Pittsfield Holiday Houses

Pittsfield Holiday Homes
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A historic building with classical architecture, a traffic light, and a yellow taxi.

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Our top choices for Pittsfield holiday homes

A wooden deck with a table and chairs, surrounded by a white railing.

A bedroom with a bed, a ceiling fan, a window with curtains, and a framed picture on the wall.

A residential area with houses, a driveway, and a body of water in the background.

A living room with a sofa, a coffee table, and a television. There are curtains on the windows, and a lamp is on a side table.

1. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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

Pittsfield

8.4 out of 10, Very good, (10 reviews)

8.4/10

Very good

(10 reviews)

"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."

Stephen L.

The price is NZ$846

NZ$846

includes taxes & fees

26 Oct - 27 Oct

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

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

A large white house with black shutters, surrounded by snow-covered trees and a fence.

A modern kitchen with wooden cabinets, a central island, a refrigerator, a sink, and pendant lighting.

A wooden cabinet with multiple compartments, including glass doors and drawers, likely used for storage.

2. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock

10.0 out of 10, Exceptional, (22 reviews)

10/10

Exceptional

(22 reviews)

"Amazing Inn. Cozy and everything we needed. "

Price F.

The price is NZ$1,978

NZ$1,978

includes taxes & fees

27 Oct - 28 Oct

Hancock Village Inn Near Jiminy Peak

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

A white house with a porch, surrounded by a grassy lawn and trees with autumn foliage.

A living room with two grey sofas, a wooden coffee table, a painting on the wall, and a lamp.

A compact kitchen with a dining table and chairs, a microwave, and a refrigerator.

3. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

8.6 out of 10, Excellent, (7 reviews)

8.6/10

Excellent

(7 reviews)

"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "

Joanna P.

The price is NZ$383

NZ$383

includes taxes & fees

9 Nov - 10 Nov

NEW RENO - Chalet-style farm loft near Tanglewood

A spacious living room with a dining area, a kitchen, and a large window.

A kitchen with white cabinets, a wooden dining table, and a large window.

A bedroom with a bed, two bedside tables, a window, a skylight, and a door leading outside.

A living room with a glass coffee table, a sofa, a TV, and a dining area with chairs and a table.

4. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

7.0 out of 10, Good, (2 reviews)

7.0/10

Good

(2 reviews)

"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"

Leslie H.

The price is NZ$390

NZ$390

includes taxes & fees

5 Nov - 6 Nov

1800s Carriage house in Berkshires / Hudson Valley

A white two-story house with a porch, surrounded by trees and a hill.

A dining room with a wooden table and chairs, a fireplace, and a chandelier.

A cozy living room with a green sofa, a patterned armchair, a wooden coffee table, and a bookshelf.

A grassy outdoor area with a seating arrangement.

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "

Christine C.

The price is NZ$860

NZ$860

includes taxes & fees

1 Nov - 2 Nov

1789 Shaker Farmhouse in Berkshires/Hudson Valley

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

A modern living room with a fireplace, white cabinetry, a large flat-screen TV, and a cozy seating area with patterned cushions.

A dining area with a wooden table and chairs, a large wooden cabinet, and a kitchen in the background.

A wooden deck with a bench and umbrella, a door, and a window.

6. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

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

Stephentown

9.4 out of 10, Exceptional, (9 reviews)

9.4/10

Exceptional

(9 reviews)

"A lovely house! Very convenient for a Tanglewood weekend."

Robert B.

The price is NZ$986

NZ$986

includes taxes & fees

25 Oct - 26 Oct

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

A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

A kitchen with wooden cabinets, a countertop, and a potted plant.

A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

A bedroom with a bed, bedside lamp, and a window with curtains.

7. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!

Richmond

The price is NZ$1,192

NZ$1,192

includes taxes & fees

7 Nov - 8 Nov

Ellie’s Overlook, best view in the Berkshires!

A bedroom with a bed, a nightstand, a lamp, a chair, and a dresser.

A kitchen with wooden cabinets, a central island, and a red door leading to another room.

A dining area with a wooden staircase leading to a bookshelf filled with books and bottles.

A cozy living room with a wooden bookshelf, a patterned sofa, and a dining table with chairs.

8. Mayas Shangrila

Mayas Shangrila

2.0 star property

Richmond

The price is NZ$2,048

NZ$2,048

includes taxes & fees

10 Nov - 11 Nov

Mayas Shangrila

A two-story house with a front porch, a small garden with autumn leaves, and a clear blue sky.

A kitchen with a central island, a built-in sink, and a ceiling fan.

A kitchen with wooden cabinets, a microwave, stove, and a bar area with wooden chairs.

9. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock

8.8 out of 10, Excellent, (12 reviews)

8.8/10

Excellent

(12 reviews)

"Host was proactive in communication and answer each and every question."

Amit

The price is NZ$946

NZ$946

includes taxes & fees

25 Oct - 26 Oct

Comfortable Berkshires retreat on mtn resort, SISO

A living room with a sofa, armchairs, a coffee table, and a television.

A rustic wooden building with a chimney, surrounded by lush greenery and flowering plants.

A dining area with a wooden table, white chairs, and a hanging light fixture.

10. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."

Patricia O.

The price is NZ$1,101

NZ$1,101

includes taxes & fees

1 Nov - 2 Nov

Sun Filled Lenox Retreat - Minutes to Tanglewood!

A cozy living room with a wooden floor, a red armchair, a patterned sofa, and a glass door leading outside.

A compact kitchen with wooden cabinets, a coffee maker, and a stove.

A loft-style room with a wooden staircase, wicker furniture, and a patterned rug.

A house with a front yard, a gravel driveway, and a stone wall.

11. Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires

Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires

Richmond

The price is NZ$2,222

NZ$2,222

includes taxes & fees

23 Oct - 24 Oct

Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires

A modern living room with a sofa, armchair, coffee table, and TV.

A porch with a bench, a potted plant, and a black door with the number 175.

A living room with a sofa, armchair, coffee table, and a staircase leading to another room.

A kitchen with white brick backsplash, stainless steel appliances, wooden cabinets, and a wooden island.

12. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups

Lee

9.6 out of 10, Exceptional, (4 reviews)

9.6/10

Exceptional

(4 reviews)

"house was very clean, spacious and well equipped with everything we needed. Great communication with the host. Perfect location for our trip to Tanglewood."

neil s.

The price is NZ$1,042

NZ$1,042

includes taxes & fees

1 Nov - 2 Nov

Spacious Central Berkshires Home for Groups

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

A spacious kitchen with wooden beams, a dining area with a long table, and a living room with a red sofa and a fireplace.

A covered outdoor deck with a wooden table and a mug, overlooking a forested area.

A house with a covered porch and a well-maintained garden.

13. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods

Stockbridge

10.0 out of 10, Exceptional, (30 reviews)

10/10

Exceptional

(30 reviews)

"We had a wonderful time, we’d be happy to come back again "

Ofer C.

The price is NZ$1,135

NZ$1,135

includes taxes & fees

22 Oct - 23 Oct

Secluded Family Home in Serene Stockbridge Woods

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

A cabin in a forest with a dirt path leading to it, surrounded by trees.

A cozy living room with a grey sofa, a patterned throw blanket, and a wooden ceiling.

A triangular-shaped building with a balcony and a wooden picnic table in front.

14. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

10.0 out of 10, Exceptional, (10 reviews)

10/10

Exceptional

(10 reviews)

"We loved it! Lots of local hiking trails and a wonderful relaxing place."

Sharon K.

The price is NZ$651

NZ$651

includes taxes & fees

26 Oct - 27 Oct

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

A wooden deck with a round table and two chairs, surrounded by a forest with autumn foliage.

A red building with a stone wall, a wooden deck, and a gravel path leading to the entrance.

A bedroom with a bed, a bench, a chair, a nightstand, a table, and a ceiling fan.

15. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"Very good trip overall. Great location. Just a few things needed to make it over the top!"

William C B.

The price is NZ$519

NZ$519

includes taxes & fees

3 Nov - 4 Nov

Real Estate: Therapy - Lake, Laundry, Love it

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

A kitchen with wooden cabinets, a stainless steel refrigerator, a gas stove, and a built-in oven.

A cozy living room with wooden walls, a floral sofa, a white table, and a patterned rug.

A small, single-story house with a porch, surrounded by a well-maintained lawn and trees.

16. Cozy Home in Pownal VT

Cozy Home in Pownal VT

Pownal

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."

Jeri R.

The price is NZ$357

NZ$357

includes taxes & fees

26 Oct - 27 Oct

Cozy Home in Pownal VT

A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

A modern kitchen with a central island, stainless steel refrigerator, and pendant lighting.

A spacious living area with a wooden dining table, a black leather sofa, and a piano.

A modern kitchen with white cabinetry, a wooden island, and pendant lighting.

17. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub

New Lebanon

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "

Anonymous traveller

The price is NZ$1,010

NZ$1,010

includes taxes & fees

27 Oct - 28 Oct

NEW RENO Historic Creamery in Berkshires w/hot tub

A staircase with a wooden handrail and a white wall with a light switch.

A kitchen with wooden cabinets, a black countertop, a window with a view, and a hanging bag.

A picnic table in a grassy yard with trees and a fence in the background.

A hallway leading to a bedroom with a dresser and a mirror on the wall.

18. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires

Great Barrington

9.6 out of 10, Exceptional, (29 reviews)

9.6/10

Exceptional

(29 reviews)

"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."

Kelly B.

The price is NZ$492

NZ$492

includes taxes & fees

26 Oct - 27 Oct

Leaf-Peeper Paradise in the Berkshires

A hot tub with a string of lights above it, set against a dark night sky.

A living room with a fireplace, a sofa, a rug, and a mirror on the wall.

A living room with a ceiling fan, a TV, a sofa, a chair, and a rug.

A rustic cabin with a gravel path leading to a bench in a forested area.

19. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

9.6 out of 10, Exceptional, (19 reviews)

9.6/10

Exceptional

(19 reviews)

"Great place and welcoming stay!"

Frank M.

The price is NZ$683

NZ$683

includes taxes & fees

29 Oct - 30 Oct

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

A camping setup with a metal chair and a table by a river in a forest.

A forested path with a building in the background.

A living room with two leather sofas, a coffee table, a patterned ottoman, and a lamp on a side table.

20. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

10.0 out of 10, Exceptional, (16 reviews)

10/10

Exceptional

(16 reviews)

"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"

Jess S.

The price is NZ$598

NZ$598

includes taxes & fees

25 Oct - 26 Oct

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

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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Top Pittsfield Hotel Reviews

Hotel On North

10/10 Excellent

"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."

Vicki 1-night trip

Posted 8 hours ago

Hotel On North

Berkshire Mountain Lodge

10/10 Excellent

"Hot tub did not work"

Tatyana 2-night trip

Posted 9 hours ago

Berkshire Mountain Lodge

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"Breakfast was great ... coffee available early!"

Robert 1-night trip

Posted 9 hours ago

Comfort Inn & Suites East Greenbush - Albany

Vacation Village in the Berkshires

10/10 Excellent

"Great apartment. Large pool. Comfortable bed. Everything we needed for a great stay."

Alicia 1-night trip

Posted 10 hours ago

Vacation Village in the Berkshires

Berkshires Untold

10/10 Excellent

"Great service"

Sonia 1-night trip

Posted 11 hours ago

Berkshires Untold

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"This place was an excellent deal. I thought I was getting a hotel room, but what I got was a 2-story townhouse. The facility includes lots to do indoors (clubhouse, movie theater) and outside (sports courts, trails along the river)"

Ted 1-night trip

Posted 12 hours ago

Holiday Inn Club Vacations Oak 'n Spruce Resort

Berkshire Inn

10/10 Excellent

"Very clean room and apparently the room had been upgraded recently by real craftsmen. Well done. You don't expect this quality from an older motel, but the owners obviously take pride in the property."

Jeff 1-night trip

Posted 13 hours ago

Berkshire Inn

The Williams Inn

10/10 Excellent

"Fantastic hotel! Would definitely stay again."

Pete 1-night trip

Posted 13 hours ago

The Williams Inn

The Yankee Inn

10/10 Excellent

"The old fashioned touches like real glasses in the rooms. The flower selections around the property. The condition of the indoor pool and whirlpool were great.The pond and surrounding land are great. Nicest motor lodge I've been to."

Erin 1-night trip

Posted 13 hours ago

The Yankee Inn

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews	204
Accommodation	416 Holiday Homes
Lowest Price	NZ$357
Highest Price	NZ$1,978

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Pittsfield on Expedia.com

Holiday Homes in Pittsfield

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pittsfield holiday homes

1. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2. Hancock Village Inn Near Jiminy Peak

3. NEW RENO - Chalet-style farm loft near Tanglewood

4. 1800s Carriage house in Berkshires / Hudson Valley

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

6. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

7. Ellie’s Overlook, best view in the Berkshires!

8. Mayas Shangrila

9. Comfortable Berkshires retreat on mtn resort, SISO

10. Sun Filled Lenox Retreat - Minutes to Tanglewood!

11. Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires

12. Spacious Central Berkshires Home for Groups

13. Secluded Family Home in Serene Stockbridge Woods

14. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

15. Real Estate: Therapy - Lake, Laundry, Love it

16. Cozy Home in Pownal VT

17. NEW RENO Historic Creamery in Berkshires w/hot tub

18. Leaf-Peeper Paradise in the Berkshires

19. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

20. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Find holiday rentals that suit your style

Top Pittsfield Hotel Reviews

Hotel On North

Find out more about Pittsfield

Pittsfield Holiday Homes information

Explore a world of travel with Expedia