27,207 properties available

Located in Pittsfield, Wisconsin, United States. Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak! Great for outdoor enthusiasts, this 3-bedroom, 2.5-bathroom vacation rental home features a balcony, a deck, a patio, and a gazebo for you to enjoy. With a Smart TV, fireplace, and in-unit laundry, this Pittsfield retreat will make you feel cozy as soon as you arrive. After settling in, head out to wander around the town and visit Park Square or Pittsfield State Forest. Then, shred some powder at Bousquet Mountain Ski Area before returning to this getaway to stargaze on the patio.-- THE PROPERTY --MassTaxConnect ID: C0449692360 | Gas Grill | FireplaceBedroom 1: King Bed | Bedroom 2: Queen Bed, Full Bed | Bedroom 3: 2 Queen BedsHOME LIVING: Fireplace, Smart TV, washer/dryer, balcony, patio, outdoor sitting area, gazeboKITCHEN Dishwasher, fridge, stovetop, 2 ovens, microwave, coffee maker, dining table, cooking basics, dishware & flatware, CrockpotGENERAL: Free WiFi, ceiling fans, central heating, linens, towels, complimentary toiletries, h

Located in Hancock, Florida, United States. Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak. 100% private free standing house with private parking and entrance. No indoor common/shared areas.Quick walk thru woods to Grouse Run ski trial. Easy access for bathroom breaks/etc so no lodge needed!The house is professionally cleaned after each guest stay.Self check in with keyless locks.This house is in a fantastic location with beautiful views!! True ski in/ski out location. Perfect house for outdoor enthusiasts and nature lovers. Take in all Jiminy and the Berkshires has to offer!!! Quick walk through the woods to ski trail (Grouse Run).High speed fiber optic internet and TV. Ideal for remote work!Big comfortable beds. Huge space. Great fireplace with fully stocked kitchen and dinning room.Terrific location in winter for skiing or snowshoeing and summer months for mountain biking, hiking, ropes course, mountain coaster, alpine slide at the Jiminy Peak base. The trails are right out the side lowe

Located in East Chatham, New York, United States. Hudson Valley Chalet Now offering sleeping accommodations for 10! Please check out my House guide for many local recommendations! Enjoy the Berkshires in this recently renovated loft style chalet on 19 acres, just outside of Chatham, NY! The house is located centrally between 4 ski resorts, 25 minutes to the shops and restaurants of Hudson, NY and 20 minutes from Tanglewood! Relax in the hot tub after a day in town and enjoy the views! Easy access to Taconic State Parkway and I90!Basement-Walk out basement. Washer and dryer1st floor- Features a huge wrap around deck, open concept kitchen/living room with sectional and fireplace, 1 guest bedroom with a full bed, 1 full bath, and a master bedroom with attached bath2nd floor- Loft with queen pullout couch and entertainment area, 1 full bath, 1 guest room with queen bed and bunk bed.5 minutes from I-90 and Taconic state Parkway2hr30 from Boston, MA and NYC10 minutes to restaurants, brewery’s, and bars in the Village of Chatham, NY.30 min

Located in Lanesborough, Massachusetts, United States. Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer! Wake up to spectacular sunrise lake views from the deck or while soaking in the hot tub. Close to all the year round activities in the Berkshires. A short drive to tanglewood, Norman Rockwell museum, Jacob’s Pillow, Mass Moca, Jiminy Peak Ski Resort, and Bosquet Ski Resort. You can hike, snow shoe, cross country ski, mountain bike and snow mobile at the numerous local state parks. Fish off and launch your paddle boat or kayak from your personal dock. You can even take a short walk down the street to the town sandy beach. The house comes with all the amenities and a fully loaded kitchen. A grill on the deck can be utilized year round. Cozy up to the outdoor fire pit while you lounge on the outdoor furniture. The yard is fenced in and pet friendly

Located in Stephentown, New York, United States. WE'RE OPEN AGAIN FOR IMMUNIZED FOLKS AND THEIR PETS We're open for business after labor day, 2021. We lived here full time through the pandemic and really enjoyed the house. Now it's your turn.No matter the season, our house is more than just a place to stay. Nestled on almost six wooded acres, complete with a pool, giant hidden separate lawn perfect for lawn games, abundant gardens, and a wrap around porch, the house has everything you need for an idyllic vacation in an idyllic location. Located on the edge of the New York, Massachusetts border, in addition to being close to skiing, the house is conveniently located close to Tanglewood (live music venue), Jacobs Pillow (dance performances) and the historic towns of the Berkshires (Lee, Lenox, Stockbridge). Other activities in the area include hiking in the New York and Massachusetts State Parks, boating, antiquing, a live weekly auction, and theater. Even if you choose to stay close to home, you will have plenty of options for

Located in Hancock, Florida, United States. Beautiful 4 Bedroom Townhouse in the Berkshires at Jiminy Peak Resort Located slope side at Jiminy Peak mountain resort in Hancock, MA, this townhouse offers guests 4 bedrooms, 3 bathrooms, and a prime location for a relaxing or adventurous stay in the Berkshires! Enjoy the mountain views and fresh air in this lovely townhome.

Located in Canaan, New Hampshire, United States. SRC-Hudson Valley/Berkshires Cultural Corridor We welcome you to explore the magic of Sunset Ridge Chalet (aka SRC). Ideally situated within the Hudson Valley/Berkshires cultural corridor, SRC offers unparalleled panoramic sunset views of the mountains. Sitting on 7 private acres the Chalet offers our guests the unique opportunity to disconnect from their busy lives and reconnect with themselves, family, or friends. Imagine starting the day with sunrise yoga on the mahogany deck and ending it with sunset cocktails on the same deck.The spaceTo be clear, this is not a peekaboo view; this is a mammoth view! The Chalet was designed in 1998 to take every advantage of its remarkable setting and was completely renovated in Fall 2022. Highlights include a brand new kitchen, a new en suite master bedroom, a self care nook with yoga supplies, and all new bedding, light fixtures, furnishings, and kitchen utensils. SRC sits majestically on 7 hilltop acres and offers stunning mountain views.Guest a

Located in Hancock, Florida, United States. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor Summary:You want to pop out of bed, walk downstairs, and be right on the mountain - this is the place for you. This 1BR, 1BA Suite features a king bed in the master bedroom that sleeps 2, plus a second fold out queen sofa bed in the living room which sleeps an additional 2. The Kitchenette comes complete with Keurig, Toaster, Air Fryer, pots, pans, etc. The unit is equipped with games for those nights in, along w two TVs. As a guest, you have full use of all of Jiminy and the Inn, w yr round heated pool etcThe Space:All of our deluxe rental suites, apartments, and condos are very different from the standard ones offered by mountain owners. Our accommodations are fully redone, privately cleaned, and all are RIGHT ON THE MOUNTAIN! Instead of dated lodgings, experience new furnishings, in-suite perks such as Keurig machines, air fryers, board games, plentiful soft premium beddings, and of course one-of-a-kind th

Located in Lenox, New York, United States. Charming, spacious country home with stunning views.....steps from Tanglewood! Just steps to Tanglewood Main Gate and Kripalu from this dramatic three-story shingle style contemporary with five bedrooms and five and a half baths. The six hundred square foot great room has a soaring ceiling, fireplace, interior balcony, and multiple French doors and windows to overlook the beautiful southeast view over Tanglewood and Lenox. The deck and screened porch, off the gourmet kitchen, offer dining al fresco and panoramic mountain views of sunset and sunrise. A very unique home based in the classics with 4500 sq ft of easy living on almost 2 acres. Situated minutes from Downtown Lenox, this country chic home is great for entertaining friends and family, while offering a calm, secluded and romantic setting upon a hill. All bedrooms are en suite for an elegant Berkshires weekend and longterm vacation getaway, year-round. Large interior doors and huge exterior windows create a loft-like feeling in

Located in Hancock, Florida, United States. 1 Bedroom Deluxe Condo, Sleeps 8, at Bentley Brook, Jiminy Peak Ski Mountain!! This spacious one-bedroom resort suite measures approximately 780 to 880 square feet. You will enjoy two queen beds in the master bedroom, plus one queen sleeper sofa and one queen Murphy bed in the living room. Additional amenities include two full bathrooms, a full kitchen, dining area and some suites feature balconies with a mountain or valley view. Maximum occupancy is eight. Private sleeping area sleeps four.Ski-in and Ski-out your front door! Club Wyndham Bentley Brook is situated right at the base of Jiminy Peak Ski Mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking, horseback riding, Tanglewood concerts and brilliant foliage. The area delivers a wealth of cultural attractions, museums, historic landmarks, shops and restaurants, making Wyndham Bentley Brook the the perfect home base for exp

Located in Hancock, Florida, United States. 2 Bedroom Deluxe Condo at Bentley Brook, Jiminy Peak Ski Mountain!! This spacious two-bedroom resort suite measures approximately 843 to 953 square feet. You will enjoy a king bed in the master bedroom, two full beds in the guest bedroom and a queen sleeper sofa in the living room. Additional amenities include, a full kitchen and dining area, two bathrooms, washer/dryer and a balcony. Maximum occupancy is eight. Private sleeping area sleeps six.Ski-in and Ski-out your front door! Club Wyndham Bentley Brook is situated right at the base of Jiminy Peak Ski Mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking, horseback riding, Tanglewood concerts and brilliant foliage. The area delivers a wealth of cultural attractions, museums, historic landmarks, shops and restaurants, making Wyndham Bentley Brook the the perfect home base for exploring nearby Berkshire County towns and attrac

Located in Hancock, Florida, United States. ONTARA.... ONTARA, Place of the New Light...in the Berkshires...on the mountainside, with the back of the property on the New York State border...once a sheep farm, now a home for rescued koi...and deer and black bear and coyotes and great horned owls...a retreat house that serves as a real treat for the body, mind , soul...able to accommodate 1 or 2 people who would be sharing the place with the homeowner, poet, author, yogi, cancer researcher- renovations currently in progress but still quite comfortable...”now he walks in quiet solitude...the forest and the streams...seeking grace in every step he takes...” ...John Denver

Located in Hancock, Florida, United States. Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More! Complete your Berkshires retreat with a stay in the spacious Studios, perfect for romantic couples and small families. Suites feature plush bedding, additional sleeper sofa and fully equipped kitchen for all your dining needs. * Minimum age to check in is 21* Daily housekeeping is not included and may be added for a nominal fee* Please note that images are representative and units may vary slightly

Located in Hancock, Florida, United States. Bentley Brook Resort 2 Bedroom At the base of Jiminy Peak Ski Mountain, Bentley Brook resort is an exceptional choice for mountainside play. The area delivers a wealth of adventures, making this the perfect home base for exploring nearby Berkshire County towns and attractions.

Located in Hancock, Florida, United States. Pres Week- Bentley Brook Resort - Your Peak Winter Escape Bentley Brook Resort stands as a winter haven, providing unmatched ski-in, ski-out grandeur. Immerse yourself in the enchantment of the snow-clad landscape, enjoying top-notch amenities, snug alpine lodgings, and invigorating outdoor escapades. Whether you're a seasoned snow aficionado or seeking a tranquil mountain refuge, our resort assures an extraordinary blend of excitement and repose. Unwind in style, embrace the crisp mountain zephyr, and craft unforgettable moments amid the breathtaking allure of Bentley Brook. Your premier ski resort sojourn awaits, where each moment unfolds as a tribute to the enchanting magic of winter allure.

Located in Lenox, New York, United States. Steps away from shops and restaurants of Lenox Village, with private forest Newly renovated and re-furnished, ''the Peach House', is a few level steps away from Lilac Park, Main Street, the Library and the boutiques, coffee shops and restaurants of the Lenox Historic District. No need for a car.. Peter Pan bus stop to and from NYC is a 5-minute walk away.Unique for Lenox village, the property has three acres of private woods with a pleasant loop walking trail. I have expanded the field, cut dead trees and renovated the walking trail..

Located in Lenox, New York, United States. Lenox House w/ Screened Patio & Mountain View Head to Massachusetts for the holiday and stay at this inviting 1-bedroom, 1.5-bathroom vacation rental house in Lenox. The property features free WiFi, a kitchen, a screened patio, and access to the outdoor pool that’s shared with the other rental on-site — rent both properties together if you want the pool to yourself! No matter what your passions are, this area offers attractions that everyone can enjoy like the Catamount Ski Resort, the Appalachian Trail, or the Boston Symphony Orchestra.-- THE PROPERTY --MassTaxConnect ID: C0391641520 | Shared Swimming Pool (Seasonal) | 1,000 Sq Ft Bedroom Suite: King BedINDOOR LIVING: Bright & airy interior, expansive windows, open layout, dining table OUTDOOR LIVING: Fire pit, patio, yard KITCHEN: Stainless steel appliances, dishwasher, stove/oven, blender, coffee maker, spices GENERAL: Free WiFi, linens/towels, books, complimentary toiletries, washer/dryer, laundry detergent, central heating & A/C

Located in Hancock, Florida, United States. Pres day weekend! STUDIO Sleeps 4 Ski in/out Wyndham Bentley Brook JIminy I pre-reserved President and MLK weekend Friday to Monday for your family. Luxury Room is right on Jiminy Peak's learning/beginner slope. It's lift brings you to the main lift. Easy walk to restaurants and ski rentals. Excellent location. No car required. Full kitchen with all supplies. Washer/dryer in unit. Huge hot tub. Indoor pool and game room. Exact unit will vary, but will be a studio, sleeps 4

Located in Hancock, Florida, United States. The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook This hotel/resort is at the base of the ski lift for Jiminy Mountain. And, when you are not on the slopes, it features an indoor and outdoor pool and a hot tub. There's also tennis courts on site. There is a full kitchen. A game room complete with a pool table offers recreational fun. A picnic area with plenty of barbecue grills is there for your use.

Located in Pittsfield, Wisconsin, United States. Stylish Berkshire Apartment conveniently located in the center of town Enjoy a stylish, all inclusive experience at this centrally-located apartment. Located in downtown Pittsfield, Ma. A quiet, spacious two bedroom apartment designed with the travel worker in mind. Whether you are a travel nurse, travel doctor, travel for theater or travel for fun we have designed our spaces for your comfort. We are located minutes from the hospital with off street parking. WiFi, smart TVs, massage chair, comfy beds and a fully stocked kitchen , just bring is yourself.

Located in Hancock, Florida, United States. 1br Deluxe Condo Jiminy Peak Skiing! Summary:This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It provides a wealth of adventures, making it the ideal home base for exploring nearby Berkshire County towns and attractions.The Space:Enjoy the peace and serenity that comes with the views of the Jiminy Peak Ski Mountain in this deluxe 1 bedroom/2 bath condo that is 781 sq ft! The spacious master bedroom has a two queen beds, and attached en suite with jetted tub. In the very open living room there is a queen sofa sleeper and a queen murphy bed, and access to the balcony(varies) where you can enjoy the beauty of nature with your guests. This condo can accommodate up to 8 guests!  A full kitchen and a dinning room, allows you the option to prepare your own meals and enjoy the convenience of dining in. It also includes a washer and dryer in-unit for your convenience. With all the necessary amenities, and so much to do in the great outdoors

Located in Hancock, Florida, United States. Studio Condo Outdoor Adventures Summary:This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It provides a wealth of adventures, making it the ideal home base for exploring nearby Berkshire County towns and attractions.The Space:Enjoy the peace and serenity that comes with the views of the Jiminy Peak Ski Mountain in this Studio and 1 bath condo that is 404 sq ft! The living has a queen sofa sleeper and a queen murphy bed, and access to the balcony(varies) where you can enjoy the beauty of nature with your guests. This condo can accommodate up to 4 guests!  A full kitchen and a dinning room, allows you the option to prepare your own meals and enjoy the convenience of dining in. It also includes a washer and dryer in-unit for your convenience. With all the necessary amenities, and so much to do in the great outdoors, you're sure to have a fun and memorable stay! Photos may not be of the specific suite you are renting and your suite may

Located in Hancock, Florida, United States. VACATION VILLAGE IN THE BERKSHIRES MA-2 BDRM CONDO Professionally decorated in a traditional New England style, Vacation Village in the Berkshires offers spacious suites with amenities such as fireplaces, jetted tubs, and fully appointed kitchens, huge indoor/outdoor heated pool

Located in Hancock, Florida, United States. 2br DX Condo Ski & Berkshire County! Summary:This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It provides a wealth of adventures, making it the ideal home base for exploring nearby Berkshire County towns and attractions.The Space:Enjoy the peace and serenity that comes with the views of the Jiminy Peak Ski Mountain in this deluxe 2 bedroom/2 bath condo that is 843-1432 sq ft! The spacious master bedroom has a king bed, and attached en suite with jetted tub. The second bedroom comes with two double beds (varies). In the very open living room there is a queen sofa sleeper, and access to the balcony(varies) where you can enjoy the beauty of nature with your guests. This condo can accommodate up to 8 guests!  A full kitchen and a dinning room, allows you the option to prepare your own meals and enjoy the convenience of dining in. It also includes a washer and dryer in-unit for your convenience. With all the necessary amenities, and so