Vacation Rentals By Owner In Pittsfield, MA

$337.97

Escape to your cozy retreat near Pontoosuc Lake and Jiminy Peak

Pittsfield, Massachusetts, United States

In the center of Lanesborough lies a cozy 2-bedroom house that provides a peaceful escape for your upcoming trip. Imagine yourself relaxing in the soothing hot tub, soaking in the stunning views and the fresh mountain air. Indulge in the convenience of high-speed WiFi and a smart TV, perfect for cozy movie nights. Refresh your wardrobe with the in-unit washer and dryer, and start your day with a freshly brewed cup of coffee from the fully stocked kitchen. Venture out and explore the nearby Jiminy Peak Mountain Resort, Tanglewood Music Center, and Hancock Shaker Village, all within a short drive. Whether you're seeking adventure or simply a peaceful escape, this vacation home offers the perfect blend of comfort and convenience to make your stay truly unforgettable.

2

Bed

2

Bath

4

Sleeps

$169.72

/ Nightly

Apartment

Cozy Renovated with 1 parking space

Pittsfield, Massachusetts, United States

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

1

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1

Bath

2

Sleeps

Select Dates for Price

Hotel Resort

Mountain Lodge Apt!

Pittsfield, Massachusetts, United States

A full kitchen, sofa bed and flat-screen cable TV are included in each guest room. The private bathrooms are equipped with a hairdryer and free toiletries.brbrGuests at the Pittsfield Berkshire Mountain Lodge can relax in the hot tub. A games room is also available.brbrBerkshire Museum is 6 minutes’ drive from the lodge. Barrington Stage Company: Mainstage is 7 minutes’ drive.brbrTanglewood is 11 minutes' drive from the lodge.

Bed

Bath

Sleeps

$288.56

/ Nightly

Cottage

Cozy Berkshire cottage with fireplace.

Pittsfield, Massachusetts, United States

Relax at this unique, tranquil getaway. Minutes from all the Berkshires' offer; Tanglewood, Bousquet and Jiminy Peak ski resorts, museums, Colonial and Barrington Theater, Shakespeare and Co, Naumkeag, and many more. Conveniently located on the Pittsfield/Lenox line, close to many restaurants and shopping areas but tucked into the woods with hiking trails on the property. Our kitchen has all your cooking essentials. We have smart TV's and WIFI to relax with after your Berkshire adventures.br The South Mountain House is a cozy one level with a nice open flow from the front driveway through the house to your own private back patio. Three bedrooms, one queen, one full, and one twin. The couch doesn't pull out but it's very comfortable. The house sits on 9.5 acres all for your enjoyment. There are cleared paths behind the house that you are encouraged to explore; from the patio, to the orchards, the fire pit to the boulders, there is plenty to do in this home away from home.br The South Mountain House has a big driveway with plenty of free parking. The house is conveniently located in the center of the Berkshires close to shopping centers, Pittsfield downtown and Lenox downtown. 1 mile to Pittsfield country club and golf, 6 miles to Tanglewood, 2.8 miles to Bousquet Ski Resort, 13 miles to Stockbridge, 14 Miles to Jiminy Peak Ski Resort and 19 miles to Great Barrington. Pittsfield has Uber for those nights you want to go out on the town with no worries.

3

Bed

2

Bath

5

Sleeps

$416.33

/ Nightly

Private Vacation Home

Solomon Ely Homestead - Charming Pittsfield Stay

Pittsfield, Massachusetts, United States

Enjoy your stay at this 1847 New England farmhouse located just steps from downtown Pittsfield. Make yourself at home with 4-bedrooms, a wraparound porch with rocking chairs, wifi, laundry and complete kitchen. The property is filled with historic charm which pays homage to our town and creates a very cozy experience. Just a 5 minute walk to theaters, museums, popular drinking holes and eateries. We’re 20 min to Tanglewood, 10 min to Bousquet Ski Area, 10 min to the Hancock Shaker Village and central to everything the Berkshires offers.

4

Bed

2

Bath

7

Sleeps

$745.33

/ Nightly

Condo

Perfect for Winter Skiing!!

Pittsfield, Massachusetts, United States

Perfect family home for all Winter activities with 4 Bedrooms and 3.5 baths, plus it is central to all the cultural activities the Berkshires has to offer. The condo sits adjacent to the newly renovated Bousquet Mountain with new high speed chair lifts and brand new snow making equipment to guarantee skiing every day. A ski slope to the chair lifts is right out the back door! And opposite Bousquet Mountain, just a half mile away, is the newly renovated Bousquet Sport Health Club with indoor tennis and pickle ball, and a complete fitness center.brbrThe condo is on 3 levels. The ground level has a 2 car garage and behind the garage is a newly renovated space that has a good size bedroom and bathroom, and a nice size family room. The second level has a light filled living room with 20' ceilings, a dining area, a kitchen with an adjacent breakfast table/eating area, a laundry room, and a half bath. The first floor also has the master bedroom suite with a walk in closet and a bathroom with a double sink and walk in shower. An enclosed screened porch off the living room looks out on a ski run. The third level has two nice sized bedrooms, a bathroom, and a large media room. Altogether about 3,000 SF. There is also a great deal of closet space throughout. The master BR has a king bed, two other bedrooms have queen size beds, and one upstairs bedroom has two twin beds.brbrWhen you step out of the front of the house, you have far reaching views to Mt. Greylock, and there are no other condos on the other side of the street providing unobstructed views. brbrWe are right on the border of Lenox. Tanglewood without traffic is 10-11 minutes away. A 3 minute drive brings you to two large Supermarkets plus Guido's, a CVS drugstore, Carr Hardware and many restaurants. We are literally next door to the newly renovated Bousquet Ski area, and 1/2 mile away is Bousquet Sport, a large health club with a pool, indoor and outdoor tennis, and a complete fitness facilities that is currently undergoing a 28 million dollar total renovation. We are also 6 minutes from the center of Pittsfield, 7 minutes to Barrington Stage, 10 minutes to Berkshire Medical center, 15 minutes to Stockbridge and 25 minutes to Jacobs Pillow.brbrAll in all, the condo offers a great combination of space, comfort, amenities, and convenience to all the Berkshires has to offer.

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Sleeps

$701.67

/ Nightly

Private Vacation Home

Hidden Oasis in the Mountains by Evergreen Home

Pittsfield, Massachusetts, United States

7 MINUTES FROM BOUSQUET MOUNTAIN SKI AREAbrEscape with family & friends to this hidden oasis in the heart of the Berkshires.brbr Enjoy the beautiful perennial gardens, unwind in the hot tub, relax on the stone patio by the fire pit, & dine on the deck. Just minutes from Lenox & Tanglewood, this attractive 5 BR home boasts a large, fully-outfitted kitchen, comfortable Tuft & Needle mattresses, & spacious living areas with stunning mountain views.brbrIf you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.brbrThe property is at the top of the hill overlooking October Mountain. You will need AWD/4WD in the winter to ascend the street and driveway. The views are gorgeous and the location is just perfect. All Berkshire attractions are easy to get to from this spot.brbrGuests will have private access to the entire home, and property.brbrA lovely colonial at the end of a quiet cul de sac with central air conditioning for summer nights & all the fixings to get warm & cozy after a day on the slopes. brbrThe main floor of this home includes a fully equipped kitchen with a viking range perfect for cooking meals at home. A small dining area in the kitchen seats 4 guests with the formal dining room seating an additional 8 guests. The family room features gorgeous mountain views, plenty of comfortable seating, large TV and sound system. and a wood burning fireplace. Enjoy your morning coffee in the light filled screened in porch off of the family room. brbrAn additional sitting room houses a wood stove and a collection of board games. It is adjacent to the music room which contains a beautiful piano and additional seating. The French doors off of this room lead into the library that houses some of the extensive book collection in the home. The library also doubles as the first floor bedroom with a queen sized bed. Also on the first floor is a full bath with a walk in shower and washer/dryer unit. brbrThe second floor of this home contains the other four bedrooms. The primary bedroom and ensuite bathroom contains a king sized bed, TV, walk in closet, and a desk perfect for a private work space. The second and third bedrooms both feature queen sized beds. The final bedroom includes two twin XL beds both with twin trundle beds, accommodating up to four guests. An additional full guest bath with a tub/shower combo is located on this floor. brbrThe basement of this home features a home gym, bar, pool table, and ping pong table. A tv area with kids games/play area is also located in the lower level.brbrThe outside of this home is just as stunning and spacious as the inside. With beautiful mountain views and perennial gardens in the front and an expansive backyard with a fire pit, hot tub, outdoor dining table and BBQ you have everything you need right at home!brbrThis property is a true gem, offering something for everyone. Hiking, skiing, shopping, theater, golf, lakes, nature preserves, museums, & amazing restaurants all close by. brbrThe house is a short drive to both downtown Lenox (7 mins) and downtown Pittsfield (9 mins). A car is recommended to get around but biking is also an option, especially in warmer seasons. Downtown Pittsfield's Joseph Scelsi Intermodal Transportation Center has a bus station (Peter Pan, Bonanza, Greyhound, BRTA) and an Amtrak train station that provide regular service throughout the region and to major cities.brbrLook no further; this is your ideal home away from home!brbrHaving a car will greatly enhance your ability to explore the Berkshires effectively.brbrbrLOCATION: The property is at the top of the hill overlooking October Mountain. You will need AWD/4WD in the winter to ascend the street and driveway. The views are gorgeous and the location is just perfect. All Berkshire attractions are easy to get to from this spot.brPETS: Small, trained, hypoallergenic pets are allowed on a case by case basis and for an additional $100 fee per pet. We have allergies in our family and do not, under any circumstances, allow pets that shed (even in the case of a service animal). Any pets must be under 50 lbs and fully housebroken/trained. If you'd like you to bring your pet, please let us know so we can ensure they are safe at our unique property.brPARKING: Free parking on premises.brHOT TUB: Please keep the hot tub closed when not in use. Make sure the jets are off before you close up. Be aware of the potential health risks associated with hot tubs before you use it, and use at your own risk.br*Please note that the fire pit may not be cleared in winter months due to heavy snows. Shovels will be available in the event that the fire pit is buried!brbr**Your reservation includes a $20 insurance fee to cover any accidental damage during your stay, allowing you to relax and enjoy your vacation with peace of mind. If any damage does occur, please let us know so we can arrange timely replacements for the next guest.

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Sleeps

$171.68

/ Nightly

Private Vacation Home

Dancing Horse Lodge

Pittsfield, Massachusetts, United States

Dancing Horse Lodge is located on Horse Farm in the heart of the beautiful Berkshire Mountains with plenty of room for family and friends or just a quiet weekend retreat. Dancing Horse Lodge is a 3 bedroom, 1 bath ranch style house with a large eat in kitchen and living room. It is surrounded by many hiking trails and right next to Bosquet ski area and Berkshire West Athletic Club. It is conveniently located close to many of the best restaurants in the area and cultural venues including Tanglewood and Barrington Stage Company. The gas-wood stove in the living room is wonderful after a cool day of outdoor activity.

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Bath

Sleeps

$152.65

/ Nightly

Hotel Resort

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!

Pittsfield, Massachusetts, United States

The Berkshire Mountain Lodge features one-bedroom condominiums equipped with modern amenities such as full kitchens and cozy living and dining areas. The Berkshires is a cultural art haven that is home to attractions like American author Edith Wharton’s self-designed estate, The Mount and Tanglewood, the summer home of the Boston Symphony. Located near Lenox, Mass., Berkshire Mountain Lodge is a family vacation destination for all seasons that will include days filled with countryside beauty, and an abundance of activities that stimulate the senses and energize the body. During the summer and spring visit the area’s many museums, theaters, concert halls, and historic homes. The county’s lakes and rivers are perfect for boating, kayaking, swimming, and fishing. Take advantage of the miles of country lanes for hiking and biking, enjoy a round of golf or go zip-lining with the kids on a nearby mountain. Many places pale in comparison to the Berkshires fall foliage season. A refuge of natural beauty; experience nature’s kaleidoscope of colors in cooler weather while you peruse though numerous outdoor bazaars and markets.br

1

Bed

1

Bath

4

Sleeps

$217.82

/ Nightly

Apartment

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Pittsfield, Massachusetts, United States

Unwind in Pittsfield at this charming corporate apartment. With AC, a washing machine, and WiFi, guests can enjoy a marvelous stay in this 1-bedroom retreat. It's easy to see why you'll be able to unwind at our place.

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$1035.46

/ Nightly

Private Vacation Home

Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake

Pittsfield, Massachusetts, United States

For 2023, a massive gut reno has been completed, adding a 24ft wide sunroom overlooking the lake, 2 new bedrooms and a bath, as well as basement game room with wet bar, pool table and shuffleboard table.brbrFor 2019, we are excited to have finished a Brand new 1700 Sq Ft Pavered Patio with lounge chairs and a Gas Fire Pit, including a covered area under the deck to enjoy the occasional rainy days, plus stone steps going down to the water for ease of access to the lake. outdoor couch and lounge chairs for maximum relaxation. brbr5 Kayaks(one being a double!) & 2 Stand up paddleboards available lakeside for your use!brbrbrThis 5 bedroom, 3 1/2 bath country home sits on beautiful Pontoosuc Lake. This lakefront property features a deep water dock for your boat. There is a public boat launch within 2 minutes of the house. The location is ideal for water sports, kayaking, fishing, or just enjoying the serenity of the lake. Boat rentals are available just across the lake. brbrMain floor:brSpacious living room, half bath, kitchen, dining area that overlooks the lake and a sprawling sunroom with a 12 foot slider off the deck. 2 outdoor tables sit 12.brbrThe second floor has 5 bedrooms:br1. King Bedbr2. King Bedbr3. queen size bedbr4. two twin bunk beds (sleeps four)br5. queen over queen bunk bed (sleeps four)brbrBedrooms sleep 14brbrHouse has a brand new kitchen with stainless steel appliances and gas range, new second floor washer/dryer and is fully stocked with linens, towels, dishes, glassware, cooking utensils for use by guests. Outdoor gas grill brbrRentals: 1 Week Min during summer period (friday to friday)brbrPontoosuc Lake, is truly in the Heart of the Berkshires and is minutes away from local area attractions/museums/theaters:brbrTanglewoodbrNorman Rockwell MuseumbrShaker VillagebrMass MOCAbrBarrington StagebrShakespeare & CompanybrBerkshire PlayhousebrThe colonial TheatrebrJacobs PillowbrChesterwoodbrClark Art InstitutebrbrGolf- several clubs within a short distancebrbrless than 5 mins to Berkshire Mall/Target/WalmartbrbrDuring the winter months it is a very short drive to skiing Jiminy Peak or Bousquet Mountain - both under a 10 min drive.brbr2 1/2 hr drive from NYC or Boston

5

Bed

4

Bath

14

Sleeps

$497.07

/ Nightly

Private Vacation Home

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield, Massachusetts, United States

Welcome.....we invite you to come enjoy the great space of our beautiful home with your family and friends in our unique 4000 sq. ft. custom built home with sleeping accommodations for up to 28. With 8 bedrooms, 2 full kitchens, 3 beautifully updated bathrooms and great outdoor space for relaxing and entertaining, we think it's the perfect gathering spot. brThe house is nestled in the heart of the Berkshire Mountains and situated between 2 beautiful lakes that have incredible views. One lake (Onota) is just a short walk down the street where you can enjoy swimming, boating, fishing, picnicking and more. Feel free to bring your Kayaks, jet skis or boat and store them at our fenced in yard. The second lake (Pontoosuc) is just a short 3 minute drive. This lake also boasts beautiful views of the surrounding mountains and aside from boat and jet ski rentals, this area also has amenities such as on the lake restaurants with a view and golfing. Plenty of wineries and brew houses within minutes of the house.brThe season changes are amazing in the Berkshire Mountains. The fall shows off the beautiful mountains in spectacular colors and all the charming country farms are bustling with hay rides, apple picking and pumpkin fests. Winter provides an abundance of snow and our house is located just minutes from some of the best ski resorts and just a walk away from ice fishing on the lake. Spring jumps alive with the new and upcoming season of summer events. The summer season provides so many different things to do you won't know where to begin. The Berkshire summer weather is almost always perfect for enjoying the many outdoor activities the area has to offer. brWe are family friendly and cater strictly to mature adults and families only. We are happy to open up our home to those who wish to gather in a homey atmosphere for reunions, holiday gatherings, work retreats and social events, whether family or friends wishing to enjoy special occasions together, such as wedding parties, work retreats and friend getaways. However, it is not a party house or a place to host young adult parties and we do not rent to high school groups wishing to host graduation gatherings.brCOMING SUMMER 2025 A/C. For the comfort of our summer guests we will be installing a few window a/c's for a few months during the higher temperature summer months. This is usually between early July and up to mid/end of August. brbr--THE PROPERTY --brbr4000 Square Feet of Living Space | Great Room W/Pool Table, Electric Fireplace, Big Screen Smart TV | 8 Bedrooms | 3 Full Bathrooms | 2 Full Kitchens | 2 Full Laundry Rooms | Fully Fenced Yard | Driveway ParkingbrbrFully equipped for a family fun, entertaining and relaxation with plenty of amenities close by sure to please everyone in your group!brbrUpstairs Bedrooms 1: King Bed-Sitting Room with Leather Sofa, Love Seat and TV | Bedroom 2: Queen Bed, Trundle Singles, Ceiling Fan | Bedroom 3: 2 Queen Beds, 1Single, Ceiling Fan | Bedroom 4: Queen Bed, Full Size Pull out Sofa Bed, Love Seat, TV | Bedroom 5: Single brGround Floor Bedroom 6: Queen Bed | Bedroom 7: Queen Bed, Futon | Bedroom 8: Captains Full Size BedbrAdditional Sleeping Accommodations: Great Room Pull out Sofa Bed | Rollaway Cot brbrOUTDOOR LIVING: 2 tiered deck, dining table, lounge chairs and conversation area furniture - seasonal. Gas grill -seasonal | Fire pit with bench seating - year round, 7 seat jetted hot tub - year round, Play Yard for kids, Fenced in yard, Outdoor covered seating smoking areabrbrINDOOR LIVING: Big screen Smart TV, Dining tables - seating enough for 25+, Electric fireplace, Pool table - converts to dining table, Ground floor storage closet for ski gear etc., homey updated decor and comfortable beds and furniture brbrKITCHENS: 2 Fully equipped w/ cooking basics, stainless steel appliances, microwave, dishwasher, coffee maker, Kueirg, ice maker, hand mixer, dishware/flatware, pots, pans, cooking utensils, bakeware, toaster, Crock-PotbrbrGENERAL: Free WiFi, complimentary initial toiletries, towels & linens, hair dryer, washer/dryer, cleaning essentials, central heating, beach towels, beach chairs, yard toysbrbrFAQ: Stairs but not required - ground floor has a few step ups but everything needed is on the ground floor. Property does not have central A/C but is supplied with many fans - the mountain air typically brings cooler weather, even through the summer months. We cater strictly to mature adults and families. We do not rent to high school kids or party groupsbrbrPARKING: Driveway - 6 vehicles Street Parking - 2 vehicles - Extra Yard Parking - information upon request brbr-- THE LOCATION --brbrAREA ATTRACTIONS: Only minutes from golf, boating, hiking, shopping, fine dining, Hancock Shaker Village, The Colonial Theatre and Pittsfield's historic baseball park and team. Jiminy Peak Ski Resort (12 miles) and Bousquet Mountain (7 miles) both also cater to summer fun. Lee Premium Outlets (15 miles) Tanglewood (12 miles) Also close by : The Norman Rockwell Museum, Berkshire Theater Festival, Jacobs Pillow, Barrington Stage, Cranwell Spa, Kripala, Shakesphere Theater and The Mount. brbrGOLF: Within minutes: Country Club of Pittsfield, GEAA Golf Course, Berkshire Hills Country Club, Skyline Country Club, Black Rose Golf Club, The Golf Club at Wyndhurst ManorbrbrGREAT EATING: Proprietor's Lodge - Lakeside Dining (1.0 miles), Zucchinis (1.6 miles), Lakeside Bar & Grill - Lakeside Dining (2.4 miles), Old Forge Restaurant (4.5 miles), The Roasted Garlic (23.5 miles), Trattoria Rustica (3.0 miles), Mazzeos (5.6 miles), Marios -highly recommend (12.0 miles)brbrGROCERY: Harry's Supermarket (1.6 miles) Big Y (3 miles) Stop Shop (4.4 miles) Price Chopper (6.2 miles)brbrAIRPORT: Albany International Airport (50 miles) : Bradley International Airport (75 miles) : Logan International Airport (143 miles)brbrbrbr

Bed

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Sleeps

$513.99

/ Nightly

Private Vacation Home

Berkshires Lake View, Hot Tub, Large Open Great Room, Lrg Kitchen

Pittsfield, Massachusetts, United States

Families, couples, remote workers, and skiers, your Berkshires vacation rental search stops here! Bluescape is your place to reset and find calm with year-round lake views. Centrally located, start/end your outdoor or cultural adventure at this home away from home. Get more done at your distraction-free remote office with high-speed internet, including whole-home wifi with an option to be hard-wired. End each day with the quiet of the night while relaxing in the jacuzzi or by the fire table.brbrComments from previous guests:brKristine’s house was perfect for our family ski getaway. It is very spacious and everyone was happy with their bedrooms and every common area. The massage chair and hot tub were huge bonuses after a day of skiing. Everything was clean and well-appointed. We will definitely be back!! brbrThis home was perfect! Very spacious for our family gathering. The house is much bigger than it appears! Huge living room/dining area was great for keeping everyone in our group comfortable and entertained while we cooked Thanksgiving dinner in the large kitchen. Well-stocked and modern kitchen and baths, and fun extras like the massage chair and the jacuzzi! Host was very responsive and so helpful. Lake was beautiful and although the neighboring houses are close by, we felt it was peaceful and private. We can’t wait to visit again!brbrHouse with Lake Views and Accessbr4 Bedrooms, 2 Baths (1 Bedroom/1 Bath Downstairs, 3 Bedrooms/1 Bath Upstairs)brCapacity: 10 People, including infants and childrenbrBeds: 1 King, 2 Queen, 2 Sets of Twin Bunks - 7 beds total)brParking: In the driveway for up to 4 cars.brHOST/OWNER ACCESSIBILITY: We will give you space and hope you enjoy the use of our home, the lake, and all that the Berkshires has to offer! We are available if you need us ... either in-person for emergencies or through messaging. Please be aware that the 2-car garage and outside area directly to the right of the garage is restricted from guests. The two access points into the garage from inside the home are locked. Our property management supplies are inside the garages. Although limited, if at all, you may see us on the property to access the garages during your stay.brbrAmenities: Window Air conditioning (seasonal, Cleaning products, Cooking basics, Dedicated workspace, Dishes and silverware, Dryer, Hair dryer, Heating, Hot tub, Kitchen, TVs in every bedroom, livingroom, and entrance, Washer, Wifi, Bathtub, Body soap, Conditioner, Hot water, ShampoobrShower gel, Bed linens, Clothing storage, Drying rack for clothing, Extra pillows and blankets, Hangers, Iron, Room-darkening shades, Books and reading material, Ethernet connection, Exercise equipment, Children's playroom, Board games, Children’s books and toys, Outdoor playground, Pack ’n play/Travel crib, Ceiling fan, Portable fans, Carbon monoxide alarm, Fire extinguisher, First aid kit, Smoke alarm, Baking sheet, Barbecue utensils, Blender, Coffee, Coffee maker, Dining table, Dishwasher, Freezer, Hot water kettle, Microwave, Oven, Refrigerator, Stove, Toaster, Wine glasses, Lake access, Private entrance, Backyard, BBQ grill, Fire pit, Outdoor dining area, Outdoor furniture, Patio or balcony, Free parking on premises, Long term stays allowedbrbrAlbany International Airport, Albany, NY: 1 HourbrBradley International Airport, Hartford, CT: 1 Hour 40 MinutesbrBoston Logan International Airport, Boston, MA: 3 HoursbrPittsfield Municipal Airport, Pittsfield, MA: 20 MinutesbrAlbany, NY: 1 HourbrDalton, MA: 15 MinutesbrGreat Barrington, MA: 45 MinutesbrLee Premium Outlets, Lee, MA: 30 MinutesbrNew York City, NY: 3 HoursbrNorth Adams, MA: 35 MinutesbrProvincetown, MA: 4.5 HoursbrSaratoga Casino & Race Track, Saratoga, NY: 1 Hour 20 MinutesbrTanglewood, Stockbridge, MA: 30 Minutesbr-Quiet, residential, walkable, lakeside neighborhood.br-Skiing - Jiminy Peak (15-Minute Drive) + 20 minutes to Bousquet, 45 minutes to Berkshire East, and 45 minutes to Butternut Ski Area. You will find areas for snowshoeing and cross-country skiing too (Notchview 30-Minutes)br-Icefishing access across the street as long as the lake is frozen and safe for walking!br-Public park and playground (7-Minute Walk)br-Dollar General, Dunkin Donuts, Target, Starbucks, Mobil Gas Station, and Gulf Gas Station under 10-minute drive!

Bed

Bath

Sleeps

$323.62

/ Nightly

Private Vacation Home

Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b

Pittsfield, Massachusetts, United States

Beautiful, spacious, 3 bedroom, 2 bathroom, family home in the Berkshires located on a private road on crystal clear Richmond Pond with private dock for swimming and boating. Our home in the Berkshires is comfortable and clean with hardwood floors, skylights, spacious closets, and wood paneling. We have a new shower bath combination in the master bedroom (on the main floor), energy efficient washer and dryer, new Weber gas grill, and lush landscaping. There are air conditioners in each of the 3 bedrooms and one downstairs in the living/dining room. There are many books, games, a fully equipped kitchen with a table and six chairs plus additional dining room table which seats up to 8. We provide clean linens, a rowboat, 2 kayaks, life preservers, and many water toys. The house sleeps 7 people in comfortable bedrooms. The master bedroom with queen bed and twin bed and full bath (with shower/tub) are on the main floor. The additional 2 bedrooms and a bathroom with toilet and sink are upstairs. There is a second shower in an adjacent building with changing room and electricity and plenty of hot water (with a separate water tank). There is a large wooden deck with a table, umbrella, and chairs and Weber gas grill. No smoking. Good quality Spectrum Wireless Internet is provided, plus cable TV (flat screen). (Note that WIFI was installed in 2016 so earlier reviews do not list it.) Fishing is excellent in Richmond Pond; it is stocked with a variety of perch, pumpkinseed, bream, bluegill, rock bass, bullhead, brook trout, brown trout, crappie, largemouth bass and pickerel . It is a 15 minute drive to Tanglewood (summer home of the Boston Symphony); also close to Berkshire Theatre Festival, Stockbridge; Barrington Stage, Pittsfield; Lenox; Great Barrington; Jacob’s Pillow; and Williamstown. Albany airport is 1 hour away. Hiking, biking, and water skiing are all available.brbrbrKeywords: Cottage. Country house

4

Bed

3

Bath

7

Sleeps

Select Dates for Price

Private Vacation Home

Central Berkshire Craftsman - Long Terms Welcome!

Pittsfield, Massachusetts, United States

This cute as a button cottage in a walkable residential neighborhood, is the perfect home base to explore the Berkshires. In under 20 minutes, you can pop over to Tanglewood to enjoy a concert on the lawn or catch a live show at Barrington Stage Co. For our skiers- 25 minutes to Jiminy Peak, 10 minutes to Bousquet Mountain and just over 30 minutes to Butternut Basin. Hiking, golf, shopping, museums, adventure and fabulous restaurants await! br**Inquire about long term stay discounts!**br*Small dogs allowed with owner approval, no dogs under 2 years old. Please reach out for owner approval on the dog prior to booking. No multiples. $100 fee will be applied if approved.br* We can accommodate 5 adults or 6 guests including children.brIf you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.brThis residential neighborhood is super walkable with nearby parks, shops and restaurants. Check out our information book upon arrival for dining, shopping and activity recommendations!brGuests will have private access to the entire home, and property.brThis house has that craftsman style charm with beautiful wood floors and original wood moulding and doors. An enclosed front porch is the perfect spot to enjoy your morning coffee or just curl up with a good book. Two bedrooms upstairs can accommodate 4 or 5 guests, with a king size bed in the primary bedroom then a full and a twin bed in the guest bedroom. The first floor den has a futon that can accommodate one additional guest. One full bath with tub and shower is on each floor. There is a nicely equipped kitchen with separate dining room for meals at home and if you feel like eating under the stars enjoy dinner on the deck. The living room has a large flat screen TV with cable and smart streaming features and a cozy sofa to stay in for a movie night!brYou will need a car to navigate the Berkshires efficiently.

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Sleeps

$79.68

/ Nightly

Apartment

Apartment Newly Remodeled Super Location

Pittsfield, Massachusetts, United States

Large 2nd floor fully furnished apartment in 2 story corner house with plenty of parking and separate back entrance/staircase. Eat in Kitchen with all new appliances including a washer and dryer. Freshly refinished hardwoods throughout and new kitchen vinyl planking. All new furniture and bedding including area rugs. An additional bonus room that can be used as a sitting room or study. Plenty of closet and storage space. Large covered porch off the living room. Downtown Pittsfield Is 2 miles. Close to lakes and 5 minutes from Bousquet ski area.

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Sleeps

$692.23

/ Nightly

Private Vacation Home

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield, Massachusetts, United States

6 MINUTES TO BOUSQUET SKI AREAbrThis charming, newly remodeled Colonial home, nestled in the heart of the Berkshires, is perfect for your next family retreat! Explore top attractions, including museums, Tanglewood, theaters, hiking, skiing, golf, shopping, and dining. Featuring central AC, four bedrooms, three gorgeous baths, a generous bonus room, brand-new appliances & a large deck overlooking a private backyard. Enjoy the serenity of nature while being minutes from life in town! brbrbrbrIf you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.brbrThis home is located at the end of a cul de sac in a quiet residential neighborhood, offering the perfect balance of seclusion and convenience. Enjoy the tranquility of a country setting while being just a 10-15 minute drive from the vibrant downtowns of Lenox and Pittsfield.brbrGuests will have private access to the entire property.brbrThis spacious Colonial home, nestled in a quiet neighborhood, is ideal for family getaways. brbrThe large, modern kitchen is equipped with state-of-the-art appliances and everything needed to enjoy meals at home. Choose between the sunlit breakfast nook or the formal dining room, which comfortably seats eight. The cozy family room invites relaxation with its large sectional, TV, and wood-burning fireplace, while books and games on the shelves ensure entertainment on rainy days.brbrAt the front of the home, the formal living room is bathed in natural light through numerous windows. Just off the family room, the sunroom is perfect for sipping your morning coffee. A convenient half-bath is also located on the first floor.brbrUpstairs, the master suite features a king bed, ensuite bathroom with a luxurious marble shower, soaking tub, and a small desk for an office space. Three additional bedrooms offer ample sleeping arrangements with a king bed, queen bed, and two twin beds, along with a full guest bathroom on the second floor.brbrThe bonus room above the garage provides a larger office space and additional fold-out sofas for guests, with stairs leading down to the laundry room for added convenience.brbrOutside, the home opens up to a private 2-acre wooded backyard. The swing set is a delight for younger guests, while the deck is perfect for barbecues and outdoor dining.brbrIn under 30 minutes, you can reach Jiminy Peak, Bousquet, or Butternut Mountains for skiing and winter fun. Cross-country skiing, ice skating, ice fishing, and more await nearby. Enjoy culture and entertainment just minutes away, with The Colonial Theatre, Barrington Stage Co., the Berkshire Museum, shopping, and fantastic restaurants all within reach. Tanglewood is just 10 minutes away for an unforgettable experience.brbrHaving a car will greatly enhance your ability to explore the Berkshires effectively.brbrLOCATION: This home is located at the end of a cul de sac in a quiet residential neighborhood, offering the perfect balance of seclusion and convenience. Enjoy the tranquility of a country setting while being just a 10-15 minute drive from the vibrant downtowns of Lenox and Pittsfield.brPETS: A dog may be allowed with owner approval. Reach out with info about your pet prior to booking including size, age, breed, and overall temperament. A $100 pet fee will be incurred upon pet approval and booking. No multiples. brPARKING:br*Home has central air conditioning.br*2 acres of woods behind the home.brbr**Your reservation includes a $20 insurance fee to cover any accidental damage during your stay, allowing you to relax and enjoy your vacation with peace of mind. If any damage does occur, please let us know so we can arrange timely replacements for the next guest.

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12

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Select Dates for Price

Private Vacation Home

A Cozy 100 yr old New England Berkshires Dutch Colonial.nnLong term available.

Pittsfield, Massachusetts, United States

Cozy New England Dutch Colonial on a large corner 1/2 acre lot, closed in with fence and gate to close in driveway, surrounded by a canopy of trees. Close to all amenities.brbrEnjoy being a leaf peeper in the fall foliage, apple picking, the many fall parades and festivals.brbrSummer nights in Tanglewood with the Boston Symphony Orchestra, while relaxing on the lawn with food and wine, or enjoying our lakes, hiking, cultural history. brbrWinter sports, Christmas lights and Norman Rockwells recreated Stockbridge Main Street at Christmas brbrBerkshire Medical Center 4 min. General Dynamics 5 min, Lenox 7 min. Tanglewood 10 min, Stockbridge 20 min, Great Barrington 30. Norman Rockwell Museum, Barrington Stage Company, Edith Wharton’s The Mount (home of author Edith Wharton who wrote, The Age of Innocence, Ethan Frome, and The House of Mirth, to name a few), the recreation of Norman Rockwell's Stockbridge Main Street at Christmas painting in December in Stockbridge, Colonial Theater, Mass Moca, Naumkeag, Botanical Gardens. Herman Melville's Arrowhead (novelist of Moby Dick), Hancock shaker village ( walk back in time to the 1780’s of a former Shaker commune), Chesterwood (Home of american sculptor Daniel Chester French , who sculpted the Lincoln Memorial of our 16th President), State Forests, multiple lakes, boating, pontoon boat rentals, kayaking ( 2 kayaks available on property) hiking, biking, white water river rafting, zip-lining, ski resorts, Mt Greylock, Monument Mountain.

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$176.75

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Cottage

Charming Lakeview Cottage in Heart of the Berkshires

Pittsfield, Massachusetts, United States

Relax in your island cottage overlooking beautiful Onota Lake in the heart of the Berkshires. Take in 180 degree pristine lake and mountain views from the cozy living room. Custom kitchen with everything you need. Peaceful and spacious queen bedroom. Comfortable living room has full size sofa bed to accommodate whole families. Convenient lake access with beach and boat launch just a few steps away to launch your very own kayak. Beautiful deck, patio and gardens offer lots of outdoor space to unwind. Cottage is completely updated with open floor plan, stylish details and fully equipped for short- and long-term getaways. Central AC, WIFI, and gas heating for year-round comfort.

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$532.81

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Private Vacation Home

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield, Massachusetts, United States

Conveniently located near a lake, off of Route 7 on the way to attractions in both North Berkshire County and Southern Berkshire County. A perfect home base for Berkshire visit. 3 Bedroom, 2 bath plus furnished basement with all amenities needed for a comfortable stay to explore Western Mass! Brand new Central A/C for maximum comfort. New deck to enjoy with BBQ grill.brbrNote: this home does have stairs which would need to be climbed to get to the main part of the house.

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Vacation Rentals By Owner In Pittsfield, MA

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$79.68

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