Private suite holiday rentals in Berkshire County

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Top-rated Self-Contained Units in Berkshire County

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Guest favourite

Guest suite in Egremont

4.93 out of 5 average rating, 30 reviews

Retreat for All Seasons

Newly constructed apartment getaway with full kitchen, bath and queen size bed. 150 feet from Prospect Lake with swimming and boating access. Enjoy coffee or morning yoga on your private deck with a lake view. Owner lives on property (above apartment) Apartment is ground level, separate entrance-- and private parking is on side of house next to apartment entrance. Walk out past parking area - turn right toward lake access. Ten minutes from downtown Great Barrington and cultural events

Guest favourite

Guest suite in Richmond

4.93 out of 5 average rating, 193 reviews

Fall Foliage/Private Ranch/Kid&Pet Friendly/Horses

Pet-Friendly, Child-Friendly Getaway! Modern suite with full kitchen on private horse ranch. Wake to horses in the fields, hiking, breakfast on your patio. Perfect location for individuals, couples, families animal lovers. Near all ski areas (Jiminy Peak/Catamount/Bousquet /Butternut), shopping, museums (Norman Rockwell/Mass MoCA) wine tasting (Balderdash Cellars, Hilltop Orchards) Tanglewood, Jacobs Pillow, Miraval, Kripalu, Canyon Ranch. Trail ride lessons /Horse activities available by appt!

Guest favourite

Guest suite in Great Barrington

4.94 out of 5 average rating, 50 reviews

The Serendipity Spot

Greetings from the Serendipity Spot where old meets new in this charming, elegant & peaceful space where you may rest, laugh & play in the beauty of The Berkshires. Nestled in Great Barrington, this convenient spot has easy access to hiking, skiing, cultural events and restaurants galore. We are a 15-minute drive to Tanglewood and Shakespere & Co in Lenox, 12 minutes to the Norman Rockwell Museum in Stockbridge, 13 miles to Jacob's Pillow, and Ski Butternut is around the corner 2 miles away.

Top Guest favourite

Guest suite in Sheffield

5 out of 5 average rating, 88 reviews

The Sunset Suite~Great South Berkshire Location!

Welcome to the Sunset Suite, a recently completed, air-conditioned spacious upstairs space, surrounded by all the natural beauty of the Berkshires. Offering privacy with spectacular views and great sunsets! This perfect couple’s retreat is comfortable, quiet and serene, sitting on a hill surrounded by woods, farmlands and hiking trails. Located only a short 10 minute drive from both vibrant Great Barrington and quaint Sheffield, we are close to all Berkshire attractions including Tanglewood.

Guest favourite

Guest suite in South Lee

4.98 out of 5 average rating, 90 reviews

Rooms on the RIVER Free WIFI and Parking

Enjoy the entire first floor in a circa 1830 house located on the Housatonic River. The apartment offers a new bath, a dining area, and a galley kitchen with a single induction cooktop, a full-sized refrigerator, oven, and microwave. We have a coffee station, and varied electrical appliances too. Convenient to Berkshires’ cultural attractions on a noted fly fishing section of the river, near golfing, hiking, kayaking, biking, and shopping. Three miles to the local grocery store & shopping.

Top Guest favourite

Guest suite in Williamstown

4.96 out of 5 average rating, 248 reviews

Berkshire Guest Suite

Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

Top Guest favourite

Guest suite in Great Barrington

4.98 out of 5 average rating, 122 reviews

Hillside Haven

Ideally located on “the hill” in a beautiful and quiet neighborhood just a short walk to downtown Great Barrington’s amazing cafes, restaurants, ice cream, and Lake Mansfield’s beach and loop trail. The perfect hillside haven for those looking to be in the center of it all. This private, modern, and clean space is completely new as of mid-2021 and has a well-appointed kitchen, outdoor patio with a firepit, fast internet, covered parking, radiant heat floors, and an air conditioning unit.

Guest favourite

Guest suite in South Lee

4.91 out of 5 average rating, 212 reviews

Sunny Riverside Apartment

The Berkshires are a perfect spot for a getaway week or weekend. You will enjoy this cozy 2-story apartment, easily accessible to all that the region has to offer. The apartment has a fully equipped kitchen, dining space, living area, and two bedrooms, overlooking the Housatonic River. Every town in South County is 5-15 minutes drive, and in 50 minutes you could be at The Clark Museum or Mass MOCA in North County. Several ski areas are nearby, and Kripalu is just an easy 10 minute drive.

Top Guest favourite

Guest suite in Richmond

4.95 out of 5 average rating, 42 reviews

Berkshire Mountain Retreat

Studio apartment with private entrance nestled in bucolic Richmond. Located on a quiet mountain road adjacent to miles of hiking and biking trails. Close to 4 ski areas and minutes to Tanglewood, Kripalu, Clark Art Museum, Mass MoCA, Hancock Shaker Village, the Mass Audubon Wildlife Sanctuary and more. A short drive to Lenox, Stockbridge, and Great Barrington where shopping and fine dining await. Your relaxing vacation begins here with an expansive yard, views and in ground pool!

Top Guest favourite

Guest suite in Dalton

4.99 out of 5 average rating, 69 reviews

Berkshires getaway: nature, culture & relaxation

King bed and birch beams rule this nature inspired space. You have sole access to a mahogany deck, perfect for morning coffee or wine at night by a gas fire pit. Skylights, large windows, as well as plenty of light fixtures will brighten up your stay. Radiant heat, 3 ceiling fans and A/C will keep you comfortable. You will be surrounded by nature, yet ten minutes from county’s largest supermarket, and centrally located from all Berkshires’ cultural venues and hiking trails.

Superhost

Guest suite in Lee

4.77 out of 5 average rating, 132 reviews

Cozy Guesthouse Near Downtown, Lee

Welcome and enjoy our renovated Guesthouse at Lee, MA, staying on main street (15 minutes from Great Barrington and 20 minutes from Pittsfield). It is also 3 mins to Outlet and 19 mins to the closest Ski area.The master bedroom has a queen size soft mattress, and the second bedroom has a queen bed also. The kitchen has a brand new refrigerator, a gas range, and units for cooking. You will enjoy the comfortable stay! Owners live upstairs and be friendly to all visits.

Guest favourite

Guest suite in Pittsfield

4.9 out of 5 average rating, 89 reviews

Newly Renovated Red Door Annex

Private keypad entrance with parking. Large bedroom with full bathroom. The spacious room features a high-end queen bed and a small table for dining and working, a small frig, microwave, toaster oven, and pour-over coffee in a nook outside the bedroom. Popcorn, oatmeal 1/2 and 1/2 are provided. The Annex is in a tranquil neighborhood between Great Barrington and Williamstown/North Adams and ski areas.1 mile to Berkshire Medical Center. 20 minutes to Lenox. Fire Pit.