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Jul 18 - Jul 20
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Jul 25 - Jul 27
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Aug 8 - Aug 10
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Sep 5 - Sep 7

Cottages in Chestertown

The Heron's Nest at Atlantic Marina
Situated on a grassy area, this cottage offers a peaceful retreat with a porch for relaxation or dining.

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (294)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Relax in a serene outdoor space with a comfortable seating area and picturesque views of the surrounding forest.

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

10.0 out of 10, Exceptional, (48)
"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
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Set against a serene backdrop, this house features a beautifully lit facade and a decorative reindeer sculpture on the lawn.

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

10.0 out of 10, Exceptional, (90)
"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!
Perfect location for USNA Commissioning Week
Relax in this open-plan living area featuring a central island, dining space, and comfortable seating.

Perfect location for USNA Commissioning Week

10.0 out of 10, Exceptional, (83)
"Nice small property. Great for get aways and amazing service."
Perfect location for USNA Commissioning Week
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Situated by a serene body of water, this bench offers a tranquil view of the surrounding shoreline.

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

9.8 out of 10, Exceptional, (29)
"Tranquil cottage by the river to relax and reconnect for couples. Quick drive to Annapolis mall and downtown. Lots of outdoor seating to enjoy. Hosts were very responsive to our questions and request for bikes. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
House w/Water Views of Rock Creek 2BA 2BA Cottage
Relax in this serene outdoor space with a wicker sofa, glass table, and wooden bench.

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

10.0 out of 10, Exceptional, (28)
"Very quiet street, our stay was relaxing and just what we needed! "
House w/Water Views of Rock Creek 2BA 2BA Cottage
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Relax in this stylish living room with a large sofa, armchair, and ottoman, perfect for unwinding in comfort.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (51)
"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
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Kitchen area with a stove, dishwasher, refrigerator, sink, and countertop with a kettle.

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (101)
"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
Peaceful getaway convenient to local amenities including beach, boating & food
Guests can enjoy breathtaking views of the calm body of water from the rocky outcrop.

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

9.8 out of 10, Exceptional, (114)
"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
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
Enjoy serene sunsets over a peaceful lake or sea from a tranquil beach with a tree and rocks.

Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

10.0 out of 10, Exceptional, (32)
"Really like this place "
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Surrounded by lush greenery, this charming fence features a carved stone face at its center.

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!
Secluded Cozy Cottage in Historic Downtown
Stroll along the pathway to an entrance surrounded by lush greenery and a curved brick wall.

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (12)
"Perfect little cottage for 4 adults and an infant. Loved its location! "
$703 nightly
The price is $801
Jul 14 - Jul 15
Total includes taxes and fees
Secluded Cozy Cottage in Historic Downtown
Eastern Shore beach cottage get-away
Enjoy a serene beach experience with a gentle shoreline and peaceful surroundings.

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (136)
"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
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Relax on the dock with Adirondack chairs and enjoy the serene view.

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
$583 nightly
The price is $665
Jul 14 - Jul 15
Total includes taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Relax by the serene pool surrounded by lush greenery and vibrant flowers.

Charming cottage with Pool Access and WiFi in lovely Rock Hall

Charming cottage with Pool Access and WiFi in lovely Rock Hall
2 Mi to Sandy Point State Park: Home w/ Deck!
Enjoy cooking in this well-equipped kitchen with an oven, stainless steel refrigerator, and large island with a sink.

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!
Rock Creek Cottage, Waterfront, Serene Views
Terrace/patio

Rock Creek Cottage, Waterfront, Serene Views

10.0 out of 10, Exceptional, (5)
"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
Chesapeake Cottage
1 bedroom, iron/ironing board, WiFi, bed sheets

Chesapeake Cottage

Chesapeake Cottage
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Enjoy a serene lakeside retreat with a deck, perfect for outdoor dining and taking in the tranquil views.

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

Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Waterfront Annapolis Home: Fire Pit & Fishing Pier
House (3 Bedrooms) | Interior

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
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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Frequently asked questions

Why book your cottage in Chestertown with Expedia?
We think that traveling should be stress-free, so if you're chasing cottages in Chestertown at a competitive rate, Expedia delivers. Save cash and select a wallet-friendly option surrounded by nature, or book an upmarket cottage to pamper your favorite people.
How can I find cheap cottages in Chestertown?
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What is there to do in Chestertown near my cottage?
If you'd like to fill up your itinerary in Chestertown, find your way to Rolphs Wharf Marina. It's a winner with locals and tourists alike.