Holiday Rentals in Caroline County

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Our top choices for Caroline County holiday rentals

Property grounds

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 €528
includes taxes & fees
4 May - 5 May
Turnbridge Manor
House (3 Bedrooms) | Interior

3 Mi to Dover Motor Speedway: Pet-friendly Retreat

3 Mi to Dover Motor Speedway: Pet-friendly Retreat
3.0 star property
Dover
The price is €363
includes taxes & fees
13 May - 14 May
3 Mi to Dover Motor Speedway: Pet-friendly Retreat
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
Millington
9.6 out of 10, Exceptional, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is €111
includes taxes & fees
6 May - 7 May
Guest Suite for up to 2 in a Victorian on the Chester River
1 bedroom, desk, iron/ironing board, WiFi

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Frederica
10.0 out of 10, Exceptional, (19 reviews)
"Super cute and clean place, the host was very responsive to my questions. "
United States
Gosha R.
The price is €166
includes taxes & fees
5 May - 6 May
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
"Every thing was great"
United States
lesia k.
The price is €139
includes taxes & fees
7 May - 8 May
First Floor Studio Apartment in Historic Chestertown
Terrace/patio

Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape

Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
Lincoln
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
Marina

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 €324
includes taxes & fees
1 Jun - 2 Jun
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Outdoor dining

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, (7 reviews)
"Loved the Poe themed quirky charm. Convenient parking. We were attending a soccer tournament and it was a super easy 11 minute drive to DE Turf. We love old houses and it felt like our previous home in New Orleans. Cat was very responsive after an initial problem with the Vrbo app. Would stay again!"
United States
John
The price is €238
includes taxes & fees
13 May - 14 May
Poe Themed Home Close to Beaches and DE Turf
Marina

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (12 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is €369
includes taxes & fees
5 May - 6 May
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
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is €373
includes taxes & fees
5 May - 6 May
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Interior

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
The price is €135
includes taxes & fees
18 May - 19 May
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Marina

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

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Downtown Cambridge
10.0 out of 10, Exceptional, (11 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is €383
includes taxes & fees
5 May - 6 May
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Property grounds

Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville
Queen Anne
10.0 out of 10, Exceptional, (28 reviews)
"Really cute little place - very clean and owners are great about checking in on you to make sure things are great."
United States
Cheryl
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Terrace/patio

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.2 out of 10, Wonderful, (10 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 €246
includes taxes & fees
7 May - 8 May
Amazing Modern house with a full kitchen and parking
Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (25 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is €216
includes taxes & fees
13 May - 14 May
Sailwinds Loft at Cambridge Creek
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.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Great overnight stay for a wedding nearby. Would highly recommend!"
United States
Kevin F.
The price is €361
includes taxes & fees
7 May - 8 May
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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
Milford
10.0 out of 10, Exceptional, (3 reviews)
"The unit is tiny but knowing we wouldn’t be spending much time there, it was fine for our use. I liked that we could walk to locations in town. Her directions for use were very clear and precise."
United States
Rebecca N.
The price is €195
includes taxes & fees
3 May - 4 May
Cozy Unit in Milford, Delaware -Close to DE Turf
Fridge, microwave, oven, stovetop

Spacious 5 Bedroom w/Pool, Patio and Theater

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.8 out of 10, Exceptional, (8 reviews)
"The host was very accommodating and the house was excellent and served our needs perfectly."
United States
John K.
Spacious 5 Bedroom w/Pool, Patio and Theater
Interior

Luxury 2 bedroom Apt. Near DE Turf & Beaches!

Luxury 2 bedroom Apt. Near DE Turf & Beaches!
Milford
The price is €291
includes taxes & fees
5 May - 6 May
Luxury 2 bedroom Apt. Near DE Turf & Beaches!
Iron/ironing board, WiFi, bed sheets

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Downtown Cambridge
The price is €209
includes taxes & fees
19 May - 20 May
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Caroline County Hotel Reviews

Hampton Inn Salisbury

Hampton Inn Salisbury

10/10 Excellent
"Parking was safe. Yogurt, hard boiledeggs and coffee were the only edible items om the breakfast bar. Everything was fresh, but inedible"
Mark 1-night trip
Posted 10 hours ago
Hampton Inn Salisbury

Find out more about Caroline County

Holiday Homes in Caroline County

Search for holiday homes in Caroline County on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Caroline County using one of the methods below: 

  • View our selection of featured holiday homes in Caroline County
  • Use the map to find apartments and other holiday rentals in the Caroline County neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday homes in Caroline County while they last

Look no further and take a look at our great range of rental properties in Caroline County!