Vacation Rentals By Owner In Stockbridge, MA

$272.05

Stockbridge pied-à-terre

Stockbridge, Massachusetts, United States

Enjoy our new in-town stylish pied-à-terre , a block from the Red Lion. Off the main thoroughfare just enough but an easy walk for a cocktail on the porch! a stand alone building, large open window filled living/kitchen area, small 2nd floor balcony with chairs to relax, spacious bdrm with king size bed, and a modern tiled bathroom. Central HVAC, great water pressure, all new everything and a well appointed kitchen. July and August are by the week rental only.

Bed

Bath

Sleeps

$335.1

/ Nightly

Private Vacation Home

Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!

Stockbridge, Massachusetts, United States

Our home is nestled on 2.6 acres in the heart of the Berkshires! We are within 2 miles to Tanglewood & Kripalu while just minutes away from many local attractions! brbrWe are excited to be hosting short term guests again as we've had long term tenants for the last 2 years. We recently refinished the hardwood floors, replaced the stove, installed a new kitchen floor and repainted the interior.brbrThe main floor includes a fully stocked kitchen, living room, full bath, bedroom (king) and another bedroom (twin) / office. brbrThe upper level includes the master bedroom (queen), another bedroom (2 twins) and a full bath. brbrThe basement has another TV lounge area and is where the washer/dryer are located.brbrThere is a huge deck that spans the length of the house with outdoor furniture & a BBQ for your enjoyment.brbrGuests have use of the entire house. There is an apartment above the garage where our long term tenants reside (nice couple). There are separate entrances to ensure privacy for both parties.brbrLinens, towels, soap, shampoo and spare toiletries are available in the bathrooms. High speed / wireless internet, cable tv and all utilities are included.

4

Bed

2

Bath

7

Sleeps

$489.39

/ Nightly

Private Vacation Home

Seeking school year Sept-June. Please inquire!

Stockbridge, Massachusetts, United States

This light and bright home has been beautifully remodeled to be the perfect rental for you to enjoy the Berkshires! Whether you are relaxing on the sunny back deck, or cozying up to the wood burning fireplace after a day of skiing, you'll love every minute you spend at this fabulous home no matter what time of year you are visiting!brbrAmenities include: 3 bedrooms, 2 full baths, main floor primary bedroom (for one level living), high speed cable internet and WIFI, 2 Smart TVs with both Spectrum cable channels and streaming channels like Netflix and Hulu, an outdoor fire pit, sun deck with oodles of outdoor seating, all new kitchen appliances, washer/dryer, wood burning fireplace insert, window unit ACs and mini splits to keep you cool, large BBQ grill and more! brbrMain Floor: This freshly renovated home has so much to offer its guests! The kitchen is open and bright with all new cabinets and appliances including a fantastic induction cooktop oven, large refrigerator, dishwasher, microwave, toaster, standard drip coffee maker and electric tea kettle. There is a nice sized kitchen island for even more space to prep your meals, as well as a stool for someone to sit on and keep you company while you cook. The dining room table is set up for 6, but can easily accommodate 8 guests, and there is also a separate game table close by that can be used for overflow, as long as you have finished your puzzle or monopoly game. The living room has a large sectional sofa to relax on and a smart TV with both spectrum cable channels and streaming channels like Netflix, Hulu, and Prime Video available. Or, you can cozy up to the fireplace in one of the comfy chairs to warm up your feet. Just down the hall is the shared full bathroom with a tub/shower combo and the washer and dryer. Continue down the hall to find the primary bedroom with a king size bed, en suite full bath with walk-in shower, dresser and 2 closets for all of your clothes. Just off of the primary bedroom you will discover the office/bonus room with another Smart TV, desk, and plenty of seating. This room is bright and sunny with 3 large windows looking out to the backyard and can be used in a variety of ways, including floor space to spread out on for yoga or meditation, etc. This could also be a fun kid's space! brbrUpstairs: On the 2nd floor you will discover the 2 additional bedrooms at the house. One has a queen size bed, a wardrobe and dresser for your clothes. The other bedroom has a full size bed with cubbies to tuck your belongings into. brbrOutside: Just off the kitchen is the sundeck with oodles of outdoor seating, a large umbrella, fire pit, and large propane BBQ grill. The deck overlooks the backyard and has a lovely view of the wetlands and occasional beaver sightings. The large backyard has plenty of space for outdoor games and a large fire pit perfect for stargazing and roasting marshmallows (or a hot dog on a stick). brbrLocation: Centrally located, this terrific rental is close to all of the Berkshire attractions and venues you want to visit! Just 2 miles to Tanglewood, less than 5 minutes to the Stockbridge Town Beach (on Laurel Lake), 5 minutes to downtown Stockbridge, 15 minutes to Great Barrington, and about 15 minutes to Ski Butternut.

Bed

Bath

Sleeps

$740.51

/ Nightly

Private Vacation Home

Serene and Refined Berkshires Retreat, Close to Kripalu, Gardens & 3 Ski Resorts

Stockbridge, Massachusetts, United States

This stylish Berkshires retreat is ideally located between downtown Stockbridge and Lenox, just minutes from Great Barrington. Thoughtfully designed for relaxation and connection, this spacious home offers 4 bedrooms, 2.5 bathrooms, two inviting living rooms, a formal dining room, and a screened porch, blending upscale finishes with cozy elegance.brbrSet on over 2 private acres, the property invites you to enjoy a refined comfort, slow down and reconnect with nature. Begin your mornings to the soothing sounds of a nearby brook, enjoy coffee on the enclosed patio, and take peaceful walks across the lush grounds; perfect for rest, reflection, and renewal.brbrYou’ll be close to Kripalu Center for Yoga & Health for restorative R&R, morning pastries from Lost Lamb Bakery, and live music evenings at The Red Lion Inn’s Lion’s Den. Stroll through the nearby Berkshire Botanical Garden, or spend your days exploring Stockbridge, Lenox, and Great Barrington’s renowned dining, shopping, and cultural attractions.brbrIn winter, Butternut Ski Resort, Jimmy Peak Catamount are just a short drive away, making this an ideal home base for skiing and après-ski relaxation. The Stockbridge Bowl and Olivia's Overlook, both nearby, offer breathtaking views and scenic hikes.brbrWith world-class wellness, outdoor adventure, culture, and dining all within easy reach, your biggest challenge will be choosing how to spend each day. Whether you’re seeking a peaceful wellness escape, a ski weekend, or a luxurious Berkshires getaway, this home delivers comfort, style, and an exceptional location.brbrbrbr1. The Berkshire Botanical Garden - a short walk awaybr2. Norman Rockwell Museum - 2.4 miles away br3. Tanglewood - 3 miles away br4. Naumkeag - 3 miles awaybr5. Red Lion Inn Lion's Den - 3 miles awaybr5. Chesterwood - 3.3 miles away br6. Berkshire Theatre Group - 3.3 miles awaybr7. Kripalu Center for Yoga - 3.3 miles awaybr8. Turn Park Art - 4.4 miles awaybr9. The Mount, Edith Wharton's Home - 5 miles away br10. Shakespeare & Co - 5.5 miles away br11. Mahaiwe Performing Arts Center - 10 miles awaybr12. Jacob's Pillow Dance Company - 16.7 miles awaybrbrbrPattiserie Lenox - 5 milesbrFrankie's in Lenox - 4 miles away brHigh Lawn Farm - 7 miles awaybrBizen Sushi - 10 miles away brPixie Boulangerie - 9 miles away

Bed

Bath

Sleeps

$477.01

/ Nightly

Private Vacation Home

Stockbridge Landings | 3 Mins To Tanglewood

Stockbridge, Massachusetts, United States

Welcome to our rustic summer cottage—quaint, quirky, and perfectly imperfect! Nestled right at the Stockbridge Bowl in the Berkshires, it’s the spot for water lovers and Tanglewood fans alike. With more charm than shiny new, this cozy retreat is ideal for those who appreciate rustic charm and a splash of personality. Just 3 minutes from Tanglewood, it’s a step back in time where moments with family abound and good times float freely!brbr✔ Lake Accessbr✔ High-speed Wi-Fibr✔ TVbr✔ Fully equipped kitchenbr✔ Washer & dryerbr✔ Free parkingbr✔ Sun loungersbr✔ BBQ Grillbr✔ Pet-friendlybr✔ Pack n Play Travel Crib (Upon request)brbr➥ 1 min to Mahk Shores Private Beachbr➥ 3 mins to Tanglewoodbr➥ 6 mins to The Mount, Edith Wharton`s Homebr➥ 7 mins to Shakespeare & Companybr➥ 7 mins Olivia`s Overlook at Yokun Ridge Reservebr➥ 7 mins to Berkshire Botanical Gardenbr➥ 7 mins to The Lion`s Denbr➥ 8 mins to Kennedy Parkbr➥ 8 mins to The Berkshire Theaterbr➥ 9 mins to Norman Rockwell Museumbr➥ 10 mins to Laurel Lakebr➥ 10 mins to Chesterwoodbrbr✦BEDS & BATHS✦brInside we have 3 bedrooms and 2.5 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 Twin bed & 1 Double bedbrBedroom 2 - 1 Queen bedbrBedroom 3 - 1 Double bedbrShared Space - 1 Twin bedbrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a mornings worth of coffee to get you startedbr - Learn more @berkshire vacation rentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbr• DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 2 dogs. No other types of animals are authorized.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area.brbrParking is VERY TIGHT in Mahkeenac Shores. Please carpool whenever possible. There is parking FOR TWO CARS MAXIMUM in the designated spot directly in front of the home. There is no additional parking inside Mahkeenac Shores. Any cars beyond two will need to be parked in the town of Stockbridge. brbr***IMPORTANT NOTE, WE ARE NOT ALLOWED TO HAVE TRASH CANS AT THE COTTAGE. ALL GUESTS WILL NEED TO BRING THEIR TRASH TO THE TOWN DUMP, JUST A FEW MINUTES DOWN THE ROAD.brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrplease respect all quiet hoursbrPlease see guest packet for more information.

Bed

Bath

Sleeps

$500.66

/ Nightly

Private Vacation Home

Mac Shores | 5 min to Tanglewood ! • Shared Beach

Stockbridge, Massachusetts, United States

Welcome to our funky little summer cottage! Tucked in a stone`s throw from the Stockbridge Bowl and just down the street from Tanglewood, this home offers convenient access to fun in The Berkshires. Whether you’re at the lake, Tanglewood, or relaxing on the porch, there`s something for everyone. Bright, modern, and charming, it`s the ideal spot to make memories with loved ones.! Enjoy the best that The Berkshires have to offer at this peaceful and centrally-located cottage.brbr✔ Self check‑inbr✔ Lake accessbr✔ High-speed Wi-Fibr✔ TVbr✔ Fully equipped Kitchenbr✔ Coffee makerbr✔ Washer & dryerbr✔ Free parkingbr✔ BBQ Grillbr✔ Pack n Play Travel Crib (Upon request)brbr➥ 1 mins to Mahk Shores Private Beachbr➥ 3 mins to Tanglewoodbr➥ 5 mins to The Mount, Edith Wharton`s Homebr➥ 6 mins to The Lion`s Denbr➥ 7 mins to Berkshire Botanical Gardenbr➥ 7 mins to Shakespeare & Companybr➥ 7 mins to Kennedy Parkbr➥ 8 mins to The Berkshire Theatrebr➥ 9 mins to Norman Rockwell Museumbr➥ 10 mins to Chesterwoodbr➥ 12 mins to October Mountain State Forestbr➥ 13 mins to Bousquet Mountain Ski Areabrbr✦BEDS & BATHS✦brInside we have 3 bedrooms and 1 bathroom, all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 Queen bedbrBedroom 2 - 1 Full bedbrBedroom 3 - 2 Twin bedsbrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a mornings worth of coffee to get you startedbr - Learn more @berkshirevacationrentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbrNo pets of any kind allowed at this home. Emotional support animals are not allowed. By law service animals are allowed. If you are planning on bringing a service animal please reach out to us ahead of time so we can verify paperwork. If a pet is brought on the premises without alerting us the reservation will be cancelled.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area.brbrParking is VERY TIGHT in Mahkeenac Shores. Please carpool whenever possible. There is only parking FOR TWO CARS MAXIMUM in the driveway. There is no additional parking inside Mahkeenac Shores. Any cars beyond two will need to be parked in the town of Stockbridge. brbr***IMPORTANT NOTE, PER OUR HOA REGULATIONS WE ARE NOT ABLE TO HAVE ANY TRASH BINS OUTSIDE. ALL TRASH NEEDS TO BE BROUGHT BY GUESTS TO THE TOWN TRANSFER STATION, JUST A SHORT DRIVE DOWN THE ROAD.brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrplease respect all quiet hoursbrPlease see guest packet for more information.

3

Bed

1

Bath

6

Sleeps

$398.46

/ Nightly

Private Vacation Home

Stockbridge house 17 minutes from Tanglewood. Four bedroom, three bathroom.

Stockbridge, Massachusetts, United States

Recently built 4-bedroom, 3-bathroom Cape Cod style house set apart from neighbors. Very close to Norman Rockwell museum, a fast drive to Tanglewood. Ideal location. Air conditioning throughout. Large dining and living area area. One bedroom on first floor. Garage parking for several cars.brbrGrand piano is a Bosendorfer 200 from 1968 in good regulation.brbrAvailable high seasons, which would be June - October. brbrPlease contact me via VRBO prior to renting. I want to show you the latest photos from the redecorating and for me to be certain you have what you wish. Also ask about shoulder season availability and lower pricing.

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Bath

Sleeps

$357.12

/ Nightly

Private Vacation Home

Stockbridge Village in Summer

Stockbridge, Massachusetts, United States

This 1900 farmhouse in the village of Stockbridge offers all the convenience of walking to restaurants, shops, the Red Lion Inn, the public tennisbrcourt, while providing a sense of privacy and serenity from its backyard views to the Berkshire Hills across flower-filled mature plantings. It is easy walking distance to the Berkshire Theater Festival, the Red Lion Inn, and only short drive to Tanglewood, the Norman Rockwell Museum, and the the Berkshire Botanical Garden. Walk downbrthe sloping lawn to the banks of the Housatonic and listen to the breeze in the trees while taking in the scent of mountain air. When the weather's fair, sit out on the terrace with friends for dinner and watch the stars. brThe kitchen has all new appliances, fully supplied for the ambitious chef. brbrCozy up in the living room or enjoy playing the baby grand Yamaha piano.brOne bedroom offers a full canopy bed, and the larger bedroom has 2 twin beds. It's blissfully quiet at night.br[Folks, this is Main Street and there is traffic sound in the daytime, but the vast majority of guests have found it very livable.]brbrThe small upstairs sitting room has cable TV but you might prefer to just read a book or write at the window with a sweeping view to the hills over the treetops. There are two full bathrooms, one on each floor.brbrWe welcome you to enjoy the farmhouse for a memorable stay with your friends or family.

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Bath

Sleeps

$969.56

/ Nightly

Private Vacation Home

Historic Stockbridge Villa on 25 acres sleeps 23

Stockbridge, Massachusetts, United States

At the end of a tree-lined driveway, this huge private eleven bedroom villa sits by the edge of a field with garden and blackberry patch surrounded by 25 acres of woods. Walking paths reveal rocky knolls and paths circling through pine and maple trees. The private estate has ample space for a retreat, a workshop, a grand party or just family togetherness in a beautiful place, far from the madding crowd but close to highways, shopping, spas and everything you might need.brbrVilla Favorita is ideal for a large extended family, with 6 bedrooms that can comfortably sleep couples with multiple children, and 5 bedrooms comfortable for couples or individuals.brbrFive large rooms on the first floor are homey and rich in historic detail. The dining room with large French doors is joined to the modern kitchen through the butler’s pantry. The utility room has a new washer and dryer and a half bath. The living room with built-in bookshelves opens into a spacious front hall with a grand piano and a harpsichord. The first floor also has a comfortable wheelchair-accessible bedroom with handicap shower.br brThe second floor has five enormous bedrooms overlooking fields and forests; three of these are master bedrooms with en suite baths, and the dimensions of all but one are over 220 square feet.br brThe third floor, originally servants' quarters, has one shared bath and five more bedrooms, two approaching the size of the master bedrooms, and one that can double as a quiet study with desk and flat-panel monitor.

11

Bed

6

Bath

23

Sleeps

$318.35

/ Nightly

Private Vacation Home

Cozy, welcoming Berkshires cottage – perfect home base & place to unplug!

Stockbridge, Massachusetts, United States

Charming, comfortable cottage tucked away in a serene setting in Mahkeenac Heights. Step back to a time when things were simpler, less hurried. The cottage features an open living and dining room with fieldstone fireplace, galley kitchen, glass enclosed 3 season porch, 2 bedrooms, and a sleeping loft with 2 single beds. Back yard with deck, hammock and fire pit. Prime location between Stockbridge and Lenox villages, 2 miles to Tanglewood, short walk or 2-minute drive to Stockbridge Town Beach. brbrThe open living and dining room has vaulted ceilings with exposed beams and a fieldstone, wood-burning fireplace where you can enjoy a cozy fire and while away the evening. There is a sofa conversation group under the large picture window and a round dining table at the other end of the room. brbrA glass enclosed 3-season room stretches across the front of the house. It includes a second dining table and second conversation group comprised of rattan furniture and a hanging swing. Note the 2 dining tables could be put together and chairs rearranged to better accommodate a group together. brbrThe galley kitchen includes all the essentials such as refrigerator, freezer, range, microwave, an assortment of small appliances, plus all the pots and pans and dishes you should need to cook and enjoy your meals at home. brbrThe larger bedroom has a queen-sized bed, half bathroom, closet and shelves.brbrThe second bedroom has a full-sized bed and closet – and a desk should you have work to do or just want to sit and journal.brbrA ship ladder brings you to the sleeping loft with 2 single beds, both with storage drawers. brbrThe sofa could sleep 1 person if another bed on the main level is preferred.brbrThe hall bath includes shower.brbrThe cottage is 936 square feet plus the sleeping loft. Pine walls and ceilings and wood floors add to the warm ambience of this delightful cottage. brbrOut back are a wooden deck with a conversation group of furniture and a hammock.brbrThere is a fire pit that also has a grill attachment.brbrThe cottage does not have a central heating system and is therefore offered for seasonal rentals. We will accept bookings from May 1 through October 31. If the weather is unseasonably cold at the end of the season, we can provide space heaters. Alternatively, we would allow you to cancel bookings between October 15 and 31 without penalty if the weather has turned cold.brbrNote that this cottage was furnished and has been used by its owners as a getaway from the hustle, bustle and business of New York City. It is the antithesis of and antidote for the busy-ness of their lives there. The furniture is older, and a bit mismatched. The sun shining through the picture window has faded the sofa cushions. There is nothing fancy about this cottage. It is simple and has all the basics needed for a relaxing time at home, or to serve as a home basis for exploring the Berkshires’ beauty. As described elsewhere, it has W-Fi for screens you may bring, but no TV. All of this is reflected in the nightly rate. It is spotlessly clean – and ready to provide you with a place to step back in time a bit and relax and unplug and create some wonderful memories. If that is your aim, this may be the perfect place for your vacation homebase! brbrIn addition to what makes the property itself special, its location is also cherished by its owners. It is the perfect jumping off point for daytrips to places like Tanglewood, Jacob’s Pillow, Berkshire Botantical Gardens, The Clark, Mass Moca, Chesterwood, Norman Rockwell Museum, Arrowhead, not to mention all of the beautiful outdoor places to hike and explore. brWe are happy to answer questions about the property! brbrTop 4 Ski ResortsbrBousquet Mountain: 8.2 milesbrSki Butternut: 12.2 milesbrOtis Ridge Ski Area: 18.4 milesbrCatamount Mountain Resort: 19.2 milesbrbrLenox Center – 6.7 milesbrTanglewood – 1.9 milesbrJacobs Pillow – 14.5 milesbrbrGuests may enjoy the entire cottage, porch, deck, and the yard. This is a single-family home; no one else is living at the property.brbrWe provide you with an exclusive code to access the house during your stay.brbrEntire circular driveway is for your use and parks 4 cars easily, or even more cars in a pinch.brbrThe owner uses the house infrequently and does not keep many things in the closets or on the shelves, making more space for guests to use during your stay. brbrWe are a professional property management company with team members available to assist you throughout your stay. You can easily message us through your booking platform. Those messages are monitored 7 am to 8 pm seven (7) days a week. We will provide you with a number to call or text for emergencies outside these hours.brbrCheck-in and check-out are contactless. We will provide you with a custom code for your stay a couple of days before you arrive. We change the code after each guest checks out.brbrYou will receive automated, scheduled emails with helpful information before and throughout your stay, as well as customized messages about things related to you.brbrBy request we can provide things such as a portable playpen, highchair, portable crib, air mattress or dog crate for you prior to your arrival.brbrAnd if you think of things you’d like to have after you arrive, just reach out.brbrWe want to ensure you have a 5-star stay. Please let us know how we can assist with this.brbrbrOTHER DETAILS TO NOTE brbrMAX. NO OF GUESTS This home can accommodate 5 people, based on the rules of the Town of Stockbridge. These are options of where people could sleep: Each of the bedrooms could sleep 2; there are 2 twin beds in the sleeping loft, and 1 person on the sofa in the living room if another main level sleeping space is desired.brbrPETS Dogs musts be at least one year old; sorry, no puppies. 2 dogs are allowed. The cost is $65 per stay at the time of booking. Cats are not permitted. The owner has a cat that visits the property infrequently.brbrPARKING Parking is off street in a private driveway.brbrEQUIPMENT AVAILABLE We have a portable crib, high chair, booster seat, dog crate and air mattresses. Please request in advance if you need any of these.brbrBRING YOUR OWN SCREENS In keeping with the back-in-time and unplugging theme, there is no TV on site. There is Wi-Fi, so bring your own screens, if you want screen time.brbrbrMIN NO OF NIGHTS If you’d like to book for fewer nights than the minimum on the platform, please message us to request owner approval.brbrFUTURE BOOKINGS If you’d like to book further out than 6 months, on dates when the calendar has not been opened yet, please message us for owner approval.brThis is a seasonal cottage, usually available from mid-April through mid-October. brbrLONG-TERM BOOKINGS This property can be reserved for long-term bookings. Please reach out if you are interested in a long-term stay and we will provide the discounted rates if the property is available.brbrKITCHEN We want our guests to easily enjoy preparing meals at home. Therefore, our homes have well-stocked kitchens. Not just the things you’d expect like microwave, dishwasher, and basic dishes, but plenty of dishes, drinking glasses, flatware, pots & pans, cooking utensils, and other tools and small appliances.brbrCLEANING All of the properties we manage are impeccably clean. We often receive feedback that our properties are “spotlessly clean.” This house is cleaned with green products.brbrBASIC RULES:brbr-No smoking in the propertybr-No events, parties or large gatheringsbr-Must be 25+ to bookbrbrTOWN OF STOCKBRIDGE LICENSE NUMBERbrbrPROFESSIONALLY MANAGED Our principal is a real estate broker from the Greater Boston Area with 30 years’ experience renovating and caring for properties, now running a property management business in the beautiful Berkshires, providing comfortable places for people to stay while they are spending time in the area.brbrOur team takes great pride in caring for the properties we manage and in attending to details so our guests thoroughly enjoy their vacations at our properties.brbrWe have earned the Superhost status for years and Guest Favorite on some of our properties.brbrWe hope to welcome you to our Stockbridge / Berkshires retreat!brbrThe Bespoke Property Management Team

Bed

Bath

Sleeps

$534.43

/ Nightly

Private Vacation Home

Secluded Family Home in Serene Stockbridge Woods

Stockbridge, Massachusetts, United States

***WE ALSO HAVE 55 5-STAR REVIEWS ON AIRBNB***brbr***NEW SUMMER DATES NOW OPEN***brbrPrivate Forest Retreat | Heart of the Berkshires | Mins to Stockbridge, Lenox + GB | Kids Area | OfficebrbrNestled on over an acre of tranquil forest land, our property offers a serene escape down a charming dirt road, with nature walks right outside the door.brbr- Fast, reliable Wi-Fibr- Dedicated workspacebr- Covered back porch with comfortable furniturebr- Perfect for couples, families, or creative retreatsbrbr**Spacious | Modern | Cozy | Inviting | Secluded | Nature**brbrOur home, nestled in the heart of the Berkshires, is close to attractions for all ages: Tanglewood, Kripalu, Norman Rockwell Museum, ski areas, hiking, dining, and more. Enjoy a serene environment with modern conveniences and abundant natural light.brbr**Main Area:**br- Open floor plan with cathedral ceilingsbr- Gas fireplace, heat/AC, ceiling fansbr- Large dining table (seats 6-8)br- Ample natural light and wood floorsbrbr**Kitchen:**br- Large island with seatingbr- Gas stove, large fridge/freezerbr- Fully equipped for cookingbrbr**Bedrooms + Bathrooms:**br- Main floor: 1 Queen bedroom, 1 full bathroom with large tubbr- Upstairs: 1 King bedroom, 1 bedroom with 2 Full beds, 1 full bathroombrbr**Office:**br- Private office with natural light and WiFibrbr**Entertainment Areas:**br- Cozy TV roombr- Colorful basement with kids' activities and laundrybrbr**Outside:**br- Covered back porch with seating and dining areabr- BBQ grill, large yard surrounded by woods

Bed

Bath

Sleeps

$405.41

/ Nightly

Private Vacation Home

Renovated Colonial on the River! Fantastic Views

Stockbridge, Massachusetts, United States

Blue House on the Bendbr Built around 1820, the Blue House on the Bend, an historic eyebrow colonial located on an idyllic bend of the Housatonic river, has been updated and outfitted for modern day convenience but retains its charm and unique appeal, Enjoy hypnotic views of the river and wildlife from the comfortable living area, breakfast area, master bedroom or outside terrace area. The open floor plan and lovely views make this historic mill worker house seem much larger than its 1100 sq. ft, and comfortably accommodates 5 people. The three season sun porch adds more room for relaxing, eating and even sleeping! brbrWell equipped kitchen with full size appliances will make preparing meals and entertaining easy. Many dining area options available including main room, sun porch and alfresco on the river’s edge. brbrDownstairs master bedroom with new king Casper bed and bay window overlooking the river makes for a great night sleep. New downstairs bathroom includes a tiled tub /shower combination. Up a short flight of stairs, two charming bedrooms await, one with a new queen Casper and one with a twin size bed. These rooms share a new full size bath with a tiled shower. During warm months the sun porch daybed is also comfortable for sleeping!br brFull laundry facilities available in basement; off street parking for two cars. br brHouse is located on a quiet , non through street with only 7 neighboring houses. Adding to the historic Berkshire charm, hopefully you will be treated to the occasional train chugging by. Be sure and wave to the engineer! brbrAttractionsbrbrLocated in the heart of the Berkshires; the Appalachian trail, Tanglewood, Shakespeare and Company, Norman Rockwell museum, Chesterwood, summer stock theater, music and dance are all just minutes away. Easy access to Butternut Ski – 7 miles and Catamount – 14 miles. brbrFoodies can enjoy the neighborhood options including Pleasant and Main, Barrington Brewery, ExtraSpecialTeas and the fabulous Berkshire Mountain Bakery with delicious french pastries, bread and take away pizzas for easy meals. Taft Organic Farms is a short drive for local products and produce. brbrRatesbrbrRate based on 4 person occupancy; each additional person (up to 6)$25 per night br brHigh summer season rate: (mid June – mid September ) - 7 night minimum $2,700/weekbrbrThanksgiving , Christmas, New Years' – 3 night minimum- $350/night; $2,400/weekbrbrLow season rate: (mid September – mid June ) – 3 night minimum - $325/night;$2200/week brbrCleaning fee: $185brRefundable security deposit: $500 brbrHouse RulesbrbrPlease treat our home as if it was your own and please let us know of any problems immediately. brNo smoking of any kind allowed on the premisesbrNo pets allowedbrOnly registered guests allowed to stay overnight on the premises. Any other person on the property is the sole responsibility of the guest. brHomeowner is not responsible for any accidents, injuries, or illness that occurs while on the premises or its environs. brHomeowner is not responsible for the loss of personal belongings or valuables.brKeep the property and all furnishings in good order. A security deposit is required to cover any damages that might occur or excessive cleaning that might be necessary.brOnly use appliances for their intended use. brThe Blue House is on a septic system and users must be diligent about following posted rules about what can and cannot be disposed of. Rules will be posted by the sinks and toilets. brPark in designated parking area. Guests are allowed temporary parking along the road. brThere is no daily housekeeping service, however additional housekeeping can be arranged for an hourly rate. brBy accepting this reservation, it is agreed that all guests are expressly assuming the risk of any harm arising from their use of the premises or others whom they invite to use the premises. br

Bed

Bath

Sleeps

$320.7

/ Nightly

Private Vacation Home

Stockbridge Home: Walk to Town Beach!

Stockbridge, Massachusetts, United States

Escape to a lake retreat with this 3-bedroom, 2-bathroom vacation rental home in Stockbridge. Stockbridge Bowl's grassy beach is just a short walk away, promising days of fun boating, swimming, and kayaking on the water. For entertainment on dry land, explore the nearby Koussevitzky Music Shed or Norman Rockwell Museum. There's more outdoor fun to be had on various hiking trails located within 5 miles or less! After a long day, relax on the screened-in porch with a home-cooked meal.brbr-- THE PROPERTY --brbrMassTaxConnect ID C0372932830 | Free WiFi | Walk to Lake | Family Friendly | 0.2 Miles to BeachbrbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Twin Bed w/ Twin Trundle BedbrbrINDOOR LIVING: Fireplace, Smart TV, washer/dryerbrOUTDOOR LIVING: Screened-in porch, gas grill (propane provided), seatingbrKITCHEN: Stainless steel appliances, gas range, coffee maker, dishware & flatwarebrGENERAL: Keyless entry, complimentary toiletries, towels & linens, central heatingbrFAQ: 2 exterior security cameras (facing driveway and side of home), stairs required for accessbrPARKING: Driveway (3 vehicles)brbr-- THE LOCATION --brbrSTOCKBRIDGE BOWL: Stockbridge Town Beach (0.2 miles - 10-min. walk), BSO Beach (1.8 miles), Stockbridge Bowl Boat Ramp (2.6 miles), boating, swimming, fishing, kayaking, paddle boarding, canoeingbrOUTDOOR EXPLORATION ( 5 miles): Brothers Trail, Parsons Marsh Reserve, Olivia's Overlook, Burbank Trail, Stevens Glen Trail Head, Butternut Ski Area and Tubing CenterbrLOCAL ATTRACTIONS ( 5 miles): Koussevitzky Music Shed, Seiji Ozawa Hall, Frelinghuysen Morris House & Studio, Tanglewood, Ventfort Hall Mansion and Gilded Age, Norman Rockwell Museum, Chesterwood, Berkshire Theatre Group, Barrington Stage CompanybrAIRPORT: Albany International Airport (49.8 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: Your safety matters. This property features 2 exterior security cameras located on the screened-in porch and side of the home, facing outward. They do not look into any interior spaces. The cameras record video and sound when activated by motion. They will record when they first sense motion and 30 seconds after the last motion is detectedbr- NOTE: The property requires stairs to access

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$837.75

/ Nightly

Private Vacation Home

InTown Victorian Front House 5 Bd 3.5 Ba Back House 6 Bd 4 Ba Both 11 Bd 7.5 Ba

Stockbridge, Massachusetts, United States

The Front 5 Bedroom 3.5 Baths Norman Rockwell Feel Home offers a Living Room, Den, Fully Stocked Kitchen, lovely screened porch & outside gas grill on the main level. Upstairs are 5 bedrooms - Two Queen Bedrooms & One Full Bedroom share a large hallway bathroom. One Queen Bedroom has its own bathroom & one bedroom with two full beds has its own bathroom. Natural Gas heat and airconditioning. House Sleeps 11 guests per town by-laws. $700 per night (nonholiday rate). brbrThe Back 6 Bedroom 4 Bath House offers a brand new fully stocked eat-in kitchen with granite counters and center island, oversized great room, large dining room, screened porch, side yard & outside gas grill. A brand new fully accessible ADA Compliant Handicap 1st floor Queen Bedroom with private bath - roll-in shower, folding seat in shower, handicap toilet and sink. 2 King Suites upstairs with new private baths. Three other bedrooms with Queen Beds share one newly renovated hallway bathroom. House sleeps a maximum of 13 guests per town bylaws. New natural gas furnace. Window airconditioning units. Nightly (nonholiday) rate is $850 per night. brbrThe booking on this site is for the front 5 Bedroom house. $700 per night at the nonholiday rate) If you would like to book the 6 Bedroom House ($850 per night at the nonholiday rate) or to book the entire 11 Bedrooms ($1550 per night at the nonholiday rate) please message me and I will update your booking quote. brbrOur home is a No smoking of any kind inside & on property grounds. We do allow dogs at $150 per dog per stay. No cats. brbrOur Victorian home is centrally located, an easy one block stroll to Norman Rockwell's Main Street Red Lion Inn (Live music and Dining), Restaurants, Shopping and Berkshire Theatre, Tanglewood, Jacobs Pillow, Stockbridge Theatre.br3.5 miles to Swim, Fish, Kayak, relax on the Town Beach on Stockbridge Bowl. Ski Butternut, Catamount, Bousquet, Jiminy Peak.

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$307.99

/ Nightly

Cottage

Beachwood Cottage

Stockbridge, Massachusetts, United States

Unique small cottage in the sought-after Beachwood community situated 2 miles from Tanglewood on Stockbridge Bowl. Features open ceilings, skylights, 2 full bathrooms and large living room. Close to Kripalu, Lenox, Stockbridge, restaurants, hiking and everything else in the Berkshires. It’s only a short five minute walk to the private beach with access to swimming and an area to launch your own kayak, canoe or paddle board.

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$322.49

/ Nightly

Cabin

Cozy Cabin on Lake Mahkeenac

Stockbridge, Massachusetts, United States

Cozy cabin located in the popular Beachwood community which is 2 miles from Tanglewood on Stockbridge Bowl, close to Kripalu, Lenox, Stockbridge, restaurants, hiking and everything else in the Berkshires. Large open yard, good size bedrooms and spacious living room area perfect for entertaining. It’s only a short five minute walk to the lake and private beach with access to swimming and an area to launch your own kayak, canoe or paddle board.

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$340.69

/ Nightly

Apartment

Clean & Modern space with a mix of original warmth and charming renovation.

Stockbridge, Massachusetts, United States

Welcome to The Hideaway On Main in Stockbridge Center. brOur recently renovated 2 bedroom unit offers a clean mix of modern elegance and cottage charm. With a private rear entrance and a charmingly modern ambiance full of delightful surprises, you will feel like you have been transported to a secret Hideaway.brbrOur rental is perfect for 2-4 people. Please Note: brWe have a strict No Pets, No Smoking policy!brbrPlease watch our VIDEO TOUR of the property. Find it in the third position of the photo gallery. If you are having trouble finding it please message me.brbrThe Hideaway on Main Highlights Include:brbrBEDROOMS-brbr*Best sleep of your life Purple queen mattress in the rear bedroom--plush feel.br*Decadent cool gel memory foam Novafirm King mattress in the front bedroom--medium to firm feel.br*Cozy 100% cotton bathrobes to enjoy while you are our guest.br*100% cotton sheets and bedding washed in **UNscented detergent, all you will smell is 'Clean' !br*Wood headboard panels that are wiped and cleaned between guests.brbrbrKITCHEN-brbr* A Gaggia Brerra Italian espresso & coffee machine for making truly delicious coffee. Tea pot, fancy tea cups, an assortment of tea bags and loose tea are also available.br*All new stainless steel appliances: easy clean glass top stove including oven with air fry & convection, dishwasher, disposal, microwave, digital hood vent and full size refrigerator/freezer.br*Full set of Cuisinart Pro Series stainless steel pans. One non-stick omelet pan.br*Lobster Pot, mixers, blender, toaster, rice cooker, crock pot, pizza pan, cookie sheet, glass baking dishes of various sizes, an electric kettle, thermal carafe, glass mixing/serving bowls with covers, huge cutting board work surface, platters, potato masher, spices, oil and vinegar, sugar/sugar substitute.br --Photos available of all kitchen supplies, just ask us : )br*We have an abundant supply of dishes, glasses and flatware ( no need to wash a dish every time you use it because you we have more than four).br*Picnic gear: melamine plates, bowls, cups, cooler, and folding chairs to lend.brbrA DEDICATED WORK AREA-brWhether you are a digital nomad or just needing to scroll through your emails, you will enjoy the office area located in a separate space from the living room which features: br*A SIT-to-STAND desk/ Herman Miller AERON desk chair/HP Monitor on swing arm/basic stationary supplies (ask for specifics), keyboard, power hub/usb ports ON the desk surface, tack board, ipad stand, swing arm task light and abundant natural light.brNote: if you are making zoom calls, the door can be closed off from the rest of the unit for privacy.brbrBATHROOM-brOur luxurious shower has both a Huge Rainfall Shower Head and Handheld shower. You will find shelves and cubbies for toiletry bags or personal items, 5 hooks for towels or clothes, a stool to dry off your feet, great lighting with two magnification mirrors (one stationary and one for a second person to use in another area), and an assortment of extra toiletries in case you have forgotten something. A hair dryer is located under the vanity and clothes hampers are in each bedroom.br* SCENT SENSITIVE” products are available and include unscented shampoo, body wash, hand soap, dish soap, moisturizers, and natural cleaning products. Look for the cobalt bottles throughout the unit. brWe never use dryer sheets or air fresheners. We believe the smell of clean is better than heavy perfumes.brbrbrLIVING/DINING ROOM-brOur center room functions perfectly as a dividing area between the bedrooms to create a sense of privacy in each room and a very functional living room and dining area with:br*Knoll Bertoia Chairs around an elliptical wood dining table.br*Our incredibly comfortable hanging egg chair--grab a blanket & a book to enjoy the morning lost in a favorite read.br*The corner sectional is extremely comfortable for four people and has a reading light near the chimney. It is a great place to watch a movie or set up a game for game night.br*A collection of books, magazines, puzzles, games, intricate coloring books with colored pencils and a Ukulele are available for your use while here.br*You will find many beautiful items from Pine Cone Hill/Annie Selke/Dash and Albert: rugs, bedding, curtains, tile, and throw pillows are all over the unit.brbrOUTDOOR SPACE-brYou will have exclusive use of the rear deck including the patio table and chairs and shared use of the rear yard and fire pit area. Then all of the Berkshires is beyond…brAsk us about our favorite hikes, ponds, and vistas.brbrbrbrThe AREA-brWe are close to everything in the village--just a short walk to fresh chocolate croissants, gourmet treats for your picnic basket at Nejaime’s Wine Cellars, an ice cream from Main Street Cafe, dinner at Once Upon a Table, live theater at the The Unicorn Theatre, or a visit to historic Mission House or the Sedgewick Pie. brWe are centrally located in the Berkshires with easy access to north and south counties near cultural attractions of all kinds, four ski areas and hundreds of hiking trails within 15 minutes driving time. Tanglewood, Kripalu and Shakespeare & Company are all just ten minutes away.brThis vacation rental is located on the first floor (not basement) of our vacation home, our unit is on the second floor (each unit has a private entrance). We are available for help with restaurant and sightseeing suggestions or with any emergencies. We also have a local property manager available when needed if we aren't available. brThe amount of interaction with us will be up to the guest.brbrPlease note: We have exterior entry Blink doorbell cameras for your convenience and general preventative security. If you are having difficulty opening the door lock or forget your code, simply buzz the bell and it will call my cell phone. I can identify who is buzzing and remotely open the door for you. This is our second home and we are often in the second floor apartment. We will not be intrusive, but we are happy to offer suggestions for restaurants or to lend equipment if needed.brThere are three areas with steps within the unit. One step in the bathroom, two steps from the rear bedroom to the living room, and one step from the kitchen to the living room.

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$758.44

/ Nightly

Private Vacation Home

Brand New Barn House w/ EV charger

Stockbridge, Massachusetts, United States

*Beyond the north side of the property lies the turnpike, so there is some road noise. We rarely notice it, especially inside the house, but we want to point this out to those who are sensitive to traffic noise.*brbrThe story of this house is so cool! But first ... This *brand new* barn house with vintage furnishings and woods, meadow, and stream sits on 3 acres in a prime Berkshires location - just minutes to Stockbridge, Tanglewood, Lenox. While one can hear the ambient hum of the highway, there is ample privacy with landscaping, wooden fences, and a private deck.brbrThis house is perfect for a couple or for a family.brbrFor a couple, it offers one-level living, with primary bedroom and bathroom, laundry room, den all on the first floor.brbrFor a family, there's ample room upstairs for the kids - two large bedrooms, a full bath, and a hang-out space.brbrLarge windows let in views and lots of light. Radiant concrete floors on first floor are cool in the summer and warm in the winter. Kitchen boasts marble countertops, Rohl faucet, Kohler cast iron sink, Subzero fridge, full-height pantry, long bench for taking in the view. The sitting room opens onto the large cedar deck, perfect for coffee in the morning, drinks at night, or watching the kids play. The den offers plenty of seating, perfect for reading a book or watching a movie on the large screen TV. The primary bedroom is cozy and tucked away, right next to the full bathroom with a 5-foot shower with terrazzo floor and microcement walls.brbrThis all-wood FirstDay Cottage house kit was built in the summer of 2024 by college students and our teenage son with some professional oversight. See the whole process at my blog, Modern Shaker. It is stylish, simple, super-insulated. Come experience how good it feels to live in!

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$473.8

/ Nightly

Private Vacation Home

Stockbridge Bowl Lake Community

Stockbridge, Massachusetts, United States

Charming new construction home located in neighborhood community that has a private beach on the Stockbridge Bowl. Just completed in Spring of 2020, the home is open and airy and the perfect place to relax and enjoy being in the country while having all the modern conveniences of a brand new home. Whether you enjoy walks, hikes, swimming, kayaking, skiing, museums, shows, concerts or dining at great restaurants, it is all just minutes away. brbrThis four bedroom, two bath home has an open kitchen, dining, living room layout with high ceilings and great light. The master bedroom and a second bedroom are also on the first floor, with two kids bedrooms and play/lounge areas upstairs, creating a bit of separation when it is time to wind down. The home is a short walk to the community beach, where you are free to use our kayaks located right at the lake on the neighborhood’s kayak rack or just lounge at the beach. Downtown historic Lenox and the town of Stockbridge are each 3 miles from the home, with dozens of food options, great shopping and many area attractions. brbrThe home is equipped with central heat/air conditioning, internet, washer/dryer, gas fireplace, dishwasher and a tankless water heater, ensuring a comfortable stay.

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$953.37

/ Nightly

Private Vacation Home

Stylish 5 bed/5 bath Hilltop Manor + Cottage - EV charger - Amazing location!!

Stockbridge, Massachusetts, United States

*This listing is for the 4-bedroom, 4-bath house. The 1-bedroom, 1-bath guest cottage with full kitchen is available for an additional $200/night.*brbr*Beyond the north side of the property lies the turnpike, so there is some road noise. We rarely notice it, especially inside the house, but we want to point this out to those who are sensitive to traffic noise.*brbrRoom/bed breakdown:brbrMain House - Downstairs:brRoom 1: 1 queenbrbrMain House - Upstairs:brRoom 2: 1 kingbrRoom 3: 2 twinsbrRoom 4: 2 twins + 1 twin mattress in loftbrbrGuest Cottage (should you choose to add it on) - Upstairs:brRoom 5: 1 queenbrbrJust minutes to Tanglewood! This recently renovated historic homestead in Stockbridge has it all: a Revolutionary-era 4-bed, 4-bath Colonial home and 1-bed, 1-bath detached guesthouse that sit on a 9+ acre hill with an impressive view of Monument Mountain, a gentle-sloping lawn, abundant woods, and a gentle stream. brbrA spacious and luxurious retreat for family and friends, the main house offers multiple living spaces with an open kitchen and living room with wood-burning stove, library, billiard room, den/TV room with games and puzzles, and an attached greenhouse with a far infrared sauna that seats 5. An old house lover’s dream, it boasts ultra-wide-plank floors, three fireplaces, wrought iron rim locks, thumb latches, strap hinges, and heavy brass door knobs on hand-planed doors.brbrThe guesthouse with full kitchen is an adorable wooden cottage that feels bright, open, and spacious with its double-high living room. The space was crafted out of a former barn by a local carpenter and has modern amenities alongside its rustic charm. While it is closely-sited to the main home, there is ample privacy with a separate parking spot, walkway, landscaping, and a private deck. It is the perfect place for hosting extended family and visitors, to be used as a writer’s sanctuary, or for a bridal suite. Everyone who steps inside adores it!brbrCome experience the best the Berkshires has to offer! Take a walk or a bike ride to the Berkshire Botanical Garden or Naumkeag - or drive a few minutes to downtown Stockbridge, Stockbridge Bowl, Norman Rockwell Museum, Tanglewood, downtown Lenox, West Stockbridge, and Great Barrington.

5

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5

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11

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