Best B&Bs Middlebury
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Best-rated
Sinclair Inn Bed & Breakfast
- In-room breakfast
- Free parking
- Housekeeping
- Air conditioning
- Skiing
- Sun terrace
The 3-star Sinclair Inn Bed & Breakfast Jericho offers 10 rooms in the vicinity of Fishing Pond, about 15 minutes' walk away. The inn offers a beautiful garden with showers.
Residents can have breakfast in the garden. Poorhouse Pies is in close proximity to this property.
Sinclair Inn Bed & Breakfast
- In-room breakfast
- Free parking
- Housekeeping
- Air conditioning
- Skiing
- Sun terrace
Sinclair Inn Bed & Breakfast
The 3-star Sinclair Inn Bed & Breakfast Jericho offers 10 rooms in the vicinity of Fishing Pond, about 15 minutes' walk away. The inn offers a beautiful garden with showers.
Residents can have breakfast in the garden. Poorhouse Pies is in close proximity to this property.
Downtown Middlebury Bed and Breakfast
Stay At Jimmy'S
- In-room breakfast
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Terrace
The comfortable Stay At Jimmy'S Woodstock hotel offers guests access to the award-winning outdoor Billings Farm History Museum, which is approximately 25 minutes' walk away. The 3-star bed & breakfast boasts views of the garden and offers Wi-Fi throughout the property.
The Stay At Jimmy'S Woodstock is not far from Angkor Wat Restaurant, serving Cambodian cuisine.
Stay At Jimmy'S
- In-room breakfast
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Terrace
Stay At Jimmy'S
The comfortable Stay At Jimmy'S Woodstock hotel offers guests access to the award-winning outdoor Billings Farm History Museum, which is approximately 25 minutes' walk away. The 3-star bed & breakfast boasts views of the garden and offers Wi-Fi throughout the property.
The Stay At Jimmy'S Woodstock is not far from Angkor Wat Restaurant, serving Cambodian cuisine.
Romantic Bed and Breakfast in Middlebury
The Woodstocker B&B
- In-room breakfast
- Free parking
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Terrace
The 4-star The Woodstocker B&B is located around a 10-minute ride from the Marsh-Billings-Rockefeller National Historical Park, offering 9 rooms along with a sauna, a library, and a golf course.
You can dine at Red Rooster, just 13 minutes' walk from The Woodstocker Woodstock.
The Woodstocker B&B
- In-room breakfast
- Free parking
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Terrace
The Woodstocker B&B
The 4-star The Woodstocker B&B is located around a 10-minute ride from the Marsh-Billings-Rockefeller National Historical Park, offering 9 rooms along with a sauna, a library, and a golf course.
You can dine at Red Rooster, just 13 minutes' walk from The Woodstocker Woodstock.
Cheap B&B in Middlebury
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Beach access
The Fern Lodge
- In-room breakfast
- Free parking
- Express check-in/ -out
- Air conditioning
- Sauna
- Sun terrace
The comfortable The Fern Lodge Chestertown hotel, positioned 4.2 km from Loon Lake Public Beach, offers 8 spa tubs for the best experience. Located about 15 minutes' drive from the Rustic Charm, this 4-star bed & breakfast features 6 rooms with views of the garden.
Visitors can have a drink at the lounge bar, which has a happy hour and a TV.
The Fern Lodge
- In-room breakfast
- Free parking
- Express check-in/ -out
- Air conditioning
- Sauna
- Sun terrace
The Fern Lodge
The comfortable The Fern Lodge Chestertown hotel, positioned 4.2 km from Loon Lake Public Beach, offers 8 spa tubs for the best experience. Located about 15 minutes' drive from the Rustic Charm, this 4-star bed & breakfast features 6 rooms with views of the garden.
Visitors can have a drink at the lounge bar, which has a happy hour and a TV.
Are you in a hurry?
Here is a quick list of Bed and Breakfast in Middlebury, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Sinclair Inn Bed & Breakfast |
9.7 / 10 (124 Reviews) |
From 232$ | |
| Stay At Jimmy'S |
9.4 / 10 (80 Reviews) |
From 449$ | |
| The Woodstocker B&B |
9.6 / 10 (12 Reviews) |
From 538$ |
Frequently Asked Questions
Which romantic bed and breakfasts near Lake George offer unique experiences?
The Fern Lodge features private evening boat tours on Friends Lake, perfect for couples. They also provide gourmet breakfasts and cozy lake views, enhancing the romantic atmosphere.
Book a private boat tour before sunset for a truly unforgettable experience under the stars.
What romantic bed and breakfasts in Woodstock are good for outdoor adventures?
The Woodstocker B&B offers unique adventures such as curated local experiences and easy access to Mount Tom for hiking. Couples can enjoy a cozy stay with a mix of romance and nature.
Plan your hiking trip during the early morning for cooler temperatures and stunning views of the sunrise.
Which bed and breakfasts near downtown Jericho provide family-style accommodations?
Sinclair Inn Bed & Breakfast has spacious rooms that cater to families while keeping historical charm. Plus, it offers a tranquil environment with its beautiful gardens and nearby outdoor activities.
Visit during midday for the best light for family photos in the picturesque gardens.
What bed and breakfasts in Woodstock are near ski resorts for winter getaways?
Stay At Jimmy's is a cozy option located near Killington Mountain, providing access to ski slopes. The hotel offers comfortable rooms and a friendly atmosphere for ski enthusiasts.
Book your ski package at least two weeks in advance to secure better pricing on lift tickets.
Which romantic bed and breakfasts with balconies in Middlebury are best for scenic views?
The Fern Lodge has intimate guest rooms with balconies overlooking scenic landscapes, perfect for couples. Enjoy a private morning coffee while soaking up the views.
Opt for a room on the upper floors for the best view of Friends Lake at sunrise.
Which bed and breakfasts are pet-friendly and offer outdoor spaces for families?
Stay At Jimmy's welcomes pets and features a relaxing garden area where families can spend time together. Enjoy nature while creating memories with your four-legged friends.
Visit Gifford Woods State Park just moments away for pet-friendly walking trails and fresh air.
Which eco-friendly bed and breakfasts in Woodstock are near cultural attractions?
The Woodstocker B&B combines eco-friendly practices with local experiences, and it's located close to Billings Farm and Museum. It's a great base for exploring local culture while being kind to the environment.
Attend the farm's educational programs on weekdays for a quieter, more informative experience.
What unique local experiences can I find in Middlebury?
Middlebury is home to various local festivals like the Middlebury Maple Festival in spring, celebrating the town's maple syrup heritage. This event includes tastings, crafts, and family activities.
Plan your visit for the first weekend of April to fully enjoy all festival activities and flavors.
How can families enjoy outdoor activities in the Jericho area?
Families can explore Mills Riverside Park for picnics and hiking, plus skiing in winter. Nearby Smugglers' Notch also provides skiing and fun in all seasons.
Visit Mills Riverside Park on weekends for community events and activities, which are engaging for kids.
Where can I find family-friendly dining options in Woodstock?
Restaurants like Bentley's have family-friendly menus and cozy atmospheres. They are perfect for enjoying a hearty meal after a day of exploring.
Visit during lunchtime for special deals on kids' meals and a quieter dining experience.