
Holiday rentals with breakfast in Cheshire County
Find and book unique rentals with breakfast on Airbnb
Top-rated rentals with breakfast in Cheshire County
Guests agree: these breakfast rentals are highly rated for location, cleanliness and more.

Historic Bed & Breakfast with Original Folk Art!
Welcome to the Copper Pot, with wonky walls, floors and doors. It will have you stepping back in time to the year 1810. We have original Moses Eaton stenciling from 1815, The old world tavern for playing games and artifacts we found around the property! You will be staying in the MOSES EATON room! We have near by, large lakes and ski resorts. The room has a private bathroom, a panted mural and four poster bed! Your special Breakfast is made with great ingredients and free range chicken eggs!
5.0 out of 5 average rating, 7 reviews
Divol Pond Cabin
Family friendly rustic style interior home tucked away on a private dead end road. Small private pond with only three houses with access. Stunning deck with waterview connected to master bedroom with cathedral ceiling and skylights. Small fire pit. Grill. Dual heat propane fire pit table. Dock, kayak, paddle boat, hammock. Mount Watatic five minutes away. Mount Monadnock 20 minutes away. Restaurants, grocery stores/shopping close by. Perfect place to relax and enjoy quite times of nature.
4.98 out of 5 average rating, 60 reviews
"Country Comfort" in Hillsborough, NH.
Enjoy your own private apartment on a quiet country road in Hillsborough, NH. This comfortable 2nd floor apt in a separate building on the owners’ property showcases original stone walls and colorful perennial gardens. With 2 King bedrooms and a 3rd room set up with a desk and sitting area, there is ample space for 4 guests. A fully equipped kitchen will make cooking-in an enjoyable experience. Modern amenities including Wifi and Smart TV will help you stay as connected as you wish.
5.0 out of 5 average rating, 66 reviews
Country Bed & Breakfast, 2 Bedroom Hillside Suite
Get away from the hustle and bustle of the urban life and enjoy a relaxing country setting in rural New Hampshire at His & Hers Farm. We are located within an hour’s drive to several ski areas and are close to trails that can be used for snow shoeing, cross country skiing and even snowmobiling. The Gowen's Guest House is a restored and updated historic 1850s/early 1900s farmhouse that is a licensed Bed & Breakfast and has four (4) unique guest rooms each with their own private bath.
5.0 out of 5 average rating, 11 reviews
Peaceful country homestay overlooking pond
Historic 1910 schoolhouse (with large addition) with idyllic, verdant space on all sides. Classic homestay set-up. Quiet pond view from room. Here you can relax into Vermont country life. Perfect space for boarding school or college-visit families, foliage lovers, skiers. Located on a beautiful road popular for long walks and cycling. Very clean home, following COVID cleaning protocols - all household members vaccinated and boosted. LGBTQPI-celebrating home. No cleaning fee.
4.95 out of 5 average rating, 43 reviews
Swiss Chalet Family Retreat!
Welcome to our family's Swiss style chalet! Inspired by trips to Davos, Switzerland, my grandparents built the chalet in the 1950s to be a family playhouse and gathering spot for their 6 children. It's kind of magical. Today, our large extended family still enjoys holiday celebrations here every year. Our kids love exploring the woodland trails and swimming in Center Pond. We hope you love it as much as we do! Note: the building also has two apartments on the first floor.
4.88 out of 5 average rating, 112 reviews
The Historic Copper Pot B&B
Welcome to the Copper Pot historic B&B! Step back in time to the year 1810, with wonky walls, doors and floors. The Nest room is a historic room! We are home to the original folk art Moses Eaton stencils dating back to 1815! Enjoy our outside patio with firepit and grill while looking out at our wooded venue! We offer a country breakfast with free range chicken eggs! We are centralized to many attractions, like shopping, lakes, and ski resorts.
4.93 out of 5 average rating, 27 reviews
Eva's Room/Ensuite bath with One Double Bed
Do you like the experience of staying in historic homes? Welcome to the Eva Blake House. Full menu breakfast is served in the dining room between 8 and 10 AM. Three common areas. Abundant amenities. A walk or short drive to The Square with its shops, art galleries, restaurants and 1927 Opera House movie theater. Eva's Room has one double bed. Private ensuite bathroom with a claw foot bathtub. and hand-held shower spray.
5.0 out of 5 average rating, 82 reviews
Eva Blake House-Margaret's Room
Do you like the experience of staying in historic homes? Welcome to the Eva Blake House. A full menu breakfast is served in our dining room between 8 and 10 AM. Three common areas. Abundant amenities. A walk or short drive to The Square with its shops, art galleries, restaurants and our 1927 Opera House movie theater. Margaret's Room has one double bed. A walk down the hall: your large, private bathroom with walk in shower.
5.0 out of 5 average rating, 139 reviews
Country Bed & Breakfast, Green Meadow Room
Get away from the hustle and bustle of the urban life and enjoy a relaxing country setting in rural New Hampshire at His & Hers Farm. For those looking to for an authentic and comfortable country experience, this is your place! The Gowen's Guest House is a restored and updated historic 1850s/early 1900s farmhouse that is a licensed Bed & Breakfast and has four (4) unique guest rooms each with their own private bath.
5.0 out of 5 average rating, 4 reviews
Country Bed & Breakfast, White Birch Room
Get away from the hustle and bustle of the urban life and enjoy a relaxing country setting in rural New Hampshire at His & Hers Farm. For those looking to for an authentic and comfortable country experience, this is your place! The Gowen's Guest House is a restored and updated historic 1850s/early 1900s farmhouse that is a licensed Bed & Breakfast and has four (4) unique guest rooms each with their own private bath.
5.0 out of 5 average rating, 6 reviews
Country Bed & Breakfast, Sugar Maple Room
Get away from the hustle and bustle of the urban life and enjoy a relaxing country setting in rural New Hampshire at His & Hers Farm. For those looking for an authentic and comfortable country experience, this is your place! The Gowen's Guest House is a restored and updated historic 1850s/early 1900s farmhouse that is a licensed Bed & Breakfast and has four (4) unique guest rooms each with their own private bath.
5.0 out of 5 average rating, 69 reviewsPopular amenities for rentals with breakfast in Cheshire County
House rentals with breakfast

Terrace Room at the Tartan Fox

Divol Pond Cabin
4.98 out of 5 average rating, 60 reviews
Cozy, comfortable Ranch Home
4.82 out of 5 average rating, 89 reviews
Peaceful country homestay overlooking pond
4.95 out of 5 average rating, 43 reviews
Stewart Room at the Tartan Fox Inn
Bed and breakfast rentals with breakfast

Country Bed & Breakfast, Cold River Room
5.0 out of 5 average rating, 33 reviews
Eva Blake House-Margaret's Room
5.0 out of 5 average rating, 139 reviews
Eva's Room/Ensuite bath with One Double Bed
5.0 out of 5 average rating, 82 reviews
Country Bed & Breakfast, Sugar Maple Room
5.0 out of 5 average rating, 69 reviews
The Historic Copper Pot B&B
4.93 out of 5 average rating, 27 reviews
Country Bed & Breakfast, Green Meadow Room
5.0 out of 5 average rating, 4 reviews
Historic Bed & Breakfast with Original Folk Art!
5.0 out of 5 average rating, 7 reviews
Country Bed & Breakfast, 2 Bedroom Hillside Suite
5.0 out of 5 average rating, 11 reviewsOther holiday rentals with breakfast

Swiss Chalet Family Retreat!
4.88 out of 5 average rating, 112 reviews
Apartment on Main Street
4.83 out of 5 average rating, 227 reviews
Divol Pond Cabin
4.98 out of 5 average rating, 60 reviews
"Country Comfort" in Hillsborough, NH.
5.0 out of 5 average rating, 66 reviews
Eva Blake House-Margaret's Room
5.0 out of 5 average rating, 139 reviews
Eva's Room/Ensuite bath with One Double Bed
5.0 out of 5 average rating, 82 reviews
Country Bed & Breakfast, Sugar Maple Room
5.0 out of 5 average rating, 69 reviews
The Historic Copper Pot B&B
4.93 out of 5 average rating, 27 reviewsDestinations to explore
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- Okemo Mountain Resort
- Stratton Mountain
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Snhu Arena
- Ragged Mountain Resort
- Bear Brook State Park
- Hildene, The Lincoln Family Home
- Mount Monadnock
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- University of Massachusetts Amherst
- Massachusetts Museum of Contemporary Art
- Mount Sunapee Resort
- Mount Holyoke College
- Camp Plymouth State Park
- The Montague Bookmill
- Quechee Gorge
- New Hampshire Motor Speedway
- Jamaica State Park
- Bridge of Flowers





