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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Cottages in Chestertown

The Heron's Nest at Atlantic Marina
Exterior

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (290)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
View from property

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

10.0 out of 10, Exceptional, (44)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
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, (49)
"This was our second time staying at the property with our two kids and the accommodations continue to impress. We will happily stay again."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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
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, (27)
"Great location and very clean property. Cyndi was responsive and a great host. Would definitely stay again."
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Water taxi just mins to Downtown Annapolis from waterfront home with a beach, dog-friendly
On the beach, sun loungers, beach towels

Water taxi just mins to Downtown Annapolis from waterfront home with a beach, dog-friendly

10.0 out of 10, Exceptional, (31)
"Really like this place "
Water taxi just mins to Downtown Annapolis from waterfront home with a beach, dog-friendly
Rock Creek Cottage, Waterfront, Serene Views
Fridge, microwave, oven, stovetop

Rock Creek Cottage, Waterfront, Serene Views

10.0 out of 10, Exceptional, (3)
"My husband and I enjoyed our stay. The property was actually quite beautiful. The view was lovely as the home sits on a creek. The home provided everything we needed. Shopping and restaurants were very close. If you need to be in the Baltimore/Annapolis area as we had, this property is perfect."
Rock Creek Cottage, Waterfront, Serene Views
Perfect location for USNA Commissioning Week
View from property

Perfect location for USNA Commissioning Week

10.0 out of 10, Exceptional, (82)
"Charming, clean, comfortable and relaxing. Great hosts."
Perfect location for USNA Commissioning Week
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, (99)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Chesapeake Cottage
Exterior

Chesapeake Cottage

Chesapeake Cottage
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, (27)
"Very quiet street, our stay was relaxing and just what we needed! "
House w/Water Views of Rock Creek 2BA 2BA Cottage
Secluded Cozy Cottage in Historic Downtown
Terrace/patio

Secluded Cozy Cottage in Historic Downtown

9.6 out of 10, Exceptional, (10)
"Perfect little cottage for 4 adults and an infant. Loved its location! "
The price is AEDĀ 1,487
AEDĀ 2,512 total
includes taxes & fees
18 Jun - 19 Jun
Secluded Cozy Cottage in Historic Downtown
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, (8)
"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!
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Outdoor pool

Charming cottage with Pool Access and WiFi in lovely Rock Hall

Charming cottage with Pool Access and WiFi in lovely Rock Hall
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Property grounds

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is AEDĀ 1,322
AEDĀ 2,441 total
includes taxes & fees
18 Jun - 19 Jun
Chesapeake Cottages- 2 Quaint Waterfront Retreats
2 Mi to Sandy Point State Park: Home w/ Deck!
Interior

2 Mi to Sandy Point State Park: Home w/ Deck!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was clean and nice. The beds choices were comfortable and keyless checkin was convenient. "
2 Mi to Sandy Point State Park: Home w/ Deck!
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Exterior

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

10.0 out of 10, Exceptional, (87)
"Pat and Ken were very accommodating for our visit over the holidays. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
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, (28)
"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
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Property grounds

Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills

Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Eastern Shore beach cottage get-away
Sun loungers

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (133)
"This house was the cutest little place right across the street from the beach with a beautiful view. The house was clean and had all the amenities needed for our stay. We would definitely stay there again!"
Eastern Shore beach cottage get-away
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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