27,207 properties available

Located in Boothbay Harbor, Maine, United States. Spa + Pool Access! Bright Woodland View Room Escape to Boothbay Harbor for a relaxing and tranquil escape! Enjoy days kayaking, whale watching, or paddle boarding on the water.• Lodge Room with 2 Queen beds• Sofa bed to accommodate additional guests• Private Porch• Woodland View!• Watch your favorite show on the TV• Fireplace• iPod Docking Station• Shared Outdoor Pool + Hot Tub• On-Site Spa• Complimentary shuttle to downtown• FREE ParkingBoothbay Harbor is a charming coastal town in Maine that is perfect for those who love nature. The town is surrounded by forests, mountains, and waterways, and is home to some of the region's most beautiful gardens and aquariums. There are also plenty of great restaurants and bars in town, as well as plenty of opportunities for quiet relaxation. Our charming 600-700 sq.ft. room is the perfect base for your next stay.Retreat to our comfortable air-conditioned LODGE ROOM with 2 Queen beds and an additional Sofa bed. Curl up in front of the gas fireplace

Located in Southport, Connecticut, United States. PIFFI BIFF ON SOUTHPORT ISLAND | 5 Bed, 3 Bath THIS PROPERTY RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER4 NIGHT STAYS AVAILABLE IN THE SHOULDER SEASON.______________________________________________________________Welcome to Piffi Biff, a beautiful cottage located on the historic Southport Island on the Boothbay peninsula. With incredible views of the Atlantic Ocean, Squirrel Island, Boothbay Harbor, Burnt Island, you will also see porpoises, whales, migratory shorebirds, sailboats, yachts and lobster boats! The endless parade of nature- made and man-made oceanic wildlife and vessels will provide endless entertainment!_____________________________________________THE HOUSE: Gorgeous views of the ocean are the hallmark of this classic Maine summer cottage. It also offers a large living room with a field-stone fireplace to be enjoyed by all along with the incredible views! A dining room and breakfast room offer even more visual delights. A covered open deck offers another dining ar

Located in Chatham, New Jersey, United States. Harmony House in Hudson Valley- Pet Friendly Welcome to the Harmony House, located within walking distance of the charming and historic Chatham town square. This cozy countryside getaway overlooks 10 acres of beautiful forest and open plains. The property is newly renovated and stocked with all the amenities that we hope will make our home feel like yours. With many attractions such as hiking, biking, skiing, and swimming all within close proximity, the Harmony House is the perfect family vacation spot.All living spaces are completely renovated; newly refinished wood floors on the ground level & new carpet upstairs. The rooms are freshly painted with inviting colors and all the mattresses are brand new.The kitchen is very spacious and has a classic rustic look. The kitchen is equipped with 2 ovens (Whirlpool), a 5 burner gas stove, a large double sink with garbage disposal, ample pots & pans, a coffee maker, an ice maker, a blender, a toaster, a dishwasher, and a large microwave. The k

Located in Chatham, New Jersey, United States. Spacious Serviced Apartment above Chatham Staple Enjoy the privacy of this spacious, 3 bed serviced apartment with the convenience of a charming, full-service restaurant/tavern located 2 flights down. This newly renovated space is located in a private section on the third floor of what was once known as the historic 'Chatham House', a resort for artists, writers and tourists of the Catskill Mountains. With the quaint Main St of Chatham just steps away, the apt is also only a 20 min drive from downtown Hudson, as well as many other attractions.

Located in Stockbridge, Wisconsin, United States. Stockbridge Home, Come Experience The Berkshires! Summary:Beautifully 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.The Space:Living 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. Very nice flow and layout in the kitchen; easy to use with updated appliances and well equipped; leads right to the dining area i

Located in Great Barrington, Massachusetts, United States. Apartment in Gorgeous Stonybrook Farm This apartment is located in a renovated barn on a large private estate, centrally located in the heart of the Berkshires, on fifty acres of beautifully landscaped farming land. The property has a large pond, woodland trails, and abuts onto Beartown Forest with large boating lake and picnic areas. It is located less than five miles from Stockbridge and Great Barrington town centers, and ten miles drive from Lenox and Tanglewood.The apartment consist of living-room, Kitchen, 1 bedroom with a full size bed and a full size sofa bed, and 1 bathroom. Minutes drive to restaurants, shops, art galleries and other local attractions including: The Berkshire Theater, Barrington Stage, Shakespeare and Company, Jacob's Pillow, Norman Rockwell Museum, Mass MOCA, Berkshire Botanical Garden, Hancock Shaker Village, Edith Wharton 'The Mount' and other cultural venues.Year-round outdoor activities include hiking, biking, canoeing, golfing, nature tours, and histo

Located in Lee, New Hampshire, United States. Gateway to the Berkshires - Renovated downtown apartment 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, along with comfy pull down queen size Murphy bed that sleeps two. Bed room is equipped with a queen size bed & plenty of space for storage. Central air & heat provided. All linens & towel are provided. All you need is to unpack, relax & enjoy.

Located in Sheffield, Montana, United States. Waterview Home in the Berkshires: Near Hiking Take a break from the city and relax at this charming Sheffield vacation rental in the Berkshires! The 3-bedroom, 2-bath house sits right on Mill Pond and boasts a retro interior, a Smart TV, a full kitchen, a dining room, an enclosed porch with seating, stellar pond views, and more! Conveniently located near Great Barrington, Butternut Ski Area, the Appalachian Trail, and several waterfalls, this home is the perfect choice for active families seeking all-season adventure. Book today!-- THE PROPERTY --MassTaxConnectID: C0383872670 | 2,262 Sq Ft | Ping Pong Table | Wood-Burning Fireplace | Bedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: 2 Twin Beds OUTDOOR LIVING: Waterfront, Solo Stove Yukon fire pit, private yard, enclosed porch, small covered deck, dining setINDOOR LIVING: Smart TV w/ cable, board games, books, dining table, en-suite bathroom, natural lightKITCHEN: Dishwasher, stove/oven, drip coffee maker, cooking utensils, pots

Located in Valatie, New York, United States. Camp Kinderhook Lake House This house is on a quiet cove on Kinderhook lake. It has been newly renovated within the past two years. And has a great old time camp feel. There are two full bedrooms on the main floor, including a loft with two twin beds. Downstairs there are also two bedrooms; one with two twin beds and the other with two triple bunk beds. 2 full bathrooms, one upstairs, one downstairs. This house is about a scenic 2 hour drive from NYC, and about 30 minutes from Albany.Prefect for a weekend getaway. In the winter, nearby Jiminy Peak and Catamount make for a perfect opportunity to ski or snowboard. The house also has a fireplace, full kitchen, and living room. Outside, there is an upper and lower deck, perfect for barbecues and summer fun. Nearby are villages Chatham and Hudson, perfect for antiquing and exploring, with lots of great places to eat. Possible summer activities include kayaking, fishing,hiking and golfing. Good for families looking for a relaxing vacation. C

Located in Kinderhook, Pennsylvania, United States. Spacious Cottage Retreat on Beautiful 2-Acres About this spaceFeatured by BUSINESS INSIDER as one of the 12 best Airbnbs near New York City this is your spotEnjoy peace & quiet with your spacious private guest house. There are multiple workspaces with high speed wifi. A giant kitchen. Relax and get some sun on your own deck. Wake up across from an apple orchard!Go for a stroll or bike ride down the Empire Trail. Amble into town & check out the farmers market, tons of shops and restaurants. The reviews say it: this is THE serene oasis for youThe spaceNestled on a back road with a field and an orchard for neighbors, you won't find a quieter haven. You have the entire guest house to yourself, private parking and deck, and a beautiful yard to explore.Guest accessYou have full access to the space, yard and wonderful bike routes and country roads!

Located in Lee, New Hampshire, United States. Centrally Located Historical Home Summary:Come 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!The Space:All our guests tell us the best part of the house are the view. Rolling hillsides and unobstructed mountain views for miles! The first floor has an open floor plan from the kitchen to the dining room to the living room. The 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

Located in Great Barrington, Massachusetts, United States. Great Barrington, Cabin Sleeps 14, Walk To Town Summary:You and your family cannot beat this PRIME location in downtown Great Barrington while still feeling remote and in the rolling hills of The Berkshires. Quick 20 minute drive to Tanglewood, 5 minutes to Ski Butternut, 15 minutes to Catamount Ski Mountain, 350 feet walking distance to all the great restaurants and shops of downtown Great Barrington and plenty more! Short walk to a great lake with a beach area - bring your dogs and family to swim in or walk around and enjoy the nature reservation!The Space:Your home away from home has everything you need to enjoy all that the Berkshires have to offer from relaxing to being active with a hike or shopping and eating in town.The kitchen has all new stainless steel refrigerator, gas stove, microwave, and Bosch dishwasher. The kitchen is open to the living room and dining area.Kitchen is stocked with all the cooking/serving necessities including: cookware, pots, pans, plates, cups, and si

Located in Lee, New Hampshire, United States. Relax between your Berkshire adventures! Easy walk to town! Centrally located! Owner operated with pride 😊 Our vacation home in Lee Massachusetts is centrally located to ALL THINGS BERKSHIRES! In the middle of the beautiful Berkshire Mountains but also just a short walk into town with restaurants, shopping, and pubs. Our home boasts 1800 square feet on a dead end street, three bedrooms (two queen bedrooms and a third with a full and a twin) and one bath with luxurious soaking tub and skylight. Our home is open concept so you can enjoy your family from just about anywhere in the house. The house flows wonderfully from the covered front porch, through the open concept living area, through the sunroom and sliders to the back deck to bring together the outdoor and indoor living spaces. Two living room areas! A basement theatre and game room gives you a place to let the kids have fun while you enjoy your own space in the sunroom. Adults will also enjoy a friendly game of poker or bumper p

Located in Sand Lake, Wisconsin, United States. Enchanting Modern Farmhouse with Picturesque Views This 1875 farmhouse on old homestead, renovated inside & out, offers a serene getaway for family & friends.Open floor plan perfect for cooking, dining, entertaining & relaxing. Cozy nooks, both upstairs & down, provide plenty of places to work, read & play. Wide-plank hardwood ash floors add a sophisticated touch to this woodland farmhouse. Whimsical art accents give charm to a highly functional layout. 4BR and 3BA (one soaking tub and 3 showers), W/D, Mudroom & Sun room. 3-season porch. 2 exterior porches. Patio, outdoor eating area and fire pit. One outdoor “Ring” doorbell camera on roadside door facing road. Indoor gas fireplace/unit in living room. Beautiful views of fields, barns, woods, mountains & stars.~20 min to June Farms, Jiminy Peak & Pineridge Cross Country Ski Areas. Nearby Cherry Plain State Park, Mount Greylock, Clark Art Institute, MASSMoCA, Tanglewood and more!Plentiful fans and mountain breezes (no AC) in spring/sum

Located in Stockbridge, Wisconsin, United States. Modern Cottage in the heart of the Berkshires with new exterior flex space! 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 s

Located in Stockbridge, Wisconsin, United States. Rockspring by AvantStay | Huge Berkshires Estate This charming Berkshires estate consists of a beautiful main house, an ample separate recreation space, and a private pool area. Welcome to Rockspring! located in Stockbridge, your group will be surrounded by all of the area's natural beauty while enjoying a bright, contemporary design and tons of amenities. Rockspring features three kitchens: two in the main house and one in the recreation space. The large rec building also has a sitting area with dual sectionals, foosball, and a full bathroom. Back at the main home, you'll find double living rooms, multiple fireplaces, and bedrooms with private balconies and ensuite bathrooms. Enjoy an al fresco meal at the outdoor dining space on the patio, lounge near the pool, or head into town for even more dining, shopping, and entertainment options. No matter what brings your group to the Berkshires, Rockspring is ready to show you an unforgettable stay!AvantStay provides an upscale experience wi

Located in Great Barrington, Massachusetts, United States. 5 BD, 3 Baths, sleeps 12 - the pool is open & a few openings for Summer 2024 ! NOTE: Our street name has changed to Woodland Hill (from Squaw Peak). Same house, same house number - different street name.)BOOKING FOR THE REST OF 2024 AND THROUGH 2025! After a fully booked summer 2023, and bookings into September 2024, we are booking for the remainder 2024 and all of 2025 We are excited to see returning guests as well as new ones. Our five bedroom, three bath, two fireplaces, and two large 'family' rooms are ready for you and your guests. Almost three acres of property give you privacy, but you are less than 2 miles from Great Barrington, 5 minutes from Ski Butternut, and inches away from a spectacular views of New England 'country' life. Local restaurants for all tastes abound, our kitchen has all the implements you need for staying at 'home' for a meal. And the house you'll be renting - about that: A week, a month, a weekend, or a few days in the beautiful Berkshires - -

Located in Sheffield, Montana, United States. Family Friendly in Sheffield, private yet close to everything! Your perfect country escape. Clean, spacious, light and airy home set in the middle of a meadow on 20 acres. Complete privacy, yet 10 minutes to downtown Great Barrington. Close to skiing at both Catamount and Butternut. There is room for everyone, with 4 bedrooms, including two master suites. The first floor features an open concept kitchen/living/dining, along with a powder room, spacious mudroom and a gorgeous newly added 4 season sun room with radiant heat. There is also a queen bedded master suite on the first floor with a walk in closet and bathroom featuring a Jacuzzi tub. The second floor has 3 additional bedrooms including a second master suite that has both a king sized bed and a twin bed, and a bathroom with a walk in shower (no tub). An additional bedroom features a full size bed, and the last bedroom has a twin over full bunk. An additional bathroom with tub completes the second floor. Luxury bamboo sheets on

Located in Stockbridge, Wisconsin, United States. Walk into town, soak up sun on enclosed porch & steps away from nature trails! Prior guests of this charming house next to the forest trails have already reserved their return stay for next year to ensure its availability!Beautifully 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.The house has heating & air-conditioning, a dedicated office, laundry room and 3 bedrooms, including: Master Bedroom (White Room)- This en suite room has a highly-desirable

Located in Stockbridge, Wisconsin, United States. Find your Sanctuary at The Rectory at Stockbridge In the heart of Stockbridge, Massachusetts, the rectory at St. Joseph's Church offers guests a truly divine retreat. This historic gem has been transformed into an exquisite short-term lodging, inviting you to experience a blend of timeless elegance and modern comfort. With beautifully appointed rooms and a tranquil garden, it's the perfect sanctuary for those seeking solace and rejuvenation. For a spiritual journey, the Divine Mercy Shrine beckons, offering a place of reflection and devotion. Sleeps 8-12 guests.

Located in West Stockbridge, Massachusetts, United States. Perfect setting for Family Vacations Short and Long Term Stays Welcomed. Private Estate Centrally located to all Berkshire attractions and just mins. from the Mass Pike.Perfect for any event. Wedding, Reunions, Business get aways. Large chefs kitchen with 60" Wolf Range, Subzero Refrigerator/Freezer, and massive island with white marble thru out.A screened porch off the kitchen with BBQ grill right outside makes enjoying the Berkshire weather a perfect place to have meals or an afternoon snack. Easy access to Tanglewood, Stockbridge, Great Barrington, Lenox. Great restaurants are a few minutes drive along with shopping and Museums. All attractions and summer theater are very close by.4 Bedrooms, a Den with Queen pullout couch and bathBedroom Descriptions(2) Masters both with King Beds 1 on first floor the other on 2nd floor both with full baths 1 room Queen Bed other King share full bath on 2nd floorDen with pull out queen sleeper with bathLower level i

Located in West Stockbridge, Massachusetts, United States. Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox) Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This 2BR home can sleep up to 6 people. All of our mattresses have been replaced in June '21.Enjoy a nice cup of hot chocolate by the fireplace in the living room after a day of exploring the town. ★ LOCATION ★We're conveniently located in the middle of these major attractions: • Kripalu Center For Yoga & Health (4 minutes away)• Tanglewood (5 minutes away)• Stockbridge Bowl - has a cute beach and boat launch ramp (3 minutes drive, 10 minutes walk)• Norman Rockwell Museum (7 minutes away)• Butternut - great for skiing (20 minutes away)• Jacob's Pillow (30 minutes away)★ GUESTS ★Our cute and convenient condo is perfect for:• couples on a romantic getaway• families on a ski trip• friends on a long overdue trip to reconnect• performing artists from Tanglewood• those looking for longterm or temporary housingAll are welcom

Located in Sheffield, Montana, United States. 12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room Beautiful country home with 3 bedrooms plus a kids loft, 6 minutes to Great Barrington with lots to discover. 12 minutes to Butternut Skiing, 15 minutes to Catamount Skiing. Electric car charger, hot tub, fire place, game room with pool table and pac man- loads of hiking, skiing, shopping, lakes and waterfalls, Sheffield is an amazing location in the Berkshires and a great vacation spot! We love our home and know you will too!

Located in Stockbridge, Wisconsin, United States. Modern Family Retreat in Serene Stockbridge Woods ***WE ALSO HAVE 31 5-STAR REVIEWS ON AIRBNB******NEW SUMMER DATES NOW OPEN***Private Forest Retreat | Heart of the Berkshires | Mins to Stockbridge, Lenox + GB | Kids Area | OfficeNestled on over an acre of tranquil forest land, our property offers a serene escape down a charming dirt road, with nature walks right outside the door.- Fast, reliable Wi-Fi- Dedicated workspace- Covered back porch with comfortable furniture- Perfect for couples, families, or creative retreats**Spacious | Modern | Cozy | Inviting | Secluded | Nature**Our home, nestled in the heart of the Berkshires, is close to attractions for all ages: Tanglewood, Kripalu, Norman Rockwell Museum, ski areas, hiking, dining, and more. Enjoy a serene environment with modern conveniences and abundant natural light.**Main Area:**- Open floor plan with cathedral ceilings- Gas fireplace, heat/AC, ceiling fans- Large dining table (seats 6-8)- Ample natural light and wood floors**Ki