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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 40 Cottages in Chestertown with updated reviews, rates, and availability.

Waterfront River Cottage for 2, dog-friendly
Welcome to the waterfront cozy River Cottage!

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

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

9.8 out of 10, Exceptional, (109)
"We were in town for the local triathlon and had a great stay! My kids (3&4) and I were able to walk to the finish line from the location. The house was clean and large enough that we were all comfortable. If you have kids, it’s across the street from a cool boat playground. Diane was very responsive to my questions and provided plenty of towels, blankets, etc. Overall, a great stay! "
Peaceful getaway convenient to local amenities including beach, boating & food
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Amazing views, short walks to great dining!
"The design is probably my favorite thing about the place—it’s well thought out and has an excellent flow. I also slept very deeply. Can’t wait to return." Melissa - April 2021

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
Property grounds

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
Secluded Cozy Cottage in Historic Downtown
Living area

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (7)
"Such a wonderful experience staying in this poperty for a couple of days. Walking distance to everything. Jennifer was a pleasure and very responsive. May make this an annual visit! Loved Annapolis!"
The price is AED 1,469
AED 2,470 total
includes taxes & fees
24 Feb - 25 Feb
Secluded Cozy Cottage in Historic Downtown
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Room

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,
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
Welcome to the renovated kitchen at Oh Happy Bay!

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
Regularly cleaned and maintained hot tub perfect for cool nights

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
Eastern Shore beach cottage get-away
Early morning crabbing with Bay Bridge 12 miles away over the water.

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 detail

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
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Welcome to the Coastie Cottage!

Rare find! Chic cottage, salt water heated pool May 15-Oct15.

10.0 out of 10, Exceptional, (50)
"The house was even nicer than in photos or descriptions. The house very spacious, the pool and pool area were perfect for our needs. The hosts were very gracious, communicative, and easy to work with. I would definitely recommend this property."
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Outdoor seating area just off the kitchen.

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

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

10.0 out of 10, Exceptional, (24)
"The house provided a clean, bright, spacious, well-equipped place for a family Thanksgiving gathering. It made for a very comfortable few days. The host was very responsive when we had questions before our stay."
House w/Water Views of Rock Creek 2BA 2BA Cottage
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
Vintage Waterfront Cottage with Stunning Sunsets
Beach

Vintage Waterfront Cottage with Stunning Sunsets

10.0 out of 10, Exceptional, (5)
"thoroughly enjoyed our time at this lovely property. the quiet location, attention to detail, and communication with owners all made for an delightful stay. "
Vintage Waterfront Cottage with Stunning Sunsets
Rock Creek Cottage, Waterfront, Serene Views
Water view from Deck

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
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Terrace/patio

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Sunny Glen Burnie Home - On-site Water Access
Exterior

Sunny Glen Burnie Home - On-site Water Access

3.0 star property
Sunny Glen Burnie Home - On-site Water Access
Grasonville Home w/ Private Pool on the Water
Pool

Grasonville Home w/ Private Pool on the Water

3.0 star property
Grasonville Home w/ Private Pool on the Water
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

'At Fells Point' CitySide - 'Tons better than a hotel!'
CitySide Living Room & Sofa Bed

'At Fells Point' CitySide - 'Tons better than a hotel!'

9.8 out of 10, Exceptional, (185)
"The property is compact but cute. They have a door that slides across doorway between the bedroom and the living room that blocks noise from the outside. We did find the property chilly but when we contacted the owner, he had one of his staff come over, wait a few minutes for us outside, and provide us with space heaters that warmed the place up very effectively and quietly. We felt valued and cared for. I highly recommend this cozy little place and the people who manage it!"
The price is AED 323
AED 747 total
includes taxes & fees
25 Feb - 26 Feb
'At Fells Point' CitySide - 'Tons better than a hotel!'
Cass-N-Reel Luxury Houseboat
Exterior

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (21)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
Chesapeake Houseboat Getaway on Kent Island, Maryland
Exterior

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.6 out of 10, Exceptional, (20)
"We had a wonderful stay on this luxurious houseboat! Clean, comfortable & fun and Julia is an excellent host. We highly recommend Julia's Arc!"
Chesapeake Houseboat Getaway on Kent Island, Maryland
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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