Journeys Advisor

The Most Beautiful Towns with Affordable Winter Home Vacations

Winter can be boring sometimes, especially if you live in the city. You either spend your days sitting behind the desk at work or lying on your sofa, stuffing popcorn into your face and miserably watching the same movie again and again. What a life!

Perhaps it’s the perfect time to escape the hustle and the bustle of city life and make your boring winter days a little bit more interesting! DEAL?

If you agree, click on Next to find out about affordable havens to buy where you can kill the routine and renew yourself and energy

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#1 – Pine Plains, NY

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© Houlihan Lawrence

Important Information: $1.1 million | 4 Cedar Drive

Pine Plains is a town situated in the Dutchess County. It was once known for dairy farms but is still known today for horse farms. The town is offering a large choice of modest properties for sale.

Among the properties that are available for sale, we have chosen for you this uniquely designed woody house by the architectural designer Karl Crnobori and his wife, Carol who is an interior decorator. The latter was built in 2001 on Twin Island Lake.

And it contains three bedrooms and bathrooms. What makes this house even greater is the dramatic great room and the fireplace, which is handcrafted with special local stone. To add to your information, the house doors are of solid maple, beamed ceiling is also included.

For any additional information, contact: Charles G. Vetter and Jill L. Rose, Houlihan Lawrence, 845-464-1687, and 914-204-0124

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#2 – Lenox, Mass

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Important Information: $695,000 | 232 Kemble St.

Whether it is spring, summer, autumn or winter, Lenox is a vivid, active town that is always in motion. Known for its fancy restaurants and galleries, Lenox attracts hundreds and thousands of visitors all year around.

Lenox is located in the center of the region and it is just a great and lovely place to stay. In addition to this, once you visit Lenox you will definitely want to visit it for the second and third times, or even choose to move there. Who knows, you might feel the urge to buy yourself a house there and benefit from all what Lenox has to offer.

In case you have thought about it, let us take you on a very quick trip from downtown Lenox, where the majestic and royal Colonial-style house is located. The latter nearly covers 2 acres of land. It has 3½-bathroom, five bedrooms and they all contain beamed ceilings and wood-burning fireplaces.

The house also affords an in-ground swimming pool that you and your family can enjoy in the warm months. During summer, Lenox town hosts the Boston Symphony Orchestra in Tanglewood while in winter visitors enjoy skiing in the Berkshires.

If you need any further details, don’t hesitate to contact the following address:
Contact: Patrice Melluzzo, William Pitt Sotheby’s International Realty, 413-446-1146

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#3 – East Jewett, NY

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© Select Sotheby’s International Realty

Important Information:$1.1 million | 285 Round Hills Road

For the outdoor enthusiasts who are addicted to practicing their activities in the open and fresh spaces of Mother Nature, your luck is in. Don’t you like swimming, snowmobiling, hiking, and skiing? All this can be found in one single place, the East Jewett town has it all for you.

Your weekends and vacations can be as sweet as your dreams with only a vacation house with no more than three bathrooms and four bedrooms. Are you interested? If you are, then maybe you should consider contacting Regina Tortorella for further information about the property she puts for sale.

According to the information she provided, the house is only two hours away from Manhattan. It is a nearly 3,778-square-foot pad with a glorious and breathtaking view. The house has an open floor that offers a perfect open space for congregating, in addition to separate guest rooms above the garage.

Here is Regina’s full address and phone numbers: Coldwell Banker Village Green (Windham), 518-734-4200 and 914-466-0329

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#4 – Westport, Conn

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Important Information: $650,000 | 55 Long Lots Road

When the weather is clear and the sky is happy, you can perfectly see New York City from the Sherwood Island State Park of Westport town. Still, the latter is a wonderful opportunity for city dwellers to escape from the hustle and the bustle of city life.

Craving the peace of mind and tranquility, you’ll never find a better opportunity than this woody house which covers about an acre of land and 2.651-square-foot abode. This house goes back to 1860 and it is said that it used to be a one-room school. Today it is a beautiful house with three bedrooms and three bathrooms.

Life here has a different taste and better meaning. Any time you decide to buy, don’t hesitate to reach Jane Jones, Berkshire Hathaway Home Services, 203-918-4751

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#5 – Greenport, NY

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Important Information: $825,000 | 147 Bay Ave.

The first thing that catches your attention when you are in downtown Greenport Village is this charming vintage yet modern house for sale. The house is located only steps from the town’s best attractions.

It has three bedrooms and bathrooms designed with century-old wood walls and modern upgrades. What adds charms to this house is the backyard with a new deck and pergola.

Buying a house in Greenport is definitely a decision you will never regret. Unlike what most people think, Greenport is not only a place where you can enjoy your alcoholic beverages but also where you can enjoy your breakfast, lunch or dinner at restaurants with bustling scenes.

You can reach the owner of the house by contacting the following address and phone number. JoAnn Wind, Daniel Gale Sotheby’s International Realty, 631-764-3847

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#6 – Delhi, NY

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Important Information: $318,000 | 14 Second St.

Unfortunately, Delhi town often goes unnoticed. It is only three hours away from New York City known for its open acres and a small one main Street. This town has a very small population, namely students of SUNY and contingent of creative types.

Delhi is also known for the attractiveness and affordability of its architecture. Therefore, we are confident that this house we have chosen for you is tempting enough to make you come over, sign the papers and declare it to be officially yours

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#7 – Tivoli, NY

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Important Information:$475,000 | 18 North Road

Once in Tivoli, you might want to allow yourself to get lost in the fields and woods to finally witness with your own eyes the glory of nature and one of the most breathtaking views of the Hudson River and the Catskill Mountains.

You should also consider visiting Tangent Theater Company and why not enjoy sipping your cup of coffee in one of the coffees along Broadway. If you are craving to experience all this, we have a better offer for you!

There is a very special eye-catching house for sale, which was built-in town’s languid style and Victorian three bedrooms. Let’s not forget to mention the front veranda that leads you to an amazing entry hall.

In general, the house is just magical, taking you back in time to make you feel like a king or Queen living in a castle.

Here is the contact information, in case you decide to give a phone call: Stephan Delventhal, Halstead Property, 518-660-1306

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#8 – Ludlow, Vt

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Important Information:$685,000 | 1585 E. Hill Road

Ludlow town is widely known for its Okemo Moutain Resort and the 121 ski trails. Right in the heart of this town, we have found one of the dream houses for you.

The house is just impressive, covering 6¹/₂ acres of land. It contains five bedrooms with cathedral ceilings and a stunning wood burning fireplace for the cold and rainy days. The house also provides a private tennis court which you can enjoy during spring and summer times.

If you are interested, you just have to contact the number given below: Contact: Suzanne Garvey, Four Seasons Sotheby’s International Realty, 802-236-4341

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#9 – Phoenicia, NY

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Important information:$475,000 |
1244 Woodland Valley Road

Both the people and social media, especially Instagram, have made Phoenicia, which is located in the West of Woodstock, the most popular destination.

It is the best place to be if you’re looking for coziness, refuge, and isolation. The wood cabin offers you the perfect and rustic view of Catskills town all along with its wood stoves and ‘’sugar house.’’

If you prefer the motion, then you might find what you are looking for in Levon Helm Studios where you’ll be only steps away from enjoying midnight life performances of Ramble.

Contact: Alfred Peavy, Ruth Gale Realty, 845-688-5610

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