Condo vacation rentals in Pioneer Valley

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Top-rated condo rentals in Pioneer Valley

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Guest favorite
An abstract painting features bold, swirling colors surrounding a muted central area. The edges are filled with vibrant hues of red, yellow, and blue, blending with darker tones to create depth and dimension.
Condo in Springfield
4.95 out of 5 average rating, 115 reviews

Welcome to Honey Spot!

Enjoy a modern 2-floor condo in a private setting. The condo is elegantly styled embracing functionality and aesthetics. It has everything you'll need to enjoy, relax, recharge, or work during your Western Mass stay. Located 4 miles off I-91 & I-90 in Springfield, MA. 4 mi from the MGM Grand Casino & Basketball Hall of Fame, 12 mi from Six Flags New England, 32 mi from Hartford CT, 70 mi from New Haven CT, 78 mi from Mount Snow VT, 86 mi from Boston MA, 88 mi from Albany, NY and 147 mi from NYC.

Guest favorite
Condo in Williamstown
5 out of 5 average rating, 6 reviews

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 living room features a spacious light-colored couch with decorative pillows and an accent ottoman. A large artwork adorns the wall, while a plant adds greenery to the space. Natural light enters through two windows, complementing the modern decor.
Condo in Springfield
4.82 out of 5 average rating, 11 reviews

5 Bedrooms Mins to Six Flags, MGM, & Hospitals.

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 .

Guest favorite
Condo in Amherst
5 out of 5 average rating, 9 reviews

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.

A modern living area features plush seating arranged around a natural stone coffee table. A smart TV is mounted on the wall, with a staircase leading to the upper floor visible in the background. Natural light illuminates the space, creating a welcoming atmosphere.
Condo in Springfield
4.96 out of 5 average rating, 23 reviews

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!

An outdoor view of a lively resort features a large swimming pool surrounded by sun loungers, with families enjoying the water. Nearby, tennis courts are visible, and a mini-golf course is positioned in the foreground, blending seamlessly with the natural landscape.
Condo in Lee
4.82 out of 5 average rating, 38 reviews

Holiday Inn Club/ Oak and Spruce, Berkshires

This resort is the Holiday Inn Club at Oak and Spruce. The rooms have been greatly upgraded since I took these pictures. I own time shares here. It is a wonderful resort with so many amenities and the most perfect location, 15 minutes from Tanglewood, 10 minutes from center of Stockbridge. You can look it up for better photos on the web site. It is on a country road but near everything and well furnished and stocked. Reservations must be made at least 30 days in advance.

Guest favorite
A well-lit bedroom features a spacious bed covered in neutral bedding. A wooden dresser and a small nightstand with a lamp are positioned beside the bed. Natural light streams through a round window highlighting the warm wood floors.
Condo in Litchfield County
4.93 out of 5 average rating, 30 reviews

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.

Condo in Holyoke
4.75 out of 5 average rating, 4 reviews

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.

A light-filled lounge area features a cozy sofa adorned with patterned cushions and a coffee table made of distressed wood. A flat-screen TV is mounted on the wall, and a stylish chandelier provides overhead illumination, enhancing the room's inviting ambiance.
Condo in Suffield
4.77 out of 5 average rating, 13 reviews

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

Top guest favorite
A modern kitchen is visible, featuring stainless steel appliances and ample storage cabinets. A dining table set for four is in the foreground, complete with glassware and decorative green accents. Natural light fills the space, highlighting the open floor plan that leads into the living area.
Condo in Lenox
4.9 out of 5 average rating, 84 reviews

Heart of Lenox!! - Renovated downtown apartment

Completely renovated 2 bedroom downtown apartment with open floor plan in Lenox MA. Enjoy walks around the downtown area and visit the many attractions in Berkshire County. Endless restaurants to choose from, golf courses within 7 miles, Kennedy Park and Tanglewood close by. Minutes down the road you will find the historic Red lion Inn in Stockbridge or Norman Rockwell Museum.

Superhost
Condo in Whitingham

The Car Barn

FREE Breakfast and lunch everyday for your entire stay! This is a unique automotive-themed large 1700 square foot apt. newly built and furnished. Three large bedrooms, large living room, mudroom for your fishing gear or skiis. Right off the Vast Trail and above and to the left of a general store and Tap room. Plenty of parking for snowmobile trailers and cars.

Superhost
A view of a downtown street, featuring a sidewalk lined with chairs and tables outside a café. Red accents can be seen on the café's exterior. Buildings of varying heights line the street, with greenery visible in the background under a cloudy sky.
Condo in Adams
4.71 out of 5 average rating, 55 reviews

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.

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