Condo holiday rentals in Pioneer Valley

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Top-rated condo rentals in Pioneer Valley

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Top Guest favourite

Condo in Northampton

4.97 out of 5 average rating, 63 reviews

Lovely 1bedrom apartment with screened in porch

Kick back and relax in this calm, stylish,clean space located in quiet residental street ,second floor of my family home.First floor is also Airbnb studio and third floor is used by owner. Short distance from Smith and downtown also bike path right on the beegining of the street. With this full apartment there is open floor plan with ample dinning and living area ,4 glass door opening onto your own private screened porch . You are welcome to use shared outdoor firepit in back of the house too.

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Condo in Hancock

4.85 out of 5 average rating, 41 reviews

All-season Berkshires ski resort condo - Sitzmark

Stay at the Jiminy Peak mountain resort near renowned museums, music, dance and theater in the beautiful Berkshires. You'll be steps from swimming, hiking, aerial adventures and thrill rides. Meals are easy with two resort restaurants, a country store and a fully equipped kitchen. Spend your days at Tanglewood, Hancock Shaker Village, Mass MoCA and other nearby attractions. Then relax on the deck or in front of TVs in each room. Return for skiing in the winter with a fireplace for extra warmth.

Top Guest favourite

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 favourite

Condo in Hancock

4.98 out of 5 average rating, 44 reviews

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.

Guest favourite

Condo in North Adams

4.89 out of 5 average rating, 28 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.

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Condo in Lenox

4.8 out of 5 average rating, 10 reviews

Tranquil Lakeside Escape in the Berkshires

Retreat to this spacious 2-bedroom condo at The Ponds at Foxhollow, nestled in the scenic Berkshires of Massachusetts. Perfect for families or small groups, this peaceful escape offers a pond-view deck, a full kitchen, fireplace, and access to resort amenities like indoor/outdoor pools and a fitness center. Explore hiking trails, waterfalls, and cultural gems nearby. Unwind with stunning views, cozy interiors, and a wealth of year-round outdoor recreation right at your doorstep.

Guest favourite

Condo in Litchfield County

4.95 out of 5 average rating, 21 reviews

Pacer's Pasture

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.

Top Guest favourite

Condo in Brattleboro

4.93 out of 5 average rating, 353 reviews

Private & Quiet Studio Apt. in Vermont

Clean, comfortable , quiet and snug, this studio apartment is a great place to come and relax in. It has a comfy QUEEN size bed with a 40” LCD at its foot, a kitchen set up for cooking and a desk with a view of a green field. This apartment is situated on the ground floor of our detached garage. Our garage sits behind our home, well away from the street. We live in a residential neighborhood that is conveniently located near I91, Route 30, Route 9 and Downtown .

Guest favourite

Condo in North Adams

4.96 out of 5 average rating, 77 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.

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Condo in Hancock

4.91 out of 5 average rating, 23 reviews

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.

Guest favourite

Condo in Hancock

4.92 out of 5 average rating, 66 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.

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Condo in New Ashford

5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

Ski-in and Ski-out your front door! Club Wyndham Bentley Brook is situated right at the base of Jiminy Peak Ski Mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking, horseback riding, Tanglewood concerts and brilliant foliage.