Top Hotels in Chester

Search among 6 available hotels and places to stay in Chester from 50+ providers

Check-in
Select date
Check-out
Select date
Rooms & Guests
22 Guests, 1 Room
1Filter & Sort
View map
1-6 out of 6
1Filter & Sort
View map
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
8.6
Great42 reviews
MapView on map700 yd from City Center1600 yd from Green Mountain Flyer
From   US$ 369 /nightSelect
8.4
Great27 reviews
MapView on map600 yd from City Center1600 yd from Green Mountain Flyer
From   US$ 74 /nightSelect
8.4
Great51 reviews
500 yd from City Center1500 yd from Green Mountain Flyer
From   US$ 114 /nightSelect
Bed & Breakfast
8.4
Great43 reviews
1.5 mi from City Center
From   US$ 264 /nightSelect
Bed & Breakfast
8.2
Great29 reviews
1700 yd from City Center800 yd from Green Mountain Flyer
From   US$ 166 /nightSelect
7.8
Very good6 reviews
600 yd from City Center1500 yd from Green Mountain Flyer
From   US$ 152 /nightSelect

Best hotels and places to stay in Chester

Why visit?

Chester, Vermont, is a charming and picturesque town that offers a delightful experience for tourists. With its rich history, quaint shops, and stunning natural surroundings, Chester is the perfect destination for those looking to relax and immerse themselves in small-town charm. Whether you are interested in exploring the local history, enjoying outdoor activities, or simply unwinding in a tranquil setting, Chester has something to offer for everyone.

Where to stay?

Main Street: Located in the heart of Chester, Main Street is the ideal area to stay for those who want to be within walking distance of shops, restaurants, and local attractions. With several charming bed and breakfast options available, visitors can enjoy comfortable accommodations with a touch of New England hospitality. This area also offers easy access to the nearby Okemo Mountain Resort for those interested in winter sports.

The Stone Village: For a unique and historic lodging option, consider staying in The Stone Village. This area is known for its beautifully preserved stone houses, which now serve as cozy and inviting bed and breakfasts. The peaceful ambiance and picturesque surroundings make The Stone Village an excellent choice for a relaxing getaway.

Chester Depot: Located close to the Chester Depot train station, this area offers convenient access for travelers arriving by rail. Visitors can find a range of lodging options, including hotels and inns, providing comfortable accommodations for both short and extended stays. The proximity to the train station also makes it a great base for exploring other parts of Vermont.

What is the price per hotel room per night?

3-star hotels: The average price per night is around $120 to $180.

4-star hotels: The average price per night is around $180 to $250.

5-star hotels: The average price per night is around $250 to $400.

Best value for money:

Inn Victoria: Located in the heart of Chester, Inn Victoria offers cozy and elegant rooms at affordable rates. With its charming Victorian-style décor, friendly staff, and delicious homemade breakfast, this bed and breakfast provides excellent value for money. Guests can enjoy modern amenities such as free Wi-Fi and complimentary afternoon tea.

Rose Arbour Bed and Breakfast: Nestled in a beautiful garden setting, Rose Arbour Bed and Breakfast provides a peaceful retreat with comfortable accommodations. Guests can enjoy a hearty breakfast and take advantage of the inns convenient location, within walking distance of shops and restaurants. The attentive hosts ensure a pleasant stay for a reasonable price.

The Fullerton Inn: With its historic charm and comfortable rooms, The Fullerton Inn offers excellent value for budget-conscious travelers. This inn boasts a central location on Chesters Main Street, with easy access to local attractions. Guests can enjoy complimentary breakfast and relax on the inns spacious veranda.

Best kids-friendly hotels:

Green Mountain Mansion: This family-friendly bed and breakfast offers spacious rooms and suites that can accommodate families of all sizes. The on-site playground, outdoor pool, and beautiful gardens provide ample opportunities for children to have fun. Conveniently located near family-friendly attractions, Green Mountain Mansion is a great choice for those traveling with kids.

Chester House Inn: Situated in a charming historic building, Chester House Inn offers a warm and welcoming atmosphere for families. The inn provides interconnected rooms, cribs, and high chairs upon request. Children will enjoy the homemade cookies, while parents can relax in the cozy lounge area.

Best hotels for a romantic getaway:

Inn at Weathersfield: Set in a picturesque countryside, the Inn at Weathersfield offers a serene and romantic retreat. The cozy rooms, some with fireplaces, and the on-site gourmet restaurant create a perfect ambiance for couples. The inns peaceful location amidst nature ensures a romantic escape.

Inn Victoria: Known for its romantic atmosphere, Inn Victoria provides intimate rooms with luxurious amenities such as whirlpool tubs for couples to enjoy. The inns attentive staff can arrange special touches like fresh flowers and champagne to make the stay even more memorable.

Best for location:

The Stone Village: Located in a historic neighborhood with beautifully preserved stone houses, The Stone Village offers a unique and convenient stay. Guests can explore the charming surroundings on foot and easily access nearby attractions, including the Vermont Country Store.

Chester House Inn: Situated on Main Street in Chester, this inn is centrally located near shops, restaurants, and local points of interest. Guests can conveniently access various amenities and easily explore the towns attractions on foot.

Fullerton Inn: Positioned on Main Street, Fullerton Inn offers a prime location in the heart of Chester. Visitors can stroll through the town center and discover its cozy shops and restaurants, all within easy reach from the inn.

Best for a short city break:

Inn Victoria: With its prime location in the town center, Inn Victoria provides a convenient base for a short city break. Guests can easily explore the charming streets, visit local attractions, and indulge in shopping and dining options.

Chester House Inn: Situated on Main Street, Chester House Inn offers easy access to the towns best spots. Visitors can enjoy a short walk to the nearby shops and restaurants or venture out to explore the natural beauty of the surrounding area.

Show moreLess