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Vacation rentals in Pittsfield, MA

Find deals on 41 vacation rentals in Pittsfield, MA

Pittsfield, MA, United States
15 May — 16 May2
Fri 10/5
Tue 14/5

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Top rentals in Pittsfield

Find the perfect vacation rental for your stay in Pittsfield
Price
C$116
C$1140
Review Score
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6+
7+
8+
9+

Hostels and cheap hotels in Pittsfield

These hotels and hostels usually make for a cheap way to stay in Pittsfield

Berkshire Cottage

Lanesborough, MA, United States

C$ 116
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Wyndham Bentley Brook at Jiminy Peak - Play in the Winter or the Summer

Wyndham Bentley Brook at Jiminy Peak - Play in the Winter or the Summer

Lanesborough, MA, United States

C$ 204
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Wyndham Bentley Brook Studio, In & Out Ski Resort At Jiminy Peak

Lanesborough, MA, United States

C$ 200
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Cozy Renovated with 1 parking space

Cozy Renovated with 1 parking space

Pittsfield, MA, United States

C$ 208
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Heart of the Berkshires

38 Holmes Road, Pittsfield, MA, United States

C$ 204
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Charming Suite in 18th c. Berkshire Farmhouse near Mt.Greylock and Jiminy Peak

Charming Suite in 18th c. Berkshire Farmhouse near Mt.Greylock and Jiminy Peak

Lanesborough, MA, United States

9.8
C$ 225
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Get the best value vacation rental in Pittsfield

These Pittsfield vacation rentals have the best prices for their ratings
Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn

Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn

Lanesborough, MA, United States

9.3
C$ 256
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Beautiful Lenox Home, 3 Mi to Shakespeare and Co!

Beautiful Lenox Home, 3 Mi to Shakespeare and Co!

Lenox, MA, United States

9.2
C$ 404
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Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

Lanesborough, MA, United States

9.9
C$ 325
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Spacious 3br 3ba Sleeps 8 Ski On Off Jiminy Mountain Resort

Spacious 3br 3ba Sleeps 8 Ski On Off Jiminy Mountain Resort

Lanesborough, MA, United States

9.5
C$ 535
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The Mill River Cabin with Fireplace and River View!

The Mill River Cabin with Fireplace and River View!

Mill River, MA, United States

9.7
C$ 414
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momondo's favourite vacation rentals in Pittsfield

Learn more about these user-preferred vacation rentals in Pittsfield

Beautiful four season lakeside log home close to all Berkshires attractions.

Becket, MA, United States

10.0
C$ 801
19th c. Barn in the Berkshires

19th c. Barn in the Berkshires

Cheshire, MA, United States

9.3
C$ 686

Ashmere Lakefront Apartment

Hinsdale, MA, United States

10.0
C$ 268

Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled

Lanesborough, MA, United States

C$ 463

Berkshire Pontoosuc Lake Beauty Too-Modern Amenities On The Lake

Pittsfield, MA, United States

9.9
C$ 1,030
Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

Lanesborough, MA, United States

9.9
C$ 325
Spacious Comfortable Charming Family Farmhouse Great Location

Spacious Comfortable Charming Family Farmhouse Great Location

Lee, MA, United States

9.5
C$ 589

Two Rooms with En-Suite in Quiet Woodland

Hillsdale, NY, United States

10.0
C$ 393

Berkshire Lake House vacation home

Pittsfield, MA, United States

9.7
C$ 741
Beautiful Lenox Home, 3 Mi to Shakespeare and Co!

Beautiful Lenox Home, 3 Mi to Shakespeare and Co!

Lenox, MA, United States

9.2
C$ 404

Book Now For Fall Foliage! Also 4 Sale! - Deluxe Condo - Jiminy Peak, Berkshires

Lanesborough, MA, United States

C$ 926

Wyndham Bentley Brook at Jiminy Peak in the Berkshires -Play in Summer or Winter

Lanesborough, MA, United States

C$ 251
The Mill River Cabin with Fireplace and River View!

The Mill River Cabin with Fireplace and River View!

Mill River, MA, United States

9.7
C$ 414

Private Peninsula 2ac Surrounded By Water Min From Hiking Skiing Theater Music

Sheffield, MA, United States

9.2
C$ 833

Featured in a Home & Garden TV Special 30 South Mountain Road

Pittsfield, MA, United States

9.6
C$ 503

Memorial Day Week Thru 6/30 Available!!!

Pittsfield, MA, United States

C$ 370

2/Br Historic District Apartment

Pittsfield, MA, United States

C$ 478

Charming Lenox cottage within walking distance to town

Lenox, MA, United States

C$ 583

Restored 1881 Farm House

Lenox, MA, United States

10.0
C$ 479

Wyndham Bentley Brook - Jiminy Peak ski in/out

Lanesborough, MA, United States

C$ 623

Useful insights on Pittsfield vacation rentals

Get a quick overview on price and accommodation trends for your visit in Pittsfield

Lowest Vacation Rental Price

C$ 116
The cheapest price for a room in Pittsfield found in the last 7 days is C$ 116/night. This rate is available with Berkshire Cottage.

When to book a vacation rental in Pittsfield

Check out the information below to find the best deal on a vacation rental in Pittsfield
Low seasonNovembercheapest month to stay
High seasonDecembermost expensive time to stay
59%expected price decrease
47%expected price increase

Price

C$ 166 - C$ 749

Cheapest day of weekMondayis the cheapest day of the week to book
Highest day of weekSaturdayis the most expensive day of the week to book
C$ 228
C$ 444

Information about staying in Pittsfield

Read these important travel tips before booking a vacation rental in Pittsfield

When is the best time to book a vacation rental in Pittsfield?

If you can be flexible on booking dates, vacation apartments and rental properties in Pittsfield can be as much as 59% cheaper in November.

How many operators does momondo search for hotels in Pittsfield?

As of May 2024, there are 53 operators available to choose from for hotels in Pittsfield.

When did momondo last update prices for hotels in Pittsfield?

Prices for hotels in Pittsfield were last updated today.

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