Compare Pittsfield Cottage Rentals

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Featured Pittsfield Cottages

The Clearing - Quiet - Close To Nature

The Clearing - Quiet - Close To Nature

At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Pool
Kitchen
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2 out of 5
Guests staying at this cottage can enjoy a gym, barbecue grills, and a garden.
Kitchen
Pet friendly
Heaven Can't Wait, On Beautiful Kinderhook Lake!!

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Pet friendly
Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

This cottage features free WiFi in public areas and a garden.
Kitchen
Free WiFi
Private Island - Largest Fresh Water Reservoir in Mass

Private Island - Largest Fresh Water Reservoir in Mass

Guests staying at this cottage can enjoy a gym, a garden, and barbecue grills.
Kitchen
Pet friendly
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Charlemont Retreat on Chickley River w/ EV Charger

Charlemont Retreat on Chickley River w/ EV Charger

3 out of 5
This cottage features free WiFi in public areas and barbecue grills. You can take advantage of free offsite parking if you drive.
Kitchen
Washer
Entire cottage in Berkshire Villiage

Entire cottage in Berkshire Villiage

3 out of 5
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Kitchen
Washer
Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres

2 out of 5
$1,625 nightly
The price is $1,647 total per night
$1,647 total
Nov 2 - Nov 3
Total with taxes and fees
Guests of Berkshires farm, 30+ guests, 50 acres enjoy a hot tub, an arcade/game room, and laundry facilities. Additional amenities include a garden and barbecue grills.
Hot Tub
Kitchen
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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.

Hotel Options in Pittsfield

    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr, Pittsfield, MA
    $113 nightly
    The price is $126 total per night from Nov 2 to Nov 3
    $126 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.8/10 Excellent! (678 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    One West Street, Pittsfield, MA
    $103 nightly
    The price is $115 total per night from Nov 2 to Nov 3
    $115 total
    Nov 2 - Nov 3
    Total with taxes and fees
    7.8/10 Good! (887 reviews)
    Best Western Plus Berkshire Hills Inn & Suites

    Best Western Plus Berkshire Hills Inn & Suites

    1350 W Housatonic St, Pittsfield, MA
    $102 nightly
    The price is $114 total per night from Nov 2 to Nov 3
    $114 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.4/10 Very Good! (1,000 reviews)

Cottages

Book a cottage in Pittsfield
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Pittsfield. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Pittsfield better.

Cottage apartments in Pittsfield range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Pittsfield
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Pittsfield and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Pittsfield cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Pittsfield. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Pittsfield Cottages essential information

Accommodation
108 Cottages
Lowest Price
$114
Highest Price
$1,647
Popular accommodation
The Clearing - Quiet - Close To Nature, Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires, Heaven Can't Wait, On Beautiful Kinderhook Lake!!, Charming historic cottage on scenic road to Mt. Greylock, Private Island - Largest Fresh Water Reservoir in Mass, Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! , Charlemont Retreat on Chickley River w/ EV Charger, Entire cottage in Berkshire Villiage, Berkshires farm, 30+ guests, 50 acres

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