Cottages in Caroline County

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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Caroline County cottages

Exterior

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Downtown St. Michaels
9.8 out of 10, Exceptional, (200 reviews)
"Perfect house close to St Michael’s attractions"
United States
Carolyn E.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Exterior

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Tilghman Island
10.0 out of 10, Exceptional, (15 reviews)
"Amazing property well presented with fantastic views in all directions"
United Kingdom
David G.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Exterior

Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier
Cambridge
10.0 out of 10, Exceptional, (265 reviews)
"The hosts were very welcoming, helpful, good communication throughout the reservation process and stay."
United States
Ann R.
Family and Pet-Friendly, Waterfront with Pier
Exterior

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Downtown St. Michaels
9.6 out of 10, Exceptional, (126 reviews)
"Ideal location to shops and attractions. Host very easy to reach. "
United States
Don N.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Exterior

Grandma's Cottage Milford Delaware

Grandma's Cottage Milford Delaware
Milford
10.0 out of 10, Exceptional, (115 reviews)
"Great host, 2nd stay and looking forward to the next one."
United States
William S.
Grandma's Cottage Milford Delaware
Exterior

Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman
9.8 out of 10, Exceptional, (241 reviews)
"A cozy cottage, definitely met our needs. Beautiful view!"
United States
Cynthia Louise C.
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior

Secluded Waterfront Cottage on 200 acre farm near Queenstown

Secluded Waterfront Cottage on 200 acre farm near Queenstown
Centreville
10.0 out of 10, Exceptional, (105 reviews)
"Great stay!"
United States
Scott L.
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Exterior

Charming Intown Cottage – The Ultimate Walkable Getaway steps from Downtown!

Charming Intown Cottage – The Ultimate Walkable Getaway steps from Downtown!
Downtown St. Michaels
9.8 out of 10, Exceptional, (59 reviews)
"It's a very nice place and the location is great. Its not a professionally managed house which is fine, but we didn't know that going in. Everything is clean, but not professionally clean i.e. the sheets are clean but the mattress pad was not. I would stay there again."
United States
Casey G.
Charming Intown Cottage – The Ultimate Walkable Getaway steps from Downtown!
Property grounds

Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC

Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC
Royal Oak
Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC
Exterior

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Downtown St. Michaels
9.4 out of 10, Exceptional, (130 reviews)
"Our dog was so comfortable and welcome at this rental!"
United States
Kathie F.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds

Lovely 2-bedroom waterfront cottage in charming Wittman

Lovely 2-bedroom waterfront cottage in charming Wittman
Wittman
10.0 out of 10, Exceptional, (1 review)
"I recently stayed at this lovely VRBO, and it exceeded my expectations in every way. From the moment I walked in, the home felt incredibly cozy and welcoming. Everything was spotless—truly one of the cleanest vacation rentals I’ve stayed in—which immediately set the tone for a relaxing visit.The space itself is bright and airy, with plenty of natural light that makes the home feel open and refreshing throughout the day. It’s thoughtfully furnished and had everything I needed for a comfortable...
United States
Mario V.
Lovely 2-bedroom waterfront cottage in charming Wittman
Exterior

Cozy, unique, historic registered cottage on the Corsica River!

Cozy, unique, historic registered cottage on the Corsica River!
Centreville
10.0 out of 10, Exceptional, (6 reviews)
"Lovely property, cool history beautiful decor"
United States
Christine C.
Cozy, unique, historic registered cottage on the Corsica River!
Outdoor dining

The Middle Point Cabin in Saint Michaels

The Middle Point Cabin in Saint Michaels
Neavitt
9.8 out of 10, Exceptional, (58 reviews)
"Beautiful cottage; wonderful location. Perfect for a quiet and relaxing long fall weekend."
United States
Er H.
The Middle Point Cabin in Saint Michaels
Property grounds

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

Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Wye Mills
9.0 out of 10, Wonderful, (6 reviews)
"We had a great stay! Ryan was a great host, and the cottage was perfect for our needs. We would certainly stay here again."
United States
Jennifer B.
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Exterior

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Downtown St. Michaels
9.6 out of 10, Exceptional, (147 reviews)
"Great location"
United States
Jody M.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds

#2 Egret Cottage Harris Cove

#2 Egret Cottage Harris Cove
Saint Michaels
10.0 out of 10, Exceptional, (1 review)
#2 Egret Cottage Harris Cove
Exterior

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Tilghman Island
10.0 out of 10, Exceptional, (13 reviews)
"Everything about the place was perfect for a getaway loved the place everything was handy and setup perfectly to relax and enjoy the scenery "
United States
David M.
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Outdoor dining

Waterfront property with private boat ramp and new dock!

Waterfront property with private boat ramp and new dock!
Cambridge
9.2 out of 10, Wonderful, (17 reviews)
"Property was charming ! Exactly what we expected. Host provided a clean, well supplied, with all the things needed. I liked that all dishes, cups and cooking utensils, pots and pans were all in great condition. Host was very nice and responsive. "
United States
Shanda M.
Waterfront property with private boat ramp and new dock!
Outdoor dining

Be persuaded to experience this vintage cottage by the Sassa

Be persuaded to experience this vintage cottage by the Sassa
Galena
9.2 out of 10, Wonderful, (11 reviews)
"We had a nice stay! The house had everything we needed and was comfortable for our trip. Overall the place was in good shape and worked well for us."
United States
Kristen P.
Be persuaded to experience this vintage cottage by the Sassa
Outdoor dining

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cambridge
10.0 out of 10, Exceptional, (16 reviews)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
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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Top Caroline County Hotel Reviews

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Gorgeous area and the view from my window overlooked their little pier. Absolutely beautiful, super clean room, whole area was lovely!! "
Ashley 1-night trip
Posted 10 hours ago
Holiday Inn Express Annapolis East-Kent Island by IHG

Find out more about Caroline County

Caroline County Cottages information

Number of reviews
1,512
Accommodation
68 Cottages
Lowest Price
Highest Price

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