
Apartment vacation rentals in Pittsfield
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Top-rated apartment rentals in Pittsfield
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Modern Copake Falls Getaway - 8 Mins to Catamount
Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

King Bed, Wi-Fi, 2m Ski Resort
Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. * 1.5 miles to Downtown * 1.3 miles to Mahaiwe Performing Arts Center * 44 miles to Albany International Airport *4.5 miles to Great Barrington Airport KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *55" Youtube TV with NFL Pack

The Beer Diviner Brewery Apartment
The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

See MoCA from your mansion+Sauna! Near SKI
Near Ski & restaurants! 4 bedroom apartment tucked away on a hilltop oasis above Mass MoCA (3 mins by foot). 10 mins drive to Williams College & Clark. Whimsically restored (fast Wi-Fi & great water pressure). Fully private with no shared spaces + outdoor Sauna! Your stay’s proceeds allow us to host refugee/immigrant musicians pro bono year-round at @chasehillartistretreat Note: more dates are often available beyond what the calendar shows. Please don’t hesitate to inquire!

Sunny, light filled loft in 1873 Colonial
Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!

Overlooking the city in a quiet 7 unit building.
This is a quiet, 7 unit, newly renovated condominium building. We welcome quiet guests who will appreciate a relaxing stay and be conscious of others around them. We are within walking distance to the countries largest contemporary art museum. The 2nd floor is an open plan divided by the stair case. Each side has a queen bed, its own closet. The full bathroom is shared with the two beds. This is a loft, there are no full walls between the two sides of the loft.

Cooper's Place
Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

Stunning studio in the heart of Troy: Raven's Den
Raven's Den is a large studio apartment with a queen sized bed, full kitchen, and an extra-deep bathtub. It is an open plan room that can be configured as needed, featuring two "aerial silk" hammocks that double as swings. It's in the heart of Downtown Troy, close to RPI, EMPAC, The Troy Music Hall, The Farmers Market, and the Takk House. Whether you need a cozy romantic getaway or simply a clean, fresh, place to lay your head, Raven's Den could be for you.

Cool Brick Basement Studio Parking Fast WiFi AC
Cool 1900 brick basement level studio with curtained off sleeping area, fast wifi, tile floors, brick walls, nearly new kitchen, granite countertops, air conditioning & shared laundry. South Central Troy (Washington Park Neighborhood) quiet street, just 1 block to Carmen's Cafe, 3 blocks to Russell Sage, within walking distance to quaint shops, dining, nightlife and everything else Downtown Troy has to offer. Close to R.P.I, H.V.C.C, and Emma Willard.

Historical Downtown 1 Bedroom Apartment
Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for two, stainless appliances, and an array of cooking essentials. The living room features a comfortable sectional and a flat screen TV for relaxing. Wi-Fi is available throughout the space. Central heat and air to provide a comfortable environment in any season. All linens and towels are provided.

Sunny Duplex at the old boarding house
Charming big vintage apartment in an old boarding house from 1900. It's a Greek Revival house on a country lane at the foot of the Berkshires. Master bedroom and full bath are downstairs, where there is also a lovely living room, fully stocked kitchen and mudroom with washer/dryer. Note that the attic bedroom gets closed in the wintertime. Small front sitting porch, big side lawn and flowery backyard with grill and table.

ALL welcome: Lovely 1 BR studio, Berkshires beauty
Come as you are - we welcome ALL visitors. Relax and soak in your surroundings in this new 1 bedroom vacation spot. Part of a barn conversion, the space is clean and bright and ideally located for those exploring all the Berkshires has to offer. Perfect for an individual or couple looking to escape to a serene and beautiful setting - a stream abuts the property and hiking/snowshoeing trails are accessible out the front door.
Popular amenities for Pittsfield apartment rentals
Weekly apartment rentals

Downtown Apartment A

Cute, Cozy and Comfortable apartment

Walnut Way basement apartment

Center of Lenox, cozy Apartment 2-bedroom

Downtown Studio in Adams

Comfortable Pittsfield Loft

Charming/Rustic Apartment with downtown views

Modern Gem in the Heart of Berkshires
Private apartment rentals

Guestrooms on the Bike Trail

The River’s Whisper

Mill Town Lodge • Spacious & Private Retreat

"Nostalgia" a spacious2 bedroom first floor unit.

Walkable Studio: Restaurants & Fun Just Steps Away

Stockbridge private apartment

Vermont Downtown Oasis

Cozy, Quiet Apt. in Housatonic, Great Barrington
Apartment rentals with a hot tub

Berkshire Mountain Top Chalet

Ski-In Ski-Out Loft Lift & MT. Views

Cozy Ski Retreat

Mt Snow 2 Bdrm Condo - Free Ski Shuttle

Jiminy Peak Ski Loft with Hot Tub

Luxe Ski Getaway Base of Jiminy

Walk to main lift! The Handle Studio @ Mt. Snow!

Snow Tree Escape | @ Base of Mt.Snow w/ Fireplace!
When is the best time to visit Pittsfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ279 | ﺩ.ﺇ279 | ﺩ.ﺇ275 | ﺩ.ﺇ275 | ﺩ.ﺇ349 | ﺩ.ﺇ312 | ﺩ.ﺇ349 | ﺩ.ﺇ349 | ﺩ.ﺇ312 | ﺩ.ﺇ342 | ﺩ.ﺇ283 | ﺩ.ﺇ283 |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Quick stats about apartment rentals in Pittsfield

Total vacation rentals
Explore 70 vacation rentals in Pittsfield

Nightly prices starting at
Pittsfield vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

Verified guest reviews
Over 3,260 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Pittsfield vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Pittsfield rentals

4.8 Average rating
Pittsfield stays are highly rated by guests—averaging 4.8 out of 5!
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- Stratton Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Thacher State Park
- Mount Snow Ski Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Kent Falls State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Bousquet Mountain Ski Area
- Taconic State Park
- Norman Rockwell Museum
- Hildene, The Lincoln Family Home
- Ski Sundown
- Opus 40
- Berkshire Botanical Garden
- Naumkeag
- Hancock Shaker Village
- Poets' Walk Park
- Millbrook Vineyards & Winery




