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Dog Friendly Hotels with Swimming Pool in Chestertown

29 HOTELS IN AND AROUND CHESTERTOWNRanking can be influenced by the commissions we receive.
Pet-Friendly Home on Chester River with Dock! main photo
Pet-Friendly Home on Chester River with Dock!
Vacation Home in Chestertown MDUS flag
0.0
$
Info
Categories
Dog Friendly
Pool
Outdoor Pool
Free Wi-Fi
19 more hotels nearby!
Thornton main photo
Thornton
3.6 km from Chestertown
Vacation Home in Kennedyville MDUS flag
0.0
$
Info
Categories
Dog Friendly
Pool
Free Wi-Fi
Mariner's Motel main photo
Mariner's Motel
11.2 km from Chestertown
Motel in Rock Hall MDUS flag
9.4
Excellent
$
Info
Categories
Dog Friendly
Pool
Outdoor Pool
Parking
Mariners Motel main photo
Mariners Motel
11.2 km from Chestertown
Accommodation in Rock Hall MDUS flag
10
Excellent
From $172
$
Info
Categories
Dog Friendly
Pool
Outdoor Pool
Free Wi-Fi
Inn at Osprey Point main photo
Inn at Osprey Point
11.2 km from Chestertown
Inn in Rock Hall MDUS flag
9.4
Excellent
From $188
$
Info
Categories
Dog Friendly
Pool
Private Pool
Outdoor Pool
Small
Blake House Historic Estate with Private Inn main photo
Blake House Historic Estate with Private Inn
11.5 km from Chestertown
Villa in Centreville MDUS flag
10
Excellent
$
Info
Categories
Dog Friendly
Pool
Private Pool
Outdoor Pool
Centreville Waterfront Farm - 170 Acres - Pool - Private Dock - Private Beach main photo
Centreville Waterfront Farm - 170 Acres - Pool - Private Dock - Private Beach
12.7 km from Chestertown
Vacation Home in Centreville MDUS flag
0.0
$
Info
Categories
Dog Friendly
Pool
Free Wi-Fi
Holiday Inn Express Annapolis East-Kent Island by IHG main photo
Holiday Inn Express Annapolis East-Kent Island by IHG
19.7 km from Chestertown
Resort in Grasonville MDUS flag
9.2
Excellent
From $140
$
Info
Categories
Dog Friendly
Pool
Outdoor Pool
Golf
Home2 Suites by Hilton Baltimore/Aberdeen MD main photo
Home2 Suites by Hilton Baltimore/Aberdeen MD
19.8 km from Chestertown
Hotel in Aberdeen MDUS flag
8.5
Very Good
From $138
$
Info
Categories
Dog Friendly
Pool
Indoor Pool
3 Star
Best Western Kent Narrows Inn main photo
Best Western Kent Narrows Inn
19.8 km from Chestertown
Hotel in Grasonville MDUS flag
8.0
Very Good
From $110
$
Info
Summary of reviews
Best Western Kent Narrows Inn is favorably regarded by guests for its prime location near the scenic Prospect Bay and Kent Narrows. Its proximity to a variety of restaurants and entertainment venues makes it a perfect choice for those looking to explore vibrant nightlife and local attractions. The strategic location provides easy access to nearby cities and event venues while offering stunning views of the bay and marinas. Additionally, the hotel is pet-friendly, catering to families and pet owners with accessibility to nearby walking trails and the Chesapeake Bay environmental center.

Guests frequently praise the breakfast experience at the
Best Western Kent Narrows Inn, lauding the wide variety of fresh and delicious options available each morning. The breakfast includes both hearty and lighter choices, ensuring satisfaction for diverse preferences. Furthermore, the hotel has adapted well to COVID-19 measures by providing convenient grab-and-go options, appreciated by guests eager to start their day.

Accommodations at the hotel are described as clean, spacious, and comfortable, with modern features and amenities like refrigerators and microwaves enhancing the stay. Many guests enjoy the beautiful bay views from their rooms, which contribute to the overall pleasant environment. Cleanliness is an outstanding aspect throughout the property, maintained by a diligent housekeeping staff, while the friendly and efficient hotel staff positively impacts guest experiences.

The indoor pool and hot tub are highlighted as inviting amenities, with extended hours and cleanliness being noted as benefits. Families find the pool area particularly enjoyable, complementing the relaxing atmosphere of the hotel. The beds receive positive remarks for their comfort, with pillows and mattresses contributing to restful nights.

The hotel's dog-friendly approach is another appreciated feature, with amenities and surrounding areas suitable for traveling with pets. Overall,
Best Western Kent Narrows Inn combines a convenient location with exceptional service and comfort, making it a preferred choice for travelers seeking both leisure and relaxation.
Categories
Pool
Indoor Pool
Dog Friendly
Rooms with Jacuzzi / Hot-Tub
Hilton Garden Inn Kent Island Marina main photo
Hilton Garden Inn Kent Island Marina
19.9 km from Chestertown
Hotel in Grasonville MDUS flag
7.7
Good
From $143
$
Info
Categories
Dog Friendly
Pool
Indoor Pool
Parking
EV charging stations
Holiday Inn - Belcamp - Aberdeen Area by IHG main photo
Holiday Inn - Belcamp - Aberdeen Area by IHG
20.2 km from Chestertown
Hotel in Belcamp MDUS flag
8.6
Very Good
From $97
$
Info
Summary of reviews
The Holiday Inn - Belcamp - Aberdeen Area by IHG receives strong praise from guests for its overall accommodation experience. The hotel's rooms are frequently highlighted for their spaciousness, cleanliness, and appealing design, ensuring a comfortable stay. Guests often mention the super comfy beds and a cozy atmosphere, contributing to a restful experience. While a few encountered issues such as a temporary lack of hot water, the hotel demonstrated its commitment to customer service by promptly addressing concerns and offering room upgrades. Additionally, the in-hotel dining options, including delicious burgers at the bar and a varied breakfast spread, enhance the stay.

The hotel staff consistently earns high marks for their exceptional service. Guests appreciate their friendly and welcoming demeanor, with the front desk staff being especially noted for their accommodating nature and treating guests like family. The team's eagerness to please and handle matters effectively contributes to a memorable guest experience. While there are rare instances of a less welcoming arrival process, the prevailing warmth and professionalism throughout the hotel leave a lasting positive impression on visitors.
Categories
Dog Friendly
Pool
Indoor Pool
Accessible
Americas Best Value Inn Edgewood, MD main photo
Americas Best Value Inn Edgewood, MD
20.4 km from Chestertown
Hotel in Edgewood MDUS flag
5.3
Rated
From $43
$
Info
Categories
Dog Friendly
Pool
Outdoor Pool
Golf
Ramada by Wyndham Edgewood Hotel & Conference Center main photo
Ramada by Wyndham Edgewood Hotel & Conference Center
20.5 km from Chestertown
Hotel in Edgewood MDUS flag
6.3
Rated
From $57
$
Info
Categories
Dog Friendly
Pool
Outdoor Pool
Accessible
Homewood Suites by Hilton Bel Air main photo
Homewood Suites by Hilton Bel Air
20.5 km from Chestertown
Hotel in Riverside MDUS flag
7.6
Good
From $134
$
Info
Categories
Dog Friendly
Pool
Heated Pool
Indoor Pool
3 Star
Candlewood Suites Aberdeen-Bel Air by IHG main photo
Candlewood Suites Aberdeen-Bel Air by IHG
20.5 km from Chestertown
Hotel in Riverside MDUS flag
8.0
Very Good
From $116
$
Info
Categories
Dog Friendly
Pool
Outdoor Pool
Honeymoon
Hilton Garden Inn Aberdeen main photo
Hilton Garden Inn Aberdeen
21.5 km from Chestertown
Hotel in Aberdeen MDUS flag
8.5
Very Good
From $154
$
Info
Categories
Dog Friendly
Pool
Indoor Pool
Accessible
Days Inn by Wyndham Aberdeen main photo
Days Inn by Wyndham Aberdeen
21.7 km from Chestertown
Hotel in Aberdeen MDUS flag
7.4
Good
From $64
$
Info
Summary of reviews
Days Inn by Wyndham Aberdeen is lauded for its prime location, conveniently situated off I-95, making it an ideal choice for travelers heading to major cities like Baltimore and Washington DC. Guests appreciate its proximity to the historic town of Havre de Grace, as well as nearby stores and restaurants, enhancing the convenience for visitors. The location's accessibility and ample free parking add to its appeal with the friendly staff and additional amenities, like the open pool, complementing the hotel's strategic position.

While breakfast receives mixed reviews with mentions of it being very basic and lacking variety, the cleanliness and organization are noted. For those desiring more substantial options, a nearby restaurant is available.

The rooms offer a blend of positive and negative feedback. Many guests praise them for being clean, spacious and comfortable with some rooms having been upgraded and renovated. However, there are reports of hard mattresses, unpleasant odors and areas requiring attention, such as dark walls, itchy bedding and noisy surroundings. Despite these issues, the rooms provide good value for the price, appealing to travelers who prioritize basic amenities and convenience.

Cleanliness reviews also vary with numerous guests noting the overall cleanliness and comfortable beds, while some point out issues like stained towels, sticky floors and dirty bathrooms. However, there is a consistent mention of clean and quiet rooms, suggesting an effort to maintain cleanliness across the hotel.

The hotel staff consistently receive high praise for their exceptional service and friendliness. Employees, especially Brandi, are commended for their accommodating and professional nature, enhancing the overall positive experience for guests.

The pool is well-maintained and appreciated, despite its small and older appearance. It provides a clean and enjoyable amenity, particularly noted for being tranquil and rarely crowded, offering a relaxing experience for guests.

Comfortable beds are frequently mentioned, contributing positively to many guests' stays. While there are some mixed experiences regarding bed quality, the majority finds the beds clean and comfortable.

In summary,
Days Inn by Wyndham Aberdeen stands out for its excellent location, friendly staff and decent amenities, offering good value for travelers looking for basic comfort and convenience.
Categories
Pool
Outdoor Pool
Dog Friendly
Sustainability Journey
La Quinta by Wyndham Aberdeen-APG main photo
La Quinta by Wyndham Aberdeen-APG
21.8 km from Chestertown
Hotel in Aberdeen MDUS flag
8.9
Excellent
From $95
$
Info
Summary of reviews
La Quinta by Wyndham Aberdeen-APG is highly regarded for its strategic and convenient location. Situated in a quiet yet fun area, it provides easy access to the highway, making it ideal for travelers on I-95. Close to the center of town and near a variety of restaurants, the hotel's location adds to its overall convenience. Guests appreciate the clean and updated facilities, making it perfect for families and groups, despite the nearby toll bridge.

The breakfast experience generally earns positive reviews for being good, great and wonderful with specific mentions of tasty coffee, eggs and sausage. The breakfast room attendant is particularly noted for their excellent service. Cleanliness in the breakfast area also contributes to a pleasant dining experience. However, some guests suggest adding more variety to the offerings and improving the replenishment of food items towards the end of breakfast hours.

Rooms at the hotel consistently impress with their cleanliness, spaciousness and comfort. Guests often describe them as clean, beautiful, very comfortable and well-maintained, highlighting the hotel's new condition and tasteful decoration. The peaceful and quiet atmosphere further enhances the overall positive experience.

Cleanliness is a notable strong point at
La Quinta by Wyndham Aberdeen-APG with many guests praising the very clean and super clean rooms. Both private and common areas are consistently maintained to high standards, adding to the welcoming and pleasant stay. Some minor issues like dirty floors and musty smells are mentioned but these are exceptions to the generally pristine environment.

The staff at the hotel receive high marks for their friendliness, helpfulness and professionalism. Specific staff members, including Ms. Rita and Shah, are frequently praised for their exceptional service. Guests describe the check-in process as quick and easy and the overall warmth and professionalism of the team contribute significantly to an enjoyable stay, despite occasional mentions of understaffing.

The beds are generally found to be quite comfortable with many guests highlighting the firmness and comfort of the mattresses. The majority of reviews indicate a satisfactory sleeping experience, although a few guests mentioned issues with bed softness and pillow comfort.

Overall,
La Quinta by Wyndham Aberdeen-APG is highly recommended for its strategic location, excellent staff, clean and comfortable rooms and generally positive breakfast experience.
Categories
Dog Friendly
Pool
Outdoor Pool
3 Star
Travelodge by Wyndham Aberdeen main photo
Travelodge by Wyndham Aberdeen
21.8 km from Chestertown
Motel in Aberdeen MDUS flag
6.4
Rated
From $49
$
Info
Summary of reviews
Travelodge by Wyndham Aberdeen receives high praise for its convenient and strategic location. Situated off I-95 and Route 95, it is an ideal stop for road trippers, providing easy access to highways and a quiet atmosphere. The hotel's proximity to Aberdeen's local attractions and shopping venues makes it a favored choice among travelers looking to explore the area, offering relaxation and convenience.

Cleanliness is where the reviews are more mixed. Some guests report very clean rooms and a satisfactory level of cleanliness, yet others note areas in need of improvement. While the commitment to maintaining clean accommodations is evident, inconsistencies in housekeeping have been mentioned, with issues such as stained towels and unpleasant odors highlighted. Travelers should be mindful of potential variations and may wish to seek confirmation for a consistently clean environment when booking.

The staff receives generally positive feedback, with guests appreciating their friendliness and attentiveness. Descriptions such as helpful, courteous, and understanding are commonly used, suggesting a welcoming atmosphere. Particular commendation is given to the front desk team for their awesome service, and specific staff members like Mahesh are noted for their exceptional hospitality. The warm and accommodating staff play a significant role in enhancing guests' experiences and contribute to a satisfactory overall stay.
Categories
Dog Friendly
Pool
Outdoor Pool
Accessible
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 29 hotels in and around Chestertown
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