Condo vacation rentals in Western Massachusetts

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Top-rated condo rentals in Western Massachusetts

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Guest favorite

An outdoor fire pit area is surrounded by several light-colored Adirondack chairs, set upon a stone circular base. A winding stone pathway leads towards a sheltered seating area with a roof in the background, framed by lush greenery and distant hills.

Condo in Dover

4.91 out of 5 average rating, 110 reviews

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim

Escape to the mountains & stay in our fully equipped 2 bedroom (ski in/out) condo. Enjoy the wood burning fire (wood provided), smart TV & boardgames as well as the fabulous Seasons on Mt Snow facilities where you can relax in a hot tub, pool or sauna. Our ski in/out location is the best on the mountain between the main face & Carinthia Freestyle Park! See below for info on activities in the warmer months which include hiking, biking, scenic rides, lakes, golf, camp, a spa & the fall colors!

Top guest favorite

A modern living room features a traditional wood-burning fireplace framed by a brick facade. A large TV is mounted above the mantle, while a plush recliner, a small seating area, and a neatly stacked firewood display complete the cozy setting.

Condo in Dover

4.99 out of 5 average rating, 120 reviews

Summer Dream! The Handle Lodge at Snowtree Condos

The Handle Lodge at Snowtree Condos is a modern 1BR condo at the base area of Mount Snow. Comfortably sleeps 6 adults and is fully equipped with everything you'll need for a fun getaway with friends and family. Make a meal in the beautiful kitchen or step out on the balcony for stunning mountain views. Our modern and cozy decor, the lovely views, and proximity to the mountain make it a great place to relax and recharge. Check us out on IG for more content: @TheHandleLodge …. 18% OFF WEEKLY STAYS

Guest favorite

A private deck is presented with two woven chairs surrounding a small table. A white vase holds artificial flowers, complementing the natural greenery in the background. The wooden railing and floor enhance the outdoor setting's relaxing ambiance.

Condo in Dover

4.91 out of 5 average rating, 104 reviews

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna

Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

Top guest favorite

An outdoor deck with wooden flooring features a glass-top dining table surrounded by six chairs. Soft string lights are draped along the wooden railing, and a backdrop of lush trees is visible in the distance, providing a serene and private atmosphere.

Condo in Dover

4.92 out of 5 average rating, 121 reviews

3 Story Condo - 5 Minutes to Mount Snow!

Charming Dover Green condo just minutes from Mount Snow Ski Resort & Lake Whitingham. This well kept 2 bedroom, 2 bathroom, plus loft unit features open concept living, dining, vaulted ceilings, natural woodwork, 65" TV, and a wood burning fireplace. With easy access to Mount Snow, the village of Wilmington, nearby lakes, hiking, and biking, there is so much to do for tremendous year round enjoyment. There is nearby access walkable from the unit to the public MOOver shuttle to get around town.

Guest favorite

A charming black exterior cottage is framed by lush green foliage and shrubs. A welcoming entrance with a light-colored door is flanked by two windows, allowing natural light to illuminate the space. A wooden signpost is visible, indicating the property name.

Condo in Hancock

4.86 out of 5 average rating, 152 reviews

Cozy Condo @ Jiminy Peak

Nestled in the majestic Berkshire mountains, this Cozy Condo is a home away from home! It features 2 bedrooms with closets & dresser space. The master bedroom connects to a full bathroom and has a TV for when it's time to unwind in the comfort of bed! The fully equipped kitchen/dining area opens into a spacious living room. It's the perfect place for evening gatherings with friends or a romantic night in front of the fireplace! Free access to 2 heated pools, hot tubs, sauna & fitness center.

Superhost

A clear glass bowl filled with an assortment of seashells is prominently displayed on a countertop. Behind the bowl, two elegant bottles are visible, suggesting a serene and curated atmosphere.

Condo in New Britain

4.82 out of 5 average rating, 122 reviews

New Britain "Joy of Small Space" Condo

This condominium will give you a warm feeling of home away from home with a European flair. Its colorful kitchen dining area, the living room is warm and inviting , wood fire place, hand picked chairs/seating, wall to wall carpets . Queen Bed master bedroom, soothing and calming , other BR with under storage bed and additional comfortable foton lounging /bed. New washer dryer in the unit, latest in technology wood planks vinyl flooring , Bathroom is spacious with walking shower.

Guest favorite

A natural swimming area features calm green water surrounded by rocky cliffs. Several individuals are seen swimming and enjoying the sun, while others are climbing and preparing to jump from the rocks. Lush greenery frames the scene, enhancing the outdoor atmosphere.

Condo in Stratton

4.94 out of 5 average rating, 170 reviews

Updated Ski in/Ski out Stratton Condo!

Enjoy our cozy ski-in ski -out condo in the Ober Tal complex at Stratton. This newly renovated condo offers a warm, welcoming stay with modern farm house charm! Located just above the base of the mountain, our condo is a stones throw from the nearest lift ( 200 ft) and a ski lovers dream. Unwind after a long day of skiing/snowboarding or take convenient 5 minute stroll to the Village for a bite to eat or some shopping. *Mountain biking & concerts offered in the summer season.*

Guest favorite

The outdoor pool area features a large swimming pool with clear blue water, surrounded by lounge chairs. Green trees line the perimeter, creating a serene backdrop. A building with large windows stands nearby, providing shelter and amenities for guests.

Condo in Dover

4.84 out of 5 average rating, 119 reviews

Walk to Mt. Snow-Spa-Summer Pool

*Amenity rich studio only a 5 minute walk to Mt. Snow's famed Magic Carpet (runs on weekends) *Gas Fireplace *Queen memory foam Murphy bed *Queen pull out with memory foam mattress *Well appointed kitchen *65" curved UHD TV *25Mbps Wifi *USB wall outlets *Blue tooth music streaming to TV *Ample closet space *Patio with rocking chair *Easy 1st floor access *Fitness center access *Hot tub *Outdoor pool seasonal *Loaner amenities such as phone charger

Superhost

The entryway features warm wooden paneling and a spacious wooden bench. A large mirror is mounted above the bench, while hooks are attached to the wall for convenience. Natural stone tiles complete the floor, providing a rustic and welcoming atmosphere.

Condo in Stratton

4.96 out of 5 average rating, 102 reviews

Luxury Stratton condo just steps to the lift!

Enjoy this beautifully renovated 1 bed/1 bath condo with a live fireplace conveniently located steps from the mountain and Stratton Village! The Tamarack chair lift is only a few hundred yards away! Washer and dryer in unit to warm up your wet clothes after a long day of skiing or mountain biking. Fully stocked kitchen, 50’ TV w/ AppleTV, cable, Amazon Alexa, 5G WiFi, Firewood and more! This is one of the nicest Ober Tal condos available for rent!

Superhost

An indoor pool area is featured with a clear, inviting pool and wooden beams accentuating the high ceiling. Large windows allow natural light to illuminate the space, providing a view of the surrounding landscape.

Condo in Dover

4.92 out of 5 average rating, 102 reviews

Seasons at Mount Snow ski on/off condo in Vermont

Pool and Sports Center is open. Hours vary by day BBQ available for use by the outdoor pool pavilion WiFi upgrade to fiber optics On Mount Snow, Across from the Tin Lizzy trail leading to the Sundance Base Lodge and access to the Seasons Pass trail leading back to the condo. Very unique Condo in seasons as it has high vaulted ceilings. Condo is a 2 bedroom, 2 bathroom with 2nd bedroom on 2nd floor. Plenty of tennis and pickleball courts

Guest favorite

A light-colored kitchen with cabinetry in grey tones features modern appliances, including a stainless steel refrigerator, microwave, and stove. A granite countertop with a sink integrates seamlessly into the design, while a basket sits on the counter, adding a touch of warmth.

Condo in Dover

4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

Beautiful 2Bd/2Ba condo with a gorgeous view of the mountain. It takes 10 min to walk to the ski area or even faster with the free Moover bus. Every room features different art design while living room's fireplace creates warm and cozy vibe. Apartment is equipped with smart lock for your convenience. Possible to use as Work from Home space. Condo is located within quick drive to coffeeshop, restaurants and seven eleven.

Guest favorite

A spacious lobby area features a high ceiling with wooden beams. A large stone fireplace serves as a focal point, surrounded by comfortable seating options including brown leather sofas and blue accent chairs. Large windows provide natural light, enhancing the inviting atmosphere.

Condo in Stratton

4.95 out of 5 average rating, 147 reviews

Cozy condo within walking distance to the slopes.

Cozy condo within walking distance of the slopes and restaurants and shops at Stratton Mountain Village. After a day on the slopes relax in the hot tub or take a dip in the heated pool or maybe enjoy some time in the sauna. Then enjoy sitting in front of the gas fireplace and maybe watch a movie. TV is a smart TV, basic cable is included - personal password needed for Netflix, Hulu, etc.