94,639 properties available

Located in Becket, Montana, United States. Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards! Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. NOW WITH SUPER HIGH SPEED INTERNET (1GB service!)We are located close to Lenox, Stockbridge, Lee, Great Barrington and more.Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our local lake is a beautiful respite and available for picnicking and swimming all day long. We also have a tennis court in town that is public.A scenic drive away from the iconic Berkshires destinations including: Jacob's Pillow, Tanglewood, the Norman Rockwell Museum and historic Lenox, Stockbridge and Great Barrington where you will find dining, music, and culture. Near Williamstown where you can enjoy The Clark and Shakespeare Festivals. Fall foliage, spring in bloom, and picturesque winters are what keep us tied to the splendor of the Berkshires. Is skiing your thing

Located in Lee, New Hampshire, United States. Romantic Boutique Hotel / Bed and Breakfast - Standard King With Gas Fireplace La Chambrette is our economy oriented "Little Chamber," a room as charming as its name. Its private bath with a whirlpool tub, a small sitting area with a gas-operated fireplace, telephone, television and room-delivered breakfast provide for all your basic needs.With French-inspired design and nine exceptional rooms, this nineteenth-century parochial school turned country inn possesses a unique character that celebrates it as a truly distinctive landmark in the beautiful Berkshire Hills. Located in the heart of Lee, Massachusetts, this unique historic hostelry has delighted guests since its opening in 1990. The Inn offers spacious 500-square foot suites which include elegant canopied beds, comfortable sitting areas with warming fireplaces to end a day on the slopes, private baths with soothing whirlpool tubs, a desk, phone, and cable television. Eight-foot windows and embossed thirteen-foot ceilings, desi

Located in Austerlitz, New York, United States. Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape! Welcome to Chester! Fall head over heels in love with this gorgeous country home in the tranquil town of Austerlitz, NY. High vaulted ceilings, large view-facing windows, a fireplace, a formal dining area, and a chef-worthy kitchen are just a few of the many amenities that make this home a vacationer's paradise. Outside, you can take in the fresh air from the large patio with breathtaking views as far as the eye can see. There's plenty of comfortable seating and a dining table to accommodate dinner with your whole crew. When you're ready, head to the Berkshires for more outdoor activities, views, hikes, museums, and art exhibits than you could ever hope to see in one visit. Book now!AvantStay provides an upscale experience with services that elevate your stay and save time so you can enjoy every moment. Guests have access to a 24/7 support team. Whether it’s fridge stocking or in-home massages, AvantStay offers a

Located in Hillsdale, Georgia, United States. Modern, private, spacious vacation home, deck, mountain views, 5 mi to Catamount Sunset views, huge deck, chef's kitchen, fireplace, high-speed WiFi. This home is fully-equipped for your comfort and relaxation.This home is located in one of the most beautiful areas of the Hudson Valley/Berkshires, on a quiet dead-end road, close to skiing, hiking, lakes, farms, and wineries, yet very private on the deck with endless mountain views. The house has been renovated to include an open, spacious living area and stunning new chef's kitchen with gas stove. 5 generous bedrooms, 3 full bathrooms, and 2 powder rooms make this a comfortable house for everyone to spread out.This is the perfect spot to bring together family or friends to eat on the screened porch, look at the stars from the deck at night, gather around the firepit, read by the fireplace, or watch movies in the media room on a 75" TV. Cable internet means everyone can study and work efficiently during your stay. 15 minutes to Great Ba

Located in Washington, Nevada, United States. Shingle style, Timber Frame, Berkshire Cottage beside babbling brook Colesbrook Manor is a timber frame, shingle-style cottage. A true retreat destination in and of itself anytime of the year. Berkshire seclusion 2 miles off Route 8. 30 acre estate with babbling brook. Cobblestone terrace, two screen porches. Delightful & relaxing level 1/2 mile walk along brook to large untouched lake. Elevation 1500 ft. 10 minutes to Jacob's Pillow, 30 minutes to Tanglewood. Appalachian Trail nearby.The 6 night Rental period begins on Saturday 3 pm to Friday 11 am. Multiple weeks are available, discount available

Located in Becket, Montana, United States. Quintessential 1860's Berkshire farmhouse with mountain views on 30 acres. Charming 1860's farmhouse with spectacular mountain & meadow views situated on more than 30 acres. Large, covered porch offers family and friends the opportunity to relax and enjoy the view and visiting wildlife. Star gazing a must! Prepare meals in the large well-stocked kitchen and warm up by the fire while streaming your favorite movies on the smart TV (high speed WIFI). Master bedroom has sweeping mountain views with newly renovated ensuite bath and separate space for home office.You'll step back in time while still enjoying the comforts of an updated home. There's plenty of room for relaxing and entertaining. The guest rooms are generous, yet cozy. In the winter, you'll appreciate the convenience of the attached garage and the circular drive. Guests have full access to home and grounds.Dining and shopping:If cooking is not your forte, there are numerous family oriented and fine dining restaurants and shopp

Located in Great Barrington, Massachusetts, United States. Lake Community - Near Town, Attractions A short drive from New York City or Boston, or a flight into Hartford or Albany and you're in a new world of peacefulness - Gemini's Place in the Berkshires. Surrounded by tall trees and flowering shrubbery, kick off your shoes and relax on the screened porch with your summer read. Or if you're feeling energetic, you're steps to the lake - swimming, fishing, boating - or minutes to the Appalachian Trail for an afternoon hike. The Berkshires are famous for their cultural opportunities - musical, theatrical and dance productions - and who could resist an evening picnic supper on the 'great lawn' of Tanglewood combined with a premiere performance of the Boston Symphony or Pops at their summer home.Many guests take advantage of the Berkshire's fine restaurants but if you prefer to cook, the pantry is stocked with basics so you can spend your vacation funds visiting places of interest like Tanglewood, the Norman Rockwell Museum and Studio, Jacob's P

Located in Monterey, California, United States. WINTER/SUMMER - ON 5 ACRES, PRIVATE LAKE GARFIELD DOCK, 5 MILES FROM BUTTERNUT We have done all we can to think of everything to ensure a great stay. Please review and let us know if you have any questions.****As Far as the House - It is beautifully renovated and designed. And having rented in the area before we bought the property, we believe we have thought to include ever appliance and comfort you would need. ****For Summer - The central air conditioned home rests on 5 acres, with beautiful private trails, littered with blackberry bushes, two fire pits, and a large red barn that was built in the 1800s. The property stretches to Lake Garfield, where a large private dock, large floating dock, and a host of boats and kayaks are available for your personal, private use. In addition to the lakefront, a large private deck, with chairs, tables, and hammocks overlook Lake Garfield for an amazing view. The house is also open to dogs and the property also has a large, private gated dog

Located in Otis, Florida, United States. mountain refuge Extended stays are welcome!Stay in our little Mobile Home, clean, sweet and unique. The house is adjacent to Breakshires and Otis Reservoir and to Otis Ridge Ski and 10 min from Ski Butternut , a region of many mountains and lakes . Enjoy in all seasons.

Located in Lee, New Hampshire, United States. Romantic Boutique Hotel / B&B - Deluxe Firespa Suite Our romantic "Firespa" suite with a Jacuzzi for two with a smokey mirrored surround, terry cloth robes and slippers, heated towel bar, period Inspired 1800's slate blackboards, king-sized bed; gas-operated fireplace; comfortable lounging chairs; a 70-inch wall mounted smart television with Blu-ray, DVD, Netflix, and HDMI port for your computer; in-room refrigerator; high speed wireless internet; Keurig coffee/tea ensemble; and setup for wine or champagne. Round out the romantic experience with a breakfast delivered to your door to share in bed. Amenities Keurig Coffee Maker Heated Towel Bar FREE High Speed Wireless USB Charging Station DVD Player Gas Fireplace Central Heat and A/C LCD TV w/ HDMI Refridgerator Single Person Whirlpool Tub Terry Robes and Slippers In-Room Massage Availible Telephone IPhone Dock Weighing Scale VCR Room Delivered Breakfast Availible Iron and Ironing Board Hair dryer Jacuzzi for Two Free Local And Long Dis

Located in Housatonic, Massachusetts, United States. Great Barrington/Housatonic Village Getaway—bring your dog! Three second-floor bedrooms, two baths (one up, one down), in my sweet, cozy village home in a quiet, safe, and walkable neighborhood. Your dog is welcome (although I can't seem to update this in the settings)! This home is family-friendly, with a fine front porch (which acts like a a deck), gardens and tall backyard trees. Located in the village of Housatonic. Great Barrington's charming secret neighborhood, it's within minutes of choice destinations in the Southern Berkshires, down the road from Tanglewood music Norman Rockwell Museum, Naumkeag gardens, theaters pubs and lots of food! Borrow my bikes to cycle, or hike right out down the street to several trails or nearby Monument Mountain. Walk to a funky little local restaurant called Pleasant and Main, Berkshire Mountain Bakery, The Commons Pub or our local tea shop. Kids and adults can also enjoy dance and yoga class at Berkshire Pulse, right down the street. As this is

Located in Lee, New Hampshire, United States. Spacious, Lake View Condo Near Tanglewood in the Heart of the Berkshires! This spacious, sunny condo at Foxhollow on the Lenox/Lee border is perfectly situated for you to enjoy the natural beauty and many cultural attractions of the Berkshires. With sweeping views of Laurel Lake and October Mountain, this two-floor, 4 BR unit includes decks on two levels for outdoor dining and relaxing, and use of an outdoor pool and tennis courts. Tanglewood, Stockbridge, Edith Wharton's Estate, and the main streets of Lenox and Lee are all less than a 10-minute drive away.The space:The Lakeside Condos at Foxhollow are located on the 220+ acre former Westinghouse and Vanderbilt estates, on a hill with stunning views of Laurel Lake. This new rental provides the ideal home base for taking in all the great music, art, theater, dance, museums, historic sites, shopping, fine dining, and outdoor activities in the Berkshires. Or just relax with family and friends while soaking in the view from the many large

Located in Lee, New Hampshire, United States. Stunning Berkshire custom luxury home in private wooded community- walk to lake *******Perfect Home for 1 to 12 People******* 5 BR's with 2 King Beds + 2 Queen Beds + 4 Twin BedsFabulous 3800 sq. ft. Lee home in a private lake community, in the welcoming Berkshires. Situated on 4 wooded acres on a quiet country road, private but seconds from your welcoming neighbors. This pristine home features two master bedroom suites plus 3 additional bedrooms plus 5 bathrooms. Especially featuring: - cozy spacious living room with vaulted ceilings & skylights - fully equipped kitchen with adjacent large kitchen dining table seating 8-10 -oversized 25 foot long dining room with hand rectangular table seating 18-20 with oversized Anderson sliding doors. -Table pads stored in hand made dining room buffet unit. - exterior 25 foot long screened porch with designer furniture, paddle fans, overhead lighting & skylights - outdoor screene

Located in Lenox, New York, United States. Renovated 1860's Farmhouse, across from the Miraval. Ideally located just two minutes from the center of Lenox and across the street from the Miraval Resort and Spa. This expanded and restored 1860’s farmhouse offers 4 bedrooms and three full baths. The main bedroom suite in on the main level has a king bed and luxurious bath with whirlpool tub. The upstairs has three bedrooms, two queen beds and one full bed. All the bedrooms have amazing windows that let in natural light. The town just installed a sidewalk and bike path so you can walk or bike to town!Our house is moving towards being as environmentally friendly as possible. We use earth friendly cleaners (including Force of Nature) and detergents, reusable products, an all organic vegetable garden (during the warm months), medicinal flowers, no chemicals used on the grounds, and composting. We are always finding new ways to lower our impact on the earth. Completely renovated… big rooms, flat panel televisions, Central Air Condit

Located in Otis, Florida, United States. Rustic-Chic Home w/ Decks: Pool + Lake Access Natural beauty and upscale amenities pair perfectly together at this vacation rental! Nestled in the Otis Wood Lands community, the 4-bedroom, 3-bathroom home features tasteful decor, a fully equipped kitchen, an all-season sunroom with cathedral ceilings, picture windows, a telescope, and more. Enjoy a glass of wine on the bedroom suite's private deck, challenge the grill master to a cook-off, or take a dip in the heated community pool. Your stress-free getaway starts here!-- THE PROPERTY --Mass Tax ID #C0377632250 | Outdoor Entertainment | One-Person Kayak | Community PerksFrom swimming in the on-site lake to shredding powder at Otis Ridge, family fun is just a hop, skip, and a jump away from your home-away-from-home!Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: King Bed | Bedroom 4: Full Bed | Sunroom: Sleeper SofaCOMMUNITY AMENITIES (open seasonally): Heated pool, hot tub, kiddie pool, clubhouse, playground, tennis court, cano

Located in Stockbridge, Wisconsin, United States. Delightful Stockbridge House, Walk to Town! Within walking distance to Main Street in Stockbridge, 38 Church St. offers a large backyard and gardens which boarder preservation land and views of Naumkeag! Freshly furnished open floorpan with all amenities including a fully outfitted kitchen, gas-grill, private terrace with outdoor furniture, and indoor sauna. Steps away from hiking, shopping, gardens, tennis courts, golf club, museums, skiing, and the local coffee shop; this house is the ideal locale for you to unplug and plug in to everything that the Berkshires has to offer. 8 minute drive to Tanglewood!

Located in West Stockbridge, Massachusetts, United States. Gorgeous Home, Nature Lover's Delight in the Heart of the Berkshires Our beautiful, spacious, comfortable, light filled contemporary home, set on 5 acres, is a nature lover’s delight, is being listed for the first time. This home is perfect for families or friends who want to share.Conveniently located less than 10 minutes to Great Barrington, West Stockbridge and Stockbridge, the house is set back off the road with a driveway that winds through lush forest to open up to the sunny, private home site. The grounds are meticulously manicured, with gardens that have been featured in the book "Great Gardens of the Berkshires.” With extensive hiking trails right out the back door, our home is truly a nature lover's paradise. A koi pond in the back with running waterfall delights the senses. Inside, the home is equally inviting, with 8 individually zoned A/C spaces. The first floor has an open kitchen befitting a gourmet chef with a 6 burner Viking Stove and extensive kitchen appliances. Th

Located in Great Barrington, Massachusetts, United States. Gem of the Berkshires. Mountain View. Short walk to lake & downtown. A lovely house with gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tanglewood & Jacob's Pillow. 6 rooms, 3 bedrooms (4 beds), 2.5 baths, sleeps 8. Rent entire two floors. Main floor has an open floor plan, making each room flow into another, including a spacious living room with a large smart TV, a fireplace pellet stove, an upscale & fully equipped kitchen, half bathroom, a dining area which opens to a deck with breathtaking view and a screened porch. The main floor also houses a master bedroom with a king size bed, an attached master bathroom (with deep bath-tub & a separate shower) and an office in a separate room. The upper floor has a bathroom with tub & shower and two bedrooms: one with king size bed, and the second bedroom has two queen beds (sleeps 4). The backyard has a large blue-stone paved patio, where you can recline, enjoy the view, barbecue, or sit by t

Located in Lee, New Hampshire, United States. 2 Bedroom/2 Bath Vacation Rental in the Berkshires Enjoy the tranquility and comfort of a four-season country getaway. This newly renovated luxury vacation rental is housed in a 200 year old Carriage House situated on 32 pastoral acres with total privacy and separate entrance. Tucked away between Lenox and Stockbridge, the quaint little town of Lee is only minutes from the Berkshires’ most famous attractions including Tanglewood Music Festival, Jacobs Pillow, Shakespeare & Company and Barrington Stage. A spacious 2 bedroom / 2 bath 875 sq. foot unit features newly decorated furniture throughout. Your private parking space is only feet away from the French doors leading into your full service, eat-in kitchen. The oversized, sunny living room connects to a secluded outdoor garden patio with tables, chairs, umbrella and BBQ. The master bedroom with its Queen bed and the guest bedroom with twin beds is ideal for a couple, a family or a 2 couple setting.Come relax and enjoy the comforts a

Located in Troutville, Pennsylvania, United States. Studio w/pool & hot tub -only minutes to Triple Crown hiking trails Do you enjoy hiking? If so this is the perfect property for you! Located in Botetourt County, only 10 minute drive to the town of Daleville, Sunnybrook Farm is nestled in the heart of the of the Famous Triple Crown Hiking Trails, with Tinker Cliffs only a mile away. Sunnybrook Farm consists of 9 plus acres where you will find a refreshing pool to relax in or if you prefer a hot tub is available. There is a koi pond you can visit and feed the fish while listening to the frogs sing. In the evening, please come and make yourself at home and join us at the fire pit. The studio apartment is located on the ground level of our home, however there is no entry access to the main house, allowing you complete privacy. Fiber internet and TV is provided. You will also find coffee, bottled water, and a few snacks available as well. Centrally located between Roanoke and Salem, 15 minutes from I81, Roanoke College is only 16 mile

Located in Salem, Illinois, United States. Roanoke Outdoor Destination Lovely ranch home tucked back in the woods with the closest residential proximity to mountain biking and hiking trails you can get! You will have this entire home to spend relaxing and exploring Carvins Cover Nature Preserve, the Appalachian Trail, McAfee Knob, Dragons Tooth and many other iconic Virginia trails Ana’s outdoor destinations. Less than 20 minutes to downtown Roanoke and 50 minutes to Virginia Tech means that you can have the best of everything in the New River and Roanoke Valley.

Located in New Castle, Colorado, United States. Cottage, Axe Throwing, Fire Pit, Creek, Close to AT and TC. Fenced yard Beautifully renovated small cottage. Close to hiking on the Appalachian Trail, mountain biking trails and hunting. 30 minutes to Roanoke and Virginia Tech, 20 minutes to Salem. Triple Crown within a few miles. 2 bedrooms- 1 queen, and 2 twin XL. One Bath. Washer and DryerRelax and unwind and bring your dogs. Fenced in yard, doggie door, dog bed and water bowl. Barn in yard has loft area w/ 2 hammock seat swings and hanging lights. Axe Throwing target with signed waiver. Please email Jessie @ [email protected] to have waiver sent to you. Axes will be left in the kitchen before checking in, if signed wavier has been returned. Relax by the creek sitting in Adirondack chairs by the fire pit. Extras- Coffee bar, Towel WarmerWater Dispenser, water has a sulfur smell, safe and tested but we provide water via water dispenser in kitchen for your drinking.

Located in Roanoke, Texas, United States. Roanoke Retreat- close to airport & downtown Newly renovated and continuously upgraded, this charming home is convenient to shopping and eating and all that Roanoke had to offer. Private big backyard and spacious rooms, located in a quaint neighborhood with sidewalks.

Located in Salem, Illinois, United States. Willow Tree Cottage Enjoy a cozy and secluded stay on a wildlife reserve. Start a fire and munch on some snacks on us. Hiking trails are located directly behind the cottage and are available for hunting, fishing. and birding. If you are looking for a challenge try out the "triple crown" (McAfee Knob, Dragon's Tooth, and Tinker's Cliff.)