358,603 properties available

Located in Lenox, New York, United States. Lenox Chalet: Walk to Town, Mobility friendly, Amazing Views. Dog Friendly! Located in a private area of Lenox, right behind Kennedy Park, this chalet has the advantage of combining a feeling of being in the woods, with the convenience of being very close to town and all the great spots Lenox is known for. The chalet steps from Kennedy park, so hiking enthusiasts will be able to walk to an array of treks. Most of the house is laid conveniently out in the first floor, which allows for mobility, and also provides a contemporary feel. A twin, ensuite bathroom makes it convenient for families with kids. The kitchen is well appointed for all types of cooking and we encourage our guests to visit local farms to purchase produce. The house also has a cozy wood stove for winter nights and a generous deck for the summer, where guests can enjoy an amazing view of Parson's Marsh Reserve. All in, it is a magical location for a quintessential Berkshires summer experience. *Note: The property has S

Located in Lanesborough, Massachusetts, United States. Historic Stone Church in The Berkshires Hinterland Hall was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Places in 1972. Ripe with history and impeccable beauty, Ian & Jane purchased the old stone church in May of 2021, completing an extensive restoration process in accordance with the Massachusetts Historical Commission. It is with great pleasure that we open our doors to you for a wondrous stay.When entering Hinterland Hall, the ground-level sanctuary is flooded with natural light from its nine twenty-foot tracery windows, two of which feature original stained glass from 1851. The sanctuary's expansive floor plan includes its original reclaimed wide plank pine flooring with rebuilt pine pews. The thirty-seven-foot cathedral ceilings feature their original shiplap finish.Impossible to miss, the historic & rare hand-pumped organ was crafted in 1862 by the famed organ maker William Johnson of Westfield. It is number 134 of 860 ever made

Located in Lanesborough, Massachusetts, United States. Chic Berkshire Retreat by Evergreen Home Feel like you have entered your own oasis in this charming retreat. A hidden gem set far back from the road, tucked away on almost 3 acres of privacy with lush nature This 3 BR, 1.5 bath home seamlessly blends modern updates with mid-century decor, and features a brand new spacious deck to relax and take in the unobstructed mountain views. Centrally located; 6 minutes to Mt Greylock, 4 minutes to Cheshire Lake and the Ashuwillticock Rail Trail, 12 minutes to adventure at Jiminy Peak.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 quiet rural community is a beautiful peaceful place in the heart of The Berkshires. Guests have full use of the property excluding a couple locked closets for owners storageThe interior of the home has been updated in a stylish, sleek mid century modern decor and vibe with all modern comforts and conveniences. This

Located in Pittsfield, Wisconsin, United States. Charming Apartment In Berkshire Victorian Home 3rd Floor Penthouse Unit (3 bed/ 1.5 bath). This charming apartment is located in the heart of Pittsfield's Historical District in a beautiful Victorian Home. Enjoy looking out the beautiful stained glass windows original to the home dating back to 1899 or sitting out on the front stone terrace. Whether it is lounging on the rooftop deck, catching up with friends & family in the open kitchen/dining/living area, or reading a book in the office nook; there is a little special spot for everyone's needs!The spaceThe Hollister House is located on a residential street surrounded by other beautiful Victorian homes. This unit is available for short & long-term rentals! The whole group will be comfortable in this spacious and unique space. It is within a short walking distance to the main strip, "North Street" with great shops, restaurants, and activities! Minutes from great entertainment: The Colonial Theater, Barrington Stage Co., & The Berkshire

Located in Canaan, New Hampshire, United States. Four season lake side oasis in the berkshirkes Four-season lakeside oasis nestled between the Berkshires and the Hudson River Valley and a short walk from family-friendly Queechy Lake. Near skiing, Tanglewood, Hudson and Berkshire towns. Town beach rights included.

Located in Hancock, Florida, United States. Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat Summary:The most unique Suite in the Berkshires - This gorgeous Disney Themed Hotel Room will bring Mickey Magic to our summer retreat or Ski Getaway. No detail was missed in this adorable 1BR 1 BA Suite which Sleeps 4 comfortably with its King Bed and Pull out Queen Sofa in main room along with Kitchenette and Full Bath. Located in the BEST location At Jiminy - The Country Inn at the base of the mountain, you need to see this suite to believe it. Fully redone for instant Magic.The Space:The Suite has a living Room, master Bedroom, Full Bathroom, and Kitchenette in 500 sq ft of Mountain Living. 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,

Located in Pittsfield, Wisconsin, United States. Berkshire Mountainside Condo Fabulous 4 season Berkshire condo rental has room for 9 guests. Ski from this condo to Bousquet Ski Area; enjoy spring rebirth and bird migration; for summer fun we are minutes to Tanglewood – summer home of the BSO, also Barrington Stage, Jacobs Pillow and world class museums are just minutes away; fall gives you the best views of fantastic foliage including a view of Mt Greylock. Ski, hike, bike and boat - you are close to it all. Let us welcome you to our 4 season vacation home. This is an uphill unit with a large deck of the living room that offers views of the Greylock mountain range and area lakes. The main level has a large great room with gas fireplace and large HD tv. The kitchen dining area is large and has seating for 8. The kitchen is fully equipped with all the necessities you would expect to find in your own home. The primary bedroom and spacious bath is on the main level with a queen canopy bed, dresser, nightstand and HD TV. A half bath is o

Located in Pittsfield, Wisconsin, United States. Beautiful Home away from Home Large comfortable spaces good for conversations, cooking together, yoga, meditation, hot tub, quiet-time and private parties.Great spaces for small pets and extra guests.We have extra bedding for drop-ins

Located in Pittsfield, Wisconsin, United States. Family-Centric Berkshire Getaway by Evergreen Home This renovated 4 BR ranch located just minutes from Lenox has everything your family needs for a relaxing getaway! Ideally located in Central Berkshire County; museums, skiing, lake life, hiking, theaters and shopping are all just a short drive away. When you're home, relax with a movie in our theater room, play corn hole in the spacious back yard, bbq on the grill, how about a game of Foosball or Pac-Man? With room for 6 adults or 8 w/kids, this lovely spot is your perfect family retreat!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 house is ideally located in Central Berkshire County, close to many activities and features a spacious private backyard.Guests have full access to the house excluding utility room.This renovated ranch home features an open concept kitchen with stainless steel appliances fully equipped for making me

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.