Great Barrington, MA
Rosecliff Estate with Pool
About the property
Rosecliff Amenities: Main House, Heated Pool with Pool house, Sleeps 13 in beds or 15 max. high speed WIFI internet and good cell service, Smart TVs with Streaming TV channels, central AC throughout, several areas for outdoor seating, sun umbrellas, (2) propane grills, mountain views, all high end appliances, sun room, washer/dryer (3), several gas and wood burning fireplaces, attached garage, easy access to all Berkshires venues - close to both Butternut and Catamount, less than 5 mins to the center of Great Barrington. NO smoking, please. Welcome to Rosecliff! We are so happy to present this exceptional Berkshire estate that includes the main house, heated pool, and pool house. The main house has 5 bedrooms with 5 ensuite bathrooms plus 2 half baths and sleeps up to 11 in beds or 13 max (with an additional sleep space sofa bed). The pool house sleeps 2 more guests with another full bathroom and is fully heated, and cooled, and can be made available year-round. The main house is 9,500 sq ft. This property is so lovely and has so much to offer. The house sits back far from the country road and is welcoming the minute you pull in. The main floor has a entry that leads into the bright open kitchen. The appliances are all stainless, with plenty of storage, gadgets and prep space that offer guests a premier cooking experience - whether they want to create their own meals or bring in a local chef. There is a large farmhouse style table for casual dining and another gracious dining room, with a cozy propane fireplace, for more formal gatherings. The kitchen has big meadow views and is sun-filled. There is a small sitting area between the kitchen and dining room that offers a cozy space, with a full wet bar consisting of a dishwasher, ice maker, sink and wine cooler. Continue past the dining room to the large living room with another fireplace and plenty of seating. There is a cozy media room with a large TV for streaming all your favorite channels. There is still more to enjoy on the main floor with a summer sun porch and another parlor for easy gatherings, with seating and beautiful views. Just outside, on the covered patio is a lovely set up with seating and a grill for taking in the late afternoon views and sunsets. Upstairs you have all 5 bedrooms - each with ensuite bathrooms - plus an additional bonus Playroom that has a fold out sofa for another guest or 2. This area has its own entrance through the back staircase and has another large TV, an efficient kitchenette with microwave, fridge, and coffee maker, etc. It also has its own full bathroom, with a shower. This is a terrific kid's space for TV viewing, gaming and is perfect for a nanny or babysitter. The 5-bedroom suites are fabulous - each with its own style and attention to detail. The primary is grand with beautiful views, a king bed, sitting area with gas fireplace and its own TV, a large dressing area and the best primary bathroom around - with a huge walk-in shower, soaking tub, 2 sinks and another sitting area. Guest room #2 has another king bed and its own brick gas fireplace. The ensuite bathroom has a luxurious clawfoot soaking tub and a walk-in shower. Guest room #3 has 2 Twin beds, built-in closets and drawers, and an ensuite full bathroom with a tub/shower combination. Guest room #4 overlooks the pool and has a Queen bed and a Twin daybed so 3 can easily sleep here. This ensuite bathroom is a “Jack n Jill' style and shares with guest room #5. The bathroom has its own walk-in shower and another glorious soaking tub. This beautiful bathroom also has a small Juliet balcony. Guest room #5, also overlooks the pool, has a Queen bed and its own TV. The bonus playroom is located on the second floor, up the back staircase, and can also be accessed on a roof deck off the primary bedroom and guest room #2. It has another TV and is a great space for kids as well as a Queen sofa bed for added guests and has its own kitchenette. The Pool house, located less than a minute's walk from the main house (heated, also with AC) offers another option to guests with a king bed, sitting room with mountain and meadow views, has its own kitchenette, TV, and full bathroom with walk-in shower. There is another terrific full kitchen just adjacent to Pool House, known as the “Cook Shack”. This area has its own fridge/freezer, range, dishwasher, utensils, set ups, etc., and another bathroom so there is no need for swimmers to drip water into the main house or pool house. Outside, there is so much to enjoy here on this 16+ acre spread. The heated pool has plenty of both lounge and table seating, umbrellas for shade, another grill, and striped pool towels are included. The pool has easy access to the pool house and cook shack. The lawn is vast and lush and offers plenty of run-around space. There is a marvelous outdoor seating area just outside the kitchen with a stone patio, grill, ultra-lux seating and a fire pit. This is a stunning way to end the day, overlooking mountain and meadow views. Location: Rosecliff is less than 5 minutes to the center of Great Barrington, less than 15 to Ski Butternut and less than 10 to Catamount. And, just about 30 minutes to Tanglewood. Rosecliff offers our guests everything possible in a luxury retreat with close access to all the Berkshire has to offer. Main House Guest Room Bed and Bath Recap : sleeps 11 in beds or 13 max (All on second floor): Primary Ensuite: King bed, soaking tub, and oversized walk-in shower. Bedroom #2, is ensuite: King bed, shower and soaking tub. Bedroom #3, is ensuite: 2 twin beds, with tub/shower combination. Bedroom #4, Queen bed and twin daybed. Bedroom #5 has a Queen bed. Guest bath is shared, Jack 'n Jill style between Guest rooms #4 and #5 Bonus Playroom has a kitchenette, full bathroom (tub/shower) and a Queen foldout bed. Pool House: Sleeps 2 more guests in a king bed, kitchenette, and full bathroom with shower. Total sleep capacity in beds is 15.
Rosecliff Amenities: Main House, Heated Pool with Pool house, Sleeps 13 in beds or 15 max. high speed WIFI internet and good cell service, Smart TVs with Streaming TV channels, central AC throughout, several areas for outdoor seating, sun umbrellas, (2) propane grills, mountain views, all high end appliances, sun room, washer/dryer (3), several gas and wood burning fireplaces, attached garage, easy access to all Berkshires venues - close to both Butternut and Catamount, less than 5 mins to the center of Great Barrington. NO smoking, please. Welcome to Rosecliff! We are so happy to present this exceptional Berkshire estate that includes the main house, heated pool, and pool house. The main house has 5 bedrooms with 5 ensuite bathrooms plus 2 half baths and sleeps up to 11 in beds or 13 max (with an additional sleep space sofa bed). The pool house sleeps 2 more guests with another full bathroom and is fully heated, and cooled, and can be made available year-round. The main house is 9,500 sq ft. This property is so lovely and has so much to offer. The house sits back far from the country road and is welcoming the minute you pull in. The main floor has a entry that leads into the bright open kitchen. The appliances are all stainless, with plenty of storage, gadgets and prep space that offer guests a premier cooking experience - whether they want to create their own meals or bring in a local chef. There is a large farmhouse style table for casual dining and another gracious dining room, with a cozy propane fireplace, for more formal gatherings. The kitchen has big meadow views and is sun-filled. There is a small sitting area between the kitchen and dining room that offers a cozy space, with a full wet bar consisting of a dishwasher, ice maker, sink and wine cooler. Continue past the dining room to the large living room with another fireplace and plenty of seating. There is a cozy media room with a large TV for streaming all your favorite channels. There is still more to enjoy on the main floor with a summer sun porch and another parlor for easy gatherings, with seating and beautiful views. Just outside, on the covered patio is a lovely set up with seating and a grill for taking in the late afternoon views and sunsets. Upstairs you have all 5 bedrooms - each with ensuite bathrooms - plus an additional bonus Playroom that has a fold out sofa for another guest or 2. This area has its own entrance through the back staircase and has another large TV, an efficient kitchenette with microwave, fridge, and coffee maker, etc. It also has its own full bathroom, with a shower. This is a terrific kid's space for TV viewing, gaming and is perfect for a nanny or babysitter. The 5-bedroom suites are fabulous - each with its own style and attention to detail. The primary is grand with beautiful views, a king bed, sitting area with gas fireplace and its own TV, a large dressing area and the best primary bathroom around - with a huge walk-in shower, soaking tub, 2 sinks and another sitting area. Guest room #2 has another king bed and its own brick gas fireplace. The ensuite bathroom has a luxurious clawfoot soaking tub and a walk-in shower. Guest room #3 has 2 Twin beds, built-in closets and drawers, and an ensuite full bathroom with a tub/shower combination. Guest room #4 overlooks the pool and has a Queen bed and a Twin daybed so 3 can easily sleep here. This ensuite bathroom is a “Jack n Jill' style and shares with guest room #5. The bathroom has its own walk-in shower and another glorious soaking tub. This beautiful bathroom also has a small Juliet balcony. Guest room #5, also overlooks the pool, has a Queen bed and its own TV. The bonus playroom is located on the second floor, up the back staircase, and can also be accessed on a roof deck off the primary bedroom and guest room #2. It has another TV and is a great space for kids as well as a Queen sofa bed for added guests and has its own kitchenette. The Pool house, located less than a minute's walk from the main house (heated, also with AC) offers another option to guests with a king bed, sitting room with mountain and meadow views, has its own kitchenette, TV, and full bathroom with walk-in shower. There is another terrific full kitchen just adjacent to Pool House, known as the “Cook Shack”. This area has its own fridge/freezer, range, dishwasher, utensils, set ups, etc., and another bathroom so there is no need for swimmers to drip water into the main house or pool house. Outside, there is so much to enjoy here on this 16+ acre spread. The heated pool has plenty of both lounge and table seating, umbrellas for shade, another grill, and striped pool towels are included. The pool has easy access to the pool house and cook shack. The lawn is vast and lush and offers plenty of run-around space. There is a marvelous outdoor seating area just outside the kitchen with a stone patio, grill, ultra-lux seating and a fire pit. This is a stunning way to end the day, overlooking mountain and meadow views. Location: Rosecliff is less than 5 minutes to the center of Great Barrington, less than 15 to Ski Butternut and less than 10 to Catamount. And, just about 30 minutes to Tanglewood. Rosecliff offers our guests everything possible in a luxury retreat with close access to all the Berkshire has to offer. Main House Guest Room Bed and Bath Recap : sleeps 11 in beds or 13 max (All on second floor): Primary Ensuite: King bed, soaking tub, and oversized walk-in shower. Bedroom #2, is ensuite: King bed, shower and soaking tub. Bedroom #3, is ensuite: 2 twin beds, with tub/shower combination. Bedroom #4, Queen bed and twin daybed. Bedroom #5 has a Queen bed. Guest bath is shared, Jack 'n Jill style between Guest rooms #4 and #5 Bonus Playroom has a kitchenette, full bathroom (tub/shower) and a Queen foldout bed. Pool House: Sleeps 2 more guests in a king bed, kitchenette, and full bathroom with shower. Total sleep capacity in beds is 15.
Availability & Pricing
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Apr 24, 2026 | $834 | Not Available | 31 |
| Apr 25, 2026 | $834 | Not Available | 31 |
| Apr 26, 2026 | $834 | Not Available | 31 |
| Apr 27, 2026 | $834 | Not Available | 31 |
| Apr 28, 2026 | $834 | Not Available | 31 |
| Apr 29, 2026 | $834 | Not Available | 31 |
| Apr 30, 2026 | $834 | Not Available | 31 |
| May 1, 2026 | $834 | Not Available | 31 |
| May 2, 2026 | $834 | Not Available | 31 |
| May 3, 2026 | $834 | Not Available | 31 |
| May 4, 2026 | $834 | Not Available | 31 |
| May 5, 2026 | $834 | Not Available | 31 |
| May 6, 2026 | $834 | Not Available | 31 |
| May 7, 2026 | $834 | Not Available | 31 |
| May 8, 2026 | $834 | Not Available | 31 |
| May 9, 2026 | $834 | Not Available | 31 |
| May 10, 2026 | $834 | Not Available | 31 |
| May 11, 2026 | $834 | Not Available | 31 |
| May 12, 2026 | $834 | Not Available | 31 |
| May 13, 2026 | $834 | Not Available | 31 |
| May 14, 2026 | $834 | Not Available | 31 |
| May 15, 2026 | $1,500 | Not Available | 31 |
| May 16, 2026 | $1,500 | Not Available | 31 |
| May 17, 2026 | $1,500 | Not Available | 31 |
| May 18, 2026 | $1,500 | Not Available | 31 |
| May 19, 2026 | $1,500 | Not Available | 31 |
| May 20, 2026 | $1,500 | Not Available | 31 |
| May 21, 2026 | $1,500 | Not Available | 31 |
| May 22, 2026 | $1,500 | Not Available | 31 |
| May 23, 2026 | $1,500 | Not Available | 31 |
| May 24, 2026 | $1,500 | Not Available | 31 |
| May 25, 2026 | $1,500 | Not Available | 31 |
| May 26, 2026 | $1,500 | Not Available | 31 |
| May 27, 2026 | $1,500 | Not Available | 31 |
| May 28, 2026 | $1,500 | Not Available | 31 |
| May 29, 2026 | $1,500 | Not Available | 31 |
| May 30, 2026 | $1,500 | Not Available | 31 |
| May 31, 2026 | $1,500 | Not Available | 31 |
| Jun 1, 2026 | $1,500 | Not Available | 31 |
| Jun 2, 2026 | $1,500 | Not Available | 31 |
| Jun 3, 2026 | $1,500 | Not Available | 31 |
| Jun 4, 2026 | $1,500 | Not Available | 31 |
| Jun 5, 2026 | $1,500 | Not Available | 31 |
| Jun 6, 2026 | $1,500 | Not Available | 31 |
| Jun 7, 2026 | $1,500 | Not Available | 31 |
| Jun 8, 2026 | $1,500 | Not Available | 31 |
| Jun 9, 2026 | $1,500 | Not Available | 31 |
| Jun 10, 2026 | $1,500 | Not Available | 31 |
| Jun 11, 2026 | $1,500 | Not Available | 31 |
| Jun 12, 2026 | $1,500 | Not Available | 31 |
| Jun 13, 2026 | $1,500 | Not Available | 31 |
| Jun 14, 2026 | $1,500 | Not Available | 31 |
| Jun 15, 2026 | $1,500 | Not Available | 31 |
| Jun 16, 2026 | $1,500 | Not Available | 31 |
| Jun 17, 2026 | $1,500 | Not Available | 31 |
| Jun 18, 2026 | $1,500 | Not Available | 31 |
| Jun 19, 2026 | $1,500 | Not Available | 31 |
| Jun 20, 2026 | $1,500 | Not Available | 31 |
| Jun 21, 2026 | $1,500 | Not Available | 31 |
| Jun 22, 2026 | $1,500 | Not Available | 31 |
| Jun 23, 2026 | $1,500 | Not Available | 31 |
| Jun 24, 2026 | $1,500 | Not Available | 31 |
| Jun 25, 2026 | $1,500 | Not Available | 31 |
| Jun 26, 2026 | $1,500 | Not Available | 31 |
| Jun 27, 2026 | $1,500 | Not Available | 31 |
| Jun 28, 2026 | $1,500 | Not Available | 31 |
| Jun 29, 2026 | $1,500 | Not Available | 31 |
| Jun 30, 2026 | $1,500 | Not Available | 31 |
| Jul 1, 2026 | $1,500 | Not Available | 31 |
| Jul 2, 2026 | $1,500 | Not Available | 31 |
| Jul 3, 2026 | $1,500 | Not Available | 31 |
| Jul 4, 2026 | $1,500 | Not Available | 31 |
| Jul 5, 2026 | $1,500 | Not Available | 31 |
| Jul 6, 2026 | $1,500 | Not Available | 31 |
| Jul 7, 2026 | $1,500 | Not Available | 31 |
| Jul 8, 2026 | $1,500 | Not Available | 31 |
| Jul 9, 2026 | $1,500 | Not Available | 31 |
| Jul 10, 2026 | $1,500 | Not Available | 31 |
| Jul 11, 2026 | $1,500 | Not Available | 31 |
| Jul 12, 2026 | $1,500 | Not Available | 31 |
| Jul 13, 2026 | $1,500 | Not Available | 31 |
| Jul 14, 2026 | $1,500 | Not Available | 31 |
| Jul 15, 2026 | $1,500 | Not Available | 31 |
| Jul 16, 2026 | $1,500 | Not Available | 31 |
| Jul 17, 2026 | $1,500 | Not Available | 31 |
| Jul 18, 2026 | $1,500 | Not Available | 31 |
| Jul 19, 2026 | $1,500 | Not Available | 31 |
| Jul 20, 2026 | $1,500 | Not Available | 31 |
| Jul 21, 2026 | $1,500 | Not Available | 31 |
| Jul 22, 2026 | $1,500 | Not Available | 31 |
| Jul 23, 2026 | $1,500 | Not Available | 31 |
Where you'll sleep
Amenities
Guests love this place
4.86
based on 7 reviews
Overall rating
Rosecliff August 2025 Beautiful house and gorgeous view from the back. The bedroom layout was good for a large extended family (13-15). Lots of bathrooms. House was clean, well stocked with dinnerware and cookware. Outdoor patio ended up being a primary gathering spot. Bedrooms and beds were very comfortable. Pool was a bonus. Also a great gathering place. Loved the well placed shade umbrellas. In general, we really enjoyed our stay. Thank you.
Superb! Just superb. Really felt like a second home, better than our regular home!
Highly Recommend It is clear the Owners took great care to build a lovely home on an ideal setting. It was meant for a large family to enjoy the peaceful setting, wonderful pool and spacious area. Would recommend highly.
4.86
based on 7 reviews
Overall rating
Rosecliff August 2025 Beautiful house and gorgeous view from the back. The bedroom layout was good for a large extended family (13-15). Lots of bathrooms. House was clean, well stocked with dinnerware and cookware. Outdoor patio ended up being a primary gathering spot. Bedrooms and beds were very comfortable. Pool was a bonus. Also a great gathering place. Loved the well placed shade umbrellas. In general, we really enjoyed our stay. Thank you.
Superb! Just superb. Really felt like a second home, better than our regular home!
Highly Recommend It is clear the Owners took great care to build a lovely home on an ideal setting. It was meant for a large family to enjoy the peaceful setting, wonderful pool and spacious area. Would recommend highly.
Excellent Our family stay during the last week of December 2023 at Rosecliff was excellent! The house and grounds are beautiful. The finishes in the main house are top-level and obviously done by the homeowner with a lot of thought and care. We had 8 adults and 6 children (ages 10 years-9 months) and there was plenty of room for everyone. The location is very convenient to town (5-10 minutes) and to Butternut (10-15 minutes, at most), as well as to restaurants and food shopping. We highly recommend this property and look forward to the possibility of using it again! Claudia and Sarah at Berkshire Rentals went above and beyond. I can't say enough about the high level of their responsiveness, attentiveness to our needs, friendliness, and overall customer service. They were incredibly helpful and professional, and an absolute pleasure to deal with.
LOVED it! Rosecliff is a very special and beautiful place. We had the whole family and experienced a wonderful and fun week here. Everyone LOVE LOVE LOVED it from the youngest to the oldest. The house and grounds are gorgeous, very spacious and well equipped. The kitchen is big and airy and had everything we needed. There are so many rooms and areas of the property to explore and use including the pool house and cook shack. The pool was the perfect place to hang out together and enjoy fun family time. The grounds are so beautifully landscaped and maintained. The house is nicely set back from the street providing privacy with a big lush green lawn, magnificent flowers and trees. You feel like you are in remote solitude but you are actually just a few minutes from the center of Great Barrington, lots of restaurants, markets, plenty of shops. We loved riding bikes around the extended beautiful neighborhood. In back of the house is a large natural area for viewing and exploring. What a great place!
Wonderful stay Our group (6 adults, 5 children) had a wonderful stay at Rosecliff. The house was charming with high quality finishes and tons of space. The kitchen was very well stocked with lots of nice equipment and made cooking large meals a breeze. Our kids loved playing in the heated pool, which was kept at a nice warm temperature and had a big shallow half that they could stand in. Overall, the house definitely exceeded expectations and we highly recommend it.
Fabulous Rosecliff! The house is in excellent shape, updated and everything works perfectly. attention to detail is superb. The location in Great Barrington is ideal, a very short drive to the town. the 16 acres are beautifully maintained as well.
Where you'll be
Great Barrington, MA, 1230, US
Discover the cultural vibrancy and natural beauty of Great Barrington, a destination where historic charm and outdoor recreation converge. Nearby, you can experience world-class performances at the Mahaiwe Performing Arts Center or browse local seasonal offerings at the Berkshire Food Co-op. Just a short drive away, adventure awaits on the slopes of Ski Butternut and the scenic hiking trails of Monument Mountain Reservation, followed by an evening of sophisticated
Discover the cultural vibrancy and natural beauty of Great Barrington, a destination where historic charm and outdoor recreation converge. Nearby, you can experience world-class performances at the Mahaiwe Performing Arts Center or browse local seasonal offerings at the Berkshire Food Co-op. Just a short drive away, adventure awaits on the slopes of Ski Butternut and the scenic hiking trails of Monument Mountain Reservation, followed by an evening of sophisticated