Top Bed and Breakfast in Chester
-
Guest favorite
Stay At Jimmy'S
- In-room breakfast
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Terrace
The comfortable Stay At Jimmy'S Woodstock hotel provides proximity to the award-winning outdoor Billings Farm History Museum, which is located approximately 25 minutes' walk away. The 3-star bed & breakfast also features Wi-Fi throughout the property.
Angkor Wat Restaurant offers a wide range of Cambodian dishes and lies not far from this Woodstock hotel.
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 provides proximity to the award-winning outdoor Billings Farm History Museum, which is located approximately 25 minutes' walk away. The 3-star bed & breakfast also features Wi-Fi throughout the property.
Angkor Wat Restaurant offers a wide range of Cambodian dishes and lies not far from this Woodstock hotel.
Chester Bed and Breakfast Downtown
-
Top location
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, situated around a 10-minute ride from the Marsh-Billings-Rockefeller National Historical Park, features a sauna, a library, and a golf course.
The nearby dining options feature Red Rooster, which is only a 13-minute walk away.
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, situated around a 10-minute ride from the Marsh-Billings-Rockefeller National Historical Park, features a sauna, a library, and a golf course.
The nearby dining options feature Red Rooster, which is only a 13-minute walk away.
Romantic Bed and Breakfast in Chester
Inn On Putney Road
- In-room breakfast
- Free parking
- Housekeeping
- Air conditioning
- Live entertainment
- Sun terrace
The comfortable Inn On Putney Road Brattleboro enjoys a convenient location, merely 1.3 km from places of worship like St. Michael's Episcopal Church, and provides guests with a library. This 4-star bed & breakfast features a sundeck, a library, and a golf course, and the rooms overlook the garden.
Guests are welcome to a lounge bar on site. Subway is 600 metres from Inn On Putney Road and specialises in American cuisine.
Inn On Putney Road
- In-room breakfast
- Free parking
- Housekeeping
- Air conditioning
- Live entertainment
- Sun terrace
Inn On Putney Road
The comfortable Inn On Putney Road Brattleboro enjoys a convenient location, merely 1.3 km from places of worship like St. Michael's Episcopal Church, and provides guests with a library. This 4-star bed & breakfast features a sundeck, a library, and a golf course, and the rooms overlook the garden.
Guests are welcome to a lounge bar on site. Subway is 600 metres from Inn On Putney Road and specialises in American cuisine.
Cheap B&B Chester
-
Great deal
Cavalier Cottage B&B
- In-room breakfast
- Free parking
- Air conditioning
- Flat-screen TV
- Ski equipment hire
- Sun terrace
Guests of Cavalier Cottage B&B Shelburne Falls can visit the art gallery "Salmon Falls", situated 10 minutes away by car. This comfortable hotel offers Wi-Fi throughout the property.
Cavalier Cottage B&B
- In-room breakfast
- Free parking
- Air conditioning
- Flat-screen TV
- Ski equipment hire
- Sun terrace
Cavalier Cottage B&B
Guests of Cavalier Cottage B&B Shelburne Falls can visit the art gallery "Salmon Falls", situated 10 minutes away by car. This comfortable hotel offers Wi-Fi throughout the property.
Are you in a hurry?
Here is a quick list of Bed and Breakfast in Chester, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Stay At Jimmy'S |
9.4 / 10 (80 Reviews) |
From 449$ | |
| The Woodstocker B&B |
9.6 / 10 (12 Reviews) |
From 538$ | |
| Inn On Putney Road |
9.3 / 10 (52 Reviews) |
From 277$ | |
| Cavalier Cottage B&B |
8.8 / 10 (19 Reviews) |
From 185$ |
Frequently Asked Questions
Which romantic bed & breakfasts near Brattleboro should I consider?
Inn On Putney Road offers a charming atmosphere for couples seeking romance. Enjoy a gourmet breakfast and intimate accommodations.
Plan a hike at nearby Mount Monadnock before breakfast to enjoy beautiful views.
What are the best historic bed & breakfasts in Woodstock?
The Woodstocker B&B is housed in a building dating back to 1830, providing a unique historic character. Guests can explore the town's rich history while enjoying modern amenities.
Visit Billings Farm and Museum nearby to learn more about the area's agricultural history.
Where can I find pet-friendly bed & breakfasts in Shelburne Falls?
Cavalier Cottage B&B offers pet-friendly accommodations with genuine care for your furry friends. Enjoy spacious rooms while surrounded by nature.
Take a walk in Catamount State Forest with your pet in the early morning for a peaceful experience.
What bed & breakfasts in Woodstock have outdoor activities nearby?
Stay At Jimmy's provides easy access to outdoor activities near Killington Mountain. Guests can enjoy skiing in the winter and hiking during warmer months.
Book your accommodations during the weekdays to avoid crowds at popular ski areas.
Which bed & breakfasts in Chester offer notable breakfast experiences?
Inn On Putney Road prides itself on a unique multi-course gourmet breakfast using local ingredients. This is a must-try for food lovers.
Request the chef's special dish in advance to keep the surprise element alive.
What scenic bed & breakfasts in Brattleboro are ideal for nature lovers?
In addition to Inn On Putney Road, visitors can enjoy outdoor adventures at Fort Dummer State Park, which is nearby and offers great hiking trails.
Plan your hike to Fort Dummer during the late afternoon when the light is perfect for photography.
Which bed & breakfasts in Woodstock are best for an eco-friendly stay?
The Woodstocker B&B focuses on eco-friendly practices and features rustic chic decor. It provides local experiences tied to sustainability.
Participate in local farm tours to learn about sustainable farming practices in the area.
What's the best time to visit Chester for outdoor activities?
The best time is from late spring to early fall for hiking and exploring. Plan your visit in June for warm weather and blooming nature.
Book accommodations before June to get better rates and more options.
How do I get around Chester easily without a car?
Local transport options may be limited; consider using rideshare apps for flexibility. Renting a bicycle also offers a fun way to explore nearby attractions.
Bring a simple map or use offline navigation to help you understand local trails and bike paths.
Are there any local events in Chester I should plan around?
Plan your visit for the Chester Winter Carnival in January, which includes festive activities, parades, and local entertainment. It's a great way to experience the community spirit.
Book your stay in advance as hotels fill up quickly during popular events like the carnival.