Vacation Rentals in Caroline County

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Top Vacation Rentals in Caroline County

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Boats docked at the marina, offering scenic views of the calm water.

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (11)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is ￥42,471
￥76,998 total
includes taxes & fees
Aug 24 - Aug 25
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Grandma's Cottage
Situated in a wooded area, this cabin-style building offers a tranquil retreat with a front porch and lush surroundings.

Grandma's Cottage

10.0 out of 10, Exceptional, (103)
"5 nights in grandsma cottage and we enjoy every things..."
Grandma's Cottage
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Guests can enjoy serene waterfront views from the end of the pier, where two Adirondack chairs await.

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

9.8 out of 10, Exceptional, (128)
"We had a wonderful long weekend here. Perfect weather let us swim and kayak and fish all weekend. House was spacious enough for two families of five plus our dog. The views were perfect!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Relax in a serene park setting surrounded by lush greenery and a central gazebo.

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

9.8 out of 10, Exceptional, (183)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Relax by the serene pool surrounded by lush greenery and a comfortable bench.

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

10.0 out of 10, Exceptional, (133)
"Great location and property. And epic crabbing to top it off!"
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Family and Pet-Friendly, Waterfront with Pier
Escape to a serene forest retreat with a cozy cabin-style lodge featuring a sheltered front porch and breathtaking natural views.

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (250)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier
Captain's Quarters
Enjoy cooking in this well-equipped kitchen with a large window offering a view of the surrounding landscape.

Captain's Quarters

9.8 out of 10, Exceptional, (94)
"This was a wonderful home walking distance to the beach. It was spacious and extremely comfortable. We recommend it to anyone interested in a beach vacation home. "
Captain's Quarters
Cass-N-Reel Luxury Houseboat
Enjoy waterfront views from the dock, surrounded by boats and a marina.

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (31)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind
Fridge, microwave, oven, stovetop

3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind

10.0 out of 10, Exceptional, (1)
"The property was lovely. The host so very accommodating, The neighborhood close to restaurants and stores. The flowers, beverages and goodie basket was really a nice touch and very much appreciated. The beds were very comfortable as well. There is access to the community Pool too. The weather did not permit us to use it. Thank You."
The price is ￥24,750
￥100,904 total
includes taxes & fees
Jul 27 - Jul 28
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Enjoy meals in the kitchen with a central island, sink, and oven, adjacent to a dining area with a table and chairs.

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

10.0 out of 10, Exceptional, (22)
"The house was amazing, and close to Killens Pond State Park where we had additional family camping."
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Stylish entrance with a wooden staircase and a mailbox.

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

10.0 out of 10, Exceptional, (5)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
Enjoy cooking in this well-equipped kitchen with a central island, sink, stove, and ample storage.

Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18

10.0 out of 10, Exceptional, (77)
"We were very impressed with the property and your place was very clean and had just about everything we needed. The location is wonderful and close to the event that we stayed in Cambridge for. I would definitely recommend this for others and will likely be renting again"
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
Relax in this open-plan living space with a kitchen, sofa, and large window offering a view of the outdoor pool and playground.

Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf

10.0 out of 10, Exceptional, (7)
"Perfect rental for our family of 6 adults! Great location on the water with a fun restaurant just steps away. Highly recommend!!"
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
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
Poe Themed Home Close to Beaches and DE Turf
Enjoy an outdoor space with a table and chairs, surrounded by potted plants and string lights.

Poe Themed Home Close to Beaches and DE Turf

10.0 out of 10, Exceptional, (2)
"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 ￥23,725
￥40,609 total
includes taxes & fees
Jul 27 - Jul 28
Poe Themed Home Close to Beaches and DE Turf
Charming Summer Cottage – Relax and Unwind Here!
Enjoy serene waterfront views with a sailboat in the distance.

Charming Summer Cottage – Relax and Unwind Here!

10.0 out of 10, Exceptional, (8)
"A delightful, quiet and peaceful spot for a family getaway."
Charming Summer Cottage – Relax and Unwind Here!
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and microwave, and dine at the wooden table.

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

9.8 out of 10, Exceptional, (40)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Enter a serene space with a large mirror and a small table featuring a bowl and flowers.

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

8.4 out of 10, Very Good, (6)
"Large house with in law suite and 2nd entrance. Clean, rustic cabin feel. Plenty of room to stretch out. Game room and bar area is nice with big tv. Hot tub fairly new. Weather didnt permit using kayaks, but they are there for use on creek to river. Anyone who would pay for 3 or 4 rooms at the resort next door is crazy. Great place for a family get together. Bathrooms all updated. Plenty of stuff you need in bath and kitchen. Laundry room even had pods and dryer sheets."
The price is ￥54,950
￥101,868 total
includes taxes & fees
Jul 27 - Jul 28
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Mini Aruba Glamper inDover with WiFi, AC and guest access to backyard oasis
Pool

Mini Aruba Glamper inDover with WiFi, AC and guest access to backyard oasis

10.0 out of 10, Exceptional, (2)
"My husband and I stayed for two nights. The oasis makes you feel like you’re vacationing in the Caribbean. The camper is clean and comfortable for two people. Everything was perfect and cannot wait to return!"
The price is ￥22,283
￥36,626 total
includes taxes & fees
Jul 30 - Jul 31
Mini Aruba Glamper inDover with WiFi, AC and guest access to backyard oasis
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Relax in a serene outdoor setting with a tranquil lawn and water view, perfect for a peaceful retreat.

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

10.0 out of 10, Exceptional, (7)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
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

Bally's Dover Casino Resort

Bally's Dover Casino Resort

10/10 Excellent
"Everything was very pleasant "
Cage 1-night trip
Posted 14 hours ago
Bally's Dover Casino Resort