Vacation rentals with breakfast in Berkshire County

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Top-rated breakfast rentals in Berkshire County

Guests agree: these breakfast rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Lee

4.89 out of 5 average rating, 235 reviews

Cozy Berkshires Cottage

Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)

Oct 7 – 14

G$26,002 GYD per night

Guest favorite

Guesthouse in North Adams

5.0 out of 5 average rating, 207 reviews

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

Sep 30 – Oct 7

G$44,678 GYD per night

Home in New Marlborough

5.0 out of 5 average rating, 8 reviews

All-Season Berkshires Escape: Ski, Hike, Swim

Explore the best of the Berkshires, then retire to this charming 4-bed, 2-bath New Marlborough home to lounge, grill, dine, and lay your heads. The Konkapot River runs next to this vacation rental, which abuts protected land and a nature preserve. Within 5 miles of the home, you can access the Gedney Farm wedding venue, warm-weather attractions like Lake Garfield Beach and the Appalachian Trail at Beartown State Forest, winter hotspots like Butternut Ski Area, and renowned farm-to-table dining.

Apr 1 – 8

G$131,567 GYD per night

Guest favorite

Apartment in Williamstown

4.96 out of 5 average rating, 299 reviews

New Studio In Town, By the Water

★ New to Williamstown? Explore our interactive guidebook. Charming studio just steps away from shops, restaurants & few minutes’ walk to Williams College. Renovated and well-equipped, this home offers a wonderful view of Water Street. If you like the outdoors, descend on the Green River back of the property. The wooded riverbank with Adirondack chairs, and picnic tables is great for relaxing while enjoying your evening sundowners by the fire pit with the sound of the river in the background.

May 22 – 29

G$32,016 GYD per night

Guest favorite

Home in Stockbridge

4.94 out of 5 average rating, 90 reviews

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

Dec 11 – 18

G$38,029 GYD per night

Superhost

Cabin in Sheffield

4.78 out of 5 average rating, 69 reviews

The Brook House at Race Brook Lodge

Cozy, private brookside bungalow sleeps four. Bright studio living space with queen and two twin beds, full kitchen, breakfast nook. Beyond the shady porch, enjoy rolling lawn, hammocks, abundant hiking. The Brook House is situated on the grounds of Race Brook Lodge, with breakfast, swimming pool, lawn games, and great hiking right on the property, including direct access to Race Brook Falls. Also just steps away from the Stagecoach Tavern Restaurant and Barnspace and DCSC performance spaces.

Jun 26 – Jul 3

G$33,546 GYD per night

Guest favorite

Home in Egremont

4.98 out of 5 average rating, 96 reviews

Bucolic Berkshires House

UNIQUE, bright, open space with a great kitchen and thoughtfully decorated. Near MANY exciting destinations such as skiing, cultural and arts destinations, vineyards, antiquing, you name it, in both the Berkshires and Hudson Valley. Located on an unpaved road and adjacent to a beautiful park and a nearby lake. There's so much to do, but if you'd prefer to take a more relaxed approach to your get-away then shop the wonderful local food stores and farms and enjoy cooking and our lovely house.

Nov 8 – 15

G$67,433 GYD per night

Guest favorite

Cabin in Lenox

4.88 out of 5 average rating, 25 reviews

Serene Lenox Hills Cottage - Berkshires

Lenox Hills Cottage is a rustic two bedroom cottage located in the heart of the Berkshires, surrounded by stunning nature views. Tranquil and secluded, yet just minutes away from major attractions like Tanglewood, Kennedy Park, Kripalu, the Mount, Miraval, and downtown Lenox - home to many great restaurants. It's the perfect getaway from the city. Ideal spot to relax and slow down. No central air though remains fairly cool during the summer. Has cieling fans and portable fans.

May 14 – 21

G$54,657 GYD per night

Home in West Stockbridge

4.86 out of 5 average rating, 14 reviews

Spacious contemporary w/ beautiful gardens!!

Beautiful, spacious, comfortable, light filled contemporary home, set on 5 acres, truly a nature lover’s delight. 3 large BR’s, all en-suite. AC throughout. Gourmet kitchen & open flr plan w/ great flow plus office and den. Private on 5 Acres, set back from road. Super convenient location. Award winning gardens w/Koi pond to delight the senses. 50" and 65” smart TV's, hi speed internet with 200 MBS. Hiking trails right from the back of the property. A special property!!

Dec 16 – 23

G$131,373 GYD per night

Guest favorite

Apartment in Stephentown

4.92 out of 5 average rating, 26 reviews

2 Bed Berkshire Getaway @ Stephentown Hotel

Welcome to the historic Stephentown Hotel in the heart of the Berkshire & Taconic Mountains. Completely gut remodeled two bedroom apartment, brand new everything! Located on the 2nd FL. Large apartment, private arcade with (x3) real arcade games, private custom kitchen, soaking bathtub, bright and spacious with plenty of windows, ductless ACs, plus a Washer Dryer in-unit. Located minutes to Jiminy Peak! Outdoor area w/ fire pits, BBQ, picnic tables, outdoor games, etc.

Dec 23 – 30

G$35,463 GYD per night

Superhost

Home in Dalton

4.74 out of 5 average rating, 76 reviews

Willowbrook: A Sun Filled, Mid-century Modern Home

Welcome to Willowbrook! Our home is the perfect getaway from which to explore all that the Berkshires has to offer. This secluded yet close to town property has access to miles of hiking trails, ski resorts, and cultural institutions. Once home to members of the Crane family who have lived in Dalton since 1799, you can stay in a piece of history and even visit the Crane paper museum in town! We are so looking forward to hosting you in this beautiful place we call home.

May 13 – 20

G$147,103 GYD per night

Home in Lenox

5.0 out of 5 average rating, 6 reviews

Whistler's Inn/The Garden Room (#9)

Whistler’s Inn is an 1870 English Tudor mansion in the heart of Lenox near Tanglewood, Shakespeare & Co., and all of the Berkshires’ most popular cultural venues. The home was once owned by Mr. and Mrs. Ross Wynans Whistler, railroad tycoon and nephew of the painter, James M. Whistler. Whistler’s Inn captures the warmth, comfort, and elegance of a bygone era. The inn has been featured on National T.V. - The Travel Channel and Fodor’s Bed and Breakfast Country Inns.

May 9 – 16

G$53,756 GYD per night