Private suite holiday rentals in Berkshire County

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Top-rated Self-Contained Units in Berkshire County

Guests agree: These Self-Contained Units are highly rated for location, cleanliness and more.

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Top Guest favourite

The exterior of a two-story brick house is showcased, featuring large windows with flower boxes. A balcony is positioned above the entrance, and seasonal foliage surrounds the property. Well-maintained landscaping is visible in the front yard, adding to the home's inviting appearance.

Guest suite in Pittsfield

5.0 out of 5 average rating, 21 reviews

Private Luxury Apt. Berkshires!

Private suite on lower level of our home. Complete separate space with own entrance. Newly renovated apartment with 2 bedrooms (1 queen, 1 full), kitchen with all the amenities, dining table, large living room with 65” TV, & large bathroom with walk-in shower. Private patio with BBQ grille, spacious yard with fire pit. Quiet street with stunning views! Located in the heart of the Berkshires. 10 minutes from Tanglewood & Kripalu, 20 mins Mt Greylock, the Rockwell Museum, MassMoCA, skiing & hiking

LocationFamilyHospitality

Top Guest favourite

A cozy living area is depicted, featuring a dark love seat with light-colored throw pillows. A wooden coffee table sits in front, accompanied by a decorative magazine. A side table holds a lamp, while a small plant is positioned in a white pot. Natural light enters through a window adorned with blinds.

Guest suite in Great Barrington

4.95 out of 5 average rating, 55 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.

LocationAmenitiesAir conditioning

Top Guest favourite

A stunning sunset skyline displays vibrant hues of orange, pink, and purple, casting a warm glow over the distant mountains. Silhouetted trees frame the scene, while soft clouds linger in the valley, enhancing the serene atmosphere.

Guest suite in Sheffield

5.0 out of 5 average rating, 97 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.

FamilyValueAir conditioning

Top Guest favourite

A serene riverside view is framed by a bare tree, showcasing a flowing river and charming buildings along its banks. Soft natural light filters through the clouds, highlighting the peaceful landscape.

Guest suite in Lee

4.98 out of 5 average rating, 103 reviews

Rooms on the River/free parking and WIFI

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.

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Top Guest favourite

A spacious bedroom features a large bed adorned with light bedding and a folded blanket. A shelf holds decorative items alongside a serene figure. Natural light enters through sliding glass doors, leading to an outdoor patio area. A standing fan is placed nearby.

Guest suite in Great Barrington

4.99 out of 5 average rating, 137 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.

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Top Guest favourite

A warm and inviting living area features two orange chairs paired with decorative pillows. A wooden dining table with matching chairs is present, complemented by a colorful artwork display on the wall. Natural light enters through a nearby window draped with patterned curtains.

Guest suite in Lee

4.91 out of 5 average rating, 230 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.

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Top Guest favourite

A modern living area features large windows allowing natural light to fill the space. A cozy sofa and a comfortable chair invite relaxation, while a country-style table accommodates dining or work. The decor is enhanced by a colorful area rug and minimalistic furnishings.

Guest suite in Richmond

4.94 out of 5 average rating, 207 reviews

Berkshires/Pet Friendly/Tanglewood/Private Ranch

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 Rides /Horse activities available by appt!

LocationFamilyPets

Top Guest favourite

A serene bedroom showcases a queen bed adorned with light bedding, set against calming green walls. A light-colored armoire and a small side table are visible, while natural light enters the room, creating a soft ambiance. A plush pillow is placed at the head of the bed.

Guest suite in Williamstown

4.96 out of 5 average rating, 268 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.

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Guest favourite

A small arrangement of green leaves and a white flower with a red center is displayed in a smooth, dark stone vase. A shallow ceramic bowl sits on a rectangular, dark tray beside the vase, with natural light illuminating the scene from nearby windows.

Guest suite in Great Barrington

4.78 out of 5 average rating, 18 reviews

Walk to Lake + Downtown • Private Studio w/ Patio

5-min walk to Lake Mansfield + 15-min walk to downtown Great Barrington. Studio apartment in peaceful backyard oasis with patio, hammock, and flower garden. Perfect for couples seeking nature + walkability. Includes: comfy queen bed, leather couch, two writing desks, kitchenette (fridge, microwave, toaster oven, sink), private bath with shower, and ample storage. Optional: single air mattress + hammock available on request (see details below). Note: sloped path to entrance. No pets.

LocationGetting aroundBackyard

Guest favourite

An outdoor deck is presented with a large wooden table surrounded by chairs. Colorful cushions add comfort, and potted flowers brighten the space. Soft string lights hang above, illuminating a hammock and lounge chairs nearby, all set against a backdrop of lush greenery.

Guest suite in Hancock

4.82 out of 5 average rating, 211 reviews

Cozy apartment near Jiminy Peak

Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

FamilyValueBreakfast

Top Guest favourite

The entrance features a red door framed by light-colored siding. A small roof provides shelter over the entry, and a lantern hangs above. A gravel pathway leads to the door, surrounded by greenery and natural landscaping.

Guest suite in Pittsfield

4.92 out of 5 average rating, 139 reviews

Newly Renovated Red Door Annex

Private keypad entrance with parking. Large bedroom with a new Queen bed, full bathroom. There is a small table for dining and working, a small fridge, microwave, toaster oven, and pour-over coffee and tea in a nook (not a kitchen) outside the bedroom. Small outdoor sitting area. The Annex is in a tranquil neighborhood between Great Barrington and Williamstown/North Adams and ski areas. 20 minutes to Lenox. The Annex is attached to the main house but is completely private.

LocationValueBathroom

Guest favourite

A historic Victorian home is presented with multiple levels and large, decorative windows. The white exterior is complemented by a wraparound porch adorned with railings. Lush greenery surrounds the house, enhancing the inviting front entrance, while flowering shrubs add a touch of color to the landscape.

Guest suite in Adams

4.87 out of 5 average rating, 128 reviews

Quaint Suite in Center of Adams

Pet Friendly mother-in law suite within a beautiful Victorian home in the center of Adams. The quaint town sits at the base of Mount Greylock with hiking and bike trails within minutes of your accommodations. Restaurants, grocery store and a 9 hole golf course are in walking distance. MASS MOCA is just a short 6 mile drive. Tanglewood music center is a 35 minute drive. Beautiful deck with gas firepit and grill. We would love you to be our guest.

LocationFamilyLaundry