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Holiday rentals in Pittsfield, MA

Find deals on 41 holiday rentals in Pittsfield, MA

Pittsfield, MA, United States
20 May — 21 May2
Wed 15/5
Sun 19/5

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Top rentals in Pittsfield

Find the perfect holiday rental for your stay in Pittsfield
Price
$128
$1260
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

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

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

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

Monthly/Yearly, All Season Vacation Rental, Minutes from Jimney Peak, MA

Monthly/Yearly, All Season Vacation Rental, Minutes from Jimney Peak, MA

Lanesborough, MA, United States

Get the best value holiday rental in Pittsfield

These Pittsfield holiday 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
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
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

momondo's favourite holiday rentals in Pittsfield

Learn more about these user-preferred holiday rentals in Pittsfield

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

Becket, MA, United States

10.0
$886
19th c. Barn in the Berkshires

19th c. Barn in the Berkshires

Cheshire, MA, United States

9.3
$759

Ashmere Lakefront Apartment

Hinsdale, MA, United States

10.0
$297

Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled

Lanesborough, MA, United States

$515

Berkshire Pontoosuc Lake Beauty Too-Modern Amenities On The Lake

Pittsfield, MA, United States

9.9
$1,149
Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

Lanesborough, MA, United States

9.9
$359
Spacious Comfortable Charming Family Farmhouse Great Location

Spacious Comfortable Charming Family Farmhouse Great Location

Lee, MA, United States

9.5
$671

Two Rooms with En-Suite in Quiet Woodland

Hillsdale, NY, United States

10.0
$435

Berkshire Lake House vacation home

Pittsfield, MA, United States

9.7
$895

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

Lanesborough, MA, United States

$1,024

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

Lanesborough, MA, United States

$277
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
$457

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

Sheffield, MA, United States

9.2
$921

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

Pittsfield, MA, United States

9.6
$563

Memorial Day Week Thru 6/30 Available!!!

Pittsfield, MA, United States

$409

2/Br Historic District Apartment

Pittsfield, MA, United States

$528

Charming Lenox cottage within walking distance to town

Lenox, MA, United States

$645

Restored 1881 Farm House

Lenox, MA, United States

10.0
$524

Wyndham Bentley Brook - Jiminy Peak ski in/out

Lanesborough, MA, United States

10.0
$689

Wyndham Bentley Brook at ski in/ ski out Jiminy Peak

Lanesborough, MA, United States

$825

Useful insights on Pittsfield holiday rentals

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

Lowest Holiday Rental Price

$129
The cheapest price for a room in Pittsfield found in the last 7 days is $129/night. This rate is available with Berkshire Cottage.

When to book a holiday rental in Pittsfield

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

Price

$184 - $828

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
$252
$490

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 holiday rental in Pittsfield?

The cheapest month to rent a holiday apartment in Pittsfield is usually November. The cost of your apartment or rental property can be around 59% cheaper in November vs. the high season.

How many operators does momondo search for hotels in Pittsfield?

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

When did momondo last update prices for hotels in Pittsfield?

Prices for hotels in Pittsfield are updated daily.

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