Vacation rentals in Pittsfield

4.93 out of 5 average rating, 101 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?!

4.87 out of 5 average rating, 292 reviews

Dancing Horse Lodge

Dancing Horse Lodge is located in the heart of the Berkshire Mountains in Pittsfield, MA, minutes from Tanglewood, Barrington Stage, Jacobs Pillow Ballet, Kripalu Yoga, Shakespeare and Co. and skiing at Bosquet and Jiminy Peak. It is a light and bright residence located on a 20-acre horse farm with nature views out of each window. It is surrounded by miles of woods, great for hiking and cross country skiing. Close to all amenities yet affords beautiful, quiet country living. Come and enjoy!

4.88 out of 5 average rating, 183 reviews

Apartment 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.

Guest suite in Pittsfield

4.9 out of 5 average rating, 67 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, 172 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!

Superhost

Home in Dalton

4.89 out of 5 average rating, 143 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.

4.95 out of 5 average rating, 191 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.

4.84 out of 5 average rating, 279 reviews

Cottage in Lanesborough

Wildlife Lakeside Cottage; views/wildlife

Fully furnished and remodeled with new upgrades in Spring 2025 including a cathedral master bedroom suite with a full bath. Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. Sleeps 6. Ther are two full and one 1/2 baths.

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, 215 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, 374 reviews

Guesthouse 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.

4.92 out of 5 average rating, 259 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.

Vacation rentals for every style

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Popular amenities for Pittsfield vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Pittsfield's top sights

Hancock Shaker Village59 locals recommend

Berkshire Museum36 locals recommend

Pittsfield State Forest12 locals recommend

Other great vacation 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.

4.9 out of 5 average rating, 21 reviews

Green 2 bedroom Downtown

FabioRating, 5 stars2 weeks ago

I highly recommend the house.

5 out of 5 average rating, 6 reviews

Sunny 1 Bedroom Apartment

Jasmine MaeRating, 5 stars3 months ago

We really loved our stay at Carrie's place in Pittsfield. She was a fantastic host: responsive, friendly, and proactive. The apartment is so cozy and well-equipped, and we felt at home right away. My dog absolutely LOVES the backyard, and has spent all winter doing snow zoomies every chance he gets. The area is peaceful, but being close to neighbors makes us feel like we're not isolated. All the everyday necessities we need (groceries, doctors, vets, car repair) are a 3-5 minute drive away, and downtown have a ton of cute shops and cafes. There's also a bunch of great sledding and skiing options nearby, and if we come back in the summer, we're going to be sure to check out the nearby trails. We truly enjoyed our time here and would come back in a heartbeat! Thank you Carrie!

4.75 out of 5 average rating, 20 reviews

Pebbled Beach Cottage

AmandaRating, 5 starstoday

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

5 out of 5 average rating, 45 reviews

Cabin in East Nassau

Luxury Cabin | Breathtaking Views & Outdoor Fun

ElaineRating, 5 stars1 week ago

Matt and Sarah’s place is wonderful. A great place to relax and enjoy the beautiful surroundings. The house is just as described and the hosts make you feel right at home. We hope to come back again!

Cottage in Great Barrington

4.94 out of 5 average rating, 133 reviews

The Cottage at The Barrington House

AliceRating, 5 stars1 week ago

Cute getaway for me and my husband as we traveled for my cousin’s wedding! The list of recommendations Katie provided was extensive and great! Best part was that we had a very long drive home and had no chores to do before checking out!!

4.94 out of 5 average rating, 47 reviews

Modern Gem in the Heart of Berkshires

ElenaRating, 5 stars2 days ago

I had a great second stay at Jon & Abby’s place. They are great hosts - proactive, clear communicators, responsive, and kind. I was so glad to find their place available for the week I needed to be in the area for work! It is comfortable, secure, well-maintained, and quiet (and very minimal noise audible between the two units based on my experience). Highly recommended.