Holiday rentals in Lenox

5 out of 5 average rating, 25 reviews

Center of Lenox, cozy Apartment 2-bedroom

The whole group will enjoy easy access to everything from this centrally located duplex apartment. Less than 300 yards away, enjoy downtown Lenox. Featuring several fine dining options or stop by the local Heritage Tavern for pub food & drafts. Enjoy the local roastery at the Lenox coffee shop or experience the Haven cafe & bakery. Several shopping boutiques along the way or visit the Lee Premium Outlets shopping center only 5 miles . Come enjoy the Berkshires and experience the town of Lenox!

Superhost

4.85 out of 5 average rating, 84 reviews

Station House 2R

Former train station, converted to apartments, is on 3 acres next to the Housatonic Railroad tracks. It is located between a chapel, the scenic Housatonic River and October Mountain. The 2 bedroom unit is on the second floor. Location is 1 mile from major route 7&20, between Lenox and Pittsfield. Museums, down hill ski areas, cross country, hiking are among area attractions. It is a short drive to restaurants and shops. Adjacent to the George Darey Housatonic Valley Wildlife Management Area.

Superhost

4.93 out of 5 average rating, 231 reviews

Heart of Lenox Walk to Town Cozy Cottage!

The cottage is a 2-minute walk to Church St., right in the heart of Lenox. Kennedy Park (1.5 miles) is a short stroll away for great hiking & biking, while multiple 5-star restaurants are all within a few minute walk. Tanglewood (2 miles), Kripalu (3 miles), Shakespeare & Co. (1 mile), Berkshire Theatre Festival & the Norman Rockwell Museum (7 miles), Butternut, Jiminy Peak (15 miles) & Bousquet (5 miles) ski area, Mahaiwe Performing Arts Center & Jacob's Pillow (14 miles) are all close by!

Superhost

4.93 out of 5 average rating, 234 reviews

The Berkshire Quintessential Cape downtown Lenox

Experience the best of the Berkshires in this charming, in-town, Lenox home! With stunning oak floors and white walls, this light-filled gem features high ceilings and abundant windows. Enjoy a cozy first-floor bedroom and full bath, while upstairs hosts two spacious bedrooms with a shared bath. The open-concept living and dining area, complete with a wood-burning fireplace, is perfect for gatherings. Just a short stroll to town, Tanglewood, and Canyon Ranch, this is your ideal getaway!

Guest house in Housatonic

4.96 out of 5 average rating, 124 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

4.94 out of 5 average rating, 36 reviews

Guest suite in Richmond

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!

4.88 out of 5 average rating, 161 reviews

Spacious 4-Bedroom Colonial Gem in Downtown Lenox

Spacious 4-Bedroom Retreat in Lenox, MA Experience your perfect getaway in this beautifully renovated home in Lenox, MA. This charming 4-bedroom, 3-bathroom retreat offers 2,089 sq. ft. of space and is designed for a comfortable stay. The deck, BBQ grill, and cozy seating make for memorable gatherings. The Wi-Fi is fast for all your streaming needs, and there are 2 Wi-Fi HDTVs. Lenox, MA, is a picturesque town in the heart of the Berkshires. Book your stay today!

4.99 out of 5 average rating, 216 reviews

Farm stay in Pittsfield

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

4.93 out of 5 average rating, 374 reviews

Guest house in Lenox

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Guest house in Stockbridge

4.95 out of 5 average rating, 234 reviews

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

5 out of 5 average rating, 35 reviews

Guest house in Lenox

Guest House at Stonover Estate

Located on historic Estate grounds, this is an aesthetically pleasing and private getaway for adults and couples. The town of Lenox hosts multiple 5-star restaurants, and the property is a 10 minute walk to town. It is 1 mile from Tanglewood, 1 mile to Shakespear & Co., and 14 miles to Jacob’s Pillow. If you like the outdoors, it is a half mile to Kennedy Park for hiking or biking.

5 out of 5 average rating, 124 reviews

Flat in Lee

Lovely Berkshire apartment with beautiful views

Kick back, relax and rejuvenate in this calm, stylish, zen new space minutes from town. Private entrance with keyless entry. Comfy crisp clean beds and spacious living room. Kitchen has everything you'll need to cook dinners or not! Friends getaway, couples, familes or remote work. Mountain views and beautiful sunsets Minutes to Tanglewood/Jacobs Pillow

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for Lenox holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Lenox

4.75 out of 5 average rating, 4 reviews

Raised Ranch Serenity

IlyaRating, 5 stars8 months ago

A great place to stay. The location is close to the town center but away just enough to be countryside peaceful. Vasiliki is a very friendly host who communicates really well. The apartment matches the description and features a really big back yard that must be a great place to spend evenings in the summer. It’s very quiet and cozy.

Cabin in West Stockbridge

5 out of 5 average rating, 7 reviews

Serene rustic mountain cabin in the Berkshires!

KellyRating, 5 stars2 weeks ago

Would love to come Back!

4.98 out of 5 average rating, 49 reviews

Flat in Stockbridge

Stockbridge private apartment

CatherineRating, 5 stars2 weeks ago

This was a great weekend getaway for two of us. The apartment is pristine and private. It was a great base camp for outings in the Berkshires. Stockbridge is just one mile away up the road and has tons of cute shops and restaurants.

5 out of 5 average rating, 24 reviews

Place to stay in Lenox

Lenox Retreat Near Tanglewood w/ Rescued Donkeys

DeborahRating, 5 stars9 months ago

Jodi is Hostess Extraordinaire! Lots of charm & comfort in a space perfect for relaxing with a friend or 2. Anything you may need for convenience is readily available. Very responsive to communications before & during our stay. Easy to set up visits with the adorable donkeys in their care. You will want to meet them, share carrots with them & gaze into their soulful eyes. We are looking forward to our next visit!

5 out of 5 average rating, 4 reviews

Cozy Home in Lenox

DavidRating, 5 stars9 months ago

We were very happy with this place. Every room is very comfortable. It was spotlessly clean. The kitchen has plenty of counter space, and every piece of cookware and appliance you could hope for. Though located near a busy road, it is far enough from the road that it is quiet - we never heard any traffic noise, or any other noise. The listing seemed to say there was no air conditioning, but there is great central air conditioning. We couldn’t possibly have been more comfortable. The location is perfect if you plan on visiting Tanglewood, The Mount, or Jacobs Pillow. We want to come back next year, and stay even longer!

Cottage in Great Barrington

4.94 out of 5 average rating, 133 reviews

The Cottage at The Barrington House

AliceRating, 5 stars1 week ago

Cute getaway for me and my husband as we traveled for my cousin’s wedding! The list of recommendations Katie provided was extensive and great! Best part was that we had a very long drive home and had no chores to do before checking out!!

5 out of 5 average rating, 6 reviews

Amadeus House-3 Bedrooms Each w Bath & Kitchenette

RachelRating, 5 stars7 months ago

We had a lovely stay at Marianne's place. The home is charming and located on a lovely street just a minute's walk to all the main shops in Lenox. The beds were comfortable with modern amenities. Would definitely recommend to those visiting the area.