Pittsfield Condos

Featured Condos in Pittsfield

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Williamstown, MA

This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Pool

Parking included

Ski-In/Ski-Out at Jiminy Peak in the Country Inn

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Ski-in/ski-out access and an outdoor pool are featured at this smoke-free condo. There's fun for all ages with a playground and an arcade/game room. A gym and a hot tub are also provided.

Pool

Hot Tub

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

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Ski-in/ski-out access and an outdoor pool are featured at this smoke-free condo. There's a gym on site, and laundry facilities and concierge services are also offered.

Pool

Hot Tub

Peaceful 1BR Condo with Pond View

3 Fox Hollow Drive, Lenox, MA

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A sauna is featured at this condo, along with laundry facilities and barbecue grills.

Pool

Kitchen

Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool

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A gym is featured at this condo, along with laundry facilities.

Air conditioning

Laundry

Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths

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This condo features a gym and a hot tub. Laundry facilities are provided for your convenience.

Pool

Hot Tub

1/2 Mi to Jiminy Peak: Condo w/ Pool & Hot Tub

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A hot tub is featured at this property, along with laundry facilities and barbecue grills.

Pool

Hot Tub

UNIQUE - 1BR Country Condo @ Jiminy Peak

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This condo features an outdoor pool and an indoor pool. Enjoy the gym and conveniences like a garden and laundry facilities.

Pool

Kitchen

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

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A gym is featured at this condo, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Pool

Kitchen

Club Wyndham Bentley Brook Resort - 2 Bedroom

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This condo features ski-in/ski-out access, a hot tub, and laundry facilities. Families will appreciate the water park and barbecue grills. Concierge services are provided for your convenience.

Pool

Hot Tub

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

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Ski-in/ski-out access and an outdoor pool are featured at this smoke-free condo. There's a gym on site, and laundry facilities and concierge services are also offered.

Pool

Hot Tub

Berkshires Getaway < 1 Mi Skiing & Hiking!

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This condo features ski-in/ski-out access, a garden, and laundry facilities. Families will appreciate the arcade/game room and barbecue grills.

Kitchen

Washer

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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.

Top Family Friendly Condos in Pittsfield

Hotel On North

297 North Street, Pittsfield, MA

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9.4/10 Exceptional! (736 reviews)

Find Condos with a Pool in Pittsfield

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street, Pittsfield, MA

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7.8/10 Good! (794 reviews)

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.

What is the price range for condos in Pittsfield?

Travelocity has plenty of tempting deals on Pittsfield condo rentals for you to choose from. They range from to . Prices and availability are subject to change. Additional terms may apply.

How many Pittsfield condos are there?

At Travelocity, there are 62 condo rentals in Pittsfield—dive into your dream vacation!

How can I find cheap beach condo rentals in Pittsfield?

It’s easy to find cheap condo rentals in Pittsfield on Travelocity. Just enter your travel dates and hit search. You can organize your results using the best filters for you and sort by price or by budget. If you want a cheaper break in Pittsfield, consider staying in —when it’s quieter and fewer people visit.

What are the benefits of Pittsfield condo rentals?

If you want the luxury of a hotel with all the comforts of home, book a Pittsfield condo rental. In your own slice of paradise, you can cook what you like and stay together with friends and family in multiple bedrooms, comfortable living spaces, and a whole lot of privacy.

What amenities are in a beachfront Pittsfield condo rental?

Pittsfield condos on the beach have all kinds of cool extras that elevate your vacation. Take your pick from a wide range of amenities from pet-friendly condos, rentals with hot tubs, oceanfront condos with astounding views, and places with pools—and much, much more.

Are any Pittsfield condo rentals pet-friendly?

Bring your four-legged friend on your Pittsfield vacation and stay in a pet-friendly condo. They’re easy to find: You just need to hit the pet-friendly filter in your search then choose the condo that fits your bill.

How can I find family-friendly condos in Pittsfield?

Whether it’s a big family get-together or a quick weekend escape with the little ones, there are loads of Pittsfield condos that welcome families with open arms. When you’ve entered your travel dates, click the family-friendly filter—you might also find it useful to enter your guest numbers, so you can find a condo that fits everyone.

Are there luxury condos available in Pittsfield?

There are some divine luxury beachfront condo rentals in Pittsfield! To find your answer to perfection, sort your results by rating, read our guest reviews, and check out the accommodation photos to know your chosen condo exceeds your expectations!

How to find the best condo in Pittsfield on Travelocity?

Finding your perfect Pittsfield condo is easy with Travelocity. Just enter your travel dates and hit search. With a fantastic selection of deals at your fingertips, all you need to do is add filters to build your dream getaway.

Pittsfield Condos essential information

Accommodation	62 Condos
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Popular accommodation	Vacation Village in the Berkshires, Ski-In/Ski-Out at Jiminy Peak in the Country Inn, SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1, Peaceful 1BR Condo with Pond View, Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool , Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths, 1/2 Mi to Jiminy Peak: Condo w/ Pool & Hot Tub, UNIQUE - 1BR Country Condo @ Jiminy Peak, 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7, Club Wyndham Bentley Brook Resort - 2 Bedroom, SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2, Berkshires Getaway < 1 Mi Skiing & Hiking!