Great Barrington, MA

Rosecliff Estate with Pool

Copied to clipboard
Click to copy
15 guests
6 bedrooms
8 bathrooms
9500 sqft

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.

  • Pool outdoor
  • Hot tub
  • Fire pit
15 guests
6 bedrooms
8 bathrooms
9500 sqft

  • Flexible check-in & out

    Check-in after 4:00 PM • Check-out before 10:00 AM

  • Easy cancellation


About this 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) AvailabilityMin Stay (nights)
Feb 24, 2026$695Available3
Feb 25, 2026$695Available3
Feb 26, 2026$695Available3
Feb 27, 2026$695Available3
Feb 28, 2026$695Available3
Mar 1, 2026$695Available3
Mar 2, 2026$695Available3
Mar 3, 2026$695Available3
Mar 4, 2026$695Available3
Mar 5, 2026$695Available3
Mar 6, 2026$695Available3
Mar 7, 2026$695Available3
Mar 8, 2026$695Available3
Mar 9, 2026$695Available3
Mar 10, 2026$695Available3
Mar 11, 2026$695Available3
Mar 12, 2026$695Available3
Mar 13, 2026$695Available3
Mar 14, 2026$695Available3
Mar 15, 2026$695Available3
Mar 16, 2026$695Available3
Mar 17, 2026$695Available3
Mar 18, 2026$695Available3
Mar 19, 2026$695Available3
Mar 20, 2026$695Available3
Mar 21, 2026$695Available3
Mar 22, 2026$695Available3
Mar 23, 2026$695Available3
Mar 24, 2026$695Available3
Mar 25, 2026$695Available3
Mar 26, 2026$695Available3
Mar 27, 2026$695Available3
Mar 28, 2026$695Available3
Mar 29, 2026$695Available3
Mar 30, 2026$695Available3
Mar 31, 2026$695Available3
Apr 1, 2026$695Available3
Apr 2, 2026$695Available3
Apr 3, 2026$695Available3
Apr 4, 2026$695Available3
Apr 5, 2026$695Available3
Apr 6, 2026$695Available3
Apr 7, 2026$695Available3
Apr 8, 2026$695Available3
Apr 9, 2026$695Available3
Apr 10, 2026$695Available3
Apr 11, 2026$695Available3
Apr 12, 2026$695Available3
Apr 13, 2026$695Available3
Apr 14, 2026$695Available3
Apr 15, 2026$695Available3
Apr 16, 2026$695Available3
Apr 17, 2026$695Available3
Apr 18, 2026$695Available3
Apr 19, 2026$695Available3
Apr 20, 2026$695Available3
Apr 21, 2026$695Available3
Apr 22, 2026$695Available3
Apr 23, 2026$695Available3
Apr 24, 2026$695Available3
Apr 25, 2026$695Available3
Apr 26, 2026$695Available3
Apr 27, 2026$695Available3
Apr 28, 2026$695Available3
Apr 29, 2026$695Available3
Apr 30, 2026$695Available3
May 1, 2026$695Available3
May 2, 2026$695Available3
May 3, 2026$695Available3
May 4, 2026$695Available3
May 5, 2026$695Available3
May 6, 2026$695Available3
May 7, 2026$695Available3
May 8, 2026$695Available3
May 9, 2026$695Available3
May 10, 2026$695Available3
May 11, 2026$695Available3
May 12, 2026$695Available3
May 13, 2026$695Available3
May 14, 2026$695Available3
May 15, 2026$695Available3
May 16, 2026$695Available3
May 17, 2026$695Available3
May 18, 2026$695Available3
May 19, 2026$695Available3
May 20, 2026$695Available3
May 21, 2026$695Available3
May 22, 2026$695Available3
May 23, 2026$695Available3
May 24, 2026$695Available3
May 25, 2026$695Available3

Top notch amenities

GUEST FAVORITES

Pool outdoor
Hot tub
Game Room
Fire pit
Fire place
BBQ Area
Patio
Balcony
Air hockey

Where you'll sleep



Explore Great Barrington, MA

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

Things to know

Here are some things which you should know before booking Rosecliff Estate with Pool

House rules

Check-in after 4:00 PM
Check-out before 10:00 AM
15 guests maximum
Pets not allowed
No smoking - fees will apply
Events not permitted
Commercial photography requires approval

Cancellation policy

This property follows Berkshire Rentals’s standard cancellation policy.