Apartment holiday rentals in Pioneer Valley

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Top-rated apartment rentals in Pioneer Valley

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Guest favourite

Apartment in Hancock

4.95 out of 5 average rating, 61 reviews

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!

Top guest favourite

Apartment in Hancock

4.94 out of 5 average rating, 88 reviews

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1

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.

Top guest favourite

Apartment 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 favourite

Apartment in North Adams

4.88 out of 5 average rating, 41 reviews

Downtown Condo - walk to MoCA

New owners but same great location! Overlooking the Historic Eagle Street district in downtown North Adams, you'll find this centrally located, 330 sq ft. condo. Sleeps 2 people (full size bed and fold out futon), Fully equipped eat in kitchen and 3/4 bath. You shouldn't need much more for your stay here in North Adams. Please note: This condo is located on the 2nd floor. Due to the antique nature of the building, there is no handicap accessible entrance, and the stairs are steep and narrow.

Guest favourite

Apartment in Hancock

4.9 out of 5 average rating, 10 reviews

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.

Guest favourite

Apartment in Litchfield County

4.93 out of 5 average rating, 28 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.

Apartment in Lenox

4.7 out of 5 average rating, 10 reviews

Peaceful 1BR Condo with Pond View

Escape to a serene retreat at this cozy 1-bedroom condo in The Ponds at Foxhollow, nestled in the heart of the Berkshires. With a scenic pond view and surrounded by breathtaking mountains, this charming unit is perfect for couples or small families seeking tranquility. Enjoy a fully equipped kitchen, warm fireplace, and access to indoor and outdoor pools, along with endless nearby hiking trails and cultural activities. Your perfect getaway awaits in beautiful Lenox, MA.

Guest favourite

Apartment in Hartford

4.98 out of 5 average rating, 140 reviews

Posh Pad in The Business District

Truly unique, spacious, and comfortable condo in the heart of the Hartford Business District!!! Big city vibes in a quiet, cozy but swanky corner unit. Truly a home away from home. The unit is very nicely appointed with all the creature comforts you can imagine (+blackout curtains). The convenience of an Elevator makes grocery-hauling in the city very easy. Located within walking distance of the very best downtown Hartford has to offer!

Superhost

Apartment in Hancock

5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

This premier Berkshires destination resort is located at the base of the ski slopes of Jiminy Peak Mountain Resort. After a day of skiing, snowboarding, hiking and other seasonal activities, return to your spacious two-bedroom resort suite designed for maximum rest and relaxation with a kitchen and spacious living/dining area. The resort's heated indoor and outdoor pool, game room, sauna, and activities center are sure to please.

Guest favourite

Apartment in North Adams

4.96 out of 5 average rating, 89 reviews

Newly renovated 2BR on historic Eagle Street.

Enjoy the comforts of a newly renovated, quiet and centrally located apartment on historic Eagle Street. Visit the unique boutiques of downtown North Adams, Mass MOCA just a few blocks away, or take a short drive to many of the cultural attractions of the northern Berkshires. One flight of stairs takes you to a 2 bedroom (+ sofa bed), 1 bath apartment featuring vaulted ceilings, a full kitchen, laundry room and tons of light.

Guest favourite

Apartment in Hancock

4.9 out of 5 average rating, 72 reviews

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.

Top guest favourite

Apartment 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.