Condo vacation rentals in The Berkshires

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 Autumn & Foliage

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.

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

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.

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.*

MountainViewBrightCondo10MinToColgateLake

Sunny and spacious condo with stunning mountains view, a perfect place to disconnect from busy life . Plush and comfortable decor , fire place , plenty of board games - perfect set up for a group or a family to unwind in the mountains, gather for home cooked dinner and drinks. Spacious deck is a sweet spot to enjoy morning coffee and listen to the frog songs. Swimming pool (communal for residents and renters only )seasonal , NOT heated, opens in June 28through September 5th.

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

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!