Holiday rentals with breakfast in Orange County

Sunset Chalet - Midcentury Views

Step into the timeless charm of Sunset Chalet, a meticulously renovated midcentury alpine retreat by Brooke and Sean. Indulge in the nostalgic ambiance, sipping cocktails and spinning vinyl records. Set on a private lot with inspiring Western ridgeline views and captivating sunsets. Outside, a spacious deck awaits, accompanied by a dining area, lounge chairs, wood fired hot tub, bocce court, pond, and trails. Escape to this mountain retreat, reconnect with nature, & create cherished memories.

Windswept Acres Homestay - Southeast Room

Windswept is an inviting and comfortable place to stay for 1 night or a week. We love to share our property and home, which includes two friendly dogs and a cat. It features a double bed with its own entrance from the east-facing deck. Bath is shared if the Northeast room is booked. The house is guest friendly as well with extra space in the refrigerator for your use and a living room available for reading or watching TV. (Be sure to check out our other rooms and our Sugar House as well!)

Howling Wolf Farm Yurt--A Magical Glamping Retreat

Our 88-acre farm spreads up a steep hillside above the village of Randolph, one mile away. The land is a mixture of open areas where we rotate our sheep flock daily, and wooded land with trails and old stone walls. You might hear the occasional car or truck on a nearby road, but more likely you'll hear our sheep baaing to one another or the cows across the valley trumpeting, or the abundance of birdsong. The energy here is calming and peaceful--we know you will love it as much as we do.

Dante’s Inferno Luxury queen bed + many extras

Gorgeous canvas bell tent in secluded setting, outfitted with luxuriously dressed queen memory foam bed, pillows, table, lighting, chairs, outdoor patio set + hammocks. Coffee and tea with cream & sugar avail all day. We provide drinking water, a cooler to use, everything but your clothes and meals (except breakfast, we have that covered!) *Solo Stove for a private Glampsite fire available to rent for $50/night, all wood provided. Limited inventory, must reserve, first come first served

Marlene’s Room

Welcome to Your Home Away from Home! Whether you're seeking a romantic getaway, an outdoor adventure, or a peaceful retreat, our cozy room has everything you need. The large windows invite abundant natural light, offering views of our beautiful backyard where we have 8 acres of land that you are welcome to explore while staying with us. We offer breakfast from 7-9 am. You are welcome to use our microwave and store your food in the small fridge that is exclusively used by our guests.

Johnnycake Flats Inn, Train Room

Johnnycake Flats is a family owned B&B, an 1800's farmhouse and former stagecoach stop. Three inviting guest rooms, each with private baths and great views. All stays include yummy, homemade breakfasts, using organic and local ingredients. XC skiing and snow shoeing can be accessed on our adjoining field with your own equipment. Sugarbush and Mad River Glen are a 1/2 hour drive via the Roxbury Gap (snow tires and winter driving skills a must) or a 55min drive via I-89, exit 9.

Glenwood, Cozy 1BR, LR/Kit, fireplace, lake

Cozy rustic 1BR cabin. One of 20 cabins at 115 acres. Family friendly, restaurant (late June-Labor Day). This cabin does not allow pets. 1BR w/queen bed, kitchenette, screen porch. fireplace, picnic table, BBQ. Shared private waterfront-kayaks & fishing, walking trails. Cook in, dine at excellent local restaurants or take-out. Rent bikes/E-bikes or just relax. Spend time with us in our spacious country setting. More options at Loch Lyme Lodge NO CLEANING FEES

Vermont Mountain View Serenity

The address is not yet GPS received. The address is 129 Cyr Heights, not Cyr road. Google Maps will bring you to Cyr Road, not to 129 Cyr Heights. Apple Maps however, will bring you to the correct physical location. The house sets on bedrock. It is a flat open concept with high ceilings and beautiful oversized garage. Being mountain-side with windows open you’ll enjoy a continuous mountain breeze. Radiant floor heating provides warmth to your feet as you walk.

The Robert Burns Suite, a 1 Bedroom Apartment

The Maplecroft Bed & Breakfast is located in the heart of downtown Barre VT, a short walk to restaurants and shopping. As the owner I would be happy to help with information about the area and I look forward to making your stay with us memorable and relaxing. There are many short day trips easily accessible from our location in Central Vermont. We use locally sourced ingredients for our hot homemade breakfast included with your stay.