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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 modern living room corner features a brown leather recliner with high backrest beside a window. A small table holds a potted plant, while a wood stack is positioned against the wall for a rustic touch. Natural light filters through brown curtains.

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, 128 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

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, 319 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, 168 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, 189 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

4.91 out of 5 average rating, 277 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, 148 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, 132 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 chalet duplex features a two-toned exterior with a dark wooden upper level and a white lower level. A spacious outdoor deck is visible, complemented by greenery and well-maintained shrubs, creating a serene setting within a natural landscape.

4.85 out of 5 average rating, 169 reviews

Mount Snow Close, Great Price, Lots of Room

This is a chalet duplex. You’re renting entire top 2 floors - no shared spaces. However, there’s an Airbnb rental in the lower unit of this house. Separate entrances & no indoor shared space. 2 bedrooms on the main level with a full bathroom and 2 bedrooms on the second level with a full bathroom. On site washer and dryer The kitchen comes equipped for cooking needs. ****The house has a lower level that has a 2 bedroom 1 bath Airbnb rental unit. No shared space but FYI.****

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, 161 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

Apartments

Convenient locations with everyday essentials

Chalets

Adventure-ready homes with après-ski style

Popular amenities for Western Massachusetts condo rentals

Free parking on premises

Air conditioning

Weekly condo rentals

An open concept living space features a dining area with wooden chairs surrounding a table, complemented by a decorative rug. The kitchen is visible in the background, equipped with modern appliances. Comfortable seating options, including couches and armchairs, create a welcoming atmosphere.

Condo in Worcester

4.97 out of 5 average rating, 71 reviews

Bright and Spacious 2BR/2BATH Condo with Parking

A spacious living room features a large sectional sofa adorned with decorative pillows. A wooden coffee table sits in front, complemented by natural light from large windows with soft curtains. Artwork adorns the walls, creating a welcoming atmosphere.

5 out of 5 average rating, 22 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

A comfortable seating area features a gray couch adorned with decorative pillows and a cozy throw. An ottoman sits in front of the couch, both situated on a soft rug. Natural light enters through two large windows, highlighting the warm wood flooring.

Condo in Waterford

4.93 out of 5 average rating, 43 reviews

Light Down at the Poet's Perch

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.

4.92 out of 5 average rating, 39 reviews

Spacious 3 bedroom apt in Lenox historic downtown

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.

4.95 out of 5 average rating, 65 reviews

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

A cozy living area features a stone fireplace framed by a wooden mantel. Comfortable brown seating is arranged around a small table, with a large window providing natural light and views of the surrounding greenery. A television and a decorative fireplace tool set enhance the space.

4.89 out of 5 average rating, 9 reviews

Seasons on Mount Snow | Walk Out / Ski Home!

A snowy street is lined with charming houses, showcasing a mix of architectural styles. The backdrop features a mountain slope with visible ski trails. A clear sky with scattered clouds enhances the peaceful winter scene.

Condo in Ludlow

4.96 out of 5 average rating, 25 reviews

Perfect Getaway! Modern & Convenient to Everything

A lush green lawn frames a serene pond, reflecting the surrounding landscape. The two-story condo units are visible in the background, showcasing a harmonious blend with the natural setting. Towering trees provide a calming backdrop, enhancing the peaceful atmosphere of the area.

4.63 out of 5 average rating, 8 reviews

Peaceful 1BR Condo with Pond View

Pet-friendly condo rentals

A well-lit bedroom features a spacious bed covered in neutral bedding. A wooden dresser and a small nightstand with a lamp are positioned beside the bed. Natural light streams through a round window highlighting the warm wood floors.

Condo in Litchfield County

4.96 out of 5 average rating, 23 reviews

Meadow View

A cast iron gas fireplace is centered on a stone hearth, providing warmth. A wooden ladder holds colorful blankets, while a woven basket filled with magazines is placed nearby. Light filters in through a window with horizontal blinds, enhancing the cozy ambiance.

Condo in Ludlow

4.89 out of 5 average rating, 38 reviews

Fully walkable 2BR condo in Ludlow’s village!

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, 103 reviews

Great 2 bedroom condo at Stratton Mountain

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

4.9 out of 5 average rating, 72 reviews

Stratton Mountain vacation spot

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, 71 reviews

LAKEFRONT: Walk to Marina, Restaurants, Near Track

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, 54 reviews

Ski Condo 5 Min from Mt Snow

An open living space features vaulted ceilings supported by exposed wooden beams. A comfortable sofa with colorful cushions is positioned beside a coffee table, while a dining table with chairs occupies the other side. Natural light floods in through large windows, creating a bright and inviting environment.

Condo in North Adams

4.96 out of 5 average rating, 82 reviews

Newly renovated 2BR on historic Eagle Street.

Top guest favorite

The exterior of a two-story duplex is presented, featuring a welcoming porch with black railings and an American flag. A vibrant garden in the foreground displays a variety of colorful flowers, while large windows enhance the airy and bright appearance of the home.

Condo in Stillwater

5 out of 5 average rating, 23 reviews

Saratoga Getaway

Condo rentals with a pool

A serene pond reflects the surrounding greenery and tall trees, with a distant mountain rising in the background. The clear blue sky above contributes to the tranquil setting, creating a peaceful landscape ideal for nature walks.

4.97 out of 5 average rating, 89 reviews

Cozy Mountain Condo - Let's Hike!

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 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

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, 12 reviews

Cozy Updated 2 Bedroom Corner Condo

A spacious living area features two patterned sofas and a wooden coffee table, complemented by a textured area rug. A dining table is positioned nearby, with a large window allowing natural light to illuminate the room. Subtle artwork decorates the walls.

4.89 out of 5 average rating, 111 reviews

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

A living room features a large stone fireplace with a wood storage basket beside it. A comfortable sofa with decorative pillows faces a wooden coffee table. Natural light floods the space through a large window, complemented by a nearby area rug.

4.87 out of 5 average rating, 241 reviews

Mt Snow Ski In/Out at Seasons

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

4.94 out of 5 average rating, 36 reviews

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

A view of an open-concept suite showcases a kitchen countertop with a sink and decorative flowers. A cozy living area is visible, featuring a red sofa and a dining table. The master bedroom is visible in the background, fitted with a king bed and soft lighting.

Condo in Ludlow

4.93 out of 5 average rating, 111 reviews

One Bedroom Suite Near Okemo

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