Holiday rentals with breakfast in Berkshire County

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Top-rated Holiday Accommodation with Breakfast in Berkshire County

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Private room in Sandisfield

4.93 out of 5 average rating, 144 reviews

Hospitality in the Berkshire Woods

Enjoy a rustic wooded retreat up in the cool Berkshire hills, surrounded by nature and wildlife, in a quiet, secluded, safe and peaceful setting, yet very close to top-notch cultural and recreational attractions. Nearby trails, pristine lakes and woods offer hiking, swimming and cycling. Experience the absence of mechanical sounds and the centering presence of rustling leaves, birdsong, and owls hooting at night. Behold a star-studded black night sky without artificial light. Breakfast included!

Home in New Marlborough

5 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.

Top Guest favourite

Guesthouse in North Adams

5 out of 5 average rating, 284 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.

Home in Great Barrington

Charming Long Pond Vacation Home in the Berkshires

Lond Pond Road is considered one of the most beautiful and peaceful roads in th Berkshires. It is the perfect location to vacation in the Berkshires, 5 minutes north of downtown Great Barrington and Lake Mansfield. Tanglewood , Shakespeare &Co, The Mount and many summer play houses are 15 minutes, 10 minutes to Stockbridge and 25 minutes to Jacob's Pillow.. The upside down house is a converted barn on 3 beautifully landscaped acres with a spa, 4 bedrooms, 2 baths, screened porch and patio.

Top Guest favourite

Private room in Pittsfield

4.96 out of 5 average rating, 70 reviews

Airy Queen Bedroom with Couch, Pittsfield

I rent 2 second-floor bedrooms in my home , w a shared bathroom. This is a roomy space, with a desk and a wicker couch. The queen bed has a comfortably firm foam mattress. Replacing a closet (which became the bathroom) are clothes stands, over-the-door hooks, a dresser, & a hall closet. Rooms shared with the host and other guests are kitchen, living room, deck and laundry room. Emma the Dog is a cute charmer and doorbell substitute. Co-host George's cat Bongo is, of course, typically quiet

Top Guest favourite

Home in Stockbridge

4.94 out of 5 average rating, 140 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.

Cabin in Sheffield

4.78 out of 5 average rating, 74 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.

Guest favourite

Private room in Sheffield

4.98 out of 5 average rating, 50 reviews

Sheffield Lodge - Ramblewood Master

The Sheffield Lodge is a warm and inviting rustic Bed and Breakfast secluded from city life nestled in a pine forest. Enjoy your home-away-from-home where there is always friendly service, delicious breakfasts, afternoon treats. The lodge features an inviting fireplace, large screen TV, game table for board games or cards and a quiet reading/living room, and ample parking. Outdoor recreation is within minutes in every direction. There are museums, shops and many great restaurants nearby.

Top Guest favourite

Private room in Pittsfield

4.98 out of 5 average rating, 431 reviews

Large guest suite w/private bath in the Berkshires

A wonderful welcoming house in a beautiful residential neighborhood with no occupancy taxes! We are 15-25 minutes from Tanglewood, Kripalu, Mt Greylock, the Rockwell Museum, MassMoCA, skiing and hiking. Our home is centrally located to all of the fun things to do in the Berkshires. We've lived here for over 20 years and are happy to provide helpful insights for your stay. One of the reasons we love the Berkshires is that each season offers wonderfully unique experiences for any visitor.

Guest favourite

Condo in Hancock

4.86 out of 5 average rating, 7 reviews

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

You want to bring your whole family to Jiminy and be in ONE CONDO, with gorgeous views, a deck, BBQ, Backyard, and be at Jiminy Peak - This condo is for you - right in the heart of Country Village. This Stylish 2BR country Condo w AC is fully updated and comes with parking in front and full access to the Country Inn Amenities ( Fitness, pools, hottub, Tennis etc). This large 900 sq ft condo features country decor, & sleeps up to 7 with a queen, two bunk beds, pull out Trundle, and Full Bed.

Top Guest favourite

Private room in Canaan

4.94 out of 5 average rating, 96 reviews

Serene Berkshire Room with breakfast

Charming room with breakfast included. This is a room in our home where we live. Private shower/bathtub/toilet and heat lamp. Netflix, Amazon and Roku in room. On 1st floor of comfortable, quiet house in rural setting. Geothermal heating and cooling. Nestled in Hudson Valley/Berkshires. Year-round cultural, scenic & recreational activities. Free pass to nearby private beach. Near 4 ski areas. Enjoy our nature trail & busy birdfeeders. 10 mins. from highway- 2.5 hours. from NYC & Boston.

Guest favourite

Apartment in Stephentown

4.95 out of 5 average rating, 42 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.