
Condo holiday rentals in Western Massachusetts
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Top-rated condo rentals in Western Massachusetts
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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

~10% OFF~Walk To Mountain~Amenities
⭐️"Beautiful place in a great location - recently renovated, super clean and across the street from town." ⇒ Center of Stratton Village, walking distance to restaurants, shops, and the lifts🚶♂️🏔 ⇒ Private balcony with amazing views 🌅 ⇒ Dedicated workspace 📝 ⇒ Gas fireplace 🔥 ⇒ Fully equipped Chef's kitchen👩🍳 ⇒ Central AC/Heat ⇒ Onsite garage parking for 1 vehicle 🅿️ ⇒ Community amenities: pools, hot tubs, sauna, fitness center, tennis court, hiking trail, washer/dryer ⇒ 67 mbps Wifi

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.

Great Amenities-Season Condo gym-sport center-pool
True ski in ski out ground floor condo w/ private entrance. Wood burning fireplace, wood included! King size bed in master, true Queen murphy bed, 1-memory foam cot, plus air mattress. Fully stocked & functional kitchen, including Keurig & Mr. coffee. Full bath w/blow dryer. Seating; kitchen counter, expandable table, wine barrel bar top. Walk out the door & down the steps to the NEW Sundance high speed lift. Take the Seasons trail home. Brand new state of the art Sports Center included.

Luxury Spacious 2BR • King & Queen Beds • 2 Baths
Family-Friendly 2BR Getaway! Spacious stay with a 🛏️ King & Queen bed, ☀️ outdoor patio, 👶 baby crib! 🐶 pet-friendly neighborhood! Great for 🩺 travel nurses & 💼 professionals with ⚡ high-speed WiFi, 📺 Roku TV & 🎬 Netflix. Easy access to UMASS and St Vincent Hospitals 🏥 for work or care for loved ones. Close to 👵 Southgate Shrewsbury—perfect for visiting Grandma & Grandpa! Close to beautiful Dean Park—perfect for walks, playtime, or just soaking up nature. We’d love to host you!

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 multiple hot tubs, and sauna. Come visit and relax in the Vermont mountains.

Cozy Mt Snow Ski In / Out
Directly on the mountain. Ski right back to door. Less than 2 minute walk to the trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and 1 in each bedroom. Ground floor with private deck with tables and chairs for relaxing. Free parking. Condo across the hall is also available for larger groups. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.

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

Historic Rondout Home | Walk to Waterfront
Welcome to our comfortable two-bedroom home in Kingston’s historic Rondout neighborhood. It’s an easy home base for couples, friends, families, and solo travelers—just a short walk from the waterfront and some of Kingston’s best restaurants and shops. *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

MountSnow 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 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 Best parking on the mountain

Dorset, Vermont mountain retreat
Relax at this peaceful, private and welcoming Dorset condo with a fireplace and spacious deck with views of the mountains. Get away from the hustle and bustle of everyday life. Sit by the fireplace and read or enjoy mountain views from the deck. Grill outside or sit indoors at the country table with family and friends. Dorset and environs (Manchester, Bromley, Stratton, Arlington) offer a number of excellent restaurants, shopping, and sports.

Walk to Mt. Snow-Spa-Summer Pool
*Amenity rich studio only a 5 min 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 chairs *Easy 1st floor access *Fitness center access *Hot tub *Outdoor pool seasonal *Loaner amenities such as phone charger
Popular amenities for Western Massachusetts condo rentals
Weekly condo rentals

Spa Dreams

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

Spacious 3 bedroom apt in Lenox historic downtown

Downtown Adams Vintage Getaway

Mtn. view, easy access to village

Jiminy Peak Country Inn - ski in/out condo MT view

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck

Summer in the mountains!
Pet-friendly condo rentals

Meadow View

2BR w/ Parking + deck - Near Downtown & MVP Arena

Elegant Grand Beam • Luxury 3BR + King Suite

Historic Gem, Fireplace,2BR/2BA,Capitol District

Walk-to-Lifts Mt Snow Ski Condo

Ski Condo 5 Min from Mt Snow

Newly Renovated Clean Comfortable Relaxing Ideal

3BR family condo - pool, sauna & balcony
Condo rentals with a pool

Mount Snow Ski Chalet

Slopes N Seasons | Trailside Condo at Mount Snow

Ski On/Off 2BR w/Pool, Fireplace & Arcade

Four Seasons Slope-side Getaway at Mount Snow

A Village location, Steps to the Lifts & Village

Cozy Mt Snow 1-bed w/ fireplace & mountain view

Slopeside Condo @ Seasons on Mt Snow (Ski-In/Out)

3BR @ Jiminy Peak | 4-Season Berkshires Retreat
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- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- June Farms
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Taconic State Park
- University of Connecticut
- Bash Bish Falls State Park
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Ski Sundown
- Hudson Chatham Winery
- Rensselaer Polytechnic Institute
- MVP Arena
- University of Massachusetts Amherst
- Naumkeag
- New York State Museum
- Massachusetts Museum of Contemporary Art
- Norman Rockwell Museum
- Connecticut Convention Center
- Mount Greylock
- Mount Holyoke College
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