.

See all hotels in Pittsfield

A lake surrounded by autumn-colored trees and a rocky shoreline.

Top reviews in Pittsfield

A spacious living room with a stone fireplace, wooden furniture, and a large potted plant.

The Trailside Inn

North Sherburne

10/10 Excellent

Grainne

A spacious living room with a fireplace, leather sofas, a wooden coffee table, and a view of the outdoors.

North Star Lodge and Resort

Killington

10/10 Excellent

Julie

A two-story house with a porch, surrounded by trees.

Inn at Neshobe River

Brandon

10/10 Excellent

Anonymous traveller

A modern room with a glass door leading to a patio, two wicker chairs, a small table, and a wooden ceiling beam.

Best Western Inn & Suites Rutland-Killington

Rutland

10/10 Excellent

Christian

A row of cabins with a river in the foreground, surrounded by trees and a snowy landscape.

Sleep Woodstock Motel

Woodstock

10/10 Excellent

Dave

A covered outdoor seating area with stone pillars and wooden beams, surrounded by a grassy lawn and trees.

My Place Hotel-Randolph VT

Randolph Center

10/10 Excellent

Kseniia

A covered outdoor area with a wooden ceiling, potted plants, and a bench.

Hampton Inn Rutland

Rutland

10/10 Excellent

Stewart

Frequently Asked Questions

How much do condos in Pittsfield cost?

The price range for condos in Pittsfield is CA $117 to CA $324 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 9.4. Silver Spring Chalet - Getaway is one highly recommended option. Guests staying at this 3-star condo will enjoy amenities such as a furnished patio and a fireplace. Slopeside Pico 3 Bedroom Condo is another popular choice. This 3-star property offers a swimming pool and ski-in/ski-out facilities.

How many condos are there in Pittsfield?

You can choose from 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.

Are there any family-friendly condos in Pittsfield?

Put your feet up at Silver Spring Chalet - Getaway, a 3-star option not far from town. Conveniences here include a furnished patio and a fireplace. Another family-friendly condo is Slopeside Pico 3 Bedroom Condo. Ski-in/ski-out facilities and a swimming pool help make this 3-star escape a hit with guests. Once you've checked in and unpacked your suitcase, there are loads of family-friendly attractions to explore in and around Pittsfield. Pico Mountain at Killington Ski Resort and Gifford Woods State Park guarantee fun for all ages.

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.

Search Condos Rentals in Pittsfield from CA $117

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Pittsfield condo rentals

1. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

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

3. Charming Killington Center Studio Condo on the Bus Route. Discounted Ski Rentals. Pool.

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

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

6. Modern Killington Farmhouse Condo: Close to it all! 412

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

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

9. Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5

10. The Suites at Killington Center

11. Trailside Loft at Pico | Ski-In/Out Condo w/ Loft + 2BR | Steps to Lift

12. Summit View at Pico | Mountain Views, Balcony, Fireplace

13. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

14. FirBear- Pool, Gym, Fireplace, Hot tub!

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

16. Mountain Green ground-floor condo with private yard off the patio

17. SnowCub- Pets Indoor Pool Hot Tub Sauna Fireplace

18. The Sunup Suite at Killington: 2RM/2BA Condo w/ Pool. Bus Route. Discounted Ski Rentals!

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

20. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Learn more about Pittsfield

Top reviews in Pittsfield

The Trailside Inn

10/10 Excellent

Frequently Asked Questions

How much do condos in Pittsfield cost?

What are the best condos in Pittsfield?

How many condos are there in Pittsfield?

Are there any family-friendly condos in Pittsfield?

Why book your condo in Pittsfield with Expedia?

How can I find cheap condos in Pittsfield?

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