Pittsfield Holiday Homes from £198: Search Holiday Homes in Pittsfield

Pittsfield Holiday Homes
Massachusetts
United States of America
Holiday Homes
Expedia.co.uk

Pittsfield Travel Guide Hotels in Pittsfield Holiday Rentals in Pittsfield Flights to Pittsfield Pittsfield Car Hire Pittsfield Holidays

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Pittsfield holiday homes

3-bedroom house in beautiful Berkshires, close to amenities!

Pittsfield

The price is £235

£235

includes taxes & fees

17 Feb - 18 Feb

3-bedroom house in beautiful Berkshires, close to amenities!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

7.8 out of 10, Good, (7 reviews)

7.8/10

Good

(7 reviews)

"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."

Liz V.

The price is £358

£358

includes taxes & fees

16 Feb - 17 Feb

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Hancock Village Inn Near Jiminy Peak

Hancock

10.0 out of 10, Exceptional, (16 reviews)

10/10

Exceptional

(16 reviews)

"Amazing Inn. Cozy and everything we needed. "

Price F.

The price is £837

£837

includes taxes & fees

10 Feb - 11 Feb

Hancock Village Inn Near Jiminy Peak

2 bedrooms, desk, iron/ironing board, travel cot

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Sherwood Forest

9.8 out of 10, Exceptional, (11 reviews)

9.8/10

Exceptional

(11 reviews)

"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"

Matthew F.

The price is £290

£290

includes taxes & fees

11 Feb - 12 Feb

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

2 bedrooms, iron/ironing board, WiFi, bed sheets

Home in Great Barrington

Great Barrington

9.8 out of 10, Exceptional, (27 reviews)

9.8/10

Exceptional

(27 reviews)

"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "

Cameron M.

The price is £199

£199

includes taxes & fees

22 Feb - 23 Feb

Home in Great Barrington

Florida Mountain Log Cabin

Florida

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Place was super clean. Beds were comfortable. Location was great."

Tristan e.

The price is £251

£251

includes taxes & fees

16 Feb - 17 Feb

Florida Mountain Log Cabin

3 bedrooms, iron/ironing board, free WiFi, bed sheets

Near Tanglewood: Historic Summer Retreat

New Lebanon

9.4 out of 10, Exceptional, (26 reviews)

9.4/10

Exceptional

(26 reviews)

"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."

Paul S.

The price is £244

£244

includes taxes & fees

10 Feb - 11 Feb

Near Tanglewood: Historic Summer Retreat

Cozy Home in Pownal VT

Pownal

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."

Jess M.

The price is £141

£141

includes taxes & fees

26 Feb - 27 Feb

Cozy Home in Pownal VT

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Very nice house and the stay was unproblematic!"

Noah K.

The price is £308

£308

includes taxes & fees

10 Feb - 11 Feb

Riverbend Berkshire East Basecamp - 3 bedrooms available

Smart TV, fireplace, books, music library

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs

9.0 out of 10, Wonderful, (21 reviews)

9.0/10

Wonderful

(21 reviews)

"Comfy beds, clean, great big deck with a view. "

Corinne T.

The price is £273

£273

includes taxes & fees

10 Feb - 11 Feb

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."

Cheryl F.

The price is £198

£198

includes taxes & fees

10 Feb - 11 Feb

Sweet Cozy Victorian in Housatonic. Close to everything.

The Greylock Cabin

Florida

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Wonderful view, peaceful quiet area, cosy cabin."

Anonymous traveller

The price is £277

£277

includes taxes & fees

3 Mar - 4 Mar

The Greylock Cabin

Family Ski Getaway in the Berkshires

Great Barrington

9.2 out of 10, Wonderful, (9 reviews)

9.2/10

Wonderful

(9 reviews)

"Close to a great bakery and near to a farm market and shopping mall. "

Cristine C.

The price is £208

£208

includes taxes & fees

8 Mar - 9 Mar

Family Ski Getaway in the Berkshires

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

9.6 out of 10, Exceptional, (4 reviews)

9.6/10

Exceptional

(4 reviews)

"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."

Sarah D.

The price is £330

£330

includes taxes & fees

10 Feb - 11 Feb

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Treat yourself at the stunning June Farms Wellness Huts!

West Sand Lake

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."

SteveS

The price is £329

£329

includes taxes & fees

10 Feb - 11 Feb

Treat yourself at the stunning June Farms Wellness Huts!

Artists’ Hideaway in Old Chatham

Old Chatham

The price is £377

£377

includes taxes & fees

10 Feb - 11 Feb

Artists’ Hideaway in Old Chatham

Renovated house. Built in 1890s. No neighbors in sight.

Chatham

The price is £231

£231

includes taxes & fees

10 Feb - 11 Feb

Renovated house. Built in 1890s. No neighbors in sight.

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

8.0 out of 10, Very good, (1 review)

8.0/10

Very good

(1 review)

"excellent communication with property manager."

Nancy H.

The price is £400

£400

includes taxes & fees

10 Feb - 11 Feb

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

10.0 out of 10, Exceptional, (33 reviews)

10/10

Exceptional

(33 reviews)

"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "

cathy c.

The price is £469

£469

includes taxes & fees

10 Feb - 11 Feb

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"

Roberta

The price is £971

£971

includes taxes & fees

10 Feb - 11 Feb

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

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.

View all properties