Pittsfield vacation rentals

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Top-rated vacation rentals in Pittsfield

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Lee

4.9 out of 5 average rating, 202 reviews

1817 Berkshire Farmhouse- Close to Everything.

*Close to ski resorts & tubing! We are nestled at the foot of October Mountain State Forest, yet close to the centers of Lee, Lenox, & Pittsfield. Our charming house was built in 1817- original wood beams, wood floors, and quite a history. Whether you enjoy skiing, exploring local restaurants & downtowns, venturing outdoors or experiencing the local art scene, the Berkshires has something for everyone. Our little farmhouse serves as the perfect "home base" for all of your Berkshire adventures.

Apr 24 – May 1

G$32,378 GYD per night

Guest favorite

Home in Canaan

5.0 out of 5 average rating, 133 reviews

Country Cottage

Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.

Mar 25 – Apr 1

G$32,191 GYD per night

Guest favorite

Home in Lee

4.89 out of 5 average rating, 235 reviews

Cozy Berkshires Cottage

Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)

Sep 25 – Oct 2

G$26,039 GYD per night

Guest favorite

Cottage in Lanesborough

4.93 out of 5 average rating, 220 reviews

Stone School Cottage

Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.

Sep 5 – 12

G$38,300 GYD per night

Guest favorite

Guesthouse in Becket

4.93 out of 5 average rating, 257 reviews

Country Cabin

Lovely private country setting. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. I only accept advance reservations of 2 nights or more. (You may reserve a single night booking within 5 days of the request.) The space is for 2 adults but I allow for flexibility, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.

Jan 2 – 9

G$25,434 GYD per night

Superhost

Home in Dalton

4.88 out of 5 average rating, 113 reviews

The Yellow House

The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. This historic small town offers many activities including Jacob's Pillow, hiking trails, skiing, Mass MoCA, and The Clark Art Institute. It is close to Tanglewood in Lenox and the Norman Rockwell Museum in Stockbridge. Located steps away from The Stationery Factory, which houses a food market, gallery spaces, artisan shops, coffee shop, and the Shire Brewhouse & pub.

Dec 1 – 8

G$23,965 GYD per night

Guest favorite

Guest suite in Hancock

4.83 out of 5 average rating, 154 reviews

Cozy apartment near Jiminy Peak

Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

Dec 3 – 10

G$17,794 GYD per night

Guest favorite

Guesthouse in Lenox

4.95 out of 5 average rating, 276 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Sep 5 – 12

G$30,637 GYD per night

Guest favorite

Farm stay in Pittsfield

4.99 out of 5 average rating, 105 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or take a walk on our hiking trail.

Jul 19 – 26

G$31,580 GYD per night

Guest favorite

Apartment in Lenox

4.88 out of 5 average rating, 169 reviews

Station House 1E Private Room & Bath

Our place is a central location in Berkshire County, short drive to restaurants and shops; art and culture, skiing and hiking also close by. You’ll love this former train station( next to the Housatonic RR tracks) which is on three acres between a chapel, the scenic Housatonic River and October Mountain. Our place is good for couples, solo adventurers, and business travelers.

Jun 17 – 24

G$15,307 GYD per night

Guest favorite

Apartment in Pittsfield

4.92 out of 5 average rating, 224 reviews

Marie's Place

This newly renovated bright sunny apartment is minutes from Bosquet ski area & also close to downtown. It has a large kitchen and pantry. Beautiful oak dining room table. Comfy living room set, with a 43 inch Roku TV. Electric fireplace. Queen size beds in both bedrooms. Large walk-in closet in. 28 minutes from Jiminy peak. Close to downtown restaurants and theaters.

Dec 27 – Jan 3

G$29,968 GYD per night

Guest favorite

Apartment in Plainfield

4.95 out of 5 average rating, 237 reviews

Sunny carriage house apartment

Our sunny apartment is located midway between Northampton and the Berkshires, in a lovely rural setting. The kitchen, bath and studio living area are in a private apartment, surrounded by 12 acres of open fields. The kitchen is well equipped and includes all the makings for tea and coffee. Orange juice, oatmeal, English muffins and homemade granola are also provided!

Dec 4 – 11

G$23,427 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Pittsfield vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Pittsfield's top sights

Walmart9 locals recommend

Berkshire Roots7 locals recommend

Big Y World Class Market80 locals recommend

99 Restaurants7 locals recommend

Colonial Theatre56 locals recommend

Berkshire Museum102 locals recommend

Other great vacation rentals in Pittsfield

Guest favorite

Home in Pittsfield

4.98 out of 5 average rating, 102 reviews

Hidden Oasis in the Mountains by Evergreen Home

Apr 25 – May 2

G$96,648 GYD per night

Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 255 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Oct 17 – 24

G$20,651 GYD per night

Guest favorite

Apartment in Plainfield

4.97 out of 5 average rating, 238 reviews

Sunny, light filled loft in 1873 Colonial

Feb 25 – Mar 4

G$24,868 GYD per night

Guest favorite

Guest suite in Williamstown

4.96 out of 5 average rating, 202 reviews

Berkshire Guest Suite

Nov 26 – Dec 3

G$20,385 GYD per night

Guest favorite

Guesthouse in Canaan

4.93 out of 5 average rating, 166 reviews

Airy cottage with meadow views in The Berkshires

Feb 13 – 20

G$34,549 GYD per night

Guest favorite

Loft in East Nassau

4.99 out of 5 average rating, 151 reviews

Dog Friendly Farm Spring bird watching

Sep 15 – 22

G$33,427 GYD per night

Superhost

Apartment in Lee

4.78 out of 5 average rating, 106 reviews

Cozy Berkshire Cottage Style Apartment

May 31 – Jun 7

G$21,376 GYD per night

Guest favorite

Guesthouse in Stephentown

5.0 out of 5 average rating, 359 reviews

Dog Friendly Studio

Aug 31 – Sep 7

G$39,935 GYD per night

Show all

Other great vacation rentals in Pittsfield

Superhost

Apartment in Pittsfield

4.83 out of 5 average rating, 18 reviews

Cozy Studio Apt in Downtown Victorian

Jun 29 – Jul 6

G$25,328 GYD per night

Guest favorite

Apartment in Pittsfield

5.0 out of 5 average rating, 41 reviews

Simply off North

Nov 10 – 17

G$17,376 GYD per night

Guest favorite

Apartment in Pittsfield

4.96 out of 5 average rating, 48 reviews

The sweet place in the beautiful Berkshires!

Dec 7 – 14

G$25,565 GYD per night

Superhost

Cottage in Pittsfield

4.9 out of 5 average rating, 69 reviews

Cottage Getaway - access all the Berkshires offer!

Jun 5 – 12

G$31,038 GYD per night

Guest favorite

Apartment in Canaan

5.0 out of 5 average rating, 83 reviews

Mountain View Getaway

Aug 27 – Sep 3

G$22,301 GYD per night

Superhost

Apartment in Lanesborough

4.85 out of 5 average rating, 62 reviews

Charming Apt. in 18th c. Berkshire Farmhouse

Jun 17 – 24

G$22,439 GYD per night

Guest favorite

Guest suite in Great Barrington

5.0 out of 5 average rating, 43 reviews

Sweet 1-bedroom with salt water pool

Jun 6 – 13

G$27,191 GYD per night

Guest favorite

Home in Becket

4.94 out of 5 average rating, 36 reviews

Nerd Preservation Sanctuary

Dec 1 – 8

G$19,317 GYD per night

Show all

Quick stats about vacation rentals in Pittsfield

Total rentals
210 properties
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
70 properties allow pets
Family-friendly rentals
120 properties are a good fit for families
Total number of reviews
7.1K reviews
Nightly prices starting at
G$2,090 GYD before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Pittsfield?
Yes! Work meets play with ease at over 110 vacation rentals in Pittsfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Pittsfield?
Four-legged friends are welcome in Pittsfield. Choose from more than 70 vacation rentals for guests traveling with pets.
Are there Pittsfield vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Pittsfield, available on Airbnb. Make a splash and soak up the sun in style!
Do cottage rentals in Pittsfield have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Pittsfield. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Pittsfield?
Pittsfield has more than 70 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Pittsfield have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Pittsfield. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Pittsfield?
Experience the best of Pittsfield with our apartment rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Pittsfield have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Pittsfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Pittsfield have a gym?
Absolutely! We offer over 10 house rentals with a gym in Pittsfield. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Cottage Rentals in Pittsfield?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Pittsfield vacation rentals

Top-rated vacation rentals in Pittsfield

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Pittsfield vacation rentals

Stay near Pittsfield's top sights

Other great vacation rentals in Pittsfield

Home in Pittsfield

Apartment in Copake Falls

Apartment in Plainfield

Guest suite in Williamstown

Guesthouse in Canaan

Loft in East Nassau

Apartment in Lee

Guesthouse in Stephentown

Other great vacation rentals in Pittsfield

Apartment in Pittsfield

Apartment in Pittsfield

Apartment in Pittsfield

Cottage in Pittsfield

Apartment in Canaan

Apartment in Lanesborough

Guest suite in Great Barrington

Home in Becket

Quick stats about vacation rentals in Pittsfield

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Pittsfield?

Are there pet-friendly vacation rentals in Pittsfield?

Are there Pittsfield vacation rentals on Airbnb with pools?

Do cottage rentals in Pittsfield have wifi?

Are there family-friendly house rentals in Pittsfield?

Do house rentals in Pittsfield have a bbq area?

How much does it cost to stay in apartment rentals in Pittsfield?

Do cottage rentals in Pittsfield have air conditioning?

Do house rentals in Pittsfield have a gym?

What are the most popular amenities for Cottage Rentals in Pittsfield?

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