Condo vacation rentals in Pioneer Valley

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Jiminy's GEM is everything you're looking for! The location is absolutely prime- steps from the highspeed 6pk lift with your balcony overlooking the beautiful mountain & apres fire pit. Enjoy 3 bdrms/3 full baths with enough beds to accommodate numerous families, sleeping a total of 10 people. Take advantage of a heated pool, hottub & gym when you're not enjoying the mountain. Summer and Leaf Peeping season are equally as entertaining and enjoyable. Let us make your trip better than imagined!

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

You want to bring your whole family to Jiminy and be in ONE CONDO, with gorgeous views, a deck, BBQ, Backyard, and be at Jiminy Peak - This condo is for you - right in the heart of Country Village. This Stylish 2BR country Condo w AC is fully updated and comes with parking in front and full access to the Country Inn Amenities ( Fitness, pools, hottub, Tennis etc). This large 900 sq ft condo features country decor, & sleeps up to 7 with a queen, two bunk beds, pull out Trundle, and Full Bed. Th

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2

Ski-in,ski-out! Unbeatable location for all seasons! Closest condo at JiminyPeak to the slopes and lifts. Located right at base of Mt. in JJ’sLodge in the heart of JiminyVillage. Mere steps to BerkshireExpress HighSpeed 6pack! Amazing pano views of the slopes surround. Designated pkg space in owner’s pkg lot. Unmatched access to all JP’s year-round activities. Skiing,MtBiking,hiking,tennis,swimming,fall foliage leaf peeping, shops,restaurants,MtAdventurePark w/ famous MtCoaster&AlpineSuperSlide.

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).

Jiminy Peak Country Inn 1 Bedroom Suite

A privately owned, older unit within Jiminy Peak's Country Inn. Located in the Berkshires, the inn is at the base of the ski slope. This unit is on the 1st floor of the last building which means you can ski to your doorstep if there's lots of snow (harder getting to the lift) . A locker room is at the end of the building to secure your equipment (key provided). The resort offers a year-round heated pool, 2 hot tubs, a gym, fireplace lounge and seasonal restaurants. Come enjoy the mountain!

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!

Luxury furnished condo. Attached garage. Fireplace

Welcome to the luxurious Simsbury retreat designed and fully equipped for displaced or relocating families and traveling professionals. Our townhouse offers 2 bedrooms with en-suite bathrooms, an attached garage, huge basement/TV/Game room, fully stocked kitchen with granite countertops, and large deck. Equipped with brand new luxury furnishings, a cozy gas fireplace, TVs and desks in each room, 2 bikes and games, it is perfect for indulging in comfort and convenience during your stay.

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.

Large one bedroom, two full bath, full kitchen

Located in the heart of Hancock's premier ski-resort, Jiminy Peak this lovely appointed self contained apartment is ski on, ski off the 45 runs of the mountain. Perfect for a cozy Fall getaway to leaf peep all of the beautiful Berkshires. Close to Williamstown, North Adams, Lee, Lenox, Pittsfield and more. This is a year round spot with loads of activities. Pool, jacuzzi, exercise room and two restaurants are on site.

Jiminy Peak Country Inn - ski in/out condo MT view

Rent your very own condo in the Country Inn at Jiminy Peak Mountain Resort.This unit is just steps away from the entrance and your ski locker. Ski in/out and never have to move your car! Spectacular view of the mountain from your windows, close to all the amenities the resort has to offer. The resort offers a year-round heated pool, 2 hot tubs, a gym, fireplace lounge and restaurants. The perfect mountain escape.