Condo holiday 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!

Family · Value · Cleanliness

Steps to Holyoke Medical Center! Remote-Work Hub

Great for School Visits & College Tours | Easy I-91 Access | 11 Mi to The Big E Experience the heart of the Knowledge Corridor from this modern Holyoke vacation rental! Whether you're in town for business or leisure, this spacious apartment offers a secure retreat perfectly nestled between Springfield and Northampton. After a day of meetings or exploring Mount Tom State Reservation, head to downtown Holyoke for dinner and boutique shopping. Lock in your Western Massachusetts getaway now!

Family · Location · Checkout

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.

Location · Family · Long 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.

Value · Location · Parking

Top Guest favourite

Guest favourite

3BR @ Jiminy Peak | 4-Season Berkshires Retreat

4-season Berkshires retreat at the base of Jiminy Peak Mountain. PRIME ski-in/ski-out in winter, mountain adventure park in summer & fall. The 3BR/2BA JPeak Condo at JJ's Lodge sleeps 8–10 in 1 King, 1 Queen, 2 Bunk Beds (Twins over Fulls) — steps from ski lifts, trails, Alpine Slide, mountain coaster & summit chairlift. Country Inn amenities (pool, hot tubs, gym, game room) open year-round. Village restaurants, fire pits, coffee shop & ski shop open ski season.

Location · Family · Kitchen

5BR 2-Level Duplex Sleeps Groups | Covered Porch

Spacious 5-bedroom, 2-level duplex perfect for families, work groups, and extended stays. Designed for comfort and group travel, with plenty of space to relax, dine, and unwind. ✨ Highlights 5 bedrooms (including 1 king bed) TVs in every bedroom 2 full bathrooms (tub + walk-in shower) Dining table seats 8 Fully equipped kitchen In-unit washer & dryer Covered furnished porch Second floor unit with 12 steps up to the entrance. Furnished back yard .

Value · Location · Getting around

The Monadnock Suite

Welcome to the Monadnock Suite, a New and beautifully appointed 2-bedroom, 1.5-bath retreat in the heart of the Monadnock Region. Sleeps up to 4 with a fully equipped kitchen, comfortable living room, high-speed Wi-Fi, Smart TV, and dedicated parking. Close proximity to Mount Monadnock, hiking, skiing, golf, restaurants, breweries, and downtown Keene. The perfect home base for work, adventure, or a relaxing New Hampshire getaway!

Family · Bathroom · Accuracy

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.

Family · Location · Sleep quality

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.

Value · Family · Condition

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.

Location · Family · Decor

The Car Barn

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.

Check-in · Breakfast · Condition

Spacious 3 bedroom apt in Lenox historic downtown

Newly renovated, spacious 3-bedroom apartment, with 2 bathrooms and free parking in the back. Centrally located in the heart of historic downtown of Lenox. Walk to restaurants and shops, or even skip the traffic and take the 15 min walk to Tanglewood, the famous summer home of Boston Symphony Orchestra .

Value · Family · Long stay