Vacation rentals in Pittsfield

4.93 out of 5 average rating, 110 reviews

A modern kitchen is displayed, featuring an arrangement of appliances including a stove, microwave, and refrigerator. A dining table sits in the center, complemented by a green patterned rug. Sunlight filters through a nearby door, illuminating the open layout and inviting atmosphere.

Apartment in Pittsfield

Downtown Apartment A

Centrally located in the Berkshires. Enjoy a beautiful day at Tanglewood, view the amazing art at Mass Moca or discover nature on one of the many hiking/biking trails the Berkshires has to offer. Located 5 mins from Bousquet and close to Jimmy Peak as well for anyone enjoying the snow! There are a variety of delicious restaurants to suit any appetite. Located in a quiet neighborhood, if your out & about all day or just looking to get away from the hustle & bustle of the city it's a perfect spot.

ValueFamilyNearby

4.95 out of 5 average rating, 480 reviews

A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.

Chalet in Otis

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

FamilyLocationAccuracy

4.98 out of 5 average rating, 86 reviews

The historic stone church exterior is framed by lush greenery and a manicured lawn. Towering above, the bell tower features intricate architectural details. A wooden fence surrounds the property, leading to a pathway that invites exploration of the beautiful grounds.

Home in Lanesborough

Historic Stone Church in The Berkshires

<b>Hinterland Hall</b> was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Places in 1972. Ripe with history and impeccable beauty, Ian & Jane purchased the old stone church in May of 2021, completing an extensive restoration process in accordance with the Massachusetts Historical Commission. It is with great pleasure that we open our doors to you for a wondrous stay. <b>Follow us @hinterlandhall</b> Please inquire about weddings & events.

LocationValueQuiet

A single-story wooden lodge with a green metal roof is set amidst a grassy area. The exterior is lined with windows, allowing natural light to fill the interior. Surrounding trees provide a backdrop, and a paved driveway leads to the entrance, enhancing accessibility.

4.87 out of 5 average rating, 327 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!

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4.99 out of 5 average rating, 395 reviews

Tiny home in Wilmington

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

LocationValueWifi

A bright living area features a yellow couch and two accent chairs, inviting relaxation. A patterned area rug centers the space, while natural light filters through large windows. A staircase is visible in the background, along with decorative plants and artwork adorning the walls.

4.96 out of 5 average rating, 228 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!

LocationFamilyAccess

4.85 out of 5 average rating, 297 reviews

A serene lake reflects a clear blue sky and lush green forests surrounding it. The water, calm and inviting, showcases the vibrant colors of autumn foliage along the banks, with tall grasses in the foreground adding to the natural landscape.

Cottage in Lanesborough

Wildlife Lakeside Cottage; views/wildlife

Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. There is an incredible amount of wildlife, especially all types of birds. Sunny views abound. The house boasts a bright wood interior with a cozy feel. It has two and a half baths. There is a first floor queen bedroom with cathedral ceiling, and on the 2nd floor another queen room and a twin room-2 single beds.The adjacent lake teams with wildlife, seasonal weeds do grow. Contact us for conditions.

FamilyLocationPets

4.99 out of 5 average rating, 313 reviews

Home in Lee

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

LocationFamilyBathroom

Guest suite in Pittsfield

The entrance features a red door framed by light-colored siding. A small roof provides shelter over the entry, and a lantern hangs above. A gravel pathway leads to the door, surrounded by greenery and natural landscaping.

4.92 out of 5 average rating, 135 reviews

Newly Renovated Red Door Annex

Private keypad entrance with parking. Large bedroom with a new Queen bed, full bathroom. There is a small table for dining and working, a small fridge, microwave, toaster oven, and pour-over coffee and tea in a nook (not a kitchen) outside the bedroom. Small outdoor sitting area. The Annex is in a tranquil neighborhood between Great Barrington and Williamstown/North Adams and ski areas. 20 minutes to Lenox. The Annex is attached to the main house but is completely private.

LocationValuePets

4.9 out of 5 average rating, 175 reviews

A quaint cottage is nestled among trees, featuring a welcoming front porch with several potted plants and outdoor seating. The light-colored exterior is complemented by blue accents on the chairs, while the wooden deck extends invitingly, creating a serene outdoor space.

Cabin in Cheshire

Private Paradise in the Berkshires

Your own private and romantic getaway behind a small orchard. A sweet running brook and outdoor shower! A short drive to all Berkshire cultural events -- Tanglewood, Jacob's Pillow, theatre festivals and more. Great dining nearby. Perfect for 2! Under COVID-19 regulations in Massachusetts, I am required to allow at least 24 hours between guests. It's a drag, but it is intended to keep us all healthy! Please forgive any inconveniences this might create in your trip plans.

ValueFamilyAmenities

4.99 out of 5 average rating, 326 reviews

A two-story home is depicted, featuring a grey wooden exterior with multiple windows. A wooden deck with stairs leads to the entrance, surrounded by green grass and vibrant yellow flowers. The clear blue sky complements the inviting structure.

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.

LocationFamilyOutdoor spaces

4.92 out of 5 average rating, 324 reviews

A cozy living room is furnished with two comfortable sofas and a coffee table set on a patterned rug. Natural light enters through a window, illuminating wall art and decorative elements. A door leads to a balcony area, enhancing the space's inviting feel.

Apartment in Pittsfield

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. Large bathroom with tub and shower. 28 minutes from Jiminy peak. Close to downtown restaurants and theaters. Ac units are installed from June through September.

LocationValueGrill

Popular amenities for Pittsfield vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

What Airbnb hosts recommend seeing in Pittsfield

Find unforgettable activities and unique points of interest near you. Our hosts share their favorite things to do and must-visit places to see in Pittsfield.

Jiminy Peak Mountain Resort

Four-season resort offering skiing, mountain biking, zip lining, and scenic chairlift rides

Summarized by AI

At Jiminy Peak Mountain Resort you can ski and snowboard on up to 45 trails for all levels, with night skiing, terrain parks, snowshoe trails, lessons, and rentals, plus cozy lodges and several on-site restaurants and shops. Ride the 3,600-foot Mountain Coaster, alpine slide, and Soaring Eagle, or explore a full Mountain Adventure and Aerial Adventure Park with ziplines and treetop obstacles. In warmer months, add hiking, mountain biking, trampolines, and scenic chairlift rides with broad valley views. The resort also runs a busy calendar of family-friendly events, including the spooky seasonal “13 Nights at Jiminy.”

Mentioned by 341 local hosts

Norman Rockwell Museum

Art museum showcasing the largest collection of Norman Rockwell's works, with engaging exhibits and scenic grounds

Summarized by AI

Explore the world’s largest collection of Norman Rockwell’s original paintings, drawings, and memorabilia, including iconic works like his Saturday Evening Post covers and “Four Freedoms.” Tour his preserved studio, watch the short films about his life and process, and join gallery talks, lectures, workshops, and family art programs. Walk the 36-acre grounds with outdoor sculptures and big valley views, then stop at the on-site café and browse the Rockwell-themed gift shop and archives.

Mentioned by 478 local hosts

Mount Edith Wharton's Home

Summarized by AI

At The Mount, explore Edith Wharton’s restored Gilded Age mansion on a self-guided or guided house tour, seeing the rooms she designed, her custom-bound books, and architecture inspired by French and Italian classical styles. Walk the formal gardens and grounds, with outdoor art installations, seasonal sculpture exhibitions, and space to wander with dogs on leash. Join literary and cultural programs, including author lectures, live storytelling, theater, music, workshops, and fall ghost tours. In winter, experience Nightwood, a nighttime light-and-music walk through the estate’s paths and gardens.

Mentioned by 251 local hosts

Hancock Shaker Village

Living history museum showcasing Shaker life, with historic buildings, farm animals, and workshops

Summarized by AI

Spend the day exploring 20 historic Shaker buildings, walking through gardens, and visiting an active farm with baby animals, piglets, goats, turkeys, and the iconic round barn. Learn how the Shaker community lived through costumed interpreters, exhibits, and demonstrations of woodworking, blacksmithing, metalsmithing, farming, cooking, and ingenious inventions. Kids can get hands-on in the Discovery Barn, trying on Shaker-style clothing and imagining life in a 19th-century school. Wrap up with locally focused food at the cafe and Shaker goods in the gift shop.

Mentioned by 229 local hosts

Naumkeag

Gilded Age estate featuring elegant gardens, seasonal events, and a preserved shingle-style mansion

Summarized by AI

Explore the 44-room Gilded Age shingle-style mansion on a guided house tour or wander the 48-acre estate at your own pace, taking in its character-filled terraces and architecture. Stroll through world-renowned gardens, from spring’s Daffodil and Tulip Festival to colorful summer plantings, and relax with a drink or light pastry from the outdoor coffee stand or cash bar. Time your visit for Naumkeag at Night with live music, Sunset Yoga, garden classes, or seasonal events like the Pumpkin Show and Winterlights holiday display.

Mentioned by 182 local hosts

Berkshire Botanical Garden

Charming 15-acre garden showcasing diverse plant species, seasonal events, and educational programs

Summarized by AI

Explore 15–24 acres of display gardens, mixed borders, perennial beds, a pond garden, a historic 1937 herb garden, woodland areas, and a children’s discovery garden showcasing over 3,000 mostly Northeastern and Berkshire-native plants. Join classes, workshops, lectures, and guided tours, or visit for rotating exhibits, plant sales, and seasonal events like the annual Fall Harvest Festival. Families can enjoy kid-friendly programming and hands-on discovery areas. Nearby, pair your visit with local museums, restaurants, and shops in Stockbridge and neighboring towns.

Mentioned by 182 local hosts

Other great vacation rentals in Pittsfield

4.89 out of 5 average rating, 18 reviews

Cottage in Pittsfield

Pine & Paddle | Pond Access • Kayaks

LocationFamilyComfort

A charming two-story home is framed by lush greenery, with a spacious deck featuring multiple seating areas. Flowering plants and shrubs add color to the landscape, while a gravel pathway leads toward the entrance, creating an inviting atmosphere amidst nature.

4.95 out of 5 average rating, 38 reviews

The Guest House at Cottage Farm

LocationFamilyHospitality

A serene view of Onota Lake is captured, showcasing vibrant autumn foliage reflected in the calm waters. Two docks are visible, with one equipped for boat access. A grassy area leads to the lake, creating a peaceful setting for relaxation.

4.92 out of 5 average rating, 49 reviews

Berkshire Lakehouse - 3 bedrooms - sleeps 5

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5 out of 5 average rating, 30 reviews

Apartment in Lenox

Historical Housatonic Street Building

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5 out of 5 average rating, 23 reviews

Home in Lebanon Springs

Modernized 1860s Getaway w/ Queechy Lake Passes*

LocationFamilyIndoor spaces

Hotel room in Pittsfield

4.65 out of 5 average rating, 43 reviews

1 BD • Berkshires Apartment • Full Kitchen/Pool

LocationFamilyAccess

5 out of 5 average rating, 25 reviews

A serene lakefront property is viewed from the water, featuring a well-maintained lawn and inviting home. The structure is flanked by mature trees, while a small private dock extends into the lake, providing easy access to the water.

Home in Lanesborough

Lakefront Home on Ponstoosuc Lake, The Berkshires

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