Photo by Assya A

Search Chestertown Cottages

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Cottages in Chestertown

The Heron's Nest at Atlantic Marina

9.8 out of 10, Exceptional, (302)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina

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

10.0 out of 10, Exceptional, (93)
"We stay at Firefly every time we go to visit our son and his family. It works perfectly for us…an oasis for us, and a fun place for the kids to visit, too. Pat and Ken have been the perfect hosts!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

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

10.0 out of 10, Exceptional, (51)
"Beautiful home with LOTS of attention to detail. The backyard was a beautiful oasis and we LOVED the “swing bed” on the screened-in porch. Mark and Karen add lots of fine touches to make your stay special. Plenty of room for two, cozy for four, and comfortable for four legged friends with the fenced in back yard. Quiet and private with a short 10 minute drive to town. Can’t wait to return!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (103)
"Secluded"
Secluded Waterfront Cottage on 200 acre farm near Queenstown

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (13)
"We had a very lovely stay . This is an excellent location . "
$651 nightly
The price is $742
Aug 24 - Aug 25
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (54)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Charming cottage with Pool Access and WiFi in lovely Rock Hall

10.0 out of 10, Exceptional, (2)
"Adorable little cottage and amenities. Owners very nice. Perfect little getaway. "
Charming cottage with Pool Access and WiFi in lovely Rock Hall

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
$583 nightly
The price is $665
Aug 25 - Aug 26
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats

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

9.8 out of 10, Exceptional, (34)
"We wanted to celebrate my wife’s birthday with some friends, and a bushel of crabs…and what an incredible house to host a special occasion. The kids had the water/mini beach and plenty of yard space to play; there was a space outside to eat the crabs; and the house was incredibly clean and inviting. "
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

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

9.8 out of 10, Exceptional, (116)
"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

Rock Creek Cottage, Waterfront, Serene Views

10.0 out of 10, Exceptional, (6)
"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

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 Cottage

10.0 out of 10, Exceptional, (2)
"Outstanding accommodations in an extraordinary neighborhood!! Many near by options for dining and outdoor activities!! Highly recommended!! "
Chesapeake Cottage

Eastern shore beachfront cottage with stunning sunset views!

10.0 out of 10, Exceptional, (1)
"Check in was a breeze. Place was clean. Simply beautiful. Most relaxing place ever. "
Eastern shore beachfront cottage with stunning sunset views!

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
$410 nightly
The price is $473
Aug 26 - Aug 27
Total with taxes and fees
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

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

10.0 out of 10, Exceptional, (30)
"Perfect location, we were in town for birthdays and a wedding shower. Short drive to our favorite spots, Two Rivers, Primos & Seaside for steamed crabs. House has everything you need. Will return on our future visits to the Dena. "
House w/Water Views of Rock Creek 2BA 2BA Cottage

Waterfront Annapolis Home: Fire Pit & Fishing Pier

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

13 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
13 Mi to Downtown Baltimore: Quiet Home w/ Porch

Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games

10.0 out of 10, Exceptional, (85)
"Nice small property. Great for get aways and amazing service."
Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games

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

10.0 out of 10, Exceptional, (11)
"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!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chestertown Hotel Reviews