Hilltop Escape with Views & Hot Tub

Summary:
Contemporary Berkshire retreat with stunning mountain views, two king suites, media room, hot tub, and wraparound deck. Enjoy sunsets, nearby skiing, hiking, Tanglewood, and Great Barrington. Features include a chef’s kitchen, gas fireplace, fast WiFi, fire pit, and office space. Surrounded by nature on 3.5 wooded acres, just minutes from top attractions. The perfect blend of luxury, privacy, and convenience.

The Space:
Welcome to Hilltop, a serene and stylish Berkshire escape where privacy, luxury, and nature come together in perfect harmony. Perched atop a wooded ridge on 3.5 acres, this contemporary two-story home offers sweeping views of the tree-covered valleys and rolling Berkshire Mountains from nearly every room. Whether you’re here for a romantic getaway, an adventurous family vacation, or a peaceful work-from-home retreat, Hilltop delivers an unforgettable experience in every season.

From the moment you arrive, you’ll feel immersed in the tranquil beauty of the Berkshires. Watch the sunset light up the hills from the expansive wraparound deck or unwind in the seven-person hot tub beneath a canopy of stars. Located just 12 minutes from downtown Great Barrington and within 20–25 minutes of Stockbridge and Lenox, you’ll enjoy quick access to top attractions like Tanglewood, Butternut Ski Resort, Lake Buel, and the area’s world-class dining, shops, hiking trails, and art venues.

Inside, Hilltop features 2,370 square feet of bright, open living space with two luxurious primary suites, 2.5 bathrooms, and a media room that doubles as a third sleeping area. The main level showcases floor-to-ceiling west-facing windows that fill the home with natural light and frame the incredible mountain views. Thoughtfully designed with a mix of modern furnishings and regional antiques, the décor reflects the character and creativity of the Berkshires.

The living room is perfect for gathering, with a soaring ceiling, cozy gas fireplace, and 70” HDTV equipped with Roku for you to connect to your favorite streaming services. The open-concept kitchen and dining area allow everyone to stay connected while preparing meals or enjoying a glass of wine. Chef’s will enjoy the four-burner gas cooktop, double oven, new smart refrigerator with ice maker and in-door filtered water, microwave, dishwasher, and Breville Smart Oven Pro. A French press, Keurig K-Duo Hot and Iced Single Serve and Carafe Coffee Maker to ensure your mornings are off to a delicious start.

The dining room comfortably seats six and is surrounded by windows, making even a casual meal feel special. For those who need to get a bit of work done, the dedicated office/library offers a small desk, computer monitor, reading nook, and 1GB speed WiFi—ideal for remote work or study. This space also connects to the lower-level primary suite and can be used for a pack-n-play if needed.

The main-level primary bedroom features a king-size bed, 55” TV, walk-in closet, and breathtaking views. The spa-inspired en suite bathroom offers dual vanities, a soaking tub, glass-enclosed rain shower with multiple spray options, and a private bidet-equipped toilet room. You’ll also find an all-in-one washer/dryer conveniently located inside the walk-in closet.

Upstairs, the second primary bedroom is a peaceful retreat with vaulted ceilings, exposed beams, four skylights, and west-facing windows that frame treetop and sunset views. A 60” HDTV provides entertainment, and a stylish shared bathroom with glass-enclosed shower and oversized vanity completes the upper level.

The media room offers a 77” HDTV and an oversized modular sectional that converts into a queen bed or two full beds, making it the perfect third bedroom or movie-night hideaway. With five TVs throughout the home, everyone can enjoy their favorite shows, games, or streaming services at any time.

Step outside to enjoy the best of outdoor living: a Blackstone gas griddle, fire pit, dining area, and of course, the private hot tub overlooking the mountain ridge. Thoughtful touches like a selection of spices, high-quality kitchenware, plush linens, and a variety of board games make it easy to settle in and feel at home.

Guests have full access to the home, with the exception of the locked, unoccupied basement. Please note: the bedroom skylights do not have window treatments—early risers will love the natural light, while light sleepers may wish to bring an eye mask.

For easy planning, here are the bedroom layouts:
Bedroom 1: King Bed (Main Level Primary Suite)
Bedroom 2: King Bed (Upper Level Primary Suite)
Media Room: Configurable Sectional (Two Full Beds or One Queen Bed)

At Hilltop, you’ll find yourself surrounded by beauty, comfort, and the rich cultural offerings of the Berkshires. Whether you’re catching a show at Tanglewood, hiking nearby trails, skiing at Butternut, kayaking on a mountain lake, or simply savoring a sunset from the deck, this special home provides the perfect setting to relax, recharge, and reconnect

The Neighborhood:
Located between the historic village of New Marlborough and Great Barrington.
Only 12 minutes from downtown Great Barrington, 25 from Lennox and 20 from Stockbridge.

Other Things to Note:
We look forward to welcoming you soon!
Standard rules like no pets, no smoking, no partying, and being respectful of the neighbors apply.

Hot Tub: You must sign the pool waiver form in order for us to access to the hot tub area. If your reservation is not in the peak summer we make no assumptions that the pool will be open during your stay. Please ask us before reserving to clarify this.

No sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.

Interaction with Guests:
Support team available 24 hours a day.