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Compare 404 Vacation Homes in Chestertown with updated reviews, rates, and availability.

Directly Across from Gate One & Steps from the Waterfront
Private rear courtyard
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (200)
"Incredible location! The process was easy and the house completely suited our needs! We would definitely stay again!"
Directly Across from Gate One & Steps from the Waterfront
Elegant Urban Retreat in Canton Baltimore
Living area
Elegant Urban Retreat in Canton Baltimore
9.6 out of 10, Exceptional, (8)
"Darling place located close to everything you need -- restaurants, coffee shops, drug stores, and Safeway. Quiet neighborhood to boot. The manager was very responsive to any questions. This place is a definite "yes"."
The price is AED 441
AED 1,069 total
includes taxes & fees
6 Nov 2024 - 7 Nov 2024
Elegant Urban Retreat in Canton Baltimore
USNA family Waterfront Paradise just minutes from Annapolis and Baltimore, MD.
Marina
USNA family Waterfront Paradise just minutes from Annapolis and Baltimore, MD.
USNA family Waterfront Paradise just minutes from Annapolis and Baltimore, MD.
Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning
Living area
Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning
3.0 star property
Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Miscellaneous
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (19)
"Our annual girls weekend was held at this property. The house was perfect. there were enough beds and Comfortable relaxing places to sit and view the lake relax around the pool Or just sit quietly and read a book. The property manager, Erin Was so helpful through the entire process And I do think the pictures did not do justice to the lovely appointed decor. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Amazing Location
Charming garden row home, easy 4 block walk to the heart of Annapolis.
10.0 out of 10, Exceptional, (108)
"We have stayed at this property multiple times since we have a son at the Naval Academy. This place is beautiful, well appointed and comfortable. The hosts are very responsive and they go out of their way to make their guests feel extra special- we will be back. "
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Charming Historic Townhouse Steps From USNA
Interior
Charming Historic Townhouse Steps From USNA
10.0 out of 10, Exceptional, (20)
"We had the best time at this rental — it was accessible, cozy, stocked with things like good toilet paper (silly, but we noticed and appreciated!), and in an amazing location! Absolutely recommend! "
Charming Historic Townhouse Steps From USNA
Idyllic Pasadena Retreat with Garden + Hot Tub!
Pasadena Vacation Rental | 1,727 Sq Ft | 3BR | 2BA | Stairs Required
Idyllic Pasadena Retreat with Garden + Hot Tub!
9.8 out of 10, Exceptional, (21)
"This place was a wonderful little getaway for my partner and I! It's even more lovely than in the photos! Spacious and very comfortable and cozy. Immaculately clean and well stocked with the essentials. The king bed was very very comfy. The hot tub was amazing and super relaxing! The patio is beautiful and the fountain in the back yard is adorable and added a lovely bit of scenery and ambiance as well. It's also in a great location, just a couple minutes away from anything you might need, like...
Idyllic Pasadena Retreat with Garden + Hot Tub!
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
8.8 out of 10, Excellent, (18)
"Loved this location as EVERYTHING is walkable - St John's college, USNA, the capitol and Main Street. One skinny parking place was appreciated and reasonable for a standard size vehicle (not super truck or SUV). Enjoyed the older character of the home and modern conveniences as well as small outdoor space that was very nicely landscaped with flowers. "
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard
Situated on a quiet street in West Annapolis, the home is walkable to shops, restaurants and Navy Stadium.
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard
10.0 out of 10, Exceptional, (15)
"Very clean, great location - easily walkable for a USNA reunion to stadium and alumni center!"
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard
Charming Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Outdoor dining
Charming Waterfront house with expansive views of the Chesapeake Bay and Sunsets
10.0 out of 10, Exceptional, (1)
"What a wonderful home, spacious just beautiful! But the view of the bay was everyone’s favorite, we spent 98% of the time outside only inside for eating and sleeping. The grandkids didn’t pick up and electronic device the entire time, they played basketball, fished, cornhole, counting boats. The only time a TV was turned on was to watch Big Blue Madness and the Kentucky/Vandy game (we’re from Kentucky). But if you like TV there is one in every room! This home is very well stocked with everything...
Charming Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Concord Point Lighthouse
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
9.6 out of 10, Exceptional, (55)
"Super cute house in a quiet neighborhood(unless the fire department has a call. It is right around the block.) Really enjoyed our stay. Just be warned, the stairs to the upstairs are not for someone older. They are a bit steep and narrow."
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
Come Relax,Enjoy,Experience,drink,and have a Exciting joyful Vacation
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
9.4 out of 10, Exceptional, (23)
"We had a great stay. Ray, the host was easy to communicate with and very hands-on and helpful. The place exceeded expectations. Really a lot of room. The garage was nice to have. Only thing the Rooftop deck needs some sprucing up and some better outdoor furniture. Otherwise the place was Great."
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Charming Home in Annapolis, MD !
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
9.6 out of 10, Exceptional, (105)
"The only downside and it was miniscule in relation to the overall experience was the amount of debris on the front porch that came from storms blowing off of the trees. Couldn't really be helped and again very minor issue. The rest of the house was fabulous!!"
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
10.0 out of 10, Exceptional, (47)
"Beautiful views and spacious comfortable living space. Well supplied kitchen. "
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
This fire pit overlooking the lake offers stunning sunset views and an even better seat for stargazing!
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
9.4 out of 10, Exceptional, (32)
"We had a great time in the pool, fishing off dock, paddle boarding, kayaking and swimming. The kids (5 under 8) loved playing in the bAsement."
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
Waterfront Oasis w/ Private Dock, 3BR/2BA
Living area
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.8 out of 10, Exceptional, (26)
"The house is spacious (more than the photos may lead you to believe), with numerous gathering centers inside and out. My guests enjoyed the dock at sunset and the fire pit by the water. The patio under the house had a charcoal grill and ample space for tables and chairs. Though our weekend had perfect weather, the covered patio made the place "weatherproof" had it rained. There is tons of parking, and a beautiful view over the water. The Host was readily available via VRBO messaging, Usually...
Waterfront Oasis w/ Private Dock, 3BR/2BA
Riverfront home with multiple decks, central AC, washer/dryer - two dogs OK
Riverfront home with multiple decks, central AC, washer/dryer - two dogs OK
10.0 out of 10, Exceptional, (36)
"Pretty house in a lovely location. Everything went very smoothly."
Riverfront home with multiple decks, central AC, washer/dryer - two dogs OK
Sunny Glen Burnie Home - On-Site Water Access
Glen Burnie Vacation Rental | 3BR | 2BA | Stairs Required | 1,800 Sq Ft
Sunny Glen Burnie Home - On-Site Water Access
9.6 out of 10, Exceptional, (12)
"The property was excellent location for our purposes of exploring the area. For future reference you should update the ‘amenities’ to clarify that the coffee maker is a Keurig type and not traditional. Also having throw blankets handy for cool evenings on the deck would nice. "
Sunny Glen Burnie Home - On-Site Water Access
Beautiful, spacious, quiet waterfront house!
Stunning view. Gorgeous sunrises. Birdwatcher's and boater's paradise.
Beautiful, spacious, quiet waterfront house!
10.0 out of 10, Exceptional, (45)
"Good"
Beautiful, spacious, quiet waterfront house!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chestertown

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (60)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Miscellaneous
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (19)
"Our annual girls weekend was held at this property. The house was perfect. there were enough beds and Comfortable relaxing places to sit and view the lake relax around the pool Or just sit quietly and read a book. The property manager, Erin Was so helpful through the entire process And I do think the pictures did not do justice to the lovely appointed decor. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from Gate One & Steps from the Waterfront
Private rear courtyard
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (200)
"Incredible location! The process was easy and the house completely suited our needs! We would definitely stay again!"
Directly Across from Gate One & Steps from the Waterfront
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.