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Caroline County Holiday Rentals

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Our top choices for Caroline County holiday rentals

Property grounds
Turnbridge Manor

Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (12 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is HK$2,807
HK$4,554 total
includes taxes & fees
19 Jan - 20 Jan
Turnbridge Manor
Marina
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
2.0 star property
Downtown Cambridge
9.8 out of 10, Exceptional, (11 reviews)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
The price is HK$1,053
HK$2,661 total
includes taxes & fees
2 Feb - 3 Feb
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very clean, and very comfortable beds."
United States
Edward R.
The price is HK$1,092
HK$2,702 total
includes taxes & fees
2 Feb - 3 Feb
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina
Station House East: Upscale Loft in the Historic District Cambridge, MD

Station House East: Upscale Loft in the Historic District Cambridge, MD

Station House East: Upscale Loft in the Historic District Cambridge, MD
Downtown Cambridge
10.0 out of 10, Exceptional, (7 reviews)
"Location very convenient, flat beautiful, clean, very friendly, respo sive and accommodating hostess! Thank you!"
United States
Solveig S.
The price is HK$1,158
HK$2,781 total
includes taxes & fees
15 Jan - 16 Jan
Station House East: Upscale Loft in the Historic District Cambridge, MD
Marina
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
2.5 star property
Downtown Cambridge
10.0 out of 10, Exceptional, (10 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is HK$1,131
HK$2,752 total
includes taxes & fees
2 Feb - 3 Feb
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Terrace/patio
Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.8 out of 10, Exceptional, (8 reviews)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is HK$1,403
HK$2,784 total
includes taxes & fees
15 Jan - 16 Jan
Amazing Modern house with a full kitchen and parking
Private kitchen
Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (24 reviews)
"What a great place to relax after exploring and enjoying the area. Definitely will visit again "
United States
Chris S.
The price is HK$1,208
HK$1,983 total
includes taxes & fees
15 Jan - 16 Jan
Sailwinds Loft at Cambridge Creek
Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!
Cambridge
10.0 out of 10, Exceptional, (50 reviews)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
The price is HK$1,228
HK$2,905 total
includes taxes & fees
18 Jan - 19 Jan
Beautiful Waterfront Retreat in Cambridge!
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is HK$772
HK$1,238 total
includes taxes & fees
15 Jan - 16 Jan
First Floor Studio Apartment in Historic Chestertown
Outdoor dining
Poe Themed Home Close to Beaches and DE Turf

Poe Themed Home Close to Beaches and DE Turf

Poe Themed Home Close to Beaches and DE Turf
Milford
9.8 out of 10, Exceptional, (6 reviews)
"Wonderful place other than no operational WiFi."
United States
William F.
The price is HK$1,263
HK$2,170 total
includes taxes & fees
15 Jan - 16 Jan
Poe Themed Home Close to Beaches and DE Turf
Fridge, microwave, dishwasher, coffee/tea maker
HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit
Centreville
10.0 out of 10, Exceptional, (8 reviews)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is HK$1,537
HK$3,472 total
includes taxes & fees
19 Jan - 20 Jan
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Dining
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is HK$1,949
HK$3,273 total
includes taxes & fees
15 Jan - 16 Jan
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior
Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (19 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is HK$530
HK$975 total
includes taxes & fees
22 Jan - 23 Jan
Guest Suite for up to 2 in a Victorian on the Chester River
Marina
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.4 out of 10, Very good, (6 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is HK$936
HK$2,215 total
includes taxes & fees
15 Jan - 16 Jan
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
1 bedroom, iron/ironing board, WiFi, bed sheets
Cozy Unit in Milford, Delaware -Close to DE Turf

Cozy Unit in Milford, Delaware -Close to DE Turf

Cozy Unit in Milford, Delaware -Close to DE Turf
Milford
10.0 out of 10, Exceptional, (2 reviews)
"Perfect place for my son and I that had a lacrosse tourney that was only 8 minutes away at the Delaware turf fields Cat was awesome and replied very fast and was super accommodating!! "
United States
Shaine L.
The price is HK$926
HK$1,763 total
includes taxes & fees
15 Jan - 16 Jan
Cozy Unit in Milford, Delaware -Close to DE Turf
Interior
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind

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

3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind
Delmar
10.0 out of 10, Exceptional, (8 reviews)
"House was as described and just was great. 5 stars all the way around!!! "
United States
Julius D.
The price is HK$1,318
HK$5,372 total
includes taxes & fees
15 Jan - 16 Jan
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind
Smart TV
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"Amazing news out of the back.Great for kayaking.We brought our own kayaksAnd also use yoursThere were four of usWe also took a nice trip over to Saint Michael’s"
United States
Sandy S.
The price is HK$2,045
HK$4,119 total
includes taxes & fees
15 Jan - 16 Jan
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (51 reviews)
"Great place, will stay again"
United States
Matt S.
The price is HK$1,793
HK$2,174 total
includes taxes & fees
18 Jan - 19 Jan
Waterfront Getaway with Dock
Smart TV
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

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

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
8.8 out of 10, Excellent, (10 reviews)
"Clean, cozy, and lovely - a winter cabin stay to remember. Kids already wanted to go back 5 days later. 10 out of 10 stars! "
United States
Mr.
The price is HK$2,424
HK$4,817 total
includes taxes & fees
15 Jan - 16 Jan
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Interior
JVA LUXURY HOUSING

JVA LUXURY HOUSING

JVA LUXURY HOUSING
Smyrna
10.0 out of 10, Exceptional, (1 review)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is HK$3,119
HK$4,538 total
includes taxes & fees
22 Jan - 23 Jan
JVA LUXURY HOUSING
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

Springhill Suites By Marriott Frederica

Springhill Suites By Marriott Frederica

10/10 Excellent
"Good service "
Jose 2-night trip
Posted 5 days ago
Springhill Suites By Marriott Frederica