Vacation Rentals in Caroline County

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Top Vacation Rentals in Caroline County

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

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

9.6 out of 10, Exceptional, (121)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Cass-N-Reel Luxury Houseboat
Marina

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (41)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
Walk to Everything House
Fridge, microwave, oven, stovetop

Walk to Everything House

10.0 out of 10, Exceptional, (83)
"Clean and nice place to stay"
Walk to Everything House
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (259)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

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

9.8 out of 10, Exceptional, (188)
"Excellent accommodations. Comfortable, good location.One way you could improve is to furnish wash cloths and hand towels. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Outdoor pool, a heated pool

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

9.8 out of 10, Exceptional, (74)
"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Private beach

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

10.0 out of 10, Exceptional, (16)
"Gorgeous views and location. "
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Marina

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

10.0 out of 10, Exceptional, (95)
"Beautiful home in a quiet community. "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Dollhouse in Central Historic St Michaels
Exterior

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (55)
"Great location. House is old and therefore a little quirky, but overall comfortable. "
Dollhouse in Central Historic St Michaels
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior detail

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

10.0 out of 10, Exceptional, (12)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Harbor View Suite Talbot County License Number STRN-25-58
Fridge, microwave, coffee/tea maker, toaster

Harbor View Suite Talbot County License Number STRN-25-58

10.0 out of 10, Exceptional, (31)
"The room and location were perfect. Very clean and comfortable space to stay and right in the heart of town. "
Harbor View Suite Talbot County License Number STRN-25-58
Poe Themed Home Close to Beaches and DE Turf
Outdoor dining

Poe Themed Home Close to Beaches and DE Turf

10.0 out of 10, Exceptional, (4)
"Comfortable beds, meticulous details of EA Poe throughout, walking distance to adorable Dolce’ for coffee and pastries, and lovely Milford charm are a few of the outstanding qualities of this home away from home. "
The price is ￥24,710
￥42,295 total
includes taxes & fees
Oct 10 - Oct 11
Poe Themed Home Close to Beaches and DE Turf
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Outdoor pool

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

9.8 out of 10, Exceptional, (7)
"Great House "
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds

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

9.6 out of 10, Exceptional, (143)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Dining

NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

10.0 out of 10, Exceptional, (26)
"Nice stay… good family home…. Lots of sleeping accommodations…. A few steps from the beach!!!!! Great host!!!!!"
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Captain's Quarters
Fridge, microwave, oven, stovetop

Captain's Quarters

9.8 out of 10, Exceptional, (100)
"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "
Captain's Quarters
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (43)
"Wonderful home in excellent location!!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (9)
"My kids and I absolutely loved our stay at the Outlook! So peaceful and relaxing. We spent a lot of time walking around the trails spotting deer and toads. We did a good amount of fishing on the dock, catching catfish. I hope to stay here again in the future."
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (102)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is ￥15,029
￥24,113 total
includes taxes & fees
Oct 14 - Oct 15
First Floor Studio Apartment in Historic Chestertown
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Sun loungers, beach towels

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

10.0 out of 10, Exceptional, (36)
"This is a beautiful property, well appointed, but not too formal for families wanting to be in the pool or on the water all day. We were a party of 12 including six grandchildren. There was plenty to do for the adults and the grandchildren and plenty of space in the home to not feel like you were on top of each other. The sunsets were spectacular. Marissa is an extremely responsive host, and all our questions were answered in a timely fashion. Saint Michaels is very close by and an absolutely...
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
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

Hampton Inn Salisbury

Hampton Inn Salisbury

10/10 Excellent
"The property is very well kept and in a convenient location."
Larry 1-night trip
Posted 2 days ago
Hampton Inn Salisbury

Find out more about Caroline County

Find out more about Caroline County

Vacation Apartments in Caroline County

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