Vacation Rentals By Owner In Stockbridge, MA

$574.14

Classic Berkshire Retreat

Stockbridge, Massachusetts, United States

One of TWO lovely dwellings for rent on nearly four private acres. See VRBO 3529604 to learn more about our Charming Berkshire Cottage for large gatherings of family and friends!brbrThe Main House is a beauty nestled in the heart of the Berkshires. An ideal home away from home for Tanglewood concert-goers, lovers of snow sports, hikers and leaf peepers, this stunning property on nearly four acres boasts all the charm folks look for when traveling to western Massachusetts. brbrJust minutes away from the Norman Rockwell Museum and Berkshire Botanical Gardens (next door to both, really!), guests will enjoy proximity to all the best of the Berkshires while tucked away from noise and crowds. Use as a cozy home base as you venture out to see the sights, or just stay home and enjoy the landscaped grounds, access to a darling playhouse, large swing, quaint fish and frog pond, corn hole, frisbee, a scooter and bike for the kids! brbrManicured gardens and a forest out back make for a most relaxing little paradise during your time away from home. The Main House offers beautiful, classic decor, generously appointed and ready to welcome you and your family! Just a hop away from Butternut, Bosquet Resort, Jiminy Peak, and Catamount for ski and tubing! brbrOur fabulous cottage is a lovely, quiet retreat just minutes from some of the most iconic spots in the Berkshires! brbrAsk about winter/spring monthly rates, Jan-May. brbrPerfect for the remote worker who would love to escape the city for beautiful Berkshires living in the wintertime. Bring your laptop, books, winter clothes, and skis and prepare to snuggle in for a beautiful season in one of the most idyllic location in western Massachusetts.

3

Bed

2

Bath

10

Sleeps

$501.56

/ Nightly

Private Vacation Home

Beautifully Restored 1860's Stockbridge Farmhouse- short walk to downtown!

Stockbridge, Massachusetts, United States

Welcome to your home away from home in beautiful, historic Stockbridge. This inviting 3-bedroom getaway offers comfort, convenience, and a peaceful atmosphere—perfect for families, couples, or small groups looking to unwind and explore the Berkshires. Best of all, you’re just a short ten-minute walk to downtown Stockbridge, making it easy to enjoy the town’s charming streets and local attractions.brbrEach bedroom is thoughtfully furnished with a plush queen-size bed, ensuring a restful night’s sleep. The well-appointed bathroom features a relaxing bathtub and a bidet for added comfort. With both heating and air conditioning, the home stays cozy and comfortable year-round.brbrRelax in the pleasant, well-equipped living spaces or plan your next adventure with some of the area’s most beloved destinations just minutes away. Enjoy world-class performances at Tanglewood Music Venue, spend the day lakeside at Stockbridge Bowl, or explore American art at the Norman Rockwell Museum. Nature lovers will appreciate the scenic Monument Mountain and October Mountain hiking trails.brbrBeyond the sights, Stockbridge offers plenty of local charm. Enjoy casual and fine dining, visit farm stands featuring local produce, browse quaint shops, or go antiquing throughout the Berkshire region.brbrWe’re always available to answer any questions and ensure your stay is smooth, comfortable, and memorable.brbrBook your Stockbridge stay today and experience the perfect blend of culture, nature, and small-town charm!

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Bath

Sleeps

$446.85

/ Nightly

Private Vacation Home

Stockbridge Home, Come Experience The Berkshires!

Stockbridge, Massachusetts, United States

Summary:brbrBeautifully renovated three bedroom in Stockbridge with a great layout and energy throughout the home. In addition to the large and very pretty screened in porch, there is a newly created area off the back that has pavers with a modern fire pit, a new Weber Genesis grill and four wood and wicker chairs - a great area to relax. Clean, updated and cozy all at once.brbrbrbrThe Space:brbrLiving room is inviting and nicely decorated. There is plenty of seating for all with a comfy couch and ottoman (that can be used to make a chaise at one end of the couch) and two swivel chairs.The large 55 inch tv has basic cable and a roku for sound and streaming apps such as Netflix, Hulu, Amazon Prime, etc with your log in information. Original artwork can be found all around the home, along with some framed vintage posters. brbrbrbrVery nice flow and layout in the kitchen; easy to use with updated appliances and well equipped; leads right to the dining area inside or the lovely screened in porch outside that has a lovely teak round dining table. Large galley kitchen with a gas stove, new appliances and lots of white quartz counter space, perfect for large meals for the whole crew. New dishwasher to make cleaning a breeze. Essentials including microwave, drip coffee maker, toaster and kettle available for use. brbrbrbrWell stocked kitchen with all the necessary cooking/serving items including cookware, pots, pans, plates, bowls, glasses, mugs, silverware and even children's dinnerware.brbrbrbrThe dining room has round table seating for eight with the table leaf. There is space for two at the kitchen island. An additional table with chairs is located in the large screened in porch. brbrbrbrThere are a total of three bedrooms to accommodate guests during your stay, for easy planning here are the bedroom layouts:brbrBedroom 1: master with king bed, dresser, desk, full length mirror, en suite bathroom and small walk in closetbrbrBedroom 2: queen size bedbrbrBedroom 3: single day bed with another single pull out trundle bedbrbrbrbrThere are two full size bathrooms. The en suite in the master has a large walk in shower with tile and marble shelves; there is one vanity with drawers and counter space and a large mirror and a medicine cabinet with mirror on the side of the vanity. brbrbrbrSeamless indoor outdoor living including, screened in porch with round teak dining table,; peaceful back yard, fire pit with plenty of seating and a new Weber Genesis grill. brbrbrbrOther things to get excited about:brbr-Only four small steps up to the front door of this one floor home, perfect for guests with limited mobility.brbr-Hardwood floors throughout the home and tile floors in bathrooms.brbr-Washer and dryer with plenty of detergent and dryer sheetsbrbr-There are two AC splits: one in the living room and one in the masterbrbr- Parking for two cars in the driveway and street parking is availablebrbr-Bring your furry friends, up to two dogs allowed, $50 per dog, must be at least 1 year old, sorry no puppies!brbrbrbrPlease keep in mind:brbr-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.brbrbrbrGuest Access:brbrEverything you need for a great stay, toiletries, linens, towels, hairdryer, iron and ironing board, washing machines, detergent, and more!brbrbrbrThe Neighborhood:brbrFood and Drink favorites:brbrRed Lion Inn, StockbridgebrbrOnce Upon a Table, StockbridgebrbrThe Lost Lamb, StockbridgebrbrBistro Zinc, LenoxbrbrAmici, West StockbridgebrbrFour Brothers Pizza, Great BarringtonbrbrAegean Breeze, Great BarringtonbrbrZichotencati, Great BarringtonbrbrCafe Adam, Great BarringtonbrbrNaji’s, Great BarringtonbrbrMarketplace Kitchen Table, Great BarringtonbrbrGreat Barrington BrewerybrbrbrbrCulture and Wellness : brbrJacob’s Pillow, Dance brbrShakespeare and Company brbrTanglewood brbrKripalu Center for Yoga and Health brbrMiraval Berkshires Resort & Spa brbrShaker Mill Books brbrTanglewood brbrDowntown Lenox brbrBerkshire Botanical Garden brbrNaumkeg brbrChesterwood brbrNorman Rockwell Museum brbrThe Mount, Edith Wharton’s Estate brbrHerman Mellville’s Arrowhead brbr brbrSkiing, Snowboarding and tubing:brbrButternut Ski Area and Tubing CenterbrbrCatamount Mountain Resortbrbr brbrLakes: Close to public lakes for swimming, kayaking, fishing or lounging by the water: brbrCard Pond brbrLake Mansfield brbrLake Garfield brbrBenedict PondbrbrUmpachene Falls brbrLake Onota brbr brbrHiking:brbrMonument MountainbrbrHousatonic FlatsbrbrOctober Mountain State ForestbrbrBeartown State Forest brbrTyringham Cobble brbrAshintully GardensbrbrHousatonic FlatsbrbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon! brbrStandard rules like no smoking, no partying, and being respectful of the neighbors apply.brbrBring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies!brbrbrbrNo sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart. brbrbrbrPets: Damage caused by pets is not covered by the accidental damage waiver.

Bed

Bath

Sleeps

$509.53

/ Nightly

Private Vacation Home

Classic Stockbridge Cottage

Stockbridge, Massachusetts, United States

Summary:brbrClassic Southern Berkshire escape, built in the early 1900s by a cartographer for the NY Times. The home boasts a living room sized for entertaining, a separate library and an additional sitting space. The wood burning fireplaces in the living room and library bring warmth to enjoy your coffee on cold mornings. Light and bright kitchen adjoins the dining room with a screened-in porch for outdoor dining. Large decks on the front, side and back invite one outside at every turn.brbrbrbrThe Space:brbrUpon arriving at the home you will see the lush landscaping and the Goshen stone steps that take you to the front door. You will notice the large deckbrbrbrbrEnjoy a quiet moment in the living room with a crackling wood burning fireplace, antique spinet piano, comfortable sofa and four lounge chairs. This room also allows you to pick up the excitement by breaking out a board game in the nook with a game table and four chairs. If you’re looking to enjoy a good book or family movie, move over to the library where you will find a loveseat, two lounge chairs, wood burning fireplace and a Roku TV that you can log into your streaming apps such as Netflix, Hulu, amazon Prime, etc. At the end of your evening, relax and enjoy a drink in the lounge between the living room and kitchen. You will find a cozy loveseat, chair and classy bar cart. .brbrbrbrThe dining area has lots of natural light with two sets of french doors leading to the outdoor wrap around deck. Easy access to the kitchen with the open peninsula to make setting up for large family meals easy. With the dining table with seating for eight and four seats at the peninsula, there is room for everyone! brbrbrbrThe large open kitchen is recently updated and has some new appliances. The open spaces allow for you to be able to cook with friends and family without bumping into one another. With a clean white palate and glass french doors that lead to the backyard makes the space bright and cheerful. Well stocked kitchen with all the necessary cooking/serving items including cookware, pots, pans, plates, bowls, glasses, mugs, silverware, and 12 cup drip coffee maker. Dishwasher makes cleaning up a breeze! brbrbrbrThe spacious primary bedroom with window seating, lounge chairs, chaise lounge and a queen bed has an adjoining ensuite. The remaining bedrooms have lots of natural light, small desk and lounge chairs that make for a peaceful retreat. brbrbrbrIn total, there are four bedrooms to accommodate up to 8 guests during your stay, for easy planning, here are the bedroom layouts: brbrMain Bedroom: Queen size bed w/ ensuite bathroom and private porchbrbrSecond Bedroom: Queen size bedbrbrThird Bedroom: Queen size bed brbrFourth Bedroom: Full size bed brbrbrbrThis home boasts two and a half bathrooms. The primary bedroom ensuite has double sinks and a tub/shower combo. The second full bath has a stand up shower with two shower heads and a handheld shower wand. The half bath powder room is on the first floor, convenient to everyone. brbrbrbrRelax on an expansive deck that has room for everyone! Enjoy your morning coffee or use the gas grill to make your favorite meal as the sun goes down. brbrbrbrOther things to get excited about:brbr-Inside the home, you will find hardwoods throughout the main and top floors with rugs in each room. brbr-Stay cool this summer with single zone central air on the first level and mini splits upstairs. brbr-Circular driveway can fit four to six cars and a side driveway to fit an additional car.brbr-New Samsung front loading washer / dryer upstairs next to all Bedrooms.brbr-Several stairs to enter the house, so it may not be the best rental for those with limited mobility.brbrbrbrPlease keep in mind:brbr-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.brbrbrbrThe Neighborhood:brbrCharming neighborhood around the corner from Chesterwood is within walking distance to beautiful nature trails, the Rockwell Museum and Main Street. This home is also a short drive from all the Berkshires has to offer. This location is only short drives to Tanglewood, Berkshire Botanical Garden, Stockbridge Bowl, West Stockbridge, Housatonic, Great Barrington, Lenox, Butternut, Lee, Shaker Village, and Jacob ' s Pillow.brbrbrbrSome of our favorite eating places are the Red Lion Inn (Stockbridge) , Once Upon A Table (Stockbridge) , Brava (Lenox), and Prairie Whale (Great Barrington)brbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon! brbrStandard rules like no smoking, no partying, and being respectful of the neighbors apply.brbrBring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies!brbrbrbrNo sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.brbr*Damage caused by pets is not covered by the accidental damage waiver.

Bed

Bath

Sleeps

$1563.3

/ Nightly

Private Vacation Home

Stockbridge Retreat w/ Pool & Hot Tub!

Stockbridge, Massachusetts, United States

Escape to the Berkshires and indulge in the ultimate experience at this luxurious 4-bedroom, 3.5-bathroom house. Situated on 22 acres of pristine land, this vacation rental offers unrivaled privacy and tranquility. Take a dip in the private pool, soak in the hot tub, shoot some hoops, play some pickleball, or a play game of ball hockey on our private court. Or, explore nearby attractions such as the Norman Rockwell Museum, Tanglewood, and the hiking trails of the Stockbridge area.brbr-- THE PROPERTY --brbrMassTaxConnect ID #: C0437672830 | 22-Acre Property | Modern Interior | Gas Fireplace | Private Heated Pool (Depth 3.5’-9’)brbrBedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: Full Bed | Bedroom 4: Queen Bed | Den: 2 Twin Futons (converts to King Bed)brbrOUTDOOR LIVING: Patio, private pool (open seasonally), screened-in porch, hot tub, basketball & pickleball court, gas grill, beach chairs, beach towels, deck, garden, hammock, outdoor shower, outdoor speakers, pool toys, patio heater, gas fire pitbrINDOOR LIVING: Board games, piano, Smart TVs, DVD player, books, ceiling fans, walk-in closet, dining table, printerbrKITCHEN: Air fryer, drip coffee maker, dishwasher, microwave, knife set, dishware & flatware, ice maker, spices, toaster, cooking basicsbrGENERAL: Free WiFi, linens & towels, hair dryer, complimentary toiletries, keyless entry, washer & dryer, central heating & air conditioningbrFAQ: Steps required, Ring doorbell (facing out), no EV chargingbrPARKING: Driveway (4 vehicles)brbr-- THE LOCATION --brbrOUTDOOR ADVENTURE: Monument Mountain Reservation (6 miles), Berkshire Rivers Fly Fishing (6 miles), Olivia's Overlook (8 miles), Otis Ridge (17 miles) brHITTIN' SLOPES: Butternut Ski Area and Tubing Center (7 miles), Bousquet Mountain Ski Area (12 miles), Catamount Mountain Resort (14 miles), Jiminy Peak Mountain Resort (28 miles) brTIME TRAVEL: Naumkeag (2 miles), Norman Rockwell Museum (3 miles), Ventfort Hall Mansion and Gilded Age Museum (7 miles), Thomas Cole National Historic Site (40 miles), Olana State Historic Site (40 miles) brAIRPORTS: Albany International Airport (51 miles), Bradley International Airport (68 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- Guests are not permitted to charge electric vehicles on-site as the electrical system is not equipped for that, and the breaker will blowbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to accessbr- NOTE: Gardeners may be on-site in the outdoor areas, and will not disturb your staybr- NOTE: Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device or when the video doorbell button is pressed

Bed

Bath

Sleeps

$421.54

/ Nightly

Cottage

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

Stockbridge, Massachusetts, United States

Furnished Deck for Coffee Moments | Fireside RelaxationbrbrNestled in the heart of Stockbridge, with easy access to restaurants, museums, and outdoor recreation, this 4-bedroom, 2-bath vacation rental puts you at the center of all your adventures! Stroll through the quaint downtown area, visit the Norman Rockwell Museum, or hit the slopes at Butternut Ski Area. As evening rolls in, gather around the fire with s’mores .brbr-- THE PROPERTY --brbrC0437672830brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 queen bedbr- Bedroom 4: 1 full bedbrbrINDOOR LIVINGbr- 4 Smart TVs, fireplacebr- Dining tablebr- Board games & booksbr- Shower/tub combo, walk-in showerbrbrOUTDOOR LIVINGbr- Furnished deck w/ dining areabr- Spacious yard, fire pit, picnic tablebrbrKITCHENbr- Refrigerator, dishwasher, stove/oven, microwavebr- Cooking basics, dishware & flatwarebr- Dual drip/pod coffee maker, coffee & tea providedbrbrGENERAL br- Free WiFibr- Electric heat, 2 window A/C units, ceiling fansbr- Linens/towels, complimentary toiletriesbrbrFAQbr- No pets allowedbr- Wildlife may be present (bears)br- 3 exterior security cameras (facing out)brbrACCESSIBILITYbr- Single-story cottagebr- 3 steps to enter from frontbr- 2 steps to enter from backbr- Grab rail in bathroombrbrPARKINGbr- Driveway (4 vehicles)br- No EV charging on-sitebrbrADDT’L ACCOMMODATIONS br- An additional property is available down the street with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbr- Quiet area, close to hiking, restaurants & barsbr- Half-mile to basketball court, recreation center & coin laundrybr- 2 miles to Norman Rockwell Museumbr- 3 miles to Berkshire Botanical Gardenbr- 8 miles to Butternut Ski Area & Tubing Centerbr- 51 miles to Albany Int’l Airport & 68 miles to Bradley Int’l Airportbrbr-- 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- Guests are not permitted to charge electric vehicles on-site as the electrical system is not equipped for that, and the breaker will blowbr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story property requires 3 steps to enter from the front and 2 steps to enter from the backbr- Gardeners may be on-site in the outdoor areas, and will not disturb your staybr- Local wildlife, including bears, may be present in the neighborhoodbr- Your safety matters. This property features 3 exterior security cameras: 1 camera is located above the back door facing the back entrance, 1 camera is located next to the front door facing the front entrance, and 1 camera is on the garage facing the driveway. The cameras are outward facing and do not look into interior spaces. The cameras are activated by motion and will record video and sound while guests are in residence

Bed

Bath

Sleeps

$911.57

/ Nightly

Private Vacation Home

Beautiful Farm House Near Family Ski Mountains And Other Fun Winter Activities

Stockbridge, Massachusetts, United States

This gorgeous farmhouse has four bedrooms each with a private full bathroom. There are six steps leading to the front door. Ground floor bedroom has a king size bed. Each bedroom upstairs has a queen size bed, sitting chair and closet or armoire .There is a fully stocked kitchen, living room with fireplace and dining room that seats 8 people. Three bedrooms are on the second floor and each has a split unit to control heat and air conditioning. There are extra sheets and towels, a washing machine and dryer and ample parking. We have an inground swimming pool ( swim at your own risk) heated during July and august. There is beautiful outdoor furniture situated on the grounds, surrounded by flower beds and lovely scenery. Minimum stay September-June is two nights. July-August minimum stay is 5 nights. Near family friendly ski mountains catamount, butternut and 30 minutes to jiminy ski resort. Golf, Lenox pickleball and tennis courts, yoga and Maravel spa nearby. Fifteen minutes to major summer activities such as Tanglewood and Jacobs Pillow. brThe owner has a full apartment downstairs on the side with a private entrance and may be present on the property at various times.

Bed

Bath

Sleeps

$418.02

/ Nightly

Cabin

Lakeshore cabin with beach and dock

Stockbridge, Massachusetts, United States

A classic Berkshire cabin nestled under maple trees, on the shore of the Stockbridge Bowl cove, next to a waterfall. Serene, peaceful and private, yet close to all area attractions. Beach and dock. Swimming and kayaking. Large lawn with lots of trees. Newly renovated. Large light-filled living room with cathedral ceiling and skylights. Main bedroom on ground floor with en suite bathroom. Second bathroom on ground floor. Two bedrooms and balcony overlooking lake upstairs. Enclosed porch and large deck with gas grill. Forest trail and waterfall next door. Easy access. Plenty of parking. 5 minutes to Tanglewood and Kripalu. Close to area ski resorts.brbrGround floor: Living room with cathedral ceiling and skylights, two sofas, chairs, electric fire and smart TV, CDs, DVDs (no cable) games, air conditioning unit & portable air conditioner, yogibo beanbag, dining room table can seat six. Bedroom with queen bed and en suite bathroom, sliding door to porch, TV monitor, work space, air conditioning unit, ceiling fan. Bathroom with shower. 2nd Bathroom with tub/shower. Laundry room. Dining areas. Fully renovated and supplied kitchen. Large deck, enclosed porch, grill.brbrUpstairs: Two bedrooms. One with full bed and access to balcony overlooking lake.brSecond with two twin beds.

Bed

Bath

Sleeps

$390.95

/ Nightly

Private Vacation Home

A Charming Mid 1800's Stockbridge Farmhouse.

Stockbridge, Massachusetts, United States

Transform yourself in to the middle of a Norman Rockwell painting. It is easy to see how so many of his paintings were inspired by homes like these and the Stockbridge locals. Cherry Hill at Farley's Crossing has been owned by the same family for over 150 years. brbrA three minute drive from the famous Red Lion Inn in downtown Stockbridge brings you over Farley's Crossing and right up to 13 Cherry Street. brbrWhether you are in town to enjoy the Boston Symphony Orchestra at Tanglewood, or a day at the Stockbridge Bowl beach you have all the best activities near by. brbrWinter sports are all around you and Winter Holidays in Stockbridge are magical.brbrAfter a day of shopping and touring the famous Norman Rockwell museum, 13 Cherry Street awaits you with the peaceful serenity of the Berkshire mountains in your own backyard.brWe can't wait to see you.

4

Bed

2

Bath

6

Sleeps

$1457.69

/ Nightly

Private Vacation Home

A Grand property in Historic Stockbridge

Stockbridge, Massachusetts, United States

The Taggart House is an grand estate in the heart of The Berkshires. The property is a 5-minute walk to the center of Stockbridge, yet quietly situated on 3 manicured acres along the Housatonic River. The Taggart House was constructed in 1850 by noted Stockbridge resident Henry Dwight Sedgwick. Recently added to the National Register of Historic Places, the Taggart House combines fine 19th century architecture with luxurious comfort and modern amenities.

Bed

Bath

Sleeps

$670.2

/ Nightly

Private Vacation Home

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge, Massachusetts, United States

Prior guests of this charming house next to the forest trails have already reserved their return stay for next year to ensure its availability!brbrBeautifully restored 1913 home features 3-season front porch for entertaining or relaxing, steps from Laurel Hill Assn preserve, and has ‘secret gardens’ where you can stroll through paths and see our fruit, veggies & flowers tended by our gardener in Spring and Summer. We have a fire pit for guests to sit around in the evenings, a lighted outdoor dining area and pergola, all situated steps from the footbridge leading to Ice Glen Trail. This amazing location is also a short stroll from Historic downtown Stockbridge where you will find plenty of bakery & coffee shops, gifts, sweets, bars and dining.brbrThe house has heating & air-conditioning, a dedicated office, laundry room and 3 bedrooms, including: brMaster Bedroom (White Room)- This en suite room has a highly-desirable King-sized bed, private bathroom w shower and skylight, plenty of closet space, and view of the river(seasonal); brQueen bedroom (Blue Room) - This room has a Queen bed, closet, and is next to the 2nd fl full bathroom with bathtub, shower & shaving mirror;brFull & Twin bedroom (Khaki & Green Room) - This room is suitable for adults with children, as it has a Full bed & a Twin-sized Day bed with a bureau and view of the gardens and river (seasonal). It is next to the laundry room and across the hall from the full bathroom with tub/shower. brbrHouse has a fully-stocked Kitchen with new gas range, dishwasher, microwave, Keurig machine, drip coffeemaker, bean grinder, teapot, cookware, wine bottle opener, utensils, china, glassware, spice collection. On the back porch, there is a smoker if you enjoy outdoor slow-cooked dinners.brbrWe are a short drive to Tanglewood, Berkshire Theatre Festival, Norman Rockwell Museum, Naumkeag, Kripalu Wellness Retreat, Chesterwood, Stockbridge Golf Club, local ski resorts (Butternut and Bousquet) & neighboring towns Gt Barrington and Lenox with many restaurants, bars, and shops to experience!

Bed

Bath

Sleeps

$288.56

/ Nightly

Private Vacation Home

Near Stockbridge Bowl in Wooded surround - Rent monthly- Cozy, Quiet, Scenic.

Stockbridge, Massachusetts, United States

We want renters to be comfortable, so we've combined taste, charm and comfort. We take pride on making our rustic house a home that combines form and function. Neighbors are not that close - but noise travels so we've placed limitations on large gatherings. We hope you understand - and we expect the same from the neighbors.brbrThis Cozy rustic Berkshire Home has an all wood inside and outside (with insulation in-between). It is surrounded by large windows for lots of light and a close up view of nature. It offers lots of charm with modern amenities for a wonderful stay in the Berkshire Mountains. For Summer: We are centrally located less than two miles from Tanglewood outside the cozy town of Lenox and a mile and a half from Kripalu. - also in the outskirts of Lenox. The house is a stone's throw from the Stockbridge bowl. Fishing in season, many walking and climbing trails, and lake swimming at the nearby Stockbridge Town beach. The Lake is private for residents. As renters you can get beach passes. Most seasons, from the nearby outlet for the Stockbridge Bowl, from the house you can hear and see a beautiful waterfall as it spills off from the lake under an overheFad footbridge on its way around the mountain. Beautifully sited opposite the waterfall, this charming loft-style, wood home has been described as a 'treehouse for adults and even has a small porch on the third floor that looks out over an expanse of green including views of the spill off from the Bowl as its river wends its way down around the perimiter of the property. brbrIn the winter there is skiing at Butternut in Great Barrington or cross-country skiing on the many available trails in the surrounding area. Hiking and climbing are also constant adventures at Monument Mountain and Greylock for more challenging hiking/climbing. There are milder walks/hikes all around the property and in neighboring towns. Winter is a wonderland on the property, especially when the waterfall from the lake freezes in motion - it's quite a sight. brbrWith an open airy design, the first floor is one continuous space, complete with small galley kitchen and modern equipment for all you will need to cook delicious meals. There is a dining area that can comfortably seat six, a living room, half bath and French doors which open to a porch and outdoor hot tub.brbrFor long term rentals we leave the hot tub running all winter but from Jan.- March because of the often freezing temperatures - we have to work around the heating mechanisms. In the living room there are three steps leading to two window-seats placed underneath a skylight. The stairs continue to the second floor which has a small cozy enclosed bedroom with a full size bed, skylight and two windows. Adjacent to that bedroom is a full renovated bath, a large airy study with a full size futon couch.. More stairs lead to the master bedroom which has a queen bed. This top floor master bedroom often grabs the title Eagle's Nest. It is well lit with several windows, a skylight and porch. It is part of the loft style open-air design but private nonetheless - a true artist's dream.brbrMidway between Stockbridge and Lenox you'll find all the cultural and recreational attractions of the Berkshires (Tanglewood, Norman Rockwell Museum, Jacob's Pillow, Chesterwood, Berkshire Theatre Festival) as are golf, tennis, horseback riding, boating, swimming, skiing - cross-country and downhill, and hiking in the state forests. In warmer weather you can Canoe or Kayak (and swim) in the nearby lake (equipment not included) or do a short car ride with kayak or canoe in tow, to other nearby lakes. There is a public boat slip a quarter mile away along with Kayak and bike rentals. Wintertime recreation includes skiing at Butternut Basin, Bousquet, Catamount and Jiminy Peak as well as snow shoeing, cross country skiing and ice skating. brbrTo make your stay more enjoyable the kitchen is stocked with teas, condiments, oils and vinegars for the salads you can make with fresh greens from the Great Barrington Outdoor Farmer's market. The lower cabinets in the kitchen and the supply closet in the downstairs half bath are stocked with paper goods (paper towels, toilet tissue) and cleaning supplies should you need them. Help yourself!brbrThe house has central air conditioning and heating. The A/C amply cools the first two floors and a heat pump and and ceiling fans cool the third floor. brWe have high speed internet, cable TV and a high quality radio. There is a CD player and about 60 CDs with a variety of music though a leaning toward classical.brbrYou'll find new ceramic dishes, bowels and cups and more than adequate wine and beverage glasses. brbrPlease take a look at the video on this site for a look at the ravine that is formed by the waterfall. It wraps around one side of the property and offers a relaxing view. Lawn chairs are available on the property to give you the convenience of sitting near this overlook or in the shade of a nearby tree. brbrIf you want a short beautiful walk without driving to one of the hiking areas enjoy the 2 mile (round trip) walk around our community on a back road that weaves around the Stockbridge Bowl. The road is private and only used by residents so you can take morning walks (or runs) while only you will enjoy this lake road that connects several houses. brbrEnjoy!!!brbrPS - Our reviews are from 2022 and before. Because of the pandemic we cut back on rentals and were using the house ouselves for a while.

2

Bed

1

Bath

6

Sleeps

$565.79

/ Nightly

Private Vacation Home

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge, Massachusetts, United States

One of a kind must see getaway. Berkshire Glamour meets Hollywood Rennaisance and Town & Country. This well-lit, newly renovated designer home was built for entertaining, family vacations, romantic getaway, and/or an outing with friends and musicians. This home was designed with every detail in mind for a comfortable and decadent getaway. Just minutes away (literally minutes) from Tanglewood, Kripalu, Downtown Lenox, Downtown Stockbridge, Norman Rockwell Museum, and many other local attractions. You can't beat the location since its central to all the local attractions. brbrThe interior of this home was designed to please for every member in your family. On approx 2 acres of land with an open backyard and layout, the main floor has a beautiful living room with a Brooklyn fireplace, velvet couch and a 2 person rocking chair, a formal dining room, a beautiful (and magazine featured) kitchen, breakfast nook full of natural light and dining table, cozy and elegant family room, washer/dryer room, and a guest bathroom with a full shower included. Nearly every room has a chandelier that adds to the charm and elegance of this residence.brbrThe 2nd floor, also hard wood floors, includes an art deco guest bathroom with shower and tub, two (2) beautiful guest bedroom with a queen bed, a bedroom with two (2) twin beds designed to be pushed together to make a queen (sheets, comforter, etc all packaged and included), a reading room with a sofa-bed, and an elegant master bedroom with a queen bed, and an enormous bathroom that will make you feel like you're in a spa with a massage tub and two shower-head standing shower. Because we were aiming for this feeling, there are no TVs in the bedrooms on the 2nd floor.brbrWe promise that when you walk into our Berkshire home you'll be impressed with the size, the layout, the natural lighting, the decor, the comfort, and the vicinity to all local Berkshire attractions. brbrAlso, linens, towels, spare toiletries, etc are available in the bathrooms. Wireless internet, satellite tv, netflix, and all utilities are included.

Bed

Bath

Sleeps

$745.2

/ Nightly

Private Vacation Home

Water front log cabin next to Tanglewood

Stockbridge, Massachusetts, United States

Log cabin in a very private setting on the water with a dock and access to the Stockbridge bowl. Waterfront property close to Tanglewood, Lenox, Stockbridge, hiking and boating. We have kayaks, a rowboat, and a stand-up paddle board for your use. Very comfortable house with a large porch with outside seating, a propane fire pit, and a propane heater. Central AC with a large fireplace, whole home generator in case of storm outages. Gentle slope to the water, watch the beavers swim by, the black bear wander across the yard with plenty of deer, fox, bald eagles, and turtles to be seen.brbr

Bed

Bath

Sleeps

$228.2

/ Nightly

Cottage

Rustic Waterfront Retreat With Private Dock, 2 kayaks & canoe. Air conditioner!

Stockbridge, Massachusetts, United States

This A-frame cottage has private waterfront access with two single kayaks and a canoe. A new 12,000 btu air conditoner keeps much of the main floor cool in summer. When the crisp Fall temperatures hit, the house has a proper forced hot air heating system w/ heat registers in the floors and a touchscreen thermostat on the wall, across from the bathroom. You have a master bedroom downstairs with a full sized bed, an upstairs bedroom with 2 twin beds and a loft area upstairs that has a pull out futon bed. There is 1 bathroom with a shower and a large living area with a futon that can sleep more people. A deck provides a beautiful view of the woods and the waterfront. The kitchen is equipped with a stove, oven, refrigerator, microwave, and utensils. (Please Note: There is no dishwasher, garbage disposal or washer/dryer. And due to allergies in the family, we do not allow pets at the A-Frame.) Our home has been rented in the summer to Tanglewood musicians for the last 20 years without interruption. The main floor is carpeted and the loft and bedroom upstairs have throw rugs.brbr(Please note that the propane fireplace in the main room is decorative only - due to insurance regulations. The 12,000 btu air conditioner and plenty of fans keeps your summer time cool. The central forced hot air heating system keeps the house quite comfortable in the Spring and Fall)brbrIf you are into Yoga, you may know that world renowned Kripalu Center for Yoga and Health is 10 minutes by car and a half hour canoe ride from the cottage. Yes, you can actually canoe/kayak to Kripalu from the cottage. It is an amazing experience!

2

Bed

1

Bath

6

Sleeps

$130.82

/ Nightly

Apartment

2 Mi to Norman Rockwell Museum: Stockbridge Apt!

Stockbridge, Massachusetts, United States

Historic Building | Pet Friendly w/ Fee | Near Stockbridge Golf ClubbrbrTrade city bustle for Berkshires bliss, stroll to Main Street shops, taste local flavors, and unwind! 'Town and County,' a 1-bedroom, 1-bath vacation rental apartment, blends inviting amenities with unbeatable walkability. Enjoy morning coffee on the private patio as the Housatonic River passes by, then head out to visit the Berkshire Botanical Garden and beloved local galleries or hike at Bash Bish Falls State Park!brbr-- THE PROPERTY --brbrC20122505brbrSLEEPING ARRANGEMENTSbr- Bedroom: 1 king bedbrbrKITCHENbr- Stove/oven, refrigerator, microwavebr- Keurig coffee maker (coffee provided)br- Cooking basics, trash bags/paper towels, dishware & flatwarebrbrINDOOR LIVINGbr- Smart TVbr- Dining tablebrbrOUTDOOR LIVINGbr- Small table & umbrella seating for 2 on historic Main Streetbr- YardbrbrGENERALbr- Central heating & A/Cbr- Iron/boardbr- Linens/towels, complimentary toiletries, hair dryerbr- Free WiFibrbrFAQbr- Pet fee (paid pre-trip)br- Homeowner on-site (separate unit)brbrACCESSIBILITYbr- Single-story apartment, 1 step to enterbrbrPARKINGbr- Shared driveway (3 vehicles, first-come, first-served)brbrADDT’L ACCOMMODATIONSbr- An additional property is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbr- Easy access to I-90br- 2 miles to Norman Rockwell Museumbr- 2 miles to Berkshire Botanical Gardenbr- 5 miles to Tanglewoodbr- 8 miles to Butternut Ski Areabr- 45 miles to Albany Int’l Airport & 51 miles to Bradley Int’l Airportbrbr-- 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- Pet friendly w/ $50 fee (+ fees & taxes, 2 pets max)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story apartment requires 1 step to enterbr- The homeowner lives on-site in a completely separate unit, and another bookable vacation rental is on-site; other guests may be present during your stay

Bed

Bath

Sleeps

$386.96

/ Nightly

Private Vacation Home

Charming home in private Beachwood Community on Lake Mahkeenac, Stockbridge

Stockbridge, Massachusetts, United States

This 3 bedroom, 1 bathroom home of 1000 square feet with an additional 200 square foot screened in porch with a table for outdoor dining and lounge furniture. It is located in the prized, private, lakefront community of Beachwood in Stockbridge, MA. The house is in a quiet location near the end of a dead end road and is surrounded in back and one side by woods. Fully equipped kitchen, access to private beach, a few miles from numerous cultural hotspots including Tanglewood, Shakespeare and Co., the Norman Rockwell Museum, Berkshire Theater, etc.

Bed

Bath

Sleeps

$493.35

/ Nightly

Private Vacation Home

Modern Cottage in the heart of the Berkshires with new exterior flex space!

Stockbridge, Massachusetts, United States

Drive down our private road to find an adorable and spacious cottage, nestled on four secluded wooded acres, with every modern amenity including central air conditioning, Internet TV and WIFI. Added for 2021 - Custom shed that serves as an office with direct ethernet connection OR for fabulous movie watching or yoga space. Stay plugged in or disconnect and enjoy the faint whooshing sound of the Housatonic River and the exquisite natural beauty around our property and in the Berkshires. Our home has three bedrooms plus a den with a pull-out couch. The three bedrooms are on the second floor. There is a spacious primary bedroom suite with a king bed and an attached, walk-out deck, private bathroom and a large walk-in closet that is big enough for a pack-in-play for the little one. The two other bedrooms have a queen bed and a full/double size bed with ample closet space and a full bath for those bedrooms to share. There is also a half bath on the main level. All of the mattresses are new and extremely high quality. On the first floor, there is a den with a full-sized pull-out couch which doubles as a peaceful reading room or a playroom for the kids. If you like to cook, enjoy the spacious open-concept kitchen. There is a lovely screened-in porch for al fresco dining and a covered porch to relax and unwind, which also has a gas grill. ADDED IN 2022 - 60 amp dedicated outlet in garage to charge your Electric Vehicle. And for added security there is a video doorbell installed on the front door.

Bed

Bath

Sleeps

$466.91

/ Nightly

Private Vacation Home

Stockbridge Village Cottage With Mountain View’s and walk to town

Stockbridge, Massachusetts, United States

Old meets new in this lovely cottage, a short walk to the Red Lion Inn. Lots of light, comfortable furniture, beautiful, fenced-in backyard with mountain views. Kitchen updated with Smeg refrigerator, gas stove, granite counters, hardwood floors throughout. Hiking trails, park and tennis courts within a 5-minute walk. Lake rights to the Stockbridge Bowl, Weber grill and Solo firepit. brThe home of Norman Rockwell, Stockbridge is the quintessential Berkshire village.brFoosball table and dart board, plus yoga mats are available for your enjoyment.

3

Bed

2

Bath

6

Sleeps

$699.35

/ Nightly

Private Vacation Home

Elegant & private light-filled privacy

Stockbridge, Massachusetts, United States

With soaring cathedral ceilings and light filled tranquility, off a quiet cul de sac road, this is the perfect place for your Berkshire retreat.brFor the past 25 years, the BSO has rented this house as a summer residence for their guest conductors and soloists. (Hence, there is only one review from the general public.) They chose this home because of it's lovely, quiet and spacious ambiance. The whole house is on one level for your ultimate comfort and convenience, brLocated only 3 miles from Tanglewood and midway between Lenox and Stockbridge, in a private setting on over three acres, this artist designed home has cathedral ceilings in all rooms. It features a private, luxurious and spacious, 1000 sq. ft. primary bedroom suite with interior jacuzzi tub plus an indoor and outdoor shower. There are two additional bedrooms in a separate wing, each with their own bathroom.brSkylights are everywhere and designed to let in the light. Mountain views are visible from many rooms. brGranite and marble countertops, white pickled hardwood floors, a fully equipped kitchen, down comforters, luxurious linens and all the amenities make this stunning house a special experience. brThere are gardens and decks surround most of the house. A redwood screened porch surrounded by lovely flower gardens complete the picture.brMany well known International musicians have stayed here and continue to return to this very peaceful, art filled and elegant home.brbrKeywords: Contemporary House/ cathedral ceilings/ private setting/ 3 plus acres/ gardens/ 3 miles to Tanglewood.

3

Bed

2

Bath

5

Sleeps

Vacation Rentals By Owner In Stockbridge, MA

$574.14

$501.56

$446.85

$509.53

$1563.3

$421.54

$911.57

$418.02

$390.95

$1457.69

$670.2

$288.56

$565.79

$745.2

$228.2

$130.82

$386.96

$493.35

$466.91

$699.35

Most popular vacation rentals in Stockbridge

$376.86

$446.85

$421.54

$418.02

$405.41

$393.18

$390.95

$272.05

$283.91

$320.70

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