Apartment holiday rentals in Pioneer Valley

Sunny, Spacious, Downtown, Main St. Duplex

Our duplex apartment is centrally located on Main St. in the middle of downtown Northampton. Steps away from restaurants, nightclubs, museums, galleries, theaters, and Smith College. Park your car and spend your day exploring our beautiful little city. You'll be staying in a sunny, spacious, private bedroom with high ceilings and windows overlooking Main St. Downstairs is an airy kitchen and living room. Central A/C & Heat. Wifi. FYI, we do have a shy kitty. Extra blanket, pillows are in room

River House: walk to campus, town, Clark & more

RIVER HOUSE: Bright, modern, fully-furnished 2+ bedroom, two bathroom, loft apartment overlooking the Green River on Water Street in the heart of Williamstown, Massachusetts, in the Berkshires. Available for Williams College graduation 6/3/26-6/8/26 (5-night minimum; earlier arrival possible from 6/2/26 & later departure possible through 6/9/26). Also available for academic-year rentals from 08/27-05/29 via Zillow (search "Unique Riverfront Condo for rent in Williamstown," or inquire here).

the NAMA nest

Cozy Condo - Walking distance to MASS MoCA Welcome to North Adams, Massachusetts (NAMA), the heart of the Northern Berkshires! This one bed, one bath, sun-drenched cozy space is nestled in the iconic Flatiron Building, a unique, wedge-shaped landmark at the corner of Eagle and Church Streets, offering a one-of-a-kind architectural experience that blends 19th-century charm with modern downtown living. This cozy 330 sq ft nest is in the ideal spot for exploring NAMA, for short and long stays!

5 Bedrooms Mins to Six Flags, MGM, & Hospitalsq

Enjoy a modern 2nd floor condo in a private setting. The 5 bedroom 2bath( 1shower, 1tub) condo is elegantly styled, embracing style and functionality. It has everything you'll need to enjoy, relax, recharge, or work during your Springfield area stay. Clean, comfortable, family, friendly , safe and as pictured. You will have the entire place to your self. Safe neighborhood full of families with diverse background. Second floor unit with 12 steps up to the entrance. Furnished back yard .

Two story condo near Amherst town center and UMass

Located within minutes of downtown Amherst, our condo offers a convenient location with grocery stores, restaurants, and nearby colleges like UMass, Amherst College, and Hampshire College. A bus stop in front of the complex provides freedom and convenience, allowing you to avoid the hassle of finding parking spaces while heading to town or nearby colleges. Most bus services in the Amherst area are free. The condo has a coin-operated laundry in the common basement, also nearby Laundromats.

1 Mi to MGM Springfield: Cozy Winter Duplex!

Open-Concept Layout | WFH Friendly | Gas Grill | 3 Mi to The Big E Embrace a New England winter at this bright and welcoming 4-bed, 2-bath vacation rental duplex in Springfield. After a day of casino fun at MGM Springfield, exploring festive downtown events, or skating at local rinks, return to a warm and comfortable home base perfect for families and groups. You can also enjoy easy access to nearby colleges and universities, and holiday happenings. Book your snowy season getaway today!

Meadow View

Nestled on a quiet country road, Pacer's Pasture has everything you need for a rejuvenating stay. Just over a mile away, Haystack Mountain State Park offers scenic hiking; while the Station Place Cafe and Norfolk Pub are great eateries to enjoy dinner before catching a concert at Infinity Music Hall -- right in Norfolk. The Berkshire Country Store, an antique store, and a liquor store offer nearby provisioning and shopping. The Yale Music School is less than a mile away.

3BR Apartment Near Holyoke Medical Center & Office

Conveniently located in Holyoke, MA, this spacious apartment offers a shared lobby area at the entrance, along with a private dedicated office/den area for your convenience. Situated across the street from Holyoke Medical Center and near Interstate 91, this home is centrally positioned between the bustling cities of Springfield and Northampton. The secure neighborhood is surrounded by various businesses and banks, ensuring a safe and convenient stay.

Historic Estate Studio Loft

EASTWOOD ESTATES – THE LOFT SUITE IDEAL FOR: • Remote Workers & Digital Nomads • Short-Term Stays & Solo Retreats • Quiet, Low-Key Staycations *Note: Stair access required – not recommended for children or guests with mobility concerns FLOORPLAN & SLEEPING ARRANGEMENTS Compact, Elevated Living • 2 Full Beds (Main Level) • Pull-Out Sofa for Extra Guests • Cozy Upper Loft Nook • 1 Full Bathroom • Access via Single Interior Staircase

1 BR Apartment Near Holyoke Medical Center & WiFi

Conveniently located in Holyoke, MA, this modern apartment offers a comfortable stay with a shared lobby area at the entrance. Situated across the street from Holyoke Medical Center and near Interstate 91, this home is centrally positioned between the bustling cities of Springfield and Northampton. Safety is a top priority in this secure area, surrounded by various businesses and banks, providing peace of mind for guests.

Modern 1BR Condo near Bradley Airport & Hartford

“Welcome to your modern Windsor retreat! This newly renovated 1BR, 1.5-bath condo is minutes from Bradley Airport and Hartford. Enjoy a cozy living room with smart TV, full kitchen, King bed with blackout curtains, and a rare extra half bath. On-site laundry, free parking, seasonal pool, and a walkable plaza with Target, dining, and more.

Downtown Adams Vintage Getaway

Your family will be close to everything when you stay at this centrally-located place. Walk to the Adams Theater, rail trail, grocery store, restaurants, shops, or take a quick drive to MassMoCA, Jiminy Peak, or Greylock Glen. This is the perfect location for all north county has to offer. One free parking spot in back of building.