Vacation rentals with breakfast in Berkshire County

Find and book unique breakfast rentals on Airbnb

Top-rated breakfast rentals in Berkshire County

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

Guest favorite
Home in Lee
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)
May 22 – 29
$117 per night
4.89 out of 5 average rating, 234 reviews
Guest favorite
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
*Close to ski resorts & tubing! We are nestled at the foot of October Mountain State Forest, yet close to the centers of Lee, Lenox, & Pittsfield. Our charming house was built in 1817- original wood beams, wood floors, and quite a history. Whether you enjoy skiing, exploring local restaurants & downtowns, venturing outdoors or experiencing the local art scene, the Berkshires has something for everyone. Our little farmhouse serves as the perfect "home base" for all of your Berkshire adventures.
Jun 23 – 30
$225 per night
4.89 out of 5 average rating, 199 reviews
Guest favorite
Guesthouse in North Adams
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 7 – 14
$192 per night
5.0 out of 5 average rating, 201 reviews

Popular amenities for Berkshire County breakfast rentals

House rentals with breakfast

Superhost
Home in Dalton
Willowbrook: A Sun Filled, Mid-century Modern Home
Aug 31 – Sep 7
$611 per night
4.73 out of 5 average rating, 75 reviews
Home in Monterey
Peaceful Berkshires Retreat
May 13 – 20
$153 per night
4.7 out of 5 average rating, 20 reviews
Guest favorite
Home in Great Barrington
Gem on The Hill
May 17 – 24
$338 per night
5.0 out of 5 average rating, 9 reviews
Home in New Marlborough
All-Season Berkshires Escape: Ski, Hike, Swim
Feb 19 – 26
$549 per night
5.0 out of 5 average rating, 8 reviews
Guest favorite
Home in Lenox
Whistler's Inn/The Garden Room (#9)
May 19 – 26
$215 per night
5.0 out of 5 average rating, 6 reviews
Home in West Stockbridge
Spacious contemporary w/ beautiful gardens!!
Dec 16 – 23
$543 per night
4.86 out of 5 average rating, 14 reviews
Superhost
Room in Sandisfield
Hospitality in the Berkshire Woods
Nov 21 – 28
$59 per night
4.92 out of 5 average rating, 133 reviews
Guest favorite
Room in Williamstown
A Beautiful Home & Gardens In The Berkshires
Oct 9 – 16
$115 per night
4.83 out of 5 average rating, 384 reviews
Guest favorite
Room in Pittsfield
Pittsfield. Large queen bedroom, second floor.
Oct 30 – Nov 6
$102 per night
4.95 out of 5 average rating, 38 reviews
Guest favorite
Room in Sheffield
Beautiful Hartfield House in The Berkshires
Mar 12 – 19
$175 per night
4.97 out of 5 average rating, 30 reviews
Guest favorite
Room in Lanesborough
Berkshire Mountain Guesthouse-Near Jiminy Peak
Sep 14 – 21
$180 per night
5.0 out of 5 average rating, 32 reviews
Guest favorite
Room in Lenox
Country home Near Kripalu & Tanglewood Lenox, MA
Sep 3 – 10
$131 per night
4.83 out of 5 average rating, 12 reviews

Apartment rentals with breakfast

Guest favorite
Apartment in Stephentown
2 Bed Berkshire Getaway @ Stephentown Hotel
Oct 9 – 16
$130 per night
4.92 out of 5 average rating, 25 reviews
Apartment in North Adams
Berkshire Hideaway
Jun 19 – 26
$101 per night
4.85 out of 5 average rating, 283 reviews
Apartment in Lenox
Guest Room with 2 Queen Beds at Berkshires Lenox
Apr 27 – May 4
$131 per night
New place to stay
Guest favorite
Room in Great Barrington
comfy, cute flat with the river in my backyard
Mar 7 – 14
$49 per night
4.78 out of 5 average rating, 49 reviews
Guest favorite
Apartment in Williamstown
Downtown | Waterfront | Walk to Shops
Jan 17 – 24
$144 per night
5.0 out of 5 average rating, 62 reviews
Apartment in Lenox
Guest Room with 1 King Bed at Berkshires Lenox
Jun 1 – 8
$182 per night
New place to stay
Guest favorite
Room in Great Barrington
queen size bed in a cozy fun riverside apartment
Aug 4 – 11
$71 per night
4.85 out of 5 average rating, 34 reviews

Bed and breakfast rentals with breakfast

Guest favorite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
Nov 22 – 29
$94 per night
4.99 out of 5 average rating, 374 reviews
Guest favorite
Nature lodge in Sheffield
Sheffield Lodge - Ramblewood Master
Jul 20 – 27
$137 per night
4.98 out of 5 average rating, 42 reviews
Superhost
Room in East Chatham
The Inn at Silver Maple Farm - Upper Lodge
Dec 4 – 11
$210 per night
5.0 out of 5 average rating, 3 reviews
Guest favorite
Room in Great Barrington
Granville House - King traditional
Feb 24 – Mar 3
$275 per night
5.0 out of 5 average rating, 20 reviews
Hotel in Lenox
Lodge Two Double Mountain View at Apple Tree Inn
Jan 10 – 17
$803 per night
4.76 out of 5 average rating, 17 reviews
Room in Stockbridge
Stockbridge #1 B&B Full Breakfast Close to Museums
Mar 16 – 23
$349 per night
4.67 out of 5 average rating, 3 reviews
Guest favorite
Room in Sandisfield
Historic and Haunted New Boston Inn Built in 1731
Aug 21 – 28
$169 per night
5.0 out of 5 average rating, 16 reviews
Room in Lenox
Room 7: Leighton Rollins Room - Apple Tree Inn
Jun 17 – 24
$999 per night
5.0 out of 5 average rating, 3 reviews
Room in Cheshire
Mountain Air- Harbour House Inn
Nov 13 – 20
$206 per night
New place to stay
Room in Lenox
Modern Apt w/Kitchen in a Classic Bed & Breakfast
Dec 10 – 17
$179 per night
New place to stay
Guest favorite
Nature lodge in Sheffield
Sheffield Lodge
Jul 13 – 20
$842 per night
5.0 out of 5 average rating, 14 reviews
Guest favorite
Nature lodge in Sheffield
Sheffield Lodge - Everett Room
Oct 25 – Nov 1
$119 per night
4.97 out of 5 average rating, 65 reviews

Destinations to explore