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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 54 Cottages in Chestertown with updated reviews, rates, and availability.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun loungers

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (45)
"Great little home away from home. A small orientation list for newcomers would be helpful. Closest groceries, gas and such. Outside of that all and all VERY pleasing. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
On the beach, sun loungers, beach towels

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

9.8 out of 10, Exceptional, (29)
"My stay was wonderful, listing just as described. Beautiful water views and enjoyed the local area. Highly recommend and plan to return. Thank you so much for a lovely stay!"
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Property grounds

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

9.8 out of 10, Exceptional, (22)
"My husband and I stayed here for 3 nights while I recovered from a surgery. It was a perfect, peaceful cottage and beautiful neighborhood. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Peaceful getaway convenient to local amenities including beach, boating & food
Beach towels

Peaceful getaway convenient to local amenities including beach, boating & food

9.8 out of 10, Exceptional, (110)
"Great location and local restaurants. Perfect side for small group to do paper crafting. Would definitely book this place again. "
Peaceful getaway convenient to local amenities including beach, boating & food
Amazing views, short walks to great dining!
View from property

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (78)
"Very well-maintained property in a quiet neighborhood. Although we didn't need anything, host was always available."
Amazing views, short walks to great dining!
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sun loungers, beach towels

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (97)
"My wife and I, and our daughter's family (including our grandkids (ages 5 and 8) spent an amazing long weekend at Spring Cove Farm. We all loved our stay so much. The house was spotlessly clean and had everything we needed and the pier/water was gorgeous with ample kayaks and paddle boards. The kids fished from the pier for hours upon hours each day, and were thrilled at the selection of toys. Our daughter and son-in-law were working remotely and the Wi-Fi and Internet worked perfectlu. Dr....
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Terrace/patio

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

10.0 out of 10, Exceptional, (26)
"Amazing house! perfect for my family and our stay in Annapolis. Perfect location to everything. We had all of the amenities we needed and everything was easy to use. If I had one thing negative to say, I wish I could have had my dogs with us, I would have gladly paid a cleaning fee to have them there. Luckily I was able to make other arrangements. Thank you for sharing your house with my family!"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
The Heron's Nest at Atlantic Marina
Exterior

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (286)
"We booked this property, along with the other property at the marina for our wedding weekend and WOW - we LOVED our stay. The views from this cute little cottage are phenomenal. We woke up each morning to watch the sunrise. The hosts were extremely accommodating and even helped secure our cake topper that we accidentally left behind in the whirlwind of check-out. This was the perfect spot for our first look as well. I would highly recommend booking this place for a cute romantic stay!"
The Heron's Nest at Atlantic Marina
Eastern Shore beach cottage get-away
Sun loungers

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (133)
"Perfect location for watching the sunsets as the house is located right across the street from the beach. Also, an easy bike ride to restaurants and shops on Main St. The house is clean and comfortable. Highly recommend to other guests!"
Eastern Shore beach cottage get-away
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break
Exterior

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break

10.0 out of 10, Exceptional, (85)
"Our eighth stay at this property was just as good as ever. It is our home-away-from-home when visiting family in Annapolis. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Property grounds

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

10.0 out of 10, Exceptional, (7)
"We really enjoyed our long weekend at The Oyster Cottage. We needed some rest and relaxation and this cottage was perfect. Very well maintained and stocked! "
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Waterfront River Cottage for 2, dog-friendly
On the beach

Waterfront River Cottage for 2, dog-friendly

9.2 out of 10, Wonderful, (7)
"It's a beautiful location and we enjoyed our visit."
Waterfront River Cottage for 2, dog-friendly
Be persuaded to experience this vintage cottage by the Sassa
Outdoor dining

Be persuaded to experience this vintage cottage by the Sassa

9.4 out of 10, Exceptional, (8)
"We had one of the best vacations ever. Our 9 and 7 year old grandchildren wanted to live there forever! We had a beautiful house and access to the outdoor spaces including a dock for gishing, crabbing and swimming. We were able to make smores over a great fire pit and enjoyed phenominal sunsets from a sitting area overlooking the river. Gene and Suzie, the hosts were on-site and so warm and welcoming. Our every need was met immediately. We will definitely be vacationing at Gregg Neck Cottage...
Be persuaded to experience this vintage cottage by the Sassa
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
View from property

Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (38)
"This weekend, we had the pleasure of staying at Mark and Karen's place, and it was truly immaculate and thoughtfully designed. They’ve considered every detail, providing everything you could possibly need for a fantastic stay.One of the main reasons we chose this house was to have a gathering with our brother, who uses a wheelchair. This house checks all the boxes for accessibility. The doors throughout the home are wide enough to easily accommodate a larger wheelchair, including the doorways to...
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Secluded Cozy Cottage in Historic Downtown
Terrace/patio

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (8)
"Perfect location for family visit at USNA! House was super clean and cozy with easy access to all downtown and academy events."
The price is SAR 1,500
SAR 2,540 total
includes taxes & fees
31 Mar - 1 Apr
Secluded Cozy Cottage in Historic Downtown
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Property grounds

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"The place has a wonderful view of the bay & a cabin-like look. The exterior (deck) is fantastic with lots of lawn chairs, bbq grills, & tables and the view of the bay. The main kitchen in the 1st house (you enter into from parking) is good with 2 ovens, 1 big stove, and 1 big refrigerator. Kuerig machines in the main & small kitchen are a nice bonus. The small kitchen in the 2nd house is also nice & functional. The 2 bedrooms & 1 bathroom in the 2nd house are in good condition (except the...
The price is SAR 1,500
SAR 2,690 total
includes taxes & fees
31 Mar - 1 Apr
Chesapeake Cottages- 2 Quaint Waterfront Retreats
House w/Water Views of Rock Creek 2BA 2BA Cottage
Terrace/patio

House w/Water Views of Rock Creek 2BA 2BA Cottage

10.0 out of 10, Exceptional, (25)
"We were not on vacation we had been displaced from our do to a pipe bursting while we were on a two week vacation.We needed a place that felt like home. It was a lovely home and very comfortable. Its open space is great for family’s. I recommend this property.!"
House w/Water Views of Rock Creek 2BA 2BA Cottage
Cozy Cottage
Terrace/patio

Cozy Cottage

10.0 out of 10, Exceptional, (1)
"Lovely home with everything you need."
Cozy Cottage
Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach
Living area

Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach

Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach
Rock Creek Cottage, Waterfront, Serene Views
Fridge, microwave, oven, stovetop

Rock Creek Cottage, Waterfront, Serene Views

10.0 out of 10, Exceptional, (1)
"Absolutely amazing place for my husband and I to relax with our midshipmen. Very clean, beautifully decorated and the view on the dock each morning was stunning! Close to restaurants (loved 3 B’s Bakery) and host was awesome! "
Rock Creek Cottage, Waterfront, Serene Views
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

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

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

10.0 out of 10, Exceptional, (209)
"Perfect Location - Easy Process - Comfortable Home!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining

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

10.0 out of 10, Exceptional, (180)
"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
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds

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

9.4 out of 10, Exceptional, (22)
"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.

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