27,207 properties available

Located in Lenox, New York, United States. Beautiful Lenox Home, 3 Mi to Shakespeare & Co! Situated in the heart of the Berkshires, this 3-bed, 2-bath vacation rental offers a modern living space, a large yard and an ideal location near many attractions. Adventure seekers will enjoy easy access to the Appalachian Trail and Catamount Ski Resort, music fans can catch the Boston Symphony Orchestra (BSO) at Tanglewood and theater lovers will be minutes from Shakespeare & Co and Barrington Stage Co. No matter what you’re seeking, this Lenox home will offer something nearby to enjoy!-- THE PROPERTY --MassTaxConnect ID C0219571520 | 2,457 Sq Ft | Free WiFi | Off-Street ParkingFrom the spacious yard to the cozy sunroom, this Lenox vacation rental offers all the comforts your family could desire in addition to the perfect location for easy access to the best of the Berkshires. Bedroom 1: King Bed | Bedroom 2: 2 Extra Long Twin Beds | Bedroom 3: 2 Extra Long Twin Beds | Family Room: Sleeper SofaKITCHEN: Fully equipped, cooking basics, sp

Located in East Nassau, New York, United States. Country Cabin- Nature preserve,Hiking, Skiing, fishing, swimming & pet friendly This quiet country cabin is located on two private acres adjacent to the Kinderhook Creek Nature preserve. There is a private trail from the property to the preserve that will lead you through the beautiful woods and to the Kinderhook Creek where you can have a picnic, do some fishing, swimming and enjoy the serenity of your natural surroundings. The private 2 acre lot has a fire pit, picnic area, outhouse, gardens and large yard for play and games. An outdoor grill and patio table is located on the deck so you and your family can enjoy meals outside. During the winter months you can enjoy your meals in the dinning room where you can warm up in front of the cozy fireplace. Or enjoy some family time in the entertainment room where you can relax on the large sofa and watch movies in front of a fire, play cards or games at the card table, or try your hand at darts or foosball. Local attractions include the L

Located in Pittsfield, Wisconsin, United States. Country Living just minutes from Everything! 2 minutes to Bartlett's Apple Orchard, Richmond5 minutes to Bousquet Ski Area, Pittsfield6 minutes to Balderdash Cellars- Pittsfield6 minutes to Hancock Shaker Village - Pittsfield9 minutes to Barrington Stage Company- downtown Pittsfield10 minutes to Tanglewood - Lenox 12 minutes to Pittsfield's State Forest 24 minutes to Jiminy Peak- Hancock29 minutes to Ski Butternut- Great BarringtonWORK FROM (our) HOMEOur home office has dual monitors, a wireless keyboard, mouse, and docking station to make working remotely a breeze (more details below).Julie and Andy have spent the last 3 years doing a complete renovation to their vacation home rental named Jandie's, to make it a clean, safe place for families and individuals to enjoy the Berkshires. The landscape is that of a storybook. A large deck sits on the front of the house overlooking the sprawling driveway lined with crab apple trees.Kids and adults of all ages will love spending time in t

Located in Hancock, Florida, United States. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn Summary:You want to pop out of bed, walk downstairs, and be right on the mountain This 1BR 1 BA Ground Floor Unit right by the entrance features a king bed in the master bedroom that sleeps 2, plus a fold out queen sofa bed in the living room that sleeps an additional 2. The kitchen comes complete with all your needs, incl Keurig, pots, pans, etc. The unit is equipped with board games , along with cable TVs that have all your favorite shows . The Inn amenities are yours including heated yr rd poolThe 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 the

Located in Stephentown, New York, United States. Berkshires Apartment at the Stephentown Hotel Welcome to the historic Stephentown Hotel located in the heart of the Berkshires & Taconic Mountains! Apartment is brand spanking new! This is a Studio Apartment featuring a King bed + queen pullout sofa. Apartment has a private entrance and private deck! King size bed, queen pullout sofa, full kitchen and more. Everything is brand new! We are minutes away from Jiminy Peak, right off Route 43 in Stephentown, minutes to so many adventures and activities! The Only Stephentown on Earth!Welcome to the Stephentown Hotel! This is the Studio Apartment, Apt. # 2. Has a private entrance with parking right outside. Private deck with a BBQ for your usage. We are located minutes away from Jiminy Peak Ski Resort in the world famous Berkshire Mountains and the Taconic Mountains! Right on the NY / MASS border in beautiful Stephentown. Surrounded by nature and serenity. Every stay includes water bottles, granola bars, oatmeal packets, coffee and tea! Parki

Located in Stephentown, New York, United States. 2 Bed Berkshire Getaway @ Stephentown Hotel Welcome to the Stephentown Hotel in the heart of the Berkshire & Taconic Mountains. Completely gut remodeled two bedroom apartment, the building reopened in 2023.Two bedroom apartment, brand new everything! Located on the 2nd FL of the historic Stephentown Hotel. Large bedrooms, custom kitchen, soaking bathtub, bright and spacious with plenty of windows, ductless ACs, arcade with x3 arcade games plus a Washer Dryer in unit. Located minutes from Jiminy Peak!The spaceThe building went through a 2.5 year complete gut remodel. We are located minutes away from Jiminy Peak Ski Resort in the world famous Berkshire & Taconic Mountains! Right on the NY / MASS border in beautiful Stephentown. Surrounded by nature and serenity. Many fun activities nearby including Tanglewood, New Lebanon Speedway, Cherry Plains State Park, Mount Greylock, Cinch Em Horse stables, multiple lakes, hiking trails and more!Beautiful 2 bedroom apartment, King Bed in the primar

Located in Lanesborough, Massachusetts, United States. Bright Boho Apt in 18th c Berkshire Farmhouse This bright 1BR/1BA is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in the 1700’s, this centuries old farmhouse has since been converted into four cute apartments. Newly updated kitchen, floors, bathroom and furniture. Enjoy exploring the sprawling 19 acre property you will be staying on which includes seasonal flower fields, thousands of berry bushes, fruit trees, creek, and walking trails full of wildlife.

Located in Richmond, Utah, United States. Lovely bright apartment in pastoral shaker barn Berkshire living at its best! This historic shaker barn on 2 open acres has three apartments. Rent one or more for your group! This apartment (#1) is a one bedroom/one en suite bath with full equipped kitchen, dining area, comfortable living room with AC and smart TV, bedroom with new queen mattress and desk. Big closet. Quiet with lots of light. Shared entry hall and laundry, but unit is completely private, charming and comfortable. Private outdoor area with seating and barbecue (summer only). Around the corner from Hancock Shaker Village where this barn was moved from 100 years ago. Minutes from Balderdash Cellars winery, and Hilltop Orchards. Use of Richmond Pond, a clear lake with a lovely beach only 8 minutes away for swimming, boating or skating. Ski at Bousquet (9 minutes) or Jiminey Peak (21 minutes) or take a picnic to Tanglewood in Lenox (13 min). Close to all Berkshire attractions-- theaters, dance, museums, restaurants, shopp

Located in West Stockbridge, Massachusetts, United States. Wellspring by AvantStay | Indoor Pool + Views Wellspring is a sprawling Berkshire escape with unparalleled views of the surrounding mountains. The crown jewel of this home is its indoor pool — a haven where you can enjoy a dip no matter the season. There is a poolside lounge area and an airy sunroom where you can enjoy a breeze space with tons of natural light. Perfect for groups, Wellspring offers a variety of indoor areas where everyone can spread out and relax. There are two living rooms, as well as a lofted game area. Between the large dining table and breakfast nook, there's seating enough for everyone. The fully-equipped kitchen is easy to keep stocked with convenient grocery shopping less than 10 minutes away.Spend your evenings on the spacious patio as you fire up the grill, dine al fresco at the outdoor table, and enjoy the surrounding views. Inside, a wide selection of sleeping arrangements ensures everyone has a comfortable space to call their own.You'll be on a large privat

Located in Pittsfield, Wisconsin, United States. Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table Welcome.....we invite you to come enjoy the great space of our beautiful home with your family and friends in our unique 4000 sq. ft. custom built home with sleeping accommodations for up to 25. With 8 bedrooms, 2 full kitchens, 3 bathrooms and great outdoor space for relaxing and entertaining, we think it's the perfect gathering spot. The house is nestled in the heart of the Berkshire Mountains and situated between 2 beautiful lakes that have incredible views. One lake (Onota) is just a short walk down the street where you can enjoy swimming, boating, fishing, picnicking and more. Feel free to bring your Kayaks, jet skis or boat and store them at our fenced in yard. The second lake (Pontoosuc) is just a short 3 minute drive. This lake also boasts beautiful views of the surrounding mountains and aside from boat and jet ski rentals, this area also has amenities such as on the lake restaurants with a view and golf

Located in Lenox, New York, United States. Restored 1881 Farm House Summary:Beautifully renovated 1881 farm house minutes from down town Lenox.The Space:Quintessential Lenox Farmhouse with 1881 charm and a shiny new finish. Lovingly renovated and restored, this house is nestled on 4.5 private acres within minutes of the town of Lenox and Tanglewood.The house boasts a chef's Kitchen with all new stainless steel appliances, large farmhouse porcelain sink, marble topped counters and center island. A small deck off the kitchen is the perfect spot for a sunset cocktail or morning coffee.Beautiful Hickory barn wood floors throughout the first floor. The two bathrooms have basket weave marble floors, Victorian vanities and fixtures. Master bath has 60" double sleeper tub, walk in glass marble shower, a relaxing rain forest shower head and a bench. Spacious guest bath has claw foot tub with shower.Master & guest bedroom are detailed with 14' vaulted white wash tonged & grove ceilings.Guest Access:Check in any time after 3pm.The Neighbo

Located in Pittsfield, Wisconsin, United States. Modern 4 bedroom lakefront house in The Berkshires. 4 Bedroom lakefront house on beautiful Richmond Pond. All new kitchen appliances and bathrooms. Just steps from our brand new private dock with 2 kayaks and a canoe. Lake views from every room. Views of Mount Greylock, the highest peak in MA. Primary bedroom with king bed and bathroom on first floor. Bedroom 2 with King bed. Bedroom 3 with Queen bed. Bedroom 4 with two twin beds. Large loft area with futon. Small loft area with futon. Three decks.50" Smart TV with cable and WiFi . Central AC. Washer and Dryer. Iron and ironing board. Lakeside fire pit. Weber gas BBQ. Lakeside picnic table. Outdoor shower. Walk to Bartlett's Apple Orchard and Balderdash Cellars Winery 6 miles to Tanglewood 6 miles to Kripalu Yoga Center7 miles to Lenox11 miles to Stockbridge and The Red Lion Inn4 miles to Bousquet Ski Area19 miles to Jiminy Peak22 miles to Butternut Ski Area24 miles to Catamount Ski Area28 miles to Mass MoCA28 miles to Williams Col

Located in Lenox, New York, United States. Heart of Lenox!! - renovated downtown apartment Completely renovated 2-bedroom downtown apartment with open floor plan, located in the picturesque historical town of Lenox MA. The apartment is fully equipped for all your needs. The kitchen provides stainless appliances and an array of cooking essentials. You will find pots, pans, cooking utensils, glassware, flatware, and dishes. There is a table that seats six and a counter-top bar for two. The living room has a Flat screen smart TV and Wi-Fi is available throughout the space. There are two bedrooms. One with a king bed and one with a Queen bed. There is a pull out sofa in the living room. All linens and towels are provided. Rest and enjoy while staying comfortable with central heat and air!The Apartment works with the Local Sohn Fine Art Gallery to feature a local artist for the enjoyment of our Guests.Completely renovated 2-bedroom downtown apartment with open floor plan, located in the picturesque historical town of Lenox MA. The

Located in East Chatham, New York, United States. Newly Renovated Cabin in the Country The Heartwood Cabin is a freshly renovated rustic retreat nestled in the sleepy hamlet of Red Rock, NY.We just lovingly rebuilt and redecorated this charming cabin as a family getaway —we set out to create a place where we would be proud to bring our family and friends.

Located in Hancock, Florida, United States. Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities! So much, So Close - Nestled in the Berkshires, a getaway to Jiminy Peak offers everything you need, so close to home. Spend less time traveling and more time on the slopes during the winter or enjoying the thrills and challenges of Mountain Adventure in the summer season. When your day is done, take a short walk back to your room to relax before heading to dinner at one of our on site restaurants. Jiminy offers all that you need in a resort experience – lodging, dining, shopping and an array of activities and entertainment.Explore the surrounding region and discover the cultural attractions, restaurants, outdoor activities and more that make the Berkshires the perfect getaway in any season. Jiminy is close to many of the region’s most popular locations including the Normal Rockwell Museum, Hancock Shaker Village, Tanglewood and so much more. Or simply park your car and enjoy all that Jiminy offers right here on property in

Located in Hancock, Florida, United States. Wyndham Bentley Brook-Ski In/Out, Pool, Next to Jiminy Peak - Only 25% Deposit! WHAT YOU’LL LOVE:Nestled among the Berkshire Mountains, you will find a true New England treasure; Wyndham Bentley Brook. Located a mere 200 feet away from the premier Jiminy Peak Mountain Resort puts you in position to take part in the area’s best skiing and snowboarding. After a full day on the slopes, warm up and relax in a cozy studio, one- and two-bedroom units. Rooms here showcase both scenic mountain and valley views, and are filled with all the comforts and conveniences of home. All units feature a full kitchen, equipped with a stove, oven, dishwasher, microwave, and all the cookware needed to put together a private feast. Well laid-out suites provide generously-sized bedrooms and living areas; two bedroom units even feature an in-suite washer and dryer.You’ll love the indoor/outdoor pool and the spacious gazebo hot tub. Bentley Brook has a cool mini cinema with real, comfortable theater chairs!Jim

Located in West Stockbridge, Massachusetts, United States. 4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town. This house is close to Everything!! Tanglewood (3 miles), Kripalu (3 miles), theaters, Jacob's Pillow, Lee Outlets, etc.This house has a NEW and very large MBR on the first floor with adjacent bathroom.. It also has 3 bedrooms and a bathroom upstairs. Sleeps 11. Highlights: Central air, private English garden and gazebo, updated eat-in kitchen, mud room, bar area, and new 1st floor bathroom. House is located on Shaker Mill Pond with dock access. Perfect for a family vacation getaway with lots of space for people to come together or to have their own space. Large sunroom off kitchen has great views of the water. Large multi tiered deck off sunroom is great for relaxing and entertaining. In addition, there is a separate living room with lots of space.There is a dock on the water for easy access for kayaking and canoeing. Not a swimming pond.It is the type of house where you walk inside and instantly r

Located in Hancock, Florida, United States. Large 1 Bedroom - Vacation Village in the Berkshires Resort - Hancock Located in Hancock with commanding views of the Jiminy Peak ski area, Vacation Village in the Berkshires offers endless recreational activities and many of the comforts of home. Lounge or swim in the indoor or outdoor pools. Go hiking, biking, or horseback riding around the resort. Enjoy a tranquil day, or take a soothing soak in the outdoor hot tub. A fitness center is available for our more active guests. Nearby you’ll find Mt. Greylock State Reservation, Pittsfield State Forest, and many opportunities to enjoy the arts; Hancock Shaker Museum, Tanglewood, Williamstown Theater, MASS MoCa and the Clark Institute and Museum!Spacious One Bedroom (765 sq ft), sleeps 4. Beautifully furnished with integrated living and dining areas for entertaining and enjoyment. Kitchen (fully equipped except for oven), private balcony, CD/DVD players, TVs in bedroom and living room; with washer and dryer located on every floor.

Located in Richmond, Utah, United States. Renovated Berkshire Cottage This is what ‘Tiny Home’ Dreams are made of!Our Chic Renovated Cottage located in rural Richmond Massachusetts is close to the NY border and all Berkshire Attractions. Vintage touches mixed with new modern upgrades make this a Unique and Comfortable renting experience! This 1940s stucco cottage has been thoughtfully reimagined and curated with recent kitchen and bathroom remodels, new high end furnishings and lighting, newly refinished screened porch and luxurious upgrades in every room. The house itself is 720 sq ft with additional Breezeway, Large Screened Porch and Private Yard with gardens and Impressive fire pit area with views to the Forest.Enjoy the ease of 1 level living as you enter through the breezeway into the brand new kitchen boasting porcelain tiled floor, new stainless appliances, quartz countertop, large farm sink and custom live-edge open shelving. 4 burner gas stove with center griddle and full size oven. Cooking utensils are provided as

Located in Lenox, New York, United States. Main Street Delight 1bedroom Located on Main Street in downtown Lenox. A beautifully space fully equipped for all your needs. The eat-in kitchen has a table for four, stainless steel appliances, and an array of cooking essentials. Provided are pots, pans, cooking utensils, glassware and dishes. The living room features a cozy setup with a smart tv, all you need is your passwords and logins for your streaming devices. High speed WIFI is also available throughout the space. Central heat and AC provide a comfortable relaxing environment. Located on Main Street in downtown Lenox. A beautifully space fully equipped for all your needs. The eat-in kitchen has a table for four, stainless steel appliances, and an array of cooking essentials. Provided are pots, pans, cooking utensils, glassware and dishes. The living room features a cozy setup with a smart tv, all you need is your passwords and logins for your streaming devices. High speed WIFI is also available throughout the space. Central h

Located in Pittsfield, Wisconsin, United States. Berkshires Colonial on 2 Acres by Evergreen Home A Berkshires grand colonial home, on 2.7 private acres is the perfect home-base for your getaway to the Berkshires. Located in picturesque Richmond, MA this home is a short drive from all the Berkshires has to offer; Tanglewood, Wineries, Apple Picking, Museums, Theatre, Skiing, Hiking, Golf, Shopping and Dining. Enjoy quiet country living, minutes from Berkshires attractions. Drive 1 minute drive to Balderdash Cellars, 10 min to Bosquet Mountain, 30 min to Butternut and 35 min to Catamount.If you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.This home is situated in one of very few 'neighborhoods' in Richmond. The street is a large circle, perfect for walks and bike riding. The neighborhood is quiet, and houses are very spaced out from each other.Guests will have access to the entire home, and property.This spacious 2,624 sq foot colonial sit

Located in Hancock, Florida, United States. Cozy Accommodations w/ Fireplace, Full Kitchen & More! Located on the resort property: At Mountainside, Village Center, Country Village, or Beaver Pond. Ideal for larger families and groups: Spacious, well-appointed, many with washer/dryers. 2 bedroom units: 2-levels, 1.5 full bathrooms, generous living rooms, queen sleeper sofa in Living Room, full kitchen, Cable/Satellite TV, plus storage. Fireplaces: Available in many units. Firewood on sale at Country Store. All of our rooms are privately owned and we cannot guarantee room locations. We are also not pet or smoke friendly in any of our room locations.We no longer offer daily housekeeping services. If you need extra supplies that can be delivered upon request. The Country Store is open daily, 7 am - 7 pm, with grocery items and everyday essentials, as well as homemade sandwiches to go.

Located in Hancock, Florida, United States. Sunshine & Summertime at Left Bank Lodge Welcome to the Berkshires and all that Jiminy Peak Mountain Resort has to offer. This spacious townhome has all that you need for the perfect getaway, Winter, Spring, Summer and Fall. Bring the whole family and all the friends because there is more than enough room for everyone. Enjoy 3 floor living with 4 bedrooms, 3 full baths, fully equipped kitchen, 2 living rooms with fireplace and brand new trex deck with views for days. Skip the hassle of parking and take advantage of skiing right out your door!Take advantage of the use of all of Jiminy's amenities; swimming pools (1 open all winter!), exercise room, tennis, restaurants, country store, alpine slide, high ropes course, mountain biking...there is something for everyone!

Located in Hancock, Florida, United States. Berkshires Living!! Beautiful Location, Breathtaking Sunsets, Fully Reno Home Enjoy your own private summer mountaintop in the Berkshires - Two story, completely renovated air conditioned home on spacious, private wooded setting steps from hiking/biking trails, across from Jiminy Peak. Short drive to Williamstown, Tanglewood, Stephentown, New Lebanon, and Lenox. Brand new master bedroom/bath suite, renovated private bedroom on second floor with Queen bed, and custom made four bunk room sleeps four more.... Two complete renovated baths with Showers in both. Easily can accomadate 8-10. Kitchen renovated, all appliances you need, brand new mudroom/laundry, and large airy deck perfect for watching the sun set over the Berkshires. The House is in perfect shape, setting is not to be missed. Additional pictures available on request. Pets - dogs upon request (inquire), but sorry no cats! Brand New Hot Tub, available upon request, conditions apply. Summer Rates (June, July, August) 1