Vacation Rentals in Caroline County

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Our top choices for Caroline County vacation 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 ￥56,891
￥96,319 total
includes taxes & fees
Jan 14 - Jan 15
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 ￥21,334
￥53,939 total
includes taxes & fees
Feb 2 - Feb 3
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 ￥22,124
￥55,279 total
includes taxes & fees
Jan 14 - Jan 15
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 ￥23,467
￥56,870 total
includes taxes & fees
Jan 14 - Jan 15
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 ￥22,914
￥55,781 total
includes taxes & fees
Feb 2 - Feb 3
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 ￥28,420
￥56,382 total
includes taxes & fees
Jan 15 - Jan 16
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 ￥24,495
￥40,203 total
includes taxes & fees
Jan 15 - Jan 16
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 ￥24,890
￥58,881 total
includes taxes & fees
Jan 18 - Jan 19
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 ￥15,631
￥25,079 total
includes taxes & fees
Jan 20 - Jan 21
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 ￥25,578
￥43,939 total
includes taxes & fees
Jan 14 - Jan 15
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 ￥31,148
￥70,540 total
includes taxes & fees
Jan 19 - Jan 20
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 ￥39,508
￥66,335 total
includes taxes & fees
Jan 14 - Jan 15
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 ￥10,737
￥19,749 total
includes taxes & fees
Feb 9 - Feb 10
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 ￥16,593
￥43,888 total
includes taxes & fees
Jan 14 - Jan 15
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 ￥18,774
￥35,739 total
includes taxes & fees
Jan 14 - Jan 15
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 ￥26,707
￥108,045 total
includes taxes & fees
Jan 14 - Jan 15
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 ￥41,459
￥83,479 total
includes taxes & fees
Jan 15 - Jan 16
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 ￥36,347
￥44,056 total
includes taxes & fees
Jan 18 - Jan 19
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 ￥49,125
￥96,965 total
includes taxes & fees
Jan 14 - Jan 15
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 ￥63,156
￥92,997 total
includes taxes & fees
Feb 1 - Feb 2
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

Hampton Inn Salisbury

Hampton Inn Salisbury

10/10 Excellent
"When having to travel unexpectedly and alone the location felt very safe. The parking lot was well lit and the front desk staff was exceptional "
Leah 3-night trip
Posted 2 days ago
Hampton Inn Salisbury

Find out more about Caroline County

Vacation Apartments in Caroline County

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