A river with a green embankment and a boat.

Cottages in Caroline County

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Top Cities in Caroline County

A calm lake surrounded by tall trees and dense reeds.
CottagesCottages

Denton

Denton

Our top choices for Caroline County cottages

Exterior

Grandma's Cottage Milford Delaware

Grandma's Cottage Milford Delaware
Milford
10.0 out of 10, Exceptional, (128 reviews)
"Comfortable clean house, everything as described. Host communicated well. Will stay again if we make it that way "
United States
Sean T.
Grandma's Cottage Milford Delaware
Outdoor dining

Life is better at the RIVER!--Cozy waterfront cottage

Life is better at the RIVER!--Cozy waterfront cottage
Galena
10.0 out of 10, Exceptional, (115 reviews)
"Great place! "
United States
michael p.
Life is better at the RIVER!--Cozy waterfront cottage
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, (21 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
Outdoor dining

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock
Bozman
Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock
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, (128 reviews)
"We had a great time. The house was so charming and the location was perfect. Can't wait to go back!"
United States
Anonymous traveler
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Exterior

Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman
9.8 out of 10, Exceptional, (249 reviews)
"We loved our stay and cannot wait to return! The place was immaculate and had everything we could possibly need or want. It was like staying at a friend’s place instead of a rental. It was perfect!"
United States
Denise S.
Relaxing Waterfront Cottage Near St Michaels, Maryland
Property grounds

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

Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Wye Mills
9.2 out of 10, Wonderful, (7 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
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)
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, (148 reviews)
"Great location"
United States
Jody M.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds

Spacious waterfront house in charming Royal Oak with WiFi, AC, dock

Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
Royal Oak
10.0 out of 10, Exceptional, (1 review)
"Place was perfect"
United States
Scott B.
Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
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, (16 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
Exterior

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

Cozy, unique, historic registered cottage on the Corsica River!
Centreville
9.6 out of 10, Exceptional, (8 reviews)
"Lovely property, cool history beautiful decor"
United States
Christine C.
Cozy, unique, historic registered cottage on the Corsica River!
House (3 Bedrooms) | Front of property

Marinafront Cottage Sunrise, Fire Pit, Fireworks

Marinafront Cottage Sunrise, Fire Pit, Fireworks
3.0 star property
Cambridge
Marinafront Cottage Sunrise, Fire Pit, Fireworks
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, (108 reviews)
"Great stay!"
United States
Scott L.
Secluded Waterfront Cottage on 200 acre farm near Queenstown
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, (204 reviews)
"We had a wonderful time and really enjoyed the back screened in porch which is where we spent a lot of time with our two little dogs."
United States
LeaAnne T.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Exterior

Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier
Cambridge
10.0 out of 10, Exceptional, (269 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

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
9.6 out of 10, Exceptional, (134 reviews)
"Lovely property with a mix of antique and contemporary comfort as well as easy and convenient access to town. Hope to be back! "
United States
Tracy M.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds

#2 Egret Cottage Harris Cove

#2 Egret Cottage Harris Cove
Saint Michaels
10.0 out of 10, Exceptional, (3 reviews)
"This place was awesome, the hosts were super friendly, and the property is right on the water with dock access. They have boats, fishing and crabbing gear, and kayaks which we used. It was great for kids too since they have a whole acre with a playground and sand that my son loved. Awesome experience would highly recommend this place."
United States
Timothy
#2 Egret Cottage Harris Cove
Outdoor dining

The Middle Point Cabin in Saint Michaels

The Middle Point Cabin in Saint Michaels
Neavitt
9.8 out of 10, Exceptional, (59 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
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)
"Had a lovely peaceful stay. Great amenities."
United States
Joe S.
Be persuaded to experience this vintage cottage by the Sassa
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

Quality Inn & Suites Harrington - Milford

Quality Inn & Suites Harrington - Milford

10/10 Excellent
"."
erick fernando 2-night trip
Posted 4 hours ago
Quality Inn & Suites Harrington - Milford