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Compare 531 Vacation Homes in Chestertown with updated reviews, rates, and availability.

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (212)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (184)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (259)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

9.6 out of 10, Exceptional, (27)
"Great stay, would do it again."
The price is AED 251
AED 908 total
includes taxes & fees
28 Apr - 29 Apr
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (35)
"This house was in a fantastic location! It is within walking distance to downtown Annapolis and anything you might need or want. It is a cute little home with all of your needed comforts. "
Historic Annapolis Home 1.5 blocks from center of town.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Entire House by the Fells Point, JHU.

9.8 out of 10, Exceptional, (21)
"Home was clean and location was convenient. Had a great stay."
The price is AED 455
AED 865 total
includes taxes & fees
27 Apr - 28 Apr
Entire House by the Fells Point, JHU.

Steps to USNA Gate 3 at historic Gatehouse, on-site parking

2.5 star property
10.0 out of 10, Exceptional, (5)
"We had a wonderful stay in this fabulous property. The location near gate 3 of USNA and the quick walk to downtown made it a perfect spot. The house was impeccably clean, comfortable and roomy. Cathy was exceptionally helpful throughout our booking process and stay. You will absolutely enjoy your stay!"
Steps to USNA Gate 3 at historic Gatehouse, on-site parking

PERFECT LOCATION in the heart of history

10.0 out of 10, Exceptional, (197)
"Great weekend at this property in Annapolis! Location is within walking distance to restaurants and shopping!"
PERFECT LOCATION in the heart of history

Bay Breeze - Charming 3BR Waterfront Home on the Chester River

10.0 out of 10, Exceptional, (1)
"As advertised. Great views, dock and decks. Inside is modern, functional and very clean. No complaints whatsoever."
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

Step into History: Charming Fells Point Retreat

10.0 out of 10, Exceptional, (2)
"This home was GORG, the size, the style, the location were all 10/10. We loved having so much space for all of us to spread comfortably. Every floor was like a mini apartment with all the extra kitchen spaces. The balcony and rooftop view, which was fully furnished, were incredible bonuses We went to school in Baltimore and were visiting for a little reunion. We know Fells Point and the surrounding areas very well but got to experience it in a whole new way with this stay. We had an amazing...
Step into History: Charming Fells Point Retreat

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

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (34)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AED 270
AED 913 total
includes taxes & fees
28 Apr - 29 Apr
Relax on Kent Island in 3 Bedroom Home w/Waterview

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (136)
"we had a short stay but wished it was longer, the views from the house and peacefulness of the location were incredible"
The price is AED 1,319
AED 2,398 total
includes taxes & fees
1 May - 2 May
5-bedroom vacation home 5 minutes from historic Charlestown

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (47)
"Great location with a great view."
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

9.8 out of 10, Exceptional, (16)
"Loved the stay, easy and functional for a larger group to get together in Annapolis. "
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

10.0 out of 10, Exceptional, (86)
"My family (9 of us ages 30-63) stayed at the sunset house for what have been our 30th family vacation. This house was perfect. Great location to St Michael’s, Easton and Oxford made for "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Charming garden row home, easy 4 block walk to the heart of Annapolis.

10.0 out of 10, Exceptional, (111)
"I visited my midshipman and I couldn’t have asked for a better place! Very comfortable & spacious-yet not too big. It was as if we were home. Location was awesome. Mike was great with immediate communication-especially in preparing us with info well before our check in day! I would definitely stay here again! "
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.8 out of 10, Exceptional, (13)
"Beautiful house, perfect for our family. The humans loved kayaking and bird watching on the river, the canine loved sitting out on the fenced in deck and relaxing in the nice cool AC"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

25-50% Off~Private Beach~Hot Tub~Fire Table~

10.0 out of 10, Exceptional, (22)
"It was the perfect romantic getaway! "
25-50% Off~Private Beach~Hot Tub~Fire Table~
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

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (212)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (23)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
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.