$0
for 0 nights

Home in Great Barrington, MA

6 bedrooms

9 beds

7 bathrooms

15 guests

9500 sq. ft.

Operated by a Wander partner

Trusted operators, vetted by Wander

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.

Property License: C0422741130

Where you’ll sleep

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

Amenities

Common Amenities

  • Arcade machine
  • Air hockey
  • Hot tub
  • Dining table
  • Free parking
  • Toys
  • Books
  • Balcony
  • Patio
  • BBQ Area
  • Outdoor pool
  • Wheelchair accessible
  • Fire pit
  • Game Room
  • Wifi
  • Dedicated workspace
  • Carbon monoxide detector
  • Fire extinguisher
  • First aid kit
  • Smoke detector

Exterior

  • Garage

Living room

  • Air conditioning
  • Fire place
  • Heating
  • Sound system
  • TV

Kitchen

  • Dishes
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Fridge
  • Spices
  • Stove
  • Toaster
  • Coffee maker

Bedroom 1

  • Bed linens
  • TV
  • Fire place

Bedroom 2

  • Bed linens
  • Fire place

Bedroom 3

  • Bed linens

Bedroom 4

  • Bed linens

Bedroom 5

  • Bed linens
  • TV

Bedroom 6

  • Bed linens

Bathroom 1

  • Hair dryer
  • Bath linens

Bathroom 2

  • Bath linens

Bathroom 3

  • Bath linens

Bathroom 4

  • Bath linens

Bathroom 5

  • Bath linens

Bathroom 6

  • Bath linens

Bathroom 7

  • Bath linens

Bathroom 8

  • Bath linens

Common area

  • TV

Laundry room

  • Dryer
  • Washer

Media Room

  • TV

Bonus Room

  • TV
  • Air conditioning

4.9 · 7 reviews

Where you’ll be

Great Barrington, MA 1230, US

Great Barrington, MA, US
42.182128-73.3824039
Timezone: America/New_York

Restaurants

The Prairie Whale

The 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

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

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

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]

Little Cat Lodge

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

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.

Attractions

Monument Mountain Reservation

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.

Ski Butternut

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.

Beartown State Forest

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]

Thom Reed - UFO Park

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]

Catamount Aerial Adventure Park

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.

Catamount Mountain Resort

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 Beach and Conservation Forest Trails

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.

Things to know

Cancellation policy

50% refund up to 30 days before check-in. No refund after that.

Property rules

Pets not allowed

No smoking - fees will apply

Events not allowed

Safety & security

Check-in after 3:00 pm

Check-out before 11:00 am

15 guests maximum

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Jul 11, 2026$1500Not Available
Jul 12, 2026$1500Not Available
Jul 13, 2026$1500Not Available
Jul 14, 2026$1500Not Available
Jul 15, 2026$1500Not Available
Jul 16, 2026$1500Not Available
Jul 17, 2026$1500Not Available
Jul 18, 2026$1500Not Available
Jul 19, 2026$1500Not Available
Jul 20, 2026$1500Not Available
Jul 21, 2026$1500Not Available
Jul 22, 2026$1500Not Available
Jul 23, 2026$1500Not Available
Jul 24, 2026$1500Not Available
Jul 25, 2026$1500Not Available
Jul 26, 2026$1500Not Available
Jul 27, 2026$1500Not Available
Jul 28, 2026$1500Not Available
Jul 29, 2026$1167Not Available
Jul 30, 2026$1333Available
Jul 31, 2026$1333Available
Aug 1, 2026$1333Available
Aug 2, 2026$1333Available
Aug 3, 2026$1333Available
Aug 4, 2026$1333Available
Aug 5, 2026$1333Available
Aug 6, 2026$1333Available
Aug 7, 2026$1333Available
Aug 8, 2026$1333Available
Aug 9, 2026$1333Available
Aug 10, 2026$1333Available
Aug 11, 2026$1333Available
Aug 12, 2026$1333Available
Aug 13, 2026$1333Available
Aug 14, 2026$1333Available
Aug 15, 2026$1333Available
Aug 16, 2026$1333Available
Aug 17, 2026$1333Available
Aug 18, 2026$1333Available
Aug 19, 2026$1333Available
Aug 20, 2026$1333Available
Aug 21, 2026$1333Available
Aug 22, 2026$1333Available
Aug 23, 2026$1333Available
Aug 24, 2026$1333Available
Aug 25, 2026$1333Available
Aug 26, 2026$1333Available
Aug 27, 2026$1333Available
Aug 28, 2026$1333Available
Aug 29, 2026$1333Available
Aug 30, 2026$1333Available
Aug 31, 2026$1167Not Available
Sep 1, 2026$1167Not Available
Sep 2, 2026$1167Not Available
Sep 3, 2026$1167Not Available
Sep 4, 2026$1167Not Available
Sep 5, 2026$1167Not Available
Sep 6, 2026$1167Not Available
Sep 7, 2026$1167Not Available
Sep 8, 2026$1167Not Available
Sep 9, 2026$1500Not Available
Sep 10, 2026$1500Not Available
Sep 11, 2026$1500Not Available
Sep 12, 2026$1500Not Available
Sep 13, 2026$1500Not Available
Sep 14, 2026$1500Not Available
Sep 15, 2026$1500Not Available
Sep 16, 2026$1800Not Available
Sep 17, 2026$1800Not Available
Sep 18, 2026$1800Not Available
Sep 19, 2026$1800Not Available
Sep 20, 2026$1800Not Available
Sep 21, 2026$1800Not Available
Sep 22, 2026$1800Not Available
Sep 23, 2026$1800Not Available
Sep 24, 2026$1800Not Available
Sep 25, 2026$1800Not Available
Sep 26, 2026$1800Not Available
Sep 27, 2026$1800Not Available
Sep 28, 2026$1800Not Available
Sep 29, 2026$1800Not Available
Sep 30, 2026$1800Not Available
Oct 1, 2026$1800Not Available
Oct 2, 2026$1800Not Available
Oct 3, 2026$1800Not Available
Oct 4, 2026$1800Not Available
Oct 5, 2026$1800Not Available
Oct 6, 2026$1800Not Available
Oct 7, 2026$1800Not Available
Oct 8, 2026$1800Not Available
Oct 9, 2026$1800Not Available