Compare Pittsfield Vacation Rentals

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Pittsfield Rentals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
2.54 mi from city center
$138 nightly
The price is $155 total per night
$155 total
Aug 30 - Aug 31
Total with taxes and fees
At Berkshire Mountain Lodge, guests have access to an indoor pool, free WiFi in public areas, and a hot tub. If you decide to drive, there's free parking. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this golf aparthotel include a business center, an arcade/game room, and laundry facilities.
Pool
Hot Tub
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

Pittsfield MA
4.06 mi from city center
At this cabin, guests have access to features like laundry facilities. Friendly staff can provide concierge services, and also offer advice about sightseeing. This smoke-free cabin also has barbecue grills.
Kitchen
Washer
Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room

Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room

Stephentown NY
8.04 mi from city center
This vacation home features a hot tub and a garden. This smoke-free vacation home also has barbecue grills.
Pool
Hot Tub
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
8.26 mi from city center
$128 nightly
The price is $143 total per night
$143 total
Aug 31 - Sep 1
Total with taxes and fees
Vacation Village in the Berkshires features an indoor pool, an outdoor pool, and a children's pool. If you decide to drive, there's free parking. The front desk is staffed 24 hours a day to help with access to locker space and concierge services. Other amenities at this family-friendly aparthotel include a gym, free WiFi in public areas, and a business center.
Pool
Parking included
Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires

Lenox MA
8.73 mi from city center
Guests staying at this condo enjoy a sauna, laundry facilities, and barbecue grills.
Pool
Kitchen
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7 Lenox MA
8.76 mi from city center
The Ponds at Foxhollow features an indoor pool, an outdoor pool, and a gym. Free parking is available if you drive. Helpful staff is there to provide a safe deposit box at the front desk, as well as offer insight about the area. Additional amenities include a sauna, free WiFi in public areas, and an outdoor tennis court.
Pool
Kitchen
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++

Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++

Lenox MA
8.78 mi from city center
Guests of this vacation home enjoy features like an indoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly vacation home include laundry facilities, local meal delivery service, and a garden.
Pool
Hot Tub
Historic Stockbridge Villa on 25 acres

Historic Stockbridge Villa on 25 acres

Stockbridge MA
10.26 mi from city center
Guests of this vacation home enjoy features like an outdoor pool, a sauna, and laundry facilities. Other amenities at this family-friendly vacation home include barbecue grills and a garden.
Pool
Kitchen
Incredible Estate: Pool, Pond, Gym, Arcade, Trails & more: Perfect Summer Vacate

Incredible Estate: Pool, Pond, Gym, Arcade, Trails & more: Perfect Summer Vacate

Old Chatham NY
17.57 mi from city center
Guests of this vacation home enjoy features like an outdoor pool, a gym, and an arcade/game room. Other amenities at this family-friendly vacation home include a library, laundry facilities, and a garden.
Pool
Kitchen
Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat

Great Barrington MA
15 mi from city center
$306 nightly
The price is $342 total per night
$342 total
Sep 8 - Sep 9
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a garden.
Kitchen
Washer
Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay

Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay

Monterey MA
18.95 mi from city center
At this vacation home, guests have access to a sauna, a hot tub, and laundry facilities. Additional amenities include a garden and barbecue grills.
Hot Tub
Kitchen
Private Island - Largest Fresh Water Reservoir in Mass

Private Island - Largest Fresh Water Reservoir in Mass

Otis MA
22.36 mi from city center
Guests staying at this cottage can enjoy a gym, a garden, and barbecue grills.
Kitchen
Pet friendly
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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.

Pittsfield Large Group Rentals

How to Book Vacation Rentals in Pittsfield



🏠 What is the best price for Pittsfield vacation rentals?

Pittsfield vacation rentals range in price, starting at $143 per night.


🏠 What types of vacation rentals in Pittsfield can I rent?

Orbitz offers a wide range of Pittsfield rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Pittsfield condo rentals.


🏠 Is it free to cancel my Pittsfield vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Pittsfield vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Pittsfield. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Pittsfield?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Pittsfield apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Pittsfield?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Pittsfield package deals will get you even more savings.