Condo vacation rentals in Berkshires

SKI IN/OUT @ Mount Snow (Hot Tub & Pool)

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

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

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.

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.

Hideaway Windham/Hunter Fireplace, Snow & Skiing

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

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.

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.

Windham Condo

This condo is right off Route 23, minutes from Windham Mountain. Head to the Catskills to enjoy the great outdoors. The complex has a pool, 2 tennis courts and a fire pit. Enjoy the mountain air while working from home with dedicated Wifi. We have a well-stocked kitchen, wood-burning fireplace, and comfy deck. You are in place to enjoy all the skiing, hiking, mountain biking, and golf Windham has to offer. Only 2.7 miles from Windham Mountain Resort. Guest ID may be required on arrival.

Cozy & walking distance to town *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

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

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

Posh Pad in The Business District

Truly unique, spacious, and comfortable condo in the heart of the Hartford Business District!!! Big city vibes in a quiet, cozy but swanky corner unit. Truly a home away from home. The unit is very nicely appointed with all the creature comforts you can imagine (+blackout curtains). The convenience of an Elevator makes grocery-hauling in the city very easy. Located within walking distance of the very best downtown Hartford has to offer!