Operated by a Wander partner
Trusted operators, vetted by Wander
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.
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
2 twin beds
Bedroom 4
1 queen bed
Bedroom 5
1 queen bed
Bedroom 6
1 king bed
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
2 twin beds
Bedroom 4
1 queen bed
Bedroom 5
1 queen bed
Bedroom 6
1 king bed
Great Barrington, MA 1230, US
Great Barrington, MA, USThe Prairie Whale is a farm-to-table restaurant in Great Barrington featuring creative, locally sourced cuisine in a rustic, wood-paneled setting with a Brooklyn-inspired aesthetic. Known for its evolving menu, nose-to-tail butchery program, and commitment to minimizing waste, it offers unfussy yet sophisticated comfort food that changes seasonally.
Barrington Brewery & Restaurant is a solar-powered brewpub in Great Barrington, Massachusetts, serving handcrafted ales and scratch-made food in a rustic barn setting since 1995. Known for its smooth, flavorful beers and locally sourced ingredients, it's a beloved destination for craft beer enthusiasts and casual diners alike.
Hy's Fried is a stylish roadhouse in South Egremont serving hormone-free, gluten-free fried chicken with a crispy exterior and juicy interior, complemented by an energetic atmosphere that doubles as a dance club on weekends.
GB Eats in Great Barrington serves creative American cafe fare all day, from house-made crab cakes and polenta bowls to Berkshire melts and Bloody Marys, all crafted with local ingredients. Enjoy generous portions in a vibrant downtown spot with stunning views of the Berkshire Hills.[1][2][3]
Nestled at the base of Catamount Mountain, Little Cat Lodge serves authentic American cuisine in a cozy Alpine chalet with a roaring fireplace, great wine list, and ski-lodge vibes. Unwind with exceptional dinners and drinks after a day on the slopes.[1][2][3][4]
Great Barrington Bagel Company serves authentic New York-style bagels made fresh daily, featuring 17 cream cheese flavors, smoked fish specialties, and homemade soups in a warm, inviting deli atmosphere that captures old-school NYC charm in the heart of the Berkshires.
Discover Monument Mountain Reservation's thrilling hikes through dense forests, past cascading waterfalls and the dramatic Devil's Pulpit, culminating in sweeping views of the Housatonic Valley from its 1,642-foot summit. Adventure seekers and nature lovers will relish this rewarding Berkshires challenge.
Discover family-friendly Ski Butternut in the Berkshires, where 22 groomed trails, terrain parks, and a dedicated beginner area with top-notch instruction create perfect snow conditions amid stunning views. Ideal for beginners, families, and relaxed skiers seeking affordable, uncompetitive fun.
Discover serene Benedict Pond at Beartown State Forest, where you can kayak, fish, or hike the Appalachian Trail amid deer, bears, and bobcats, with stunning ledges views. Nature lovers and casual adventurers will relish this tranquil Massachusetts escape.[1][3][4][5]
Discover Thom Reed UFO Park, site of America's first officially recognized UFO encounter in 1969, validated by historical society and governor with a massive granite monument near a scenic covered bridge. UFO believers, mystery seekers, and road trip adventurers will love this quirky, star-endorsed landmark.[1][3][5]
Soar through New England's largest aerial adventure park at Catamount, tackling 9 tree-top courses with over 150 ziplines, bridges, and obstacles for 3 thrilling hours. Perfect for families, first-timers, and adrenaline junkies seeking challenge and canopy views.
Soar through New England's largest aerial adventure park at Catamount Mountain Resort, tackling 9 treetop courses with bridges, ladders, and thrilling ziplines for 3 hours of heart-pounding fun. Perfect for adventure-loving families, groups, and kids ages 7+ seeking unforgettable treetop challenges.[2][3][7]
Lake Mansfield offers a perfect blend of water recreation and nature exploration, with a family-friendly beach for swimming and paddling alongside scenic forest trails through 29 acres of preserved woodlands ideal for hiking, bird watching, and peaceful walks.
50% refund up to 30 days before check-in. No refund after that.
Pets not allowed
No smoking - fees will apply
Events not allowed
Check-in after 3:00 pm
Check-out before 11:00 am
15 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Jul 11, 2026 | $1500 | Not Available |
| Jul 12, 2026 | $1500 | Not Available |
| Jul 13, 2026 | $1500 | Not Available |
| Jul 14, 2026 | $1500 | Not Available |
| Jul 15, 2026 | $1500 | Not Available |
| Jul 16, 2026 | $1500 | Not Available |
| Jul 17, 2026 | $1500 | Not Available |
| Jul 18, 2026 | $1500 | Not Available |
| Jul 19, 2026 | $1500 | Not Available |
| Jul 20, 2026 | $1500 | Not Available |
| Jul 21, 2026 | $1500 | Not Available |
| Jul 22, 2026 | $1500 | Not Available |
| Jul 23, 2026 | $1500 | Not Available |
| Jul 24, 2026 | $1500 | Not Available |
| Jul 25, 2026 | $1500 | Not Available |
| Jul 26, 2026 | $1500 | Not Available |
| Jul 27, 2026 | $1500 | Not Available |
| Jul 28, 2026 | $1500 | Not Available |
| Jul 29, 2026 | $1167 | Not Available |
| Jul 30, 2026 | $1333 | Available |
| Jul 31, 2026 | $1333 | Available |
| Aug 1, 2026 | $1333 | Available |
| Aug 2, 2026 | $1333 | Available |
| Aug 3, 2026 | $1333 | Available |
| Aug 4, 2026 | $1333 | Available |
| Aug 5, 2026 | $1333 | Available |
| Aug 6, 2026 | $1333 | Available |
| Aug 7, 2026 | $1333 | Available |
| Aug 8, 2026 | $1333 | Available |
| Aug 9, 2026 | $1333 | Available |
| Aug 10, 2026 | $1333 | Available |
| Aug 11, 2026 | $1333 | Available |
| Aug 12, 2026 | $1333 | Available |
| Aug 13, 2026 | $1333 | Available |
| Aug 14, 2026 | $1333 | Available |
| Aug 15, 2026 | $1333 | Available |
| Aug 16, 2026 | $1333 | Available |
| Aug 17, 2026 | $1333 | Available |
| Aug 18, 2026 | $1333 | Available |
| Aug 19, 2026 | $1333 | Available |
| Aug 20, 2026 | $1333 | Available |
| Aug 21, 2026 | $1333 | Available |
| Aug 22, 2026 | $1333 | Available |
| Aug 23, 2026 | $1333 | Available |
| Aug 24, 2026 | $1333 | Available |
| Aug 25, 2026 | $1333 | Available |
| Aug 26, 2026 | $1333 | Available |
| Aug 27, 2026 | $1333 | Available |
| Aug 28, 2026 | $1333 | Available |
| Aug 29, 2026 | $1333 | Available |
| Aug 30, 2026 | $1333 | Available |
| Aug 31, 2026 | $1167 | Not Available |
| Sep 1, 2026 | $1167 | Not Available |
| Sep 2, 2026 | $1167 | Not Available |
| Sep 3, 2026 | $1167 | Not Available |
| Sep 4, 2026 | $1167 | Not Available |
| Sep 5, 2026 | $1167 | Not Available |
| Sep 6, 2026 | $1167 | Not Available |
| Sep 7, 2026 | $1167 | Not Available |
| Sep 8, 2026 | $1167 | Not Available |
| Sep 9, 2026 | $1500 | Not Available |
| Sep 10, 2026 | $1500 | Not Available |
| Sep 11, 2026 | $1500 | Not Available |
| Sep 12, 2026 | $1500 | Not Available |
| Sep 13, 2026 | $1500 | Not Available |
| Sep 14, 2026 | $1500 | Not Available |
| Sep 15, 2026 | $1500 | Not Available |
| Sep 16, 2026 | $1800 | Not Available |
| Sep 17, 2026 | $1800 | Not Available |
| Sep 18, 2026 | $1800 | Not Available |
| Sep 19, 2026 | $1800 | Not Available |
| Sep 20, 2026 | $1800 | Not Available |
| Sep 21, 2026 | $1800 | Not Available |
| Sep 22, 2026 | $1800 | Not Available |
| Sep 23, 2026 | $1800 | Not Available |
| Sep 24, 2026 | $1800 | Not Available |
| Sep 25, 2026 | $1800 | Not Available |
| Sep 26, 2026 | $1800 | Not Available |
| Sep 27, 2026 | $1800 | Not Available |
| Sep 28, 2026 | $1800 | Not Available |
| Sep 29, 2026 | $1800 | Not Available |
| Sep 30, 2026 | $1800 | Not Available |
| Oct 1, 2026 | $1800 | Not Available |
| Oct 2, 2026 | $1800 | Not Available |
| Oct 3, 2026 | $1800 | Not Available |
| Oct 4, 2026 | $1800 | Not Available |
| Oct 5, 2026 | $1800 | Not Available |
| Oct 6, 2026 | $1800 | Not Available |
| Oct 7, 2026 | $1800 | Not Available |
| Oct 8, 2026 | $1800 | Not Available |
| Oct 9, 2026 | $1800 | Not Available |