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Hotels in Pittsfield

Vacation rentals in Pittsfield, MA

Find deals on 41 vacation rentals in Pittsfield, MA

Pittsfield, MA
May 5 — May 62
Tue 4/30
Sat 5/4

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Top rentals in Pittsfield

Find the perfect vacation rental for your stay in Pittsfield
Price
$85
$832
Review Score
0+
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

Cozy Renovated with 1 parking space

Cozy Renovated with 1 parking space

Pittsfield, MA, United States

Heart of the Berkshires

38 Holmes Road, Pittsfield, MA, United States

Vacation Village in the Berkshires

Vacation Village in the Berkshires

Hancock, MA, United States

8.5
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

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

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
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
Vacation Village in the Berkshires

Vacation Village in the Berkshires

Hancock, MA, United States

8.5
Beautiful Lenox Home, 3 Mi to Shakespeare and Co!

Beautiful Lenox Home, 3 Mi to Shakespeare and Co!

Lenox, MA, United States

9.2
Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

Lanesborough, MA, United States

9.9
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

momondo's favorite 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
$585
19th c. Barn in the Berkshires

19th c. Barn in the Berkshires

Cheshire, MA, United States

9.4
$501

Ashmere Lakefront Apartment

Hinsdale, MA, United States

10.0
$196

Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled

Lanesborough, MA, United States

$338

Berkshire Pontoosuc Lake Beauty Too-Modern Amenities On The Lake

Pittsfield, MA, United States

9.9
$689
Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

Lanesborough, MA, United States

9.9
$237
Spacious Comfortable Charming Family Farmhouse Great Location

Spacious Comfortable Charming Family Farmhouse Great Location

Lee, MA, United States

9.5
$430

Two Rooms with En-Suite in Quiet Woodland

Hillsdale, NY, United States

10.0
$287

Berkshire Lake House vacation home

Pittsfield, MA, United States

9.7
$541
Beautiful Lenox Home, 3 Mi to Shakespeare and Co!

Beautiful Lenox Home, 3 Mi to Shakespeare and Co!

Lenox, MA, United States

9.2
$303

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

Lanesborough, MA, United States

$676

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

Lanesborough, MA, United States

$183
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
$302

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

Sheffield, MA, United States

9.2
$608

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

Pittsfield, MA, United States

9.6
$367

Memorial Day Week Thru 6/30 Available!!!

Pittsfield, MA, United States

$270

2/Br Historic District Apartment

Pittsfield, MA, United States

$349

Charming Lenox cottage within walking distance to town

Lenox, MA, United States

$426

Restored 1881 Farm House

Lenox, MA, United States

10.0
$350

Wyndham Bentley Brook - Jiminy Peak ski in/out

Lanesborough, MA, United States

$455

Useful insights on Pittsfield vacation rentals

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

Lowest Vacation Rental Price

$82
The cheapest price for a room in Pittsfield found in the last 7 days is $82/night. This rate is available with Apartment Newly Remodeled Super Location.

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
55%expected price decrease
51%expected price increase

Price

$121 - $547

Cheapest day of weekSundayis the cheapest day of the week to book
Highest day of weekFridayis the most expensive day of the week to book
$163
$329

Information about staying in Pittsfield

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

How long do people typically book vacation apartments for in Pittsfield?

A vacation apartment rental booking of around 3 nights is most popular for those visiting Pittsfield.

How much does a vacation rental apartment in Pittsfield cost?

The price of a vacation apartment in Pittsfield depends on the number of guests, locations and required amenities - for a standard apartment in Pittsfield you can expect to pay around $197 per night.

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

Pittsfield vacation rentals are at their cheapest in November. Rental prices can be around 55% lower per night than in the high season.

How many operators does momondo search for hotels in Pittsfield?

There are 53 operators available for hotels in Pittsfield as of April 2024.

When did momondo last update prices for hotels in Pittsfield?

Prices for hotels in Pittsfield are refreshed on a daily basis.

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