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Luxury Vacation Rental in the Berkshires!

Known for its thriving art institutions, outdoor activities, fall foliage, world-class museums, and renowned annual festivals like the Boston Symphony Orchestra residency at Lenox’s Tanglewood Music Center, the Berkshires is a great rural region to visit on your Williamstown getaway. The vacation rental house, situated on 12 acres, features 3 bedrooms, 2 full baths, 2 half baths, gorgeous mountain views, an apple orchard, an outdoor fire pit, and 3,600 square feet of well-appointed living space.

Catskills Retreat: Hot Tub | Fireplace | Firepit

Year-Round Catskills Retreat Escape to Five Star Cottage in Windham, NY, just 2 hours from NYC. This spacious 4-bedroom, 2.5-bath home features stunning mountain views, a cozy wood-burning fireplace, a hot tub, and a large deck for year-round enjoyment. Ski in the winter, and explore nearby hiking trails, lakes, and waterfalls in the warmer months. Ideal for families and groups seeking adventure, wellness, or a peaceful retreat. Book your stay today and experience the beauty of the Catskills!

Cozy Log Cabin in the Woods

Scenic, cozy log cabin set back in the woods. Fully furnished & decorated. Full kitchen, 1.5 bath, washer/dryer. 1 bedroom w/full & twin bed. 1 room w/full bed. 2 twin XL cots available. See pictures for bed dimensions. Handicap accessible, Desk area, Wifi, NO landline, good verizon signal,Roku tv, Heat & AC. Pets allowed. Owner lives above garage. Dogs live on property. Hens and roosters, are housed near the cabin, they can make noise day and night. Large front porch. Bring your slippers. :-)

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

You want to bring your whole family to Jiminy and be in ONE CONDO, with gorgeous views, a deck, BBQ, Backyard, and be at Jiminy Peak - This condo is for you - right in the heart of Country Village. This Stylish 2BR country Condo w AC is fully updated and comes with parking in front and full access to the Country Inn Amenities ( Fitness, pools, hottub, Tennis etc). This large 900 sq ft condo features country decor, & sleeps up to 7 with a queen, two bunk beds, pull out Trundle, and Full Bed.

Sheffield Lodge - Everett Room

Sheffield Lodge is a warm and inviting rustic Bed and Breakfast, secluded from the stressful city life, nestled in a forest of tall pines, maples, and birch trees. Enjoy your home-away-from-home where there is always welcoming hospitality, friendly service, and delicious breakfasts. Located just a short distance from the most popular activities and entertainment the Berkshires is known for including Tanglewood, Jacob's Pillow, skiing, stage theater, hiking, museums, and antique shopping.

THE Be Jolly Bed & Pub a Unique Combination

The Be Jolly House (built in 1890) at the turn of the 19th century. It was restored with the intent to return you to that period, the late 1800's, early 1900's charm, & ambiance. We recently added a propane fire pit area with a roof over it as well as a roof over the large rear deck as well as a BBQ and refrigerator. In addition, we have added another room where we have installed a home bar area with high top tables and a 4-person cedar infrared sauna! We're located in a rural setting.

Fully Remodeled Saugerties Retreat on 7 Acres!

Make this 1-bedroom, 1-bathroom vacation rental in Saugerties your next upstate destination! The newly renovated duplex, nestled on 7 acres of wooded property with a creek, offers the perfect blend of comfort and serenity. Hit the slopes and take a hike in the scenic Catskill Mountains or stop and shop in Woodstock, and afterward, gather in the fully stocked kitchen for a home-cooked meal. With high-speed internet, modern touches, and at-home laundry, this home has everything you need!

Cozy Woodstock Retreat—Near Village & Fireplace

Say hello to your perfect vacation home! Bright and airy Woodstock home with all the amenities you will need. Located only 4 minutes from the Village of Woodstock. Four-bedroom house with 3 full bathrooms located on private roadway perfect for walking & running around neighborhood. The house features heated salt-water in ground pool, 2000sf outdoor deck with BBQ grill, fire pit, basketball court, and large tranquil garden with privacy, two wood burning fireplaces, and central air.

Winter Cabin Escape • Hunter Mtn • Xmas & NYE

Four season resort like chalet in the heart of the Catskills next to its own lake. Play a game of tennis on the private court or rejuvenate in the Swedish sauna. Vaulted ceilings, exposed stonework,oversized furniture,incredible views. Swim, fish,or stand up paddle board/raft. Outdoor fire-pit. Sit on the back deck or 3 season porch w/a cup of coffee/glass of wine watching the sunrise/set.15 scenic acres, private lake & tennis court.4 well appointed bedrooms.New fine linens.

Gore Mountain Lift View: Wade St. Apt 2

Perfectly located in the heart of the Adirondacks, North Creek All Season Rental offers a variety of units to fit the needs of just about any group imaginable. Situated only steps from North Creek's Main St. Mosaic, NC ASR offers easy access to all that downtown has to offer. The Gore Ski Bowl, Hudson River, Rafting Co, Revolution Rail Co. and many other attractions are within a quick 5-10 minute walk. Boasting perfect cell reception and lightening fast 500/500 mbps wifi.

1850's Berkshire farmhouse

2 story 1850's farmhouse in West Stockbridge of the Berkshires with original ceiling beams and 16" floor boards in much of the house. Screened in porch overlooking 4 acres of gardens, stream and wooded mountains. Centrally located :10 minutes to Tanglewood, 15 minutes to downtown Lenox, Stockbridge, and Great Barrington. 5 minutes to downtown West Stockbridge. 25 minutes to Pittsfield. Wooded and river walks/cross country skiing/snowshoeing right out the door.

Renovated Downtown Great Barrington House

Newly renovated three bedroom “on the hill” in Great Barrington awaits your next family stay. Short walk to downtown Great Barrington for dining, easy stroll to Lake Mansfield for swimming or fishing, and walking trails. Quick 20 minute drive to Tanglewood, 5 minutes to Ski Butternut, 15 minutes to Catamount Ski Mountain, 3 minute walking distance to all the great restaurants and shops of downtown Great Barrington and plenty more!