Hot Pittsfield Cottage Rates

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Featured Cottages in Pittsfield

The Clearing - Quiet - Close To Nature

The Clearing - Quiet - Close To Nature

Cummington
Located in Cummington, this cottage is in a rural location, a 1-minute drive from Westfield River and 8 minutes from Chesterfield Gorge Reservation.
The Clearing - Quiet - Close To Nature
Quiet rustic cottage with shared lake access

Quiet rustic cottage with shared lake access

New Marlborough
With a stay at this cottage in Great Barrington, you'll be on a lake, just steps from Lake Buel and a 4-minute drive from Les Trois Emme Winery.
Quiet rustic cottage with shared lake access
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

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

New Marlborough
Located in Great Barrington, this cottage is on a lake, within a 5-minute drive of Lake Buel and Les Trois Emme Winery.
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
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Family-Friendly Richmond Cottage w/ Private Yard

Family-Friendly Richmond Cottage w/ Private Yard

2 out of 5
Pittsfield
With a stay at this cottage in Richmond, you'll be on the waterfront, within a 15-minute drive of Tanglewood Music Center and Nordeen Marsh Natural Heritage ...
Family-Friendly Richmond Cottage w/ Private Yard
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Monterey
With a stay at this cottage in Monterey, you'll be within a 10-minute drive of Bidwell House Museum and Ashintully Gardens.
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Cozy cottage with pool, walking distance to lake

Cozy cottage with pool, walking distance to lake

Averill Park
Located in Averill Park, this cottage is on a lake, within a 15-minute drive of Berkshire Retreat Center and Pineridge Cross Country Ski Center.
Cozy cottage with pool, walking distance to lake
Private Island - Largest Fresh Water Reservoir in Mass....

Private Island - Largest Fresh Water Reservoir in Mass....

Otis
With a stay at this cottage in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 4-minute drive from Larkum Pond.
Private Island - Largest Fresh Water Reservoir in Mass....
Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

Lanesboro
With a stay at this cottage in Lanesborough, you'll be in the mountains, within a 10-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State ...
Charming historic cottage on scenic road to Mt. Greylock
Beachwood Cottage

Beachwood Cottage

Stockbridge
With a stay at this cottage in West Stockbridge, you'll be on a lake, within a 10-minute drive of Tanglewood Music Center and Frelinghuysen Morris House and ...
Beachwood Cottage
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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 Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Pittsfield will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Pittsfield definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Pittsfield, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Pittsfield Cottages essential information

Accommodation
105 Cottages
Lowest Price
AU$185
Highest Price
AU$229
Popular accommodation
The Clearing - Quiet - Close To Nature, Quiet rustic cottage with shared lake access, Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! , Family-Friendly Richmond Cottage w/ Private Yard, Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks, Cozy cottage with pool, walking distance to lake, Private Island - Largest Fresh Water Reservoir in Mass...., Charming historic cottage on scenic road to Mt. Greylock, Beachwood Cottage

Top trending hotels in Pittsfield

Hotel On North

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$216 per night from 6 Apr to 7 Apr
AU$216
includes taxes & fees
6 Apr - 7 Apr
With a stay at Hotel On North in Pittsfield, you'll be within a 15-minute drive of Tanglewood Music Center and Berkshire Athenaeum.
Hotel On North
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is AU$185 per night from 11 Apr to 12 Apr
AU$185
includes taxes & fees
11 Apr - 12 Apr
With a stay at Holiday Inn & Suites Pittsfield-Berkshires by IHG, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$229 per night from 4 Apr to 5 Apr
AU$229
includes taxes & fees
4 Apr - 5 Apr
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
Berkshire Mountain Lodge
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The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St., Pittsfield, MA
The price is AU$218 per night from 16 Apr to 17 Apr
AU$218
includes taxes & fees
16 Apr - 17 Apr
Located in Pittsfield, The Central Downtown Inn & Suites is a 1-minute drive from Berkshire Museum and 7 minutes from Bousquet Ski Area.
The Central Downtown Inn & Suites
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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.

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