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Condo vacation rentals in Western Massachusetts

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Top-rated condo rentals in Western Massachusetts

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Top guest favorite

A spacious living area features a large sectional sofa adorned with cozy throw pillows, complemented by a textured area rug. Natural light pours in through expansive windows, enhancing the inviting atmosphere. A side table and a plush armchair add to the comfortable seating options.

4.99 out of 5 average rating, 121 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

Top guest favorite

The exterior showcases a two-story condo surrounded by greenery. A pathway lined with gravel leads to the entrance. Flowering plants and shrubs are visible along the pathway, and a lamp post adds a lighted accent. The condo features a mix of dark and muted colors with a welcoming porch.

4.92 out of 5 average rating, 131 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 bedroom 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

Top guest favorite

An abstract painting features bold, swirling colors surrounding a muted central area. The edges are filled with vibrant hues of red, yellow, and blue, blending with darker tones to create depth and dimension.

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.

A cozy seating area features two woven chairs adorned with striped cushions. A small table holds a decorative vase with flowers, set against large windows that frame a vibrant backdrop of autumn foliage outside.

4.91 out of 5 average rating, 111 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

A modern living area features a gray sofa adorned with patterned cushions. Two sleek black tables are positioned on a striped rug, with a small plant on one of the tables. Tall, dark curtains frame the window, allowing natural light to enter the space.

Condo in Poughkeepsie

4.97 out of 5 average rating, 325 reviews

Spacious and stylish entire one bedroom apartment.

Enjoy a stylish experience at this centrally-located one bedroom apartment in Poughkeepsie. Apt is located in a quiet Victorian townhouse on the 3rd floor. Entire rental unit, Parking is included for one vehicle. Located downtown. Walking distance to: Post Office, Courts, County Bldgs, Police Station, City Hall, Nesheiwat Convention Center (fka Civic Center), Poughkeepsie Grand Hotel, Walkway Over The Hudson, Bardavon Opera House, The Academy, train station, waterfront, bus depot, and more.

A warm gas fireplace is centrally positioned against a light-colored wall, complemented by a wood mantle and slate surround. A flat-screen TV is mounted above. A window allows natural light to brighten the area, while a desk and chair provide a workspace option.

Condo in Stratton

4.97 out of 5 average rating, 169 reviews

Premier Stratton Village Location - Pool & Hot Tub

-- Walk across the street to Stratton Ski Lifts -- Conveniently located near the Stratton Village, this condo places you at the center of all the mountain activities - skiing, mountain biking, events, weddings, shopping & dining. This updated studio includes gas fireplace, AC, stainless appliances, and nice décor. Long Trail House condos boasts underground heated parking, year-round outdoor pool with patio and grill, multiple hot tubs, and sauna. Come visit and relax in the Vermont mountains.

A bright living area features vaulted ceilings with large skylights. A comfortable gray sofa and a cozy red chair provide seating, while a wooden coffee table rests on a decorative rug. The space is filled with natural light and offers a view through arched windows.

Condo in Saratoga Springs

4.96 out of 5 average rating, 193 reviews

Owl's Nest - Unique Condo in Vintage Location

This unique second floor condo is flooded with natural light. Steps from Congress Park and downtown Broadway, and a short walk to the Saratoga Race Course. Skylights, hardwood floors, keyless entry, custom lighting, complete kitchen with stainless steel appliances, air conditioning, small washer/dryer all housed in an original Skidmore College building creating a quiet space in a residential neighborhood. On-site parking is included. Intimacy surrounded by all the excitement of Saratoga.

A spacious living area is adorned with a large area rug and a comfortable blue bed. Large windows allow natural light to illuminate the room, highlighting the warm yellow walls and the vintage chandelier. A small coffee table and plush seating invite relaxation.

Condo in Albany

4.9 out of 5 average rating, 282 reviews

Elegant, spacious studio apt in historic mansion

Welcome to the Plaza Suite, a newly renovated studio condo in an historic Center Square mansion. Enter through a grand reception hall/art gallery and climb the oak staircase to the sunny and spacious second floor apartment. There's a nice view of State Street and the Empire State Plaza. Features include: a new fully equipped kitchen, comfy lounge area, dining /work table, renovated vintage bathroom, walk-in closet and new queen bed. Feel free to enjoy a glass of wine in the art gallery.

A well-lit bedroom features a spacious bed with white linens and an accent pillow. Bright light streams in through two windows adorned with sheer curtains. A side table with a small lamp adds a touch of warmth to the inviting space.

Condo in Kingston

4.91 out of 5 average rating, 151 reviews

Cozy & walking distance to town *summer/fall dates

Perfect for friends, couples, families, or solo-travelers looking for a comfortable home that’s centrally located and near some of Kingston’s best restaurants and shops! This historic two-unit home is walking distance to the waterfront and a short drive to incredible hikes and farms! *Pet-friendly (no extra fee) *Family-friendly (highchair + Pack n Play for babies, games for kids). Note: Parking onsite or arrive via Metro North to Poughkeepsie, Amtrak to Rhinebeck, or bus to Kingston

A cozy living area features a grey sofa, complemented by a vibrant orange armchair. Colorful artwork adorns the wall above, enhanced by two stylish lamps casting warm light. A sleek coffee table sits between the seating, inviting relaxation and conversation.

Condo in New Britain

4.83 out of 5 average rating, 133 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.

A cozy dining area is highlighted by a round wooden table surrounded by black chairs. The open living room features a comfortable sofa and a decorative area rug. Soft lighting is provided by a stylish chandelier, enhancing the homey atmosphere.

Condo in Stratton

4.94 out of 5 average rating, 174 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.*

The open living area is furnished with a dark sofa and light wooden accents. A round table with a beige tablecloth is paired with four chairs, while framed artwork adorns the walls. A colorful area rug adds a cozy touch, complemented by soft lighting from overhead fixtures.

Condo in Middletown

4.93 out of 5 average rating, 162 reviews

Entire place to yourself Cromwell/Middletown Line

Welcome to Cromwell / Middletown line, open space condo has living room with smart TV, Wi-Fi and sofa bed connected with dining room with four seats, the kitchen is well stocked with all the amenities you need, 24 hours keyless access to the apartment, free parking. Washer / dryer unit on - site paid through a prepaid card. Condo is located near I 91 and Route 9 ramps and just minutes from shopping, restaurants and more, 5 min drive to Wesleyan University, Middlesex Hospital

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Chalets

Adventure-ready homes with après-ski style

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Western Massachusetts condo rentals

Free parking on premises

Air conditioning

Weekly condo rentals

The exterior of a historic townhouse is displayed, featuring a brick pathway leading to the entrance. Lush greenery and vibrant yellow flowers frame the well-maintained garden, while ivy climbs the walls, adding to the charm of the property.

Condo in Hartford

5 out of 5 average rating, 7 reviews

James Colt townhouse - whole apartment

A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.

Condo in Hancock

4.95 out of 5 average rating, 61 reviews

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

A cozy living area is highlighted by a stone fireplace, featuring firewood neatly stacked beside it. A flat-screen TV is mounted above the mantel, with built-in cabinets on either side. A sectional sofa and wooden coffee table provide comfortable seating for relaxation.

5 out of 5 average rating, 24 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

The exterior of a two-story apartment building is visible, framed by trees and landscaped shrubs. The structure features a mix of stone and wood, including prominent front doors. Steps lead to the welcoming entrance, and a quiet neighborhood atmosphere is suggested by the surrounding greenery.

Condo in Worcester

4.89 out of 5 average rating, 54 reviews

SalsVista 2nd Floor Corner Apt

The image captures the snowy slopes of a mountain under a partly cloudy sky. The landscape features bare trees interspersed with patches of snow, while buildings are visible at the base, offering a picturesque view of the surrounding area.

5 out of 5 average rating, 13 reviews

Cozy Updated 2 Bedroom Corner Condo

A dining area features a light-colored table with four wooden chairs, complemented by a decorative fruit bowl. Exposed brick walls add character, while soft lighting from nearby lamps creates a bright and inviting atmosphere. A comfortable living space is also visible in the background.

4.93 out of 5 average rating, 43 reviews

Spacious 3 bedroom apt in Lenox historic downtown

A view of a downtown street, featuring a sidewalk lined with chairs and tables outside a café. Red accents can be seen on the café's exterior. Buildings of varying heights line the street, with greenery visible in the background under a cloudy sky.

4.72 out of 5 average rating, 46 reviews

Downtown Adams Vintage Getaway

The living room features a comfortable gray sofa and a recliner, accompanied by a wooden side table. Artwork of bears adorns the wall above the sofa. A dining area with wooden chairs is visible in the background, leading into the kitchen area.

4.97 out of 5 average rating, 60 reviews

Triple Tree VT 1 Level #15

Pet-friendly condo rentals

Condo in Litchfield County

4.96 out of 5 average rating, 25 reviews

Meadow View

The exterior of the condominium building is showcased, featuring three levels with large windows that allow natural light in. A central staircase leads to the entrance, flanked by green grass and small shrubs, creating a welcoming appearance.

Condo in Stratton

4.94 out of 5 average rating, 104 reviews

Great 2 bedroom condo at Stratton Mountain

A wooden dock extends across calm waters, leading into Saratoga Lake. The scene captures boats moored at various docks in the distance, framed by greenery. Gentle ripples reflect the clear blue sky, creating a serene lakeside ambiance.

Condo in Saratoga Springs

4.82 out of 5 average rating, 73 reviews

LAKEFRONT: Walk to Marina, Restaurants, Near Track

A two-story condo is shown with a snow-covered roof and a well-maintained exterior. A vehicle is parked in front, and snow blankets the surrounding area. The backdrop features a snow-covered mountain, displaying ski trails that contour the slopes.

Condo in Stratton

4.91 out of 5 average rating, 74 reviews

Stratton Mountain vacation spot

A cozy living room showcases two plush couches and a small wooden coffee table. A gas stove is nestled in a brick corner, while sliding doors offer views of the outdoors. Colorful lights frame the window, adding a touch of charm to the space.

4.91 out of 5 average rating, 55 reviews

Ski Condo 5 Min from Mt Snow

Condo in North Adams

4.97 out of 5 average rating, 87 reviews

Newly renovated 2BR on historic Eagle Street.

A multi-story gray house is shown from the street, featuring a blend of modern and traditional architectural elements. Large windows line the front, with a porch accessible from the ground level. A well-maintained green lawn and several parked cars are visible in the driveway.

Condo in Hartford

5 out of 5 average rating, 9 reviews

Comfortable Relaxing Ideal Oasis

A three-story house with a gray exterior is framed by lush greenery. Sunlight filters through the trees, casting dappled shadows on the driveway. The entrance features a front porch with steps leading to the door, and a fenced area is visible in the front yard.

Condo in Fitchburg

4.89 out of 5 average rating, 9 reviews

Cozy Apt South Fitchburg 5m from Great Wolf Lodge

Condo rentals with a pool

A circular outdoor pool is surrounded by a landscaped area, featuring several trees and bushes. The building's large glass entrances reflect natural light. Sun loungers are positioned nearby, and a set of steps leads from the pool to the patio area.

Condo in Stratton

4.97 out of 5 average rating, 65 reviews

Stratton Mt Summer: Golf, tennis, hike, bike, swim

A spacious outdoor heated pool is surrounded by a secure fence, with sun loungers positioned around the deck. Lush greenery and trees are visible in the background, providing a natural setting under a clear blue sky.

4.97 out of 5 average rating, 89 reviews

Cozy Mountain Condo - Ski In/Ski Out

A snowy landscape showcases the mountain in the background with ski trails visible. The foreground features a winter scene with snow-covered ground and trees. A building is partially visible on the left, adding to the serene atmosphere.

4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

A well-maintained outdoor pool is surrounded by sun loungers, creating a serene atmosphere. Lush greenery and trees frame the background, providing a natural setting. The concrete deck features handrails for easy access, while clear skies above invite relaxation.

4.89 out of 5 average rating, 111 reviews

Seasons Condo @ Mt Snow (Ski-in/out, hike, bike)

The exterior of the lodge features a blend of stone and wood elements, with multiple balconies and large windows reflecting the surrounding landscape. The entrance is framed by a welcoming staircase, leading to the main doorway marked with a sign that reads 'Hardwood Lodge'.

Condo in Stratton

4.92 out of 5 average rating, 38 reviews

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

A heated outdoor pool is situated in a landscaped area, surrounded by lounge chairs and colorful foliage. The adjacent building features multiple stories and large windows, creating a welcoming atmosphere in a peaceful setting.

Condo in Stratton

4.95 out of 5 average rating, 65 reviews

Renovated Stratton Mtn Studio | Walk to Lifts

A spacious living area is introduced, featuring a stone fireplace and a large sectional sofa arranged around a coffee table. A dining table and chairs are positioned nearby, with natural light filtering through large windows adorned with curtains.

4.94 out of 5 average rating, 71 reviews

Condo w/ great amenities 4-seasons! Ski in Ski out

A circular heated pool is surrounded by a paved patio, with steps leading into the water. Lush greenery and small trees are present in the background, creating a serene outdoor space. Cloudy skies are visible overhead.

Condo in Stratton

4.95 out of 5 average rating, 150 reviews

Cozy condo within walking distance to the slopes.

Destinations to explore