Windsor MA Real Estate & Homes for Rent

Just a short drive to Berkshire Health Systems or North Adams Regional campus of BHS. Working from home and want a view? Beautiful contemporary home with lake rights. Pontoosuc Lake is a motorized lake. Beach is a quick walk out your front door. Beautiful views. Large rooms. Deck off of the MBR. huge deck for entertaining. Fully furnished. Newer appliances. Short term or long term rental.Convenient to shopping, the Ashwillticook Trail and easy access to RT,7 and all of Berkshire County amenities.NOTE: There are stairs at entry to the second level where you will live. Bedrooms are on the 3rd floor.

Available July 29th through August 12th (2 week minimum).Charming and Chic Summer Rental with Pool. This home has 5 bedrooms, 3 baths with stunning westerly views to Mt Everett. Dine in or out then enjoy the sunset and big skies at night and/or unwind in the heated pool. Five minutes to Great Barrington MA. All utilities included. No pets. No Smoking.

The Winthrop Estate is a registered Great Estate built in 1875 for Henri Braem, US Ambassador to Denmark and Partner in Cunard Steamship Lines, famous for the ultra-luxurious Queen Mary ship line among others. Braem sold the property to the Winthrop family, descendants of John Winthrop, the founding governor of Massachusetts, from which the property took its current name. The manor is now freshly renovated with modern touches thoughtful of its origins and includes world-class amenities.

The Kemble Berkshires is a registered Great Estate built in the 1880s for a U.S. Secretary of State and New Jersey State Senator - now newly renovated by Shared Estates with bright minimalist finishes and world-class amenities. The property has manicured landscaping with massive rolling views of the Stockbridge Bowl. Whether you want to relax in the library room with its array of books from the early 1900s, jam out in the music room, snuggle up in front of one of the home's seven fireplaces or enjoy a drink with a friend at the private bar, you will find beautiful spaces to enjoy in groups or in solitude. 100% carbon neutral. Events up to 175.The property offers a dining room (including custom farmhouse dining table), a professional kitchen, herb and vegetable garden, fire pit and expansive multi-level stone patios and decks. Events up to 175 are permitted and a tent is provided for rain contingency (first weekend in May to third weekend in October)

Available Immediately! Second floor apartment. Three bedroom with a full bathroom and a half bathroom. In unit washer and dryer. The house is equipped with generator so you never have to worry about power outages again. Pets negotiable. First, last, security and 1 month broker fee. Employment verification, background check, credit check and references required.

Sunlit, south-facing contemporary set amidst the woodlands of the Indian Lake Association. Enjoy this sunlit, sun-facing home indoors and out. A short distance to gorgeous Indian Lake and its private, association beach. Tennis courts too. Five bedrooms make this home a true find. On the first floor you'll find the primary bedroom with en-suite bathroom and a second bedroom with two twin beds. On the lower, walk-out level there is a spacious game room, two bedrooms (one queen, one with two twins) and another full bath. On the upper level there is a fifth bedroom (Queen) and bathroom as well as a loft space. Walk the quiet roads and enjoy the cultural and natural riches of the Berkshires: Nearby you'll find Jacobs Pillow Summer Dance Festival, Tanglewood, theaters, trails, gardens and museums for hiking and biking and exploring.

PRISTINE COUNTRY OASIS!Experience this wonderful Berkshire country setting nestled in the middle of hundreds of gloriously private, open acres in a bright, airy comfortable home! Recently renovated from top to bottom this 4 bedroom, 3 bath home offers plenty of room for guests in pristine surroundings and easy living. True privacy and convenience come together with this property located on the border of Stockbridge and Lee. Available fall 2024 and beyond.

TYRINGHAM VALLEY ESTATE. Sitting high above the valley, a magical home where family and friends can unwind and enjoy the slower pace of summer. This gracious home offers large gathering spaces indoors and out. From the generous double living room to the delightful screened cottage and numerous spots in between, there is plenty of room to enjoy quiet moments and time together. Gracious gardens and the heated swimming pool offer mesmerizing views, south across the valley. Three well-appointed guest rooms are located on the first floor; one offering a private suite. A primary bedroom suite on the second floor. 10 minutes to Stockbridge, 18 minutes to the gates of Tanglewood, 15 minutes to Jacobs Pillow. Enjoy slow food, great restaurants, hiking, cycling, museums & more. Magic happens in the Berkshires. Available August 2024. Max Occupancy 8. Pets will be considered. Includes weekly housekeeping, trash removal, and all utilities.

Spend your summer at the Capt. Silvanus Brown house, a historic country home at the crossroads of Columbia and Berkshire Counties.This is the perfect location to enjoy: swimming/kayaking at Queechy Lake; hiking local trails; experiencing world class music, dance and theater performances at Tanglewood, Jacob's Pillow, MacHayden summer theater, PS 21, Barrington Stage; fine dining at restaurants in Great Barrington, Lenox, Chatham, Hudson and Williamstown; exploring farmer's markets to inspire your own meals served on your deck overlooking the vineyard and classic red barn.Plenty of room for friends and family with fabulous kitchen/family room, 4 bedrooms (2 on first floor), and 2 full baths, separate dining room, den, and fun ballroom on second floor for movies, games and relaxing. Housekeeping monthly and Queechy Lake passes included. Available monthly for $10,000/mo or stay for the season (Memorial Day through Labor Day) for $28,000.

A unique opportunity to rent this lovely furnished 5 bedroom, 4 bath home for New Years and beyond A beautiful Cape on a private road with room for 10 to live comfortably and enjoy the dramatic surrounding far reaching views. There is a large living room with a Grand Piano and fireplace, dining room, spacious eat in kitchen, main floor bedroom and bath, 4 season breeze way/porch, attached 2 car garage, and a separate wing with an enormous family room with fireplace and 2 additional bedrooms.and 2 baths. Everything you will need to enjoy a country home is at your fingertips. Close to Chatham, Berkshires and skiing makes this home perfect for your winter and spring experience..hot tub too.

Come escape the winter at this Chic Scandinavian Country Retreat! Seasonal rental available 12/1 - 5/31, no less than 30 days up to six month term available. This gorgeous Cape sits privately on a 4 acre lot set down a tree lined driveway. Tasteful refined finishes and furniture will make you feel right at home! Snuggle by the wood stove in the living room or around the outdoor fire pit. Airy open1st floor living with 2 bedrooms and a full bath. 2nd floor has 2 more generous sized bedrooms each with their own sitting areas plus a media/family room and another full bath. Whole house generator and Wifi make this a carefree setting to make this a perfect staycation for the winter. Fully furnished and equipped for easy enjoyment for a large family or a more intimate get a way for one or two people. All utilities are included in monthly rent. Heat, electric, WiFi, home phone, driveway plowing. Nestled in one of the most scenic quiet areas of Columbia County. Hike, Ski, explore the many outdoor activities practically at your doorstep. A short drive to Chatham Village, Hudson or The Berkshires with restaurants, shops, arts and entertainment. Easy access to Taconic Pkwy & I90. 2.5hrs to NYC & Boston!

This immaculately maintained, sprawling open concept ranch home is situated in the quiet picturesque community of Hatfield w/ easy access to I-91 and all points north and south. 3 Bedrooms w/ Main-Bedroom w/ Main-Bathroom and large walk-in closet. Hardwood Floors, (2) Gas Stoves, new carpeting and freshly painted throughout. Laundry on the main-level, full basement and attached 2-Car Garage. Rear deck w/ gazebo offers a great space to relax all summer long! Gas Heat, Central AC and Central Vacuum system. A great home w/ attentive owners in a great location! Rent Includes: Trash/Recycling, Lawncare, Snow Removal, Water & Sewerage. Tenant Pays: Heat & Electric. Pets negotiable. Ready for move in!

Expanded Adirondack cottage in enchanted setting. Complete and total privacy on almost 70 wooded acres. Original fieldstone fireplace anchors a spacious living room with gleaming wood floors. Huge dining room and family room spaces as well as the 2 bedroom, 1 bath guest house offer flexibility to entertain family and friends.Mature landscaping, meandering stone walls, multi-level outdoor terraces overlooking a pristine pondand beautifully landscaped perennial gardens complete the symmetry of this totally private paradise. Unfurnished. Pets possible with landlord approval. One year lease minimum.Landlord will be responsible for pond maintenance..

The Every House has the soul of an artist and offers a little something for everyone.A Pond for reflecting, a pool for a cool dip. A quiet road to walk on. Proximity to Chatham for life's essentials. The mudroom is where you'll start, shedding boots and coats. Upstairs a country kitchen looks out over the grounds, keeping things in perspective. The living room is large enough for formal and informal to coexist, anchored by the fireplace. The sunroom serves as a dining room for light filled soirees. Upstairs, large bedrooms are eclectically laid out for privacy and rest. The third floor offers storage or additional living space. The garage has a two bedroom, two living room apartment with fill bath and kitchen.

Airy, bright and light converted barn in one of the few brick Georgian estates in Columbia County. A beautifully restored and furnished carriage house. Exquisitely decorated. With many of the original historic details, this furnished barn has modern upgrades with 2 bedrooms, contemporary kitchen and spacious living room. Private entrance opens to back yard, patio and in ground pool. Off street parking. Located in the historic hamlet of Old Chatham, walk to dinner at Jacksons, The Country Store. Contact Francois at [email protected] (646) 897-6801 to schedule a showing

Charming, bright and light studio bungalow in one of the few brick Georgians in Columbia County. A beautifully restored and furnished apartment. Exquisitely decorated. With many of the original historic details, this furnished studio has modern upgrades with 2 beds, contemporary kitchen and spacious living room. Private entrance opens to back yard. Off street parking. Located in the historic hamlet of Old Chatham, walk to dinner at Jacksons, The Country Store. Contact Francois at [email protected] (646) 897-6801 to schedule a showing

**Open Sunday, 4/28 11am-1pm** Attention Renters!! 2 Bedroom 1 Bath #2 floor Home is available for $900,month plus utilities. All on 2nd level with new carpet. Freshly painted walls, overlooking the serene backyard with a pond in the distance. Responsible and responsive landlord. Background and credit check required with application. First month rent and security deposit in the same amount due at lease signing. Standard Plus Tenant Screening report must be submitted with application. https://tenantbackgroundsearch.com/ -- Good Condition

This classic picture-perfect contemporary home features an open floor plan, cathedral ceilings, updated everything, and an in-ground heated pool. In addition, this outstanding Alford property is located on 5.46 acres, and it is less than a 10 minute drive to the center of Great Barrington with all of that town's fabulous restaurants, shops and food stores. The screened porch overlooks a recently constructed stone patio and deck with a built-in top-of-the-line gas grill and an easy access to the fabulous in-ground heated pool. If you are looking to escape to the ideal vacation home, this listing should be Option #1. The famous real estate saying about location, location, location could have this property as its photography definition. Rental rates beyond the July and August period are significantly lower. Landlord fills propane tank prior to move-in, and tenant fills propane tank at time of move-out.

River Road, set amongst the rolling hills of picturesque Hillsdale you'll find this turn of the century farmhouse set on 20 acres of sprawling meadows and wildflower fields. The storybook approach follows River Road alongside the rushing Green River and up a private drive overlooking mountain ridges and whimsical tall pines. The c1890 farmhouse welcomes you with its wraparound porch and fieldstone front steps. Inside the rooms are large, the living room and master bedroom are both anchored by a magnificent stacked stone fireplace, recently restored and in use. The dining room opens to the wrap around porch through french doors, and when opened the sound of the rushing Green River flows through the house. Tucked around a corner you'll find an outdoor shower overlooking the water. The kitchen is recently redone with brand new appliances and herringbone countertops, and the ground floor features an office and a full bath, which could be used as a fourth bedroom. Upstairs, all three bedrooms have ensuite baths with wonderfully deep soaking tubs, each with beautiful views of forest, pond and river. Windows, siding, roof, insulation, HVAC and floors are all brand new, allowing the next owner to own a beautiful antique farmhouse with little to no maintenance. A separate studio lies up the hill, used for creative projects by the current owners but open for future possibilities. This incredibly charming property is just 10m to the village of Hillsdale, 15m to Great Barrington and 2h to NYC.

Things don't get much more relaxing and tranquil than this beautiful condo which sits right on the side of the greens of Haystack Golf Course. The main floor has open concept living with the kitchen, dining room and living room. There is a beautiful working fireplace for those occasional chilly nights or just use it for ambiance. On the lower level, there are three bedrooms and a very functional and completely remodeled bathroom which enables use for several people at the same time. The loft is being used as primary bedroom with it's own ensuite fully renovated bathroom. Come to Vermont this summer for your vacation. This condo is central to all summer activities from swimming, hiking, mountain biking, kayaking and golf.

Looking for an escape from the hectic life in the City? This is the place to pamper yourself for a week, a month, or longer. You can make this your vacation retreat or perhaps you would like to stay in an elegant, well appointed home while you search for property to call your own in the area. The owners have been successfully renting the property for special events and short-term rentals for many years. Just pack your clothes and the rest is provided for you. Hike/snowshoe the Old Chatham Hunt Club trails that are accessible from the property, swim in the beautiful in-ground pool or the pond, play a game of basketball or volleyball, or head inside to the game/entertainment room. Full fitness area to get your workout in during inclement weather. The owners take great care in keeping the house safe and clean so you have nothing to do but come and relax.

This is a two family home, owner/landlord lives on one side. The home for rent offers a modern kitchen with dining area, enclosed rear porch with deck, living room with propane woodstove, primary suite, half bath, and laundry area. Upstairs are 3 bedrooms and family/play room. Finished basement has family room, office, and storage. The garage is accessible by both homes. 5 acre lot. Located 2.5 hours north of NYC, and 2 hours south of the Adirondacks. Terms are flexible as property is for sale.

Enjoy this magnificence contemporary home high on a hill top right outside the lovely village of Chatham NY. This beautifully furnished and decorated two bedroom w/ sleeping loft is available for rent. Fabulous views, decks, wood stove, carport, radiant heat, gas stove & BBQ, Flat screen TV, two Queen beds, good access to internet. Enjoy this wonderful home while you shop for your Columbia County Home. Includes Internet & TV, tenant responsible for utilities & snow plowing.

Well Maintained 2 story duplex. Owner pays water, trash collection and snow removal. Tenants pay electric, gas and internet. Cat and small pets allowed. Non smoking. Tenants responsible or lawn maintenance.