Find Cheap Hotels in Chestertown, MD from CA $76

For budget-conscious travellers in Chestertown, excellent options include the Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, and Driftwood Inn.The Comfort Inn & Suites Chestertown, with its 8.6 rating, offers exceptional value with complimentary full breakfast and free WiFi, ensuring a comfortable and convenient start to your day. Guests frequently highlight the comfortable and clean rooms, as well as the friendly and helpful staff. Free self-parking is also a great bonus.Another solid choice is the Red Roof Inn & Suites Chestertown, rated 7.2. This hotel provides free WiFi and free self-parking, including ample space for RVs, buses, and trucks. Reviewers often mention the comfortable and clean rooms, along with the nice and lovely staff who are happy to assist.The Driftwood Inn offers free WiFi and free self-parking.

For families seeking affordable and highly-rated accommodation in Chestertown, the Comfort Inn & Suites Chestertown is an excellent option.The Comfort Inn & Suites Chestertown boasts an impressive 8.6 rating and offers a range of valuable amenities superb for families. Guests consistently praise the comfortable and clean rooms and beds, as well as the friendly and helpful staff. A key highlight is the complimentary full breakfast, ensuring a great start to the day without extra cost. Free WiFi and free self-parking also add to the convenience and value.The Red Roof Inn & Suites Chestertown, with a 7.2 rating, also provides good value for families. It offers free WiFi, free self-parking, and complimentary toiletries. Reviewers often mention the comfortable and clean rooms, nice staff, and easy parking. Cribs are also available free of charge, which is a great benefit for families with young children.

For budget-friendly accommodation in Chestertown that includes a complimentary breakfast, the Comfort Inn & Suites Chestertown is an excellent option.The 3-star Comfort Inn & Suites Chestertown, with an 8.6 rating, provides a free full breakfast, which is a great saving for any traveller. Guests frequently praise the comfortable and clean rooms and beds, as well as the friendly and helpful staff.

The most affordable time to visit Chestertown is typically during the off-peak seasons, specifically late autumn (November) and late winter (February to early March), outside of major holiday periods. During these months, demand for accommodation and some activities tends to be lower, leading to better deals.For solo travellers, visiting in these quieter months means you can often find reduced rates on guesthouses and smaller inns, which are plentiful in Chestertown. You'll also encounter fewer crowds, allowing for a more relaxed exploration of the historic downtown, browsing independent shops, and enjoying the scenic waterfront along the Chester River. Many local eateries might offer specials during the week to attract customers, providing opportunities for budget-friendly dining.While some seasonal events might not be running, the town's charm, historical sites like the Custom House, and natural beauty remain constant and are mostly free to enjoy.

For a cheap hotel in Chestertown with a pool, the Comfort Inn & Suites Chestertown is an excellent choice.The 3-star Comfort Inn & Suites Chestertown, with an 8.6 rating, offers a refreshing outdoor pool for guests to enjoy seasonally. This hotel provides excellent value with complimentary amenities such as free Wi-Fi, free self-parking, and a full breakfast, available free of charge every day.

For affordable hotels in Chestertown with great customer service, travellers often praise Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, and Driftwood Inn.The 3-star Comfort Inn & Suites Chestertown, rated 8.6, frequently receives compliments for its great service, with many guests highlighting the friendly and helpful front desk staff. Guests also benefit from complimentary WiFi, free parking, and a free full breakfast.Red Roof Inn & Suites Chestertown, with a 7.2 rating, is known for its lovely and nice staff. This hotel also provides free WiFi, free self-parking, and complimentary toiletries, making for an economical and convenient stay.Driftwood Inn is another option where guests have consistently commented on the friendly staff.

Yes, for budget-friendly accommodation in Chestertown offering flexibility with check-in and check-out, the Comfort Inn & Suites Chestertown is a great option.The Comfort Inn & Suites Chestertown has an 8.6 rating from our customers and is known for its accommodating policies. Reviewers often highlight the friendly and helpful front desk staff, who are typically happy to assist with early check-ins or late check-outs when possible. Guests also appreciate the comfortable and clean rooms and beds, and a complimentary breakfast is included, offering excellent value.

Chestertown offers a delightful array of free activities for budget-conscious travellers, allowing you to immerse yourselves in its charm without spending a penny.For couples, a romantic stroll along the Chester River waterfront is a must. You can enjoy the scenic views, watch the boats, and explore the historic district's beautiful architecture. The town boasts numerous historic buildings, many with informative plaques, making a self-guided walking tour an engaging way to spend an afternoon. The Chestertown Farmers Market, held on Saturdays, is also free to browse and soak in the local atmosphere, even if you're not planning on buying anything.Families will find plenty to keep them entertained. A visit to Wilmer Park provides open green space for children to play, and you can enjoy a picnic by the river. The Garfield Centre for the Arts often hosts free community events, from art exhibitions to live music performances, so it's worth checking their schedule during your visit. Additionally, the local library frequently offers free children's programmes and story times, which can be a lovely, quiet activity for younger travellers.Solo travellers can find solace and inspiration in exploring the town's art galleries, many of which offer free admission. The area around Washington College also provides pleasant grounds for a leisurely walk, and you might even catch a free lecture or student performance.