27,207 properties available

Located in Canaan, New Hampshire, United States. Secluded Mountain Top Lake View in Canaan, NY. Overlooking Queechy lake, this spacious home with a cook's kitchen and wrap-around deck is a great get-away for family and friends. Within an easy 20 minute drive you will find delicious farm fresh foods, renowned arts venues, swimming, kayaking, skiing, and hiking trails. Ideally situated between the Berkshires to the east and Hudson Valley to the west, whether you are seeking cultural attractions or natural escapes, you will be in the perfect place to soak up the best the area has to offer.Other things to noteWifi service provider: Consolidated CommunicationsWifi speed: 75 Mbps upload and download

Located in West Stockbridge, Massachusetts, United States. West Stockbridge Sanctuary by Evergreen Home Enjoy a getaway to the Berkshires in this magnificent post & beam home; newly renovated and nestled on 1 acre of land - just 3 minutes from downtown West Stockbridge, and 8 minutes to Tanglewood. Located in picturesque West Stockbridge, MA this home is a short drive from all the Berkshires has to offer. Enjoy quiet country living, minutes from all Berkshires attractions. Pack your hiking shoes and explore the Berkshires in the spring from this central location!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 is a quiet neighborhood road. The home is set back from the street.Guests will have access to the entire home, and property.This 1,821 sq foot home features an open concept main floor with a light filled living room containing a smart TV and sectional for the perfect Berkshire nights. The full kitchen includes all new stainless steel a

Located in Lanesborough, Massachusetts, United States. Charming A-Frame Near all the Best parts of the Berkshires! Our A-Frame Cabin is the perfect place to disconnect and get away from it all! A family member literally built it by hand, with every detail of beautiful wood carpentry creating a dreamy cabin experience in the woods. It's cozy and quaint, complete with a propane stove and hundreds of classic movies to watch on DVD or VCR. We provide bedding as well as towels, and just ask that you leave the beds unmade and used towels hung on hooks so the cleaning service can take care of laundering them after your stay. There is no internet, so it's truly a time to "unplug" and read, watch an old classic, or head out to any of the amazing things that are offered in the Berkshires! (You can use your own phone "hot-spot" if you need to connect to the internet). We are a 3 minute drive from the base at Jiminy Peak Mountain Resort, with skiing, snowboarding and summer mountain amusement area, as well as a quarter mile from Ramblewild, an outdoor

Located in Canaan, New Hampshire, United States. Berkshires Lake House With Private Dock, gunite pool, and Chefs Kitchen This newly updated sun drenched Berkshire lake house with newly built private in-ground pool, is the perfect place for a year-round vacation. The house is nestled within a small lakefront community where being on the lake is a pass-time in winter, spring, summer or fall. This house sits on a beautiful acre of land with a private dock and lake views. You have access to a membership-only beach within a short drive or 15 minute walk. 6 light-filled bedrooms can accommodate a family retreat or 3 families with lots of space for everyone. The master bedroom has a small bedroom attached with twin beds for a family. Spend the day at the lake and then come home to a private swimming pool, pool table, two living room areas, and wood burning fireplace inside and fire pit outside. Chefs kitchen complete with anything you need to make the perfect meal. Outdoor kitchen complete with gas grill, sink, and outdoor shower.

Located in Hancock, Florida, United States. Wyndham Bentley Brook-Ski In/Out, Indoor + Outdoor Pools - 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!Jiminy

Located in Lenox, New York, United States. Perfect location in the heart of downtown Lenox If you want to feel like you're truly away, but still have access to a great lifestyle, this is the rental for you! Stay in a charming, comfortable, renovated duplex house in a beloved Summer, Fall and Winter community just steps away from tony and charming downtown Lenox. Five star restaurants, cozy cafes, bakeries, and wonderful shopping abound. Drive just a few minutes and you'll have every activity and relaxation outlet right at your fingertips. This is not to be missed! Tanglewood Music Center - less than 2 miles Jacobs Pillow - 20 min drive Miraval Resort and Spa - 2 miles Canyon Ranch - less than 2 miles Bosquet Ski Resort - 5 milesJiminy Peak Ski Resort - 18 miles (35 minutes)Butternut Ski Resort - 15 milesCatamount Ski Resort - 22 milesPleasant Valley Wildlife Sanctuary - less than 3 milesEdith Wharton's home, The Mount, less than 3 miles

Located in Richmond, Utah, United States. Relaxing Getaway in the Beautiful Berkshires A wonderful family country escape with all the accommodations of home! Set on two sprawling acres in the beautiful Berkshire mountains, you will feel a world away while having all of the Berkshires right at your fingertips.The first floor has a large guest suite with fireplace, family room with large sectional and 60-inch SmartTV, sun room with sectional, office/den, eat-in kitchen, half bath, and washer-dryer. The second floor has a twin room with trundles (sleeps 4), a queen guest room with a full-size crib, a full bathroom, and a master with a king size bed and its own en-suite bathroom. The basement has a king-size Room and Board pull-out couch, a futon, a 40'' SmartTV, and plenty of toys to keep the kids entertained. All four bedrooms have window-unit AC for summer months. The home has two large patios., which in the summer include an outdoor couch, table and chairs, grill, lounge chairs, and hammock. Enjoy your coffee while overlooking

Located in Hancock, Florida, United States. Spacious, Family-Friendly Getaway w/ Full Kitchen & Fireplace Located on the resort property: At Mountainside, Village Center, or Country Village, Ideal for larger families and groups: Spacious, well-appointed, many with washer/dryers. 3 bedroom units: 2-levels, 2 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 West Stockbridge, Massachusetts, United States. NEW FOR 2024! Light-filled family home Light-filled modern 4 bedroom, 3.5 bath home in the Berkshires. This lovely two story home features a master bedroom on each floor with its own private bathroom. Full kitchen, breakfast nook and separate dining room that seats 8. Screened porch perfect for dining and lounging. Wrap around covered deck to enjoy sunsets in the backyard. Tons of games and books, perfect for families. In the winter the easy-to-use gas fireplace will keep you warm and toasty - perfect for relaxing with a good book. Conveniently located to all that the Berkshires has to offer, like concerts at Tanglewood, antiquing, summer festivals, apple picking in the fall and skiing in the winter.

Located in Lenox, New York, United States. Family Friendly Raised Cape in the Center of Lenox Village This renovated raised cape is in the center of historic Lenox, MA. 3 large bedrooms include: king size bed, full size bed, and full size bed. The living rooms large leather sofa also has a pullout bed. Kitchen includes: flat top stove, dishwasher, nook and bar seating. Living room includes: flat screen tv, wifi, electric fire place. Laundry room with washer and dryer. House is located in center of town with easy walking to all restaurants, boutiques, grocery and cafes. Nature trails within walking distance and area attractions a short drive.

Located in Canaan, New Hampshire, United States. Hilltop House About this spaceHilltop House is the perfect get away for your family! Located on 15 acres, it is the best place to enjoy the beautiful surroundings as well as a spacious, cozy home. For those looking for a winter escape, it is just a 20-30 minute drive to three ski resorts (Jiminy Peak, Butternut, Catamount). It is also the perfect place to host the holidays, with a lovely fireplace and the ability to hold over 9 people. Experience the magic of Columbia County/the Berkshires at Hilltop House!

Located in Hancock, Florida, United States. Wyndham Bentley Brook Condo Resort Nestled in the Berkshire Mountains at the base of Jiminy Peak Ski Mountain, Wyndham Bentley Brook takes "weekend getaway" to a whole new level! No matter what time of year that you choose to visit, you will never run out of things to do. Enjoy clean and spacious rooms and amenities that include an indoor/outdoor swimming pool, sauna, convenience store, massage services and laundry facilities.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.Top Attractions in the Berkshires:- Jiminy Peak Mountain Resort- Hancock Shaker Village- The Berkshire Mall- Skyline Country Club - The Berkshire Museum- Williams College Museum of Art- Lee Premium Outlets- Norman Ro

Located in Canaan, New Hampshire, United States. Plan your Berkshires by the lake Very comfortable three-bedroom cottage in a quiet, private association on Queechy Lake. Perfect for families. Hi-speed Spectrum internet, AllClad cookware, electric range, microwave, sharp knives, coffee maker, charcoal BBQ, and tons of places to hike. Apple TV and a Bose Bluetooth soundbar. There’s a large Solo Stove firepit as well as 2 kayaks and a paddle board for tooling around the lake. Close to supermarkets. 15 minutes to Tanglewood!The spaceThe house is decorated with vintage furniture sourced from the area. The kitchen is fully stocked with Henckel knives and All-Clad pots & pans for the induction range - we stocked it as we stock our own home (too many frustrating, random European AirBnb kitchens encountered....). Dine out on the huge deck or the screened-in porch. The area is very quiet and peaceful. The house is on a dead-end lane that is perfect for kids to ride their bikes back and forth on. There’s also a Solo Stove for marshmallow roasti

Located in Richmond, Utah, United States. Escape to The Berkshires w/Pool by Evergreen Home This 4Br home is filled with cheeky pop art, stylish comfortable spaces and all the amenities you need for the ideal Berkshire vacation. This is the perfect spot to hang with friends or bring the whole family. The private, heated saltwater pool is available May- Sept, and nearly everywhere you look are mountain views. Venture out your front door to explore the hiking trails nearby or hop in your car for a 5 minute drive to Richmond Pond;10 minutes to Tanglewood!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.Situated on a private property with beautiful mountain views and close to many attractions in the Berkshires.Guests will have private access to the entire home, and property.This stylish and remodeled ranch home is flooded with natural light and looks out onto mountain views from all positions in and outside the house. The modern ki

Located in Stephentown, New York, United States. Secluded Berkshire stunning View, 4BR, min. to swim and Jimney PK with AC/wifi Escape to a a woodland retreat, mountainside haven just 10 minutes from Queechy Lake. Perfect for nature lovers, enjoy great hikes, Tanglewood concerts, and skiing at Jiminy Peak. Set on 15 wooded acres with a landscaped yard and stunning mountain views, the home features an open floor plan, vaulted ceiling living area, screened-in porch, wood-burning stove, AC, and a fully equipped cook's kitchen. Only 2.5 hours from NYC or Boston, it's the ideal serene getaway for relaxation and adventure. The whole house is yours as is our property. Remember this is the country and there are bugs and critters who (very infrequently)make their way into the house. In case you have children--please be aware that one of the bedrooms is in an elevated loft space. See photos for detail.There is a farmers market/grocery store very close by with local produce, meat and fish. Highly recommended.

Located in Hancock, Florida, United States. Wyndham Bentley Brook Condo Resort Enjoy great year round activities from white water rafting and hiking in the summer, to skiing at the famous Jiminy Peak at this ski in ski out resort. The newly opened Ramblewild Aerial Park is the talk of the town! Your 2 bedroom private condo sleeps 8. It has a king size bed in the master bedroom for 2 along with a Jacuzzi tub, then 2 double beds in the second bedroom accommodating two more persons in each bed, giving you room for four more, then a full size sleeper sofa in the living room for two more. The unit is fully equipped for cooking with a full size kitchen complete with oven, stove, microwave, dishwasher, pots, pans, glassware, silverware, and full size refrigerator. There are flat screen televisions in each bedroom plus in the living room.Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play.

Located in Pittsfield, Wisconsin, United States. Cozy Renovated with 1 parking space 1 Bedroom, 1 bath with 1 off-street parking space. Cozy renovated unit features western and eastern exposures, eat in kitchen, stainless steel appliances,microwave, dishwasher, granite countertops, bathroom with bathtub and window, finished partial wood floors, mini splits throughout apt. and private porch. Property is conveniently located nearby to hospitals, restaurants, shops, transportation hubs, parks, lakes, gas stations, financial institutions, Skiing facilities, shops, grocery stores,car wash, restaurants, laundry and dry cleaning services.

Located in Lenox, New York, United States. Renovated Lenox Haus close to downtown This Dutch colonial home with 3 or 4 bedrooms is located in Schermerhorn Park in a quiet neighborhood setting on a dead end street, walking distance to downtown Lenox that offers shopping, cafes and restaurants. Three bedrooms (or 4 per request) and 3 full baths. The new kitchen is open to the dining area and features lots of light, white quartz counters, high end appliances and a center island with seating. The living room has a fireplace and 65 inch TV connects to the dining area and 3 season room with access to a stone patio. 1st floor bedroom with 55' TV. Upstairs is a en-suite bedroom with shower and 2 more guest bedrooms that share a bath with shower/ tub combo. (new renovated bathroom pics coming soon)Laundry with gas dryer. Central A/C and cable internet with WiFi. The Tanglewood Main gate is less than a mile away. Enjoy all that Lenox has to offer in this pristine location.

Located in East Chatham, New York, United States. Spacious & Gracious 4Br Log Chalet with Sauna, Pool and Grand Entertaining Space Grand entertaining space with large decks and fire pit located in the town of East Chatham. This spacious A-frame log chalet has vaulted ceiling and an open concept living room and kitchen space. A cedar wood sauna inside for you to enjoy at any season. A private, inground 20 x 40 Grecian pool with deck is available during the summer months. A finished walkout basement with an extra room. This home is the perfect retreat for you and your guests to escape and unwind.Rental Options:Short-Term Rental (Fall/Winter):Monthly Rent: $4,250 + UtilitiesMinimum Stay: 3 MonthsExperience the serene beauty of the area during the quieter seasons.Extended Stay:Monthly Rent: $3,750 + UtilitiesTerm: 6 - 9 MonthsIdeal for those seeking a medium-term rental with a homely atmosphere.Property Features:Bedrooms: 4 spacious bedrooms plus an extra roomKing Size Bed in the master bedroom for ultimate comfortQueen Size Bed with Temp

Located in Hancock, Florida, United States. Wyndham Bentley Brook at Jiminy Peak Jiminy Peak Ski in/ski out in Winter. Summer activities at Jiminy Peak in the Berkshires. Fully equipped kitchen, living room, dining room, and two bedrooms, jacuzzi in master bath. There is an indoor/outdoor pool, adult outdoor pool, 3 hot tubs, gym with sauna and exercise room, game room and movie theater. There are organized activities for adults and children. Nearby are Tanglewood, Hiking, golfing, great restaurants, shopping, and cultural activities. Unit pictures are a representation of the units in this complex. The unit can be any 2 bedroom unit in the complex.The units are assigned at check in by the resort. I have no control over the the floor or unit location.

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. A Private 1940s Elegant Estate, renovated to Modern-Day Luxury - Tanglewood Fox Hollow, a private 1940s estate home, renovated to modern-day luxury, located in gorgeous Berkshire County, is a 3-level home with 7,800 sq feet of living space, situated on 21 acres; including 5 acres of rolling lawn and 16 acres of forest.This gorgeous, historic home built by the prominent Samuel Colt family in 1940, has been newly renovated and has 4 bedrooms, 4 full baths and 2 half baths, top of the line Subzero / Wolf appliances, and state of the art technology throughout. Situated just 5 minutes from downtown Pittsfield, MA, within close proximity to Onota Lake, Lake Pontoosic, Tanglewood (summer home of the Boston Symphony), Norman Rockwell Museum, Clark Museum, Jacob's Pillow Dance, Barrington Stage Company, Berkshire Theatre Group, The Berkshire Museum, many local taverns and restaurants, and Jiminy Peak Ski Resort.If you are up to a picturesque drive down some country roads in nearby Lenox or

Located in Pittsfield, Wisconsin, United States. Cape Home In the Beautiful Berkshires - Near Lenox & Bousquet Cozy Cape Cod home in the beautiful Berkshires in desired neighborhood. Close to Bousquet Ski Resort, Wild Acres, Tanglewood, Lenox, museums, shopping, grocery stores, dining & hiking trails. Perfect place to relax with friends & family.

Located in Hancock, Florida, United States. Fun on the slopes with pool @Vacation Village Berkshires1.0 miles to Jiminy Peak Bring your family at this private unit at the Vacation Village in the Berkshires. Views of the Jiminy Peak Ski Resort slopes from the indoor pool and some of the units.Less than 5 min driving to the slopes, enjoy the amenities offered by the Resort: indoor pool, arcades (by pay), hot tub, grills and outdoor tables, playground, movie theater, gym, pool table (by pay)and other resort activities.Maxim 4 people per apartment - jacuzzi in the bedroom and full kitchen.Laundry room on each floor ( free of charge). No pets allowed / no elevator. Units are offered at resort's check in office discretion.Check-in is at 4 pm, check -out at 10 am. (strictly enforced by the resort).