Holiday rentals in Pittsfield

4.93 out of 5 average rating, 102 reviews

Net Zero home with rustic Berkshire charm

Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

4.88 out of 5 average rating, 185 reviews

Flat in Petersburgh

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Space is 14 x 28 feet and includes living/dining/work space, bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed with pull out twin mattress. High def TV, wifi, private deck, kitchenette has mini fridge, microwave, toaster oven, hot kettle for tea and and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

5 out of 5 average rating, 100 reviews

Cottage in Pittsfield

Cozy Berkshire cottage with indoor fireplace

Relax at this unique, tranquil getaway. Minutes from all the Berkshires' offer; Tanglewood, Bousquet and Jiminy Peak ski resorts, museums, Colonial and Barrington Theater, Shakespeare and Co, Naumkeag, and many more. Conveniently located on the Pittsfield/Lenox line, close to many restaurants and shopping areas but tucked into the woods with hiking trails on the property. Our kitchen has all your cooking essentials. We have smart TV's and WIFI to relax with after your Berkshire adventures.

Guest suite in Pittsfield

4.9 out of 5 average rating, 69 reviews

Newly Renovated Red Door Annex

Private keypad entrance with parking. Large bedroom with full bathroom. The spacious room has a high-end queen bed and a small table for eating/working. Small frig, microwave, toaster oven, and pour-over coffee in a small nook outside the bedroom. Popcorn, oatmeal and yogurt are provided. The Annex is in a tranquil neighborhood between Great Barrington and Williamstown/North Adams and ski areas.1 mile to Berkshire Medical Center. 20 minutes to Lenox. Outdoor sitting area to come this summer.

4.95 out of 5 average rating, 21 reviews

Whispering Woods Guest House

Welcome to your perfect modern urban retreat in Pittsfield, Massachusetts! Our cozy home offers a charming and comfortable stay just a quick stroll from downtown, short drive to Tanglewood, and just a minute away from BMC. Enjoy the convenience of exploring local areas such as Lenox, Stockbridge, Great Barrington, North Adam’s and more! Ideal for solo travelers, couples, or anyone seeking a delightful small city experience. Come stay with us and immerse yourself in the local culture!

4.95 out of 5 average rating, 174 reviews

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

4.95 out of 5 average rating, 192 reviews

Cottage in New Lebanon

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and table.

5 out of 5 average rating, 37 reviews

Comfy Quaint Tavern

Experience this beautifully renovated unit which is available for overnight guests. Enjoy the charm of yesteryear and the echo of laughter and friendship. This property was originally a tavern that opened in 1933 and received one of the first liquor licenses in the area after prohibition was repealed. Now a fully renovated one bedroom unit (within two-unit property) with so much of the historic charm restored for your recreation and relaxation. Off street parking.

4.99 out of 5 average rating, 219 reviews

Farm stay in Pittsfield

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 just relax out on the balcony and take in the views.

4.93 out of 5 average rating, 376 reviews

Guest house in Lenox

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.

Superhost

Cabin in Plainfield

4.92 out of 5 average rating, 170 reviews

Peaceful Cabin in the Woods

Escape the noise and come relax in the middle of the beautiful Berkshire Hills. This classic log cabin has been recently renovated so that you can unwind and connect to the picturesque landscape that envelopes this property. You can drive 30 minutes west to North Adams and visit Mass Moca or 30 minutes east to Northampton, Amherst & Hadley. (Please note, 1/2 of the bedrooms is an open loft).

4.92 out of 5 average rating, 262 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.

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Popular amenities for Pittsfield holiday rentals

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Wifi

Pool

Free parking on premises

Air conditioning

Stay near Pittsfield's top sights

Hancock Shaker Village59 locals recommend

Berkshire Museum37 locals recommend

Pittsfield State Forest12 locals recommend

Other great holiday rentals in Pittsfield

4.95 out of 5 average rating, 225 reviews

Farm stay in New Lebanon

Barn Stay at Shadowbrook Farm

JenniferRating, 5 stars1 month ago

The space was beautiful, clean, and exactly as pictured! We enjoyed a weekend away and appreciated the local recommendations shared in the guide. We spent time exploring the farm, the surrounding area, and also were able to kick back and relax in the amazing property.

4.63 out of 5 average rating, 67 reviews

Beautiful Apartment in Central Pittsfield

JanetteRating, 5 stars2 weeks ago

Carrie was very responsive and friendly. The house was clean, well stocked and well furnished. We will stay again should we find ourselves in the area again

4.91 out of 5 average rating, 22 reviews

Green 2 bedroom Downtown

FabioRating, 5 stars2 weeks ago

The house is great. We've stayed here more than once and we'll definitely be back.

Home in Lenox

5 out of 5 average rating, 4 reviews

Spacious Guest House with Pool and Walk-in Shower

JessicaRating, 5 stars6 days ago

I loved my stay in the Berkshires at Siobhan’s place. The space was clean, spacious, and perfect for a quick work trip in the area. Fun walks right from the guest house and lots to explore in the area. Highly recommend!

Farm stay in Adams

5 out of 5 average rating, 3 reviews

Berkshires/Pet Friendly farm stay w/mountain views

IsabelleRating, 5 stars2 weeks ago

My three friends and I had a wonderful weekend stay at this airbnb. From the start Jessica, the host, was in touch and responsive to any questions I had. The RV itself was perfect, exactly what my group was looking for and was as advertised. A lovely guest-ready camper, a fire pit, great views and outdoor spaces, accessibility, chairs with an umbrella, a picnic table, a hammock that could be set up, easy storage for all of these things, and friendliness from the host next door. We were able to comfortably sleep 4 people for 3 nights. My group have discussed returning when we can because we had such a positive experience. We hope that others will get the opportunity to make memories in Adams, MA as we did during our stay this summer. All I have to say are good things about this location and the people who run it. I would absolutely recommend it :)

4.75 out of 5 average rating, 20 reviews

Pebbled Beach Cottage

AmandaRating, 5 stars1 week ago

The cottage is very cute and cozy with decent views of the lake. We enjoyed the couple of nights that we stayed and will definitely book again

Cottage in Great Barrington

4.94 out of 5 average rating, 135 reviews

The Cottage at The Barrington House

GuillaumeRating, 5 stars4 days ago

We enjoyed very much our (unfortunately short) stay at Katie's cottage. It's a very cosy place and I felt that it looked much better in real than in the photos. The cottage that makes you feel at home instantly. It's very clean and all the products available and services are great. It is very conveniently located between all the main attractions areas and close to all the hikes. Katie was very responsive and communicative. We hope to come back soon!