
House vacation rentals in Pittsfield
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Top-rated house rentals in Pittsfield
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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?!

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!

Bright Stockbridge country home, near everything!
Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

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!

Steps to MoCA private house + SAUNA!
In North Adams—one of the Berkshires’ prime destinations for fall colors— Chase Hill sits on a hilltop oasis just above MoCA (3 minutes by walk). Once home to the owners of the factory that became MASS MoCA, the whimsically restored house is part of this private historic estate. Only 10 minutes’ drive to Williams College & The Clark, and steps to downtown restaurants. ✨ Your stay enables us to host refugee & immigrant musicians pro bono year-round. More info on @chasehillartistretreat.

Granite Ledge, Modern home in a unique setting
Welcome to Great Barrington, the heartbeat of the Berkshires! This newly remodeled home that sits on 3.5 acres, is conveniently located 1 min from Butternutt Ski Mountain, and a 6 min drive from downtown main street Great Barrington. Convenient to restaurants, shops, farmers markets, art galleries, Tanglewood, Stockbridge, The Norman Rockwell Museum, Simon’s Rock, etc. Enjoy a vibrantly diverse restaurant scene and cultural events while still staying in a private setting.

1890 House
Back online after renovations. This beautiful Victorian farmhouse is situated on a 1/2 acre with great views of Mount Greylock, surrounding mountains and quaint town of Adams. The wraparound porch is perfect for relaxing. It is fully furnished and has a fully equipped kitchen. There is a wood stove in living room. Walking distance to Adams/supermarket. Short drive North Adams (MASSMoCA), Williamstown (Clark Museum) and Jiminy Peak (ski resort) which is 30 minutes drive.

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 relax by the firepit- we hope you enjoy your stay and will visit us again.

North Adams Getaway-walk to MASS MoCA
BRAND NEW! Ready for guests to enjoy all the Berkshires has to offer! Whether you are visiting for work or pleasure, with family or friends this is a perfect place for you. Located in downtown North Adams you are surrounded by breath taking mountains and foliage, nestled between award winning museums, access to great food, and a short drive to ski resorts, breweries, Tanglewood, the highest peak in MA, and more. A true outdoorsman paradise. BOOK NOW!

Hidden Oasis in the Mountains by Evergreen Home
7 MINUTES TO BOUSQUET MOUNTAIN Escape with family & friends to this hidden oasis in the heart of the Berkshires. Enjoy the beautiful perennial gardens, unwind in the hot tub, relax on the stone patio by the fire pit, & dine on the deck. Just minutes from Lenox & Tanglewood, this attractive 5 BR home boasts a large, fully-outfitted kitchen, comfortable Tuft & Needle mattresses, & spacious living areas with stunning mountain views.

Tranquil mid-century modern Berkshires retreat
We love the Scandi House because of its simplicity, openness, warmth, comfort, trees, space, privacy, and convenience. We enjoy this Berkshires retreat for its close proximity to all what Berkshires has to offer in music, arts, and outdoor activities. Most of all, we treasure the tranquility and each other when we are here at the house in the woods.

GreenHouse
Relax and enjoy the Berkshires at this peaceful place to stay in the beautiful Berkshires of western Massachusetts. GreenHouse is the guest cottage for the historic Hyde House which is on the National Register of Historic Places. Located within walking distance of Lee, Ma, the house is also conveniently located near Stockbridge and Lenox.
Popular amenities for Pittsfield house rentals
House rentals with a pool

Bluestone Escape - Where everyone is at home.

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

Sunbeam Lodge: Pool+Hot Tub, 50 Acres, ‘70s Oasis

Hudson River views with pool and hot tub

Stylish Rural Sanctuary! (+ Summer Pool)

Hollywood Bungalow in the Berkshires #C0191633410

Casa Luna Country Retreat with Pool, Hudson, NY
Weekly house rentals

Modern, Renovated Lakefront Escape

Solomon Ely Homestead set in walkable downtown

Whispering Woods Guest House

Berkshire Lakehouse - 3 bedrooms - sleeps 5

Lakefront Home on Ponstoosuc Lake, The Berkshires

BB's Central Berkshire Home

Historic Stone Church in The Berkshires

Spacious 4 Br+ house in the heart of Berkshires
Private house rentals

Stunning Fall Views! Hot Tub/Movie Room/Game Room

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Spacious Farmhouse with Stunning Views

Marie’s Place unit 3

Seekonk Hill

The Red House

Ski the Berkshires at Hygge House on Richmond Pond

The Berkshires Hummingbird House
Quick stats about house rentals in Pittsfield
Total rentals
100 properties
Nightly prices starting at
€ 26 before taxes and fees
Total number of reviews
3.5K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Destinations to explore
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- Stratton Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Zoom Flume
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Taconic State Park
- Stratton Mountain Resort
- Mount Sugarloaf State Reservation
- Opus 40
- Mohawk Mountain Ski Area
- Beartown State Forest
- Mount Tom State Reservation
- Mount Snow Ski Resort
- Bousquet Mountain Ski Area
- Bright Nights at Forest Park
- Albany Center Gallery
- Talcott Mountain State Park