Vacation Rentals By Owner In Lee, MA

$278.16

Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee

Lee, Massachusetts, United States

After a day of mountain adventures, our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar.brbr• Pools, Gym, Movie Theater and mini golf br• Accommodate up to 6 people br• One guest in the party, must be at least 21 y/o or older.   brbr* U$10 PER NIGHT OF RESORT FEE(WAIVED) . br**Additional charge brbrThe spacebrWe offer multiple units at this property, all of them consistently designed to give you a beautiful place to stay. While the style is consistent, the layout and view may vary by apartment. br br• Apartment style accommodation with 823 square feetbr• Queen-size bed and pullout sleeper sofabr• Fully equipped kitchenbr• Two full bathsbr• TV in living room and bedroombr• Accommodate up to 6 people brbrBEDROOM 1 - 1 Queen bed brBEDROOM 2 - 1 Queen bed brLIVING ROOM – 1 Pullout sleeper sofa    brbr• FREE PARKINGbr• Two Outdoors Pools (opened Seasonally), Two Indoor Poolsbr• Hot Tubbr• Heating and air conditioningbr• Towels & Linenbrbrbr***** PLEASE NOTE *****brThis is a Resort Villa style unit, you will have your unit assigned upon arrival, ALL units have the same quality and specification, location may vary.brbrbr***** LONG STAYS INFO: brbrWe do provide a starter kit for each unit with toiletries, toilet paper, paper towel, dish washer, detergent, etc. brGuest accessbrYou will check in at the front desk , The person whose name is on the booking must be the one that will check in, name changes only can be made up to 7 days before arrival and have a cost of $50 American dollars.br brCheck-in time: 4:00pm brCheck-out time: 10:00am brAny late check out inquire, must be discussed direct in the property`s front desk. brbrOther things to notebrbrSECURITY DEPOSIT: Resort will require a deposit for incidentals or damages at check-in. You can use a credit or debit card, the deposit is U$115 per apartment. This is a preauthorization, not charged and released at check-out if not needed. Credit cards usually are refund in 2-3 days, while debit cards can take longer. Please contact your financial institution for more details.   brbr(WAIVED) RESORT FEE: The amount of $10 + tax will be charged per night of your stay (it is not per person) this amount will cover Wi-Fi and other amenities. This amount is NOT included in your VRBO price. br brbrThis is a timeshare resort, you are MY GUEST, that means you HAVE NOT to attend any timeshare presentation. brTimeshare tour is not required but may be offered by the resort for incentives. brWE DO NOT promote, endorse or encourage any sales pit however is up to you to accept in case it is offered, again, you are not required. br brbrPLEASE CHECK OUR CANCELATION POLICY. Always is smart to buy a travel cancelation insurance, this way you always can have full refund in case you cancel. brbr**Once the reservation is confirmed, it is NOT possible to change dates and for changing names there will be a fee of €50. br brbrRules for change of names: brbr1. Name changes may be accepted up to 7 (seven) days before check-in. Note that on some special and promotional dates the name change is not accepted. brbr2. Each name change has an additional rate of € 50.

2

Bed

2

Bath

6

Sleeps

$134.92

/ Nightly

Condo

Summer in the Berkshires: Cozy country condo in charming Stockbridge MA.

Lee, Massachusetts, United States

Your Berkshires getaway starts at this sweet 1-bedroom, 1-den condo. The picture windows in the front sitting area look out onto Heron Pond. Sunlight streams in through the skylight in the cathedral ceiling. The bedroom has a comfy queen bed. A second room can be used as a bedroom (with full-sized inflatable mattress), office or yoga studio. Attend Tanglewood concerts, kayak at the Stockbridge bowl, or enjoy music and wine at Balderdash Winery. Tour the Normal Rockwell Museum and Robber-Baron mansions from the gilded age. Feel free to reach out to us during your stay - we're happy to suggest restaurants and other local spots to check out.

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Sleeps

$1111.42

/ Nightly

Private Vacation Home

Berkshires Home Makeover ~ Immaculate Lakefront Getaway ~ Dreamy Sunsets!

Lee, Massachusetts, United States

This 4 bedroom, 6 bath home takes advantage of its prime location on Laurel Lake, offering breathtaking waterfront views from every room and featuring a long list of amenities for a relaxing stay during any season, including ensuite bathrooms for every bedroom, a rooftop deck, lakeside patio, sauna, hot tub and kayaks. brbrThis 4000+ square ft. retreat was recently updated in October of 2022 by Vrbo and The Home Depot as part of a Berkshires Home Makeover project. During the makeover, all four bedrooms, the entrance, rooftop deck, and top floor, downstairs kitchen, dining room and living spaces were updated using furniture, home décor and more from The Home Depot. brbrWhile you may never want to leave the beauty of Laurel Lake and its stunning sunsets and fall foliage, this home is centrally located to all that the Berkshires has to offer: 5min to: Lenox, Stockbridge, Tanglewood 15-20min to: Jacob's Pillow, Hancock Shaker Village, Mount Greylock, Mass MoCA, Norman Rockwell Museum, and too many hikes and trails to mention. Looking for a cozy base for your winter sports This home is an easy drive to Butternut (20min) Catamount and Jiminy Peak (35min).br_______________________________________brThis Laurel Lake retreat boasts 4000+ square feet, with 4 large bedrooms (king, queen, queen and 2 twin, all with lake views and each with a private bath. There is a wonderfully spacious family connected to a large kitchen area with a walkout to the patio on the lake.

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$415.49

/ Nightly

Apartment

Updated and inviting home in Lenoxdale

Lee, Massachusetts, United States

Welcome to this thoughtfully renovate half duplex in the village on Lenoxdale. Neat as a pin, this unit offers an inviting kitchen, formal dining room, and large living room. Featuring 3 bedrooms and 1.5 bathrooms and close to numerous attractions.brbrYou are only:br3 minutes to Wyndhurst Golf & Club/Miravalbr5 minutes to downtown Lenoxbr10 minutes to Tanglewood, Canyon Ranch, Lee Prime Outlets, Mass Pike, Lee, and Kripalu.br15 minutes to downtown Stockbridgebr20 minutes to Norman Rockwell Museum

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$608.77

/ Nightly

Private Vacation Home

Spacious 5-bedroom house in charming Lee with WiFi

Lee, Massachusetts, United States

Welcome to Lee Manor – Your Cozy Retreat in the Heart of the Berkshires. Located in the charming town of Lee, Massachusetts, Lee Manor is a spacious, stylishly renovated home designed for relaxation, connection, and comfort. Whether you’re cooking a feast, enjoying a cozy night in, or heading out to explore, this is the perfect base for your Berkshires adventure.brOur family fell in love with this area through our sons’ ski racing team, and Lee Manor quickly became our winter escape. We’re excited to now share it with guests when we’re away.brbrWhether you’re planning a ski trip, a fall foliage getaway, a summer hiking retreat, or a weekend of arts and culture, Lee Manor is the perfect place to stay.brbr Why You’ll Love Lee Manor:br • Spacious, cozy interiors ideal for families, couples, or small groupsbr • Fully equipped kitchen—perfect for cooking and gatheringbr • Central location near four ski resorts, hiking trails, and top Berkshires attractionsbr • Just 5 minutes to Lee Premium Outlets and High Lawn Farmbr • Walkable to downtown Lee, Joe’s Diner (a local favorite!), shops, and restaurantsbr • Quick access to Tanglewood, Norman Rockwell Museum, Jacob’s Pillow, and morebrbr About the Area:brbrThe Berkshires offer a rare mix of natural beauty, vibrant arts and culture, historic charm, and a thriving culinary scene. Enjoy hiking and skiing by day, then wind down with a concert, museum visit, or a farm-to-table meal.brbrLee is known as the “Gateway to the Berkshires”, and it’s easy to see why. With its historic architecture, lakeside beauty, and central location, it’s a welcoming and convenient hub for exploring the entire region.

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Sleeps

$463.0

/ Nightly

Private Vacation Home

Spacious 4BR Central-Berkshires Home with POOL!

Lee, Massachusetts, United States

Spacious and comfortable home in a serene setting and ideal location. Whether you are coming for performing arts, museums, skiing, hiking, dining, shopping or some combo of adventure, this home is conveniently located plus only minutes from the Mass Pike exit in Lee, groceries, Lee Outlets and more!!brbrRelax by the pool, grill outdoors and enjoy cooking in the well-outfitted kitchen. Enjoy walks and the vistas along the quiet country road.brbrWell-behaved pets welcomed on a case-by-case basis.

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$568.88

/ Nightly

Private Vacation Home

The Freckled Hen's Berkshire Nest

Lee, Massachusetts, United States

My home is a sweet, cozy, private, and very clean farmhouse style Cape in the safe, and quiet neighborhood of Abbey Court in the foothills of October Mountain in the beautiful Berkshire Town of Lee closely bordering Lenox. Actually just a stone’s throw from Stockbridge and Lenox! Conveniently close to the highway, but off the beaten path. A great place to work from home and getaway simultaneously in a peaceful setting. A bird watcher’s delight, because a lot of them congregate in my yard. Enjoy the view from the kitchen window. brbrPrivately, proudly and locally owned. Centrally located and a very short drive to the best places to visit in the Shire: Stockbridge (5 miles to Main Street-only 5 streets away from my house!), Tanglewood (5.5 miles!), Main Street in Lenox (5.5 miles!), Berkshire Botanical Garden (7 miles), Norman Rockwell Museum (7 miles), Jacob's Pillow (9 miles), Olivia’s Overlook (7.5 miles), Berkshire HorseWorks (12 miles) and more. A stone's throw to Berkshire Scenic Railway's Lenox Dale Depot (Saturdays May 29 to September 4th). A scenic drive to Berkshire Scenic Railway's Hoosac Valley Depot in Adams/North Adams (May 29th through October with special events after October). Close to notable hiking and mountain biking trails (Appalachian Trail, October Mtn, Ice Glen, Monument Mtn, Donato's Trail, Kennedy Park, Schermerhorn Gorge, Tyringham Cobble, Charcoal Trail and Michael H. Walsh Trail at Olivia’s Overlook in Lenox (sweet vantage spot overlooking the Stockbridge Bowl), and tennis courts around the corner. Very short drive to scenic golfing outings at Cranwell (Lenox) and Greenock Country Club (Lee) golf courses.brbrLee offers satisfying dining at restaurants like Starving Artist Creperie and Cafe (best cafe in the Berkshires with an uh-mazing and unique brunch menu), Baja Charlies (best fish tacos in the world!), 51 Park (Steak 51! Fig and Goat Salad!, or the hottest Buffalo Chicken pizza on the planet!), Morgan House (my choice is the Salmonnnnnn....), Timothy's (known for their pizzas, but my favorite dish is their shrimp salad!), Salmon Run (I’m all about the salmon), the famous Joe’s Diner (casual dining), Agave's Mexican Grill, Burmese Bowl offering Asian cuisine and sushi, and more, like Rose's Restaurant (new owners offering a swanky new breakfast/lunch menu), ice cream at Lucky’s (summertime treat)! Just two streets away from fabulous antique and apparel shopping - Main Street and/or the Lee Premium Outlets. Also noteworthy, Berkshire Mountain Bakery is a little bit of a drive in the sleepy little town of Housatonic, but worth the trip for takeout and take home to bake pizzas (I can give you directions for what is one of my favorite scenic routes to get there). Just a short 15-20 minute drive to Hilltop Orchard and Furnace Brook Winery in Richmond for cider donuts (for the kids!) and wine (for the adults!). I also highly recommend the very popular Fratelli’s in Otis for a delicious meal on Main Street in Otis (takeout might only be offered at this time), a short drive from my home, but worth it. Exciting news. If you’re looking for iconic and eclectic, the Dream Away Lodge is open again and very close by in Becket. It’s a big deal and really fun. brbrThe Town of Lee is an easy and manageable size town to navigate. It’s unique and has so much to offer, with sweet downtown shopping and dining, as well outlet shopping close to the Mass Pike. brbrThe upcoming summer attraction in Lee is July 4th. Celebrate Lee's 250th Birthday with a Spectacular Fireworks Show!! Of course, Tanglewood is a very big deal here for all of us in the Berkshires. Get your tickets for another exciting season with Yo-Yo Ma, Joshua Bell and the Boston Symphony Orchestra. I'm excited to mention that Yacht Rock Revue is performing on June 21st (They're a must see! You'll be smiling for a month after you see them!), Paul Simon June 27th & 28th. James Taylor is always featured on July 3rd and 4th. On July 14th Ziggy Marley takes the stage with Trombone Shorty & Orleans Avenue. Weird Al is there on July 21st, Jason Isbell and the 400 Unit on July 28th, Cynthia Erivo with the Boston Pops (fun!) on August 21st, the divine Carrie Underwood on August 29th, Tedeschi Trucks Band (wow!) on September 2nd and Alabama Shakes (they're gonna rock!) on September 5th. There's something for everyone musically at The Shed in Lenox, a short drive from my home.brbrMy home is nestled in the foothills of October Mountain where there’s hiking and rumors over the years of being haunted or at least inhabited by ghosts. The legendary resident ghosts include the mysterious 10 year old Anna Pease, Secretary of Navy under President Grover Cleveland William Whitney and uniformed soldiers from the Revolutionary and Civil Wars. You’ll need to google it, because that’s as much as I want to know and research on that subject! My favorite part of hiking October Mountain is bringing a picnic lunch to Felton Pond.brbrThe Lee Farmer’s Market is a great way to start your Saturdays here in the summer and fall. There’s a lot going on there in a small space on the town green with locally handcrafted items. Live music is in the background to entertain you as you nibble on tasty treats and shop for perfect plants, soap, jewelry, and more brbrFor a splash of color, there is artwork is on display at Good Purpose Gallery on 40 Main Street in Lee. Local artists are featured in exhibits daily from 10-4, closed Tuesdays. You can check out current artist’s featured lists and exhibits online for more details. The garden grounds at nearby Berkshire Botanical Garden are open seasonally and often there's a sweet exhibit in Leonhardt Galleries and weekend classes. brbrMore about my home: Small and yet spacious. Continually updating accommodations for a pleasant and calming home away from home rental experience. Cozy kitchen with a wall hung electric heater and manual dial to make the living room and kitchen instantly toasty on those chilly Berkshire mornings and nights. Three bedrooms (one is very bright and sunny with a skylight; one can be made to be very dark and; one with a combination of lightness/darkness - each bedroom can suit any sleeping and ambiance preference!) and they all have windows to let in natural light. A bright, sunny, and quiet office space if you need to get some work done away from the hustle and bustle, but also, just the right size to spread out your mat to meditate or practice yoga if you want a quiet space with a large, comfortable area rug to stretch on! Large screen TV (4 feet wide, 3 feet high) with fabulous picture quality and a Netflix app in the living room. Relaxing back stone patio with a outdoor gas grill for comfortable outdoor dining along with a portable outdoor fire pit for making s’mores. Peaceful backyard in the morning with active, chirping birds and even more peaceful in the early evening when the birds are going to bed and they’re a little quieter. The birds are busy flitting around in the backyard, especially cardinals, and can be seen investigating the little compost bin behind the garage camouflaged within the ever-expanding pollinator garden looking for fruit scraps and eggshells. The comfortable and cushioned dining table and chair set is still on the patio for some relaxing breakfast, lunch or dinners because it’s warming up out there. It's just what you need to relax while you visit the Berkshires, whether you want to get out for an adventure or prefer to spend a quiet night in the privacy of your home away from home. brbrNote: Since the start of the covid-19 pandemic, I have closely followed and adhered to any limitations on short term rentals such as mine as outlined by the Town of Lee Board of Health and the Commonwealth of Massachusetts. I appreciate your understanding as we all work together to be safe. I make every effort to not only thoroughly clean, but I also offer contactless check-in to every guest. You’ll receive a personal door code and notes about the home with all the important details prior to your arrival, such as the WiFi password and the best ways to reach me during your stay. brbrI am thoroughly dedicated and focused on providing a clean home for your stay with extra time blocked off between guests who stay at or enter my home (including me) to air it out before you arrive. In addition, the local supermarkets have shopping open to Seniors one hour before the general public to avoid crowds and potential exposure. brbrMy neighborhood is very safe for walking and bicycling, but I would also be happy to provide you with a customized list of very lovely areas for walking and cycling during your stay. brbrThank you for choosing my home. I appreciate each and every one of my guests. brbrNancy

4

Bed

2

Bath

8

Sleeps

$634.29

/ Nightly

Private Vacation Home

Historic Family Retreat on the AT & Housatonic!

Lee, Massachusetts, United States

Pet Friendly w/ Fee | Updated Home Built in 1815 | Mountain & River ViewsbrbrYour ultimate Berkshires getaway awaits! This farmhouse — part of the Historic Registry — provides easy access to Ski Butternut, Bousquet Mountain, and more! Spend your days trekking scenic ridgelines and evenings admiring river sunsets from the yard. The 3-bedroom, 2-bath vacation rental offers a rare blend of 19th-century charm and modern comfort that your family will love. Don’t miss out on this unique retreat!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 twin bedbr- Additional Sleeping: 1 portable cribbrbrPROPERTY FEATURESbr- Flat-screen TVbr- Board gamesbr- 6-person dining table, high chairbr- Shared yard w/ mountain viewsbr- Marble features (same marble used for the Washington Monument & Boston Public Library)br- Birthplace of former Supreme Court JusticebrbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Drip coffee pot, Keurigbr- Microwave, toaster, blenderbr- Cooking basics, dishware & flatwarebr- SpicesbrbrGENERALbr- Free WiFibr- Window A/C unit, central heatingbr- Linens & towelsbr- Washer & dryerbr- Complimentary toiletries, hair dryer, hangersbr- Keyless entrybrbrFAQbr- 1 doorbell camera (facing front entry)br- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- 1 step for entry, 2-story apartmentbr- 1 full bathroom on 1st floor, all bedrooms on 2nd floorbrbrPARKINGbr- Shared driveway (2 vehicles)brbrADDT’L ACCOMMODATIONSbr- An additional property is available on-site w/ a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbr- Historic property located along the Appalachian Trailbr- 2 miles to Stockbridge, famous for Norman Rockwell's 'Street Scenes'br- 3 miles to downtown Leebr- 6 miles to Goose Pond Reservation & October Mountain State Forestbr- 8 miles to Tanglewood br- 10 miles to Ski Butternutbr- 12 miles to Bousquet Mountain Ski Areabr- 12 miles to Jacob's Pillowbr- 51 miles to Albany International 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)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story apartment requires 1 step for entry; the 1st floor features 1 full bathroom, and all bedrooms are on the 2nd floorbr- There is another bookable vacation rental on-site, in a separate unit with a separate entrance and a shared yard; other travelers may be present during your staybr- Your safety matters. This property features a doorbell camera on the front door facing the exterior entry. The camera does not look into any interior spaces. The camera actively records video and sound

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$510.1

/ Nightly

Condo

Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood

Lee, Massachusetts, United States

Welcome to the beautiful Lakeside Condominiums at Fox Hollow in Lenox/Lee, MA. This newly furnished condo is spacious and light filled, overlooking the stunning hills of the Berkshires. The complex has a large pool, tennis courts and an on site property manager. There are 4 bedrooms that will sleep 8 comfortably plus a sleeper that can accommodate another 2 adults. Property is in both Lenox and Lee, but is less than 2 miles from the center of charming Lenox. You are minutes from Tanglewood Music, The Shakespeare Festival, Jacob’s Pillow and so many other cultural institutions. You are about 45 minutes from Mass MOCA and about an hour from the Williamstown Theatre Festival. The property is steps away from a beautiful lake that can be used for kayaking. You will never run out of things to do in the summer!

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$523.78

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Private Vacation Home

Centrally Located Historical Home

Lee, Massachusetts, United States

Summary:brbrCome to enjoy views from this private, country escape. Decorated with many cool antiques and theatre related objects, your two bedroom home away from home has everything you need to enjoy some peace whilst enjoying everything the Berkshires has to offer. Only ten minutes to Tanglewood, Shakespeare and Co, Jacob’s Pillow, Barrington Stage, The Mount, and more!brbrbrbrThe Space:brbrAll our guests tell us the best part of the house are the view. Rolling hillsides and unobstructed mountain views for miles! brbrbrbrThe first floor has an open floor plan from the kitchen to the dining room to the living room. brbrbrbrThe kitchen is a perfect spot to start. It has everything you need to whip up home cooked meals including a flat electric cooktop, microwave, open shelving and a garbage disposal. Kitchen is stocked with all the cooking/serving necessities including: cookware, pots, pans, plates, cups, and silverware. A coffee pot is available for your morning coffee. True dining room with seating for all six of your guests. brbr brbrThe kitchen opens to the living room which has plenty of seating for your entire group. In the living room there is a television, it's a smart TV including access to YouTubeTV, so has the ability for you to connect your streaming apps to enjoy your shows. brbrbrbrOne flight up leads to the two bedrooms. Each bedroom has a queen size bed as well as a full ensuite bathroom. One of the bedrooms has a shower while the other one has a bath/shower combo.There is also a half bathroom on the first floor. brbrbrbrOver an acre of grounds surround the house. Outdoor area features a porch, fire pit, area, and propane grill. brbrbrbrOther amenities worth noting: brbr-Central heating to keep you warm this winterbrbr-All bedrooms have window AC units to keep you cool during the summerbrbr-Hardwood floors throughout with area rugs brbr-Minimal stairs to the front door, one flight of stairs to get to the bedrooms. brbr-Laundry machines available.brbr-Fast wifi throughout the house.brbr-Plenty of parkingbrbrbrbrPlease 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.brbrLots of special antiques and personal effects, owners ask that mature groups stay only, not suitable for children.brbrbrbrGuest Access:brbrEverything you need for a great stay, toiletries, linens, towels, hairdryer, iron and ironing board, and more!brbrbrbrThe Neighborhood:brbrOnly ten minutes to Tanglewood, Shakespeare and Co, Jacob’s Pillow, Barrington Stage, The Mount, and more! brbrbrbrLaurel Beach is 1.5mi from the house. If there is not a guard at the gate the beach is closed for inclement weather. The hours are 7 days a week 10am-8pm until Labor Day.brbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon! brbrStandard rules like no smoking, no partying, no pets, and being respectful of the neighbors apply.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.

2

Bed

3

Bath

4

Sleeps

$1142.14

/ Nightly

Private Vacation Home

The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History

Lee, Massachusetts, United States

** Check out the Playhouse on the Netflix series The World's Most Amazing Vacation Rentals. It's included in the Gourmet Stays episode.**brbrThe Playhouse is the PERFECT venue to house friends and families of brides and grooms. Unfortunately WE CANNOT ACCOMMODATE WEDDINGS. brbrFeatured in Berkshire and Boston Magazines, #1 on VRBO in the Berkshires.brbrBuilt by Westinghouse and then part of a Vanderbilt Estate, and the first property in the world to be powered by AC electricity, The Playhouse is a renovated iconic Berkshires property that once served as a theater space for America's greatest innovators, with visitors from President McKinley, to Nikola Tesla and Lord Kelvin, and is now hung with fine art, and includes an in-house yoga studio, two kitchens, seven sleeping areas and five bathrooms; amenities include lakefront access (an 8 min walk), and the best Berkshire views. Come relax at this historic home under 25' cathedral ceilings, connect with friends and entertain inside (We have a Yamaha upright piano.) , or on the Victorian-style courtyard.brbrWe are close to multiple ski resorts:brBousquet 11 minbrButternut 20 minbrCatamount 30 minbrJiminy Peak 35 minbrbrFeel good about your stay: all electricity comes from our rooftop solar panels. We reduce plastic waste by using eco-friendly soaps and cleaning products (with reusable containers). brbrOne 84 smart TV and (2) 60 screens for family movie viewing (Netflix, Amazon Prime, HBO, etc). As we encourage unplugging, the house does not have cable tv.brbrNearby: Wyndhurst Manor and Club (Golf and Spa), Tanglewood, Shakespeare and Company, The Mount and Jacob's Pillow (we LOVE Jacob's Pillow) performances are all within a few minutes of this centrally located property on the Lee/Lenox border. Stockbridge and West Stockbridge are also nearby. Property management is on call to assist.brbrA welcome basket of local goods and fresh cut flowers greet your party.brbrBreakdown of sleeping areas with a number for each bed below:brbrBed 1) Primary suite with queen bed, sitting area overlooking Victorian courtyard and in-suite bath and pedestal bathtub with a viewbrbrBeds 2, 3) Main floor bedroom with two twin bedsbrbrBed 4) Main floor bedroom with a full size bedbrbrBed 5) Main floor bedroom with a queen bedbrbrBeds 6, 7) Loft / office with queen and twin sleepers (semi-private)brbrBed 8) Downstairs bedroom with queen bed and dedicated bathbrbrBed 9) Downstairs main room one convertible queen sleeperbrbrBeds 10-15) Downstairs 600 square foot yoga room is convertible to a bedroom with dedicated bath. One convertible full sleeper and five high-end queen Aerobeds can be set up therebrbrThe five bathrooms have radiant floor heating and there is a pedestal tub in the Primary Suite; all bathrooms with custom reclaimed 300-year old heart wood vanities finished in the Japanese shou sugi ban style.brbrCentral air conditioning and heating is by high efficiency heat pump.brbrThe Playhouse is for residential use only, and the rental policy includes the requirement to adhere to the Rules and Regulations noted in the Rental Agreement.brbrThe maximum number of guests is 20, but there is an additional $30/day per guest above 14.

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Sleeps

$363.03

/ Nightly

Apartment

1500 sqft private entrance with beautiful views of the Berkshire Mountains

Lee, Massachusetts, United States

Come enjoy a quiet getaway in Western Massachusetts.br2 bedrooms, (3 beds, 1 Queen, 1 Double and 1 twin) 1 bath, open kitchen, living, dining, area. Approximately 1500 total sqft. 3 season room and open private deck with commanding views of October Mountain. All new furniture, bedding, appliances and totally renovated bathroom and laundry room. YouTube TV, smart TV and high speed guest wireless on site. Backyard fire pit. Gas BBQ grill on the back deck for spring, summer and fall. Enjoy morning coffee in the sun porch or on the back deck.. Big Y Supermarket, fitness center, liquor store and access to I-90 within 1 mile. 5 miles to Tanglewood, 4 miles to Stockbridge Theater, 8 miles to Jacob’s Pillow. 11 miles to the Ashuwillticook Rail Trail.brButternut Ski Area 13 milesbrBousquet Mountain 9.8 milesbrJiminy Peak Mountain Resort 24 milesbrCatamount Mountain Resort 19 MilesbrCanterbury Farm Cross Country Ski Area 9.8 milesbrKeyless entry EV (Tesla) charging station is 1 mile away.brbr*Rest assured that we are taking extra care to disinfect frequently touched surfaces between reservations. Perfect for a stay vacation, as a work-from-home alternative, or for families.br

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$732.43

/ Nightly

Private Vacation Home

Expansive Berkshires walk to town

Lee, Massachusetts, United States

Large and elegant house built into a sunny hillside that feels both cozy and expansive. Located in the center of the Berkshires, this house is quiet yet one block walk to fabulous restaurants as well as a beautiful large park with fields and hiking trails. 5 minutes to downtown Lenox, 6 min to Stockbridge, 15 min to Great Barrington, 15 min to Pittsfield. So many gorgeous places to swim, bike, hike, and enjoy the Berkshires. It took years to find this gem of a beautiful house.

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$298.08

/ Nightly

Private Vacation Home

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

Lee, Massachusetts, United States

This lovely lakefront cottage has been a favorite family gathering place of ours for 30 years. It sits on picturesque Lower Goose Pond in the heart of the Berkshires. brbrThe property is situated on a dead end street of a private lake community. The house is just over 1,000sf with a deck overlooking a large yard and the lake. The lakefront yard is big enough for a family game of whiffle ball or to throw a frisbee around. The first floor has the kitchen, living room (with a couch to sleep 5), a full bathroom, and a bedroom with a full size bed. Ascend a wooden spiral staircase to access the spacious master bedroom and bath. Outdoor furniture and a gas grill off the kitchen make outdoor dining easy. The kitchen is stocked with pots and pans, as well as dishes and other essentials. We provide bed linens and bath towels, and there is a washing machine and dryer in the basement.brbrThere is a dock on the property, and two kayaks and a canoe are available for your use. There is a public boat launch nearby if you want to bring your own powerboat, sailboat or jet ski. Clear water makes for great swimming. The main lake is connected to Upper Goose by a small estuary. Approximately 30-45 minutes by kayak or canoe, Upper Goose is environmentally protected and free from development – just the lake, surrounding mountains, and unspoiled nature. brbrPlease note that the cottage is not winterized, so it is available in spring, summer, and fall.brbrThe cottage is walking distance to the Appalachian Trail, and a short drive to Lee (close enough to bike to), the Outlets, Tanglewood, and all that the Berkshires has to offer. We hope you will make this your base for a summer vacation, and relax, enjoy the lake, the Berkshires, and the peaceful setting as much as we do!

Bed

Bath

Sleeps

$233.45

/ Nightly

Apartment

Gateway to the Berkshires - Renovated downtown apartment

Lee, Massachusetts, United States

Completely renovated downtown second floor apartment with open floor plan, located in historical downtown Lee. This apartment is equipped with everything you need for a get away in the Berkshires. Kitchen provides new stainless appliances along with everything you would need to create a meal or snack. Kitchen is open to dining room & living room. Living room is equipped with TV and WIFI. Bed room is equipped with a queen size bed & plenty of space for storage. brCentral air & heat provided. All linens & towel are provided. All you need is to unpack, relax & enjoy.

Bed

Bath

Sleeps

$670.2

/ Nightly

Private Vacation Home

Spectacular setting on your own private lake close to it all!

Lee, Massachusetts, United States

This is the perfect Berkshire home to swim, hike, leaf-peep, ski, sled, engage in the cultural attractions of the neighborhood (Tanglwood, Jacobs Pillow, Shakespeare and Co etc.), RELAX and get away only minutes to Stockbridge main st, Lenox and Lee. brbrA 1/4 mile driveway takes you to a private vacation home on its own (2.5 acre) lake. A sophisticated aeration system runs 24/7, and keeps this one of the healthiest swimming holes in the Berkshires! The loudest sound is the water running out of the lake into the stream that empties into the Housatonic.brbrThe setting is gorgeous with a 5 person hot tub built into a large deck overlooking the water.brbrThe space:brbrA large great room with a stacked stone fireplace is the center of activity. The house is 2500 sq ft, featuring 3 bedrooms, 3 full baths, and a large sun-room with a (brand new!) sofa bed with memory foam mattress for extra company.brbrTotally open floor plan downstairs, you have a kitchen and dining area open to the Great Room, with a cathedral ceiling all overlooking the water.brbrOutside is a large wrap around deck with a hot tub built into the deck. At night, you can take a wonderful soak while studying a sky that is filled with stars.brbrThere is also a fire pit to make s'mores, and plenty of open area behind and in front of the house for activities. There is a ping pong table in the back as well.brbrThe house sits on 36 private acres, with hiking, swimming and fishing as some possible activities. Across the road is a park that has additional hiking trails. And all this is in the heart of the Berkshires, less than 5 minutes from downtown Stockbridge and Lee and less than 10 to Lenox, and just over 10 minutes from Great Barrington. But TOTAL privacy!brbrThe Massachusetts Turnpike is 5 minutes away. Driving time to Boston is 2 hours, and New York City is 2.5 hours.brbrSummer: brWe are 10 min to tanglewood, Shakespeare and Co, the Norman Rockwell Museum and 15 min to Jacobs pillow. A short drive (per above) to all the other wonders of the Lee/Lenox/Stockbridge/Great Barrington area!brbrWinter: brIn the winter there is a huge sledding hill on our property right behind the house. We are 15 min drive to the awesome Butternut and Bousquet Ski Areas and 30 min to Catamount.brbrOther things to notebrbrArrival is 5:00 pm.brDeparture is 12:00 noonbrbrCentral air, and ceiling fans in every room.brbrTurkeys, ducks, and Heron are your only neighbors.brbrFloor Area: 2500 sq. ft.brbrOccupancy: Suggest 6 (it is a three bedroom), 8 is possible comfortably (using the sun room which has a queen pull out) and there are beds for 11 but would be tight and subject to our approval (aka families with small kids this would be appropriate, 11 adults less so).brbrNon smoking onlybrbrChildren welcomebrbrLocation Type: Lake View/Lakefront, water view/waterfront brbrTheme: Away From It All, Family, Couples, Friends brbrWhat we have: brCentral A/C, Basic Soaps, Internet Access, TV, Ceiling Fans, Clothes Dryer, Fireplace, Firewood, Hair Dryer, Heating, Linens, Local maps, Local restaurant guide, parking, towelsbrbrKitchen: Blender, coffee maker, cooking utensils, dishes/utensils, dishwasher, freezer, grill, microwave, oven, fridge, stove, toasterbrbrThe master bedroom is on the main floor which has a new King Size Four Season Mattress, overlooking the water. The new (2020) hot tub is on the deck outside the master bedroom. There is a full bath in the master bedroom. Sunroom has a queen sofa-bed There is a second full bath on the main floor as well. Upstairs are two bedrooms, one with a queen and a daybed/twin, and one with a twin over full bunk bed and a daybed/twin. There is a third full bath upstairs.brbrNote that 100% of the cleaning fee is passed on directly to a local family-owned cleaning business, Berkshire Family Cleaning. brbrCapacity:br8 guests are welcome as long as at least 2 are children. No more than 6 adults.brbrLastly - know that if you are interested in MORE space close by, check out our other listing next door: Prop ID 2083033br

Bed

Bath

Sleeps

$278.16

/ Nightly

Hotel

Great Place - 2 BD - Kitchen - Pool 

Lee, Massachusetts, United States

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. brbr• Pools, Gym, Movie Theater and mini golf  br• Accommodate up to 6 people  br• One guest in the party, must be at least 21 y/o or older.    brbr* U$10 PER NIGHT OF RESORT FEE(WAIVED) .  br**Additional charge brbrWe offer multiple units at this property, all of them consistently designed to give you a beautiful place to stay. While the style is consistent, the layout and view may vary by apartment.  br  br• Apartment style accommodation with 823 square feetbr• Queen-size bed and pullout sleeper sofa br• Fully equipped kitchen br• Two full bathsbr• TV in living room and bedroom br• Accommodate up to 6 people  brbrBEDROOM 1 - 1 Queen bed  brBEDROOM 2 - 1 Queen bed  brLIVING ROOM – 1 Pullout sleeper sofa     brbr• FREE PARKINGbr• Two Outdoors Pools (opened Seasonally), Two Indoor Poolsbr• Hot Tubbr• Heating and air conditioningbr• Towels & Linenbrbrbr***** PLEASE NOTE *****brThis is a Resort Villa style unit, you will have your unit assigned upon arrival, ALL units have the same quality and specification, location may vary. brbrbr***** LONG STAYS INFO:  brWe do provide a starter kit for each unit with toiletries, toilet paper, paper towel, dish washer, detergent, etc. brbrYou will check in at the front desk , The person whose name is on the booking must be the one that will check in, name changes only can be made up to 7 days before arrival and have a cost of $50 American dollars.brbrCheck-in time: 4:00pm  brCheck-out time: 10:00am  brAny late check out inquire, must be discussed direct in the property`s front desk. brbrSECURITY DEPOSIT: Resort will require a deposit for incidentals or damages at check-in. You can use a credit or debit card , the deposit is U$115 per apartment. This is a preauthorization, not charged and released at check-out if not needed. Credit cards usually are refund in 2-3 days, while debit cards can take longer. Please contact your financial institution for more details.    brbr(WAIVED) RESORT FEE: The amount of $10 + tax will be charged per night of your stay ( it is not per person ) this amount will cover Wi-Fi, Shuttle to the Strip and other amenities. This amount is NOT included in your price.  br  brbrThis is a timeshare resort, you are MY GUEST, that means you HAVE NOT to attend any timeshare presentation.  brTimeshare tour is not required but may be offered by the resort for incentives.  brWE DO NOT promote, endorse or encourage any sales pit however is up to you to accept in case it is offered, again, you are not required.  br  brbrPLEASE CHECK OUR CANCELATION POLICY. Always is smart to buy a travel cancelation insurance, this way you always can have full refund in case you cancel.  brbr**Once the reservation is confirmed, it is NOT possible to change dates and for changing names there will be a fee of €50.  br  brbrRules for change of names:  brbr1. Name changes may be accepted up to 7 (seven) days before check-in. Note that on some special and promotional dates the name change is not accepted.  brbr2. Each name change has an additional rate of € 50.

2

Bed

2

Bath

6

Sleeps

$608.34

/ Nightly

Apartment

6 Mi to Tanglewood! High-End Lee Apartment

Lee, Massachusetts, United States

High-Speed WiFi | Upgraded Kitchen | Private Forest-View Balcony | 2010 Addition to 1738 PropertybrbrKick off your next Berkshire getaway at this Lee vacation rental, where historic soul meets modern luxury! The 2-bed, 1-bath apartment serves as a launchpad for the arts and adventure — wake up to serene views before hiking the AT, fishing, or browsing the Norman Rockwell Museum. After an evening performance at Tanglewood, return home to recharge in style. Secure this New England sanctuary today!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 queen bedbr- Additional Sleeping: 1 portable cribbrbrAPARTMENT FEATURESbr- Balconybr- Smart TV, board gamesbr- Electric fireplacebr- 2010 addition to historic property built in 1738brbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Drip coffee pot, French press (starter coffee provided)br- Toaster oven, microwavebr- Cooking basics, dishware & flatwarebr- Spicesbr- 4-person dining table, counter seating, high chairbrbrGENERALbr- Free WiFi (300 Mbps)br- Central A/C & heating, ceiling fanbr- Washer & dryer, iron/boardbr- Linens & towelsbr- Complimentary toiletries, hair dryer, hangersbr- Keyless entrybrbrFAQbr- 1 exterior security camera (facing driveway)brbrACCESSIBILITYbr- Single-story apartmentbr- 1 interior flight of stairs to accessbrbrPARKINGbr- Driveway (1 vehicle)brbr-- THE LOCATION --brbr- 0.9 miles to downtown Leebr- 2 miles to Lee Premium Outletsbr- 4 miles to Stockbridge, famous for Norman Rockwell's 'Street Scenes'br- 4 miles to Goose Pond Reservation & October Mountain State Forestbr- 11 miles to Jacob's Pillowbr- 55 miles to Albany International 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- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story apartment requires 1 interior flight of stairs to accessbr- Your safety matters. This property features 1 exterior security camera located outside the front door facing the driveway. It is outward facing and does not look into any interior spaces. The camera actively records audio and video

2

Bed

1

Bath

4

Sleeps

$324.81

/ Nightly

Apartment

Hike, Fish & Ski: Riverside Barn Loft in Lee

Lee, Massachusetts, United States

Pet Friendly w/ Fee | Part of the Historic Registry | Mountain & River ViewsbrbrLace up your boots for the ultimate mountain escape! This Lee vacation rental is a beautifully preserved 1815 barn situated right on the doorstep of the Appalachian Trail. Spend your days hiking the ridgeline at Goose Pond, fishing the Housatonic, or exploring October Mountain State Forest. Back at the 1-bathroom studio, enjoy the perfect blend of rustic charm and modern touches. Book your Berkshires home base today!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Studio Loft: 1 king bed, 1 futonbrbrPROPERTY FEATURESbr- Laptop-friendly workspacebr- 2-person dining tablebr- Covered porch w/ seatingbr- Shared yard w/ mountain viewsbr- Birthplace of former Supreme Court JusticebrbrKITCHENETTEbr- Induction stovetop, toaster oven, microwave, refrigeratorbr- Single-serve coffee maker, electric kettlebr- Cooking basics, dishware & flatwarebrbrGENERALbr- Free WiFibr- Window A/C unit, electric radiator, ceiling fanbr- Linens & towelsbr- Complimentary toiletries, hair dryerbrbrFAQbr- 1 exterior security camera (facing driveway)br- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- 3 steps for entry, 2-level studio loftbr- Bathroom on main level, sleeping area on upper levelbrbrPARKINGbr- Shared driveway (1 vehicle)brbrADDT’L ACCOMMODATIONSbr- An additional property is available on-site w/ a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbr- Historic property located along the Appalachian Trailbr- 2 miles to Stockbridge, famous for Norman Rockwell's 'Street Scenes'br- 3 miles to downtown Leebr- 6 miles to Goose Pond Reservation & October Mountain State Forestbr- 8 miles to Tanglewood br- 12 miles to Jacob's Pillowbr- 51 miles to Albany International 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/ $45 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-level studio loft requires 3 steps for entry; the bathroom is on the main level, and the sleeping area is on the upper levelbr- There is another bookable vacation rental on-site, in a separate unit with a separate entrance and a shared yard; other travelers may be present during your staybr- Your safety matters. This property features 1 camera near the front door facing the driveway. The camera is outward facing does not look into any interior spaces. The camera actively records video and sound

Bed

Bath

Sleeps

$275.89

/ Nightly

Hotel

Great Place - 2 BD - Kitchen and Pool 

Lee, Massachusetts, United States

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar.brbr• Pools, Gym, Movie Theater and mini golf  br• Accommodate up to 6 people  br• One guest in the party, must be at least 21 y/o or older.    brbr* U$10 PER NIGHT OF RESORT FEE(WAIVED) .  br**Additional charge brbrThe spacebrWe offer multiple units at this property, all of them consistently designed to give you a beautiful place to stay. While the style is consistent, the layout and view may vary by apartment.  br  br• Apartment style accommodation with 823 square feetbr• Queen-size bed and pullout sleeper sofa br• Fully equipped kitchen br• Two full bathsbr• TV in living room and bedroom br• Accommodate up to 6 people  brbrBEDROOM 1 - 1 Queen bed  brBEDROOM 2 - 1 Queen bed  brLIVING ROOM – 1 Pullout sleeper sofa     brbr• FREE PARKINGbr• Two Outdoors Pools (opened Seasonally), Two Indoor Poolsbr• Hot Tubbr• Heating and air conditioningbr• Towels & Linenbrbrbr***** PLEASE NOTE *****brThis is a Resort Villa style unit, you will have your unit assigned upon arrival, ALL units have the same quality and specification, location may vary. brbrbr***** LONG STAYS INFO:  brbrWe do provide a starter kit for each unit with toiletries, toilet paper, paper towel, dish washer, detergent, etc. brbrGuest accessbrYou will check in at the front desk, The person whose name is on the booking must be the one that will check in, name changes only can be made up to 7 days before arrival and have a cost of $50 American dollars.brbr  brCheck-in time: 4:00pm  brCheck-out time: 10:00am  brAny late check out inquire, must be discussed direct in the property`s front desk. brbrOther details to notebrbrSECURITY DEPOSIT: Resort will require a deposit for incidentals or damages at check-in. You can use a credit or debit card , the deposit is U$115 per apartment. This is a preauthorization, not charged and released at check-out if not needed. Credit cards usually are refund in 2-3 days, while debit cards can take longer. Please contact your financial institution for more details.    brbr(WAIVED) RESORT FEE: The amount of $10 + tax will be charged per night of your stay ( it is not per person ) this amount will cover Wi-Fi, Shuttle to the Strip and other amenities. This amount is NOT included in your price.  br  brbrThis is a timeshare resort, you are MY GUEST, that means you HAVE NOT to attend any timeshare presentation.  brTimeshare tour is not required but may be offered by the resort for incentives.  brWE DO NOT promote, endorse or encourage any sales pit however is up to you to accept in case it is offered, again, you are not required.  br  brbrPLEASE CHECK OUR CANCELATION POLICY. Always is smart to buy a travel cancelation insurance, this way you always can have full refund in case you cancel.  brbr**Once the reservation is confirmed, it is NOT possible to change dates and for changing names there will be a fee of €50.  br  brbrRules for change of names:  brbr1. Name changes may be accepted up to 7 (seven) days before check-in. Note that on some special and promotional dates the name change is not accepted.  brbr2. Each name change has an additional rate of € 50.

2

Bed

2

Bath

6

Sleeps

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