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

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

25.18 mi from city center
$483 nightly
The price is $512 total per night
$512 total
Jul 7 - Jul 8
Total includes taxes and fees
This vacation home includes a garden and laundry facilities.
Kitchen
Washer
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

32.72 mi from city center
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An outdoor pool is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Kitchen
Captain's Quarters

Captain's Quarters

26.05 mi from city center
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This vacation home features a water park, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

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

19.71 mi from city center
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An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site.
Pool
Kitchen
Grandma's Cottage

Grandma's Cottage

19.22 mi from city center
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This cottage features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!

30.63 mi from city center
$506 nightly
The price is $536 total per night
$536 total
Jul 14 - Jul 15
Total includes taxes and fees
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

25 mi from city center
$144 nightly
The price is $159 total per night
$159 total
Jul 17 - Jul 18
Total includes taxes and fees
This apartment features an outdoor pool and a gym. There's a hot tub on site, and laundry facilities and barbecue grills are also offered.
Pool
Hot Tub
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

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

30.55 mi from city center
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A hot tub is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Kitchen
Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat

23.26 mi from city center
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Stay at this houseboat in Grasonville. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Chesapeake Bay Environmental Center and Paul Reed Smith Guitars are located nearby.
Kitchen
Free WiFi
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

22.09 mi from city center
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This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

22.34 mi from city center
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This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf

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

25.97 mi from city center
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A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
Secluded Waterfront Cottage on 200 acre farm near Queenstown

Secluded Waterfront Cottage on 200 acre farm near Queenstown

20.6 mi from city center
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This cottage featured laundry facilities and barbecue grills.
Kitchen
Washer
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

22.45 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

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

22.38 mi from city center
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This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Waterfront Property, kayaks, private dock, near town

Waterfront Property, kayaks, private dock, near town

21.12 mi from city center
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This vacation home features a water park, a garden, and laundry facilities. Families will appreciate the playground and barbecue grills.
Kitchen
Washer
Poe Themed Home Close to Beaches and DE Turf

Poe Themed Home Close to Beaches and DE Turf

21.5 mi from city center
$271 nightly
The price is $278 total per night
$278 total
Jul 7 - Jul 8
Total includes taxes and fees
A garden is available at this vacation home.
Kitchen
Air conditioning
Charming Summer Cottage – Relax and Unwind Here!

Charming Summer Cottage – Relax and Unwind Here!

30.73 mi from city center
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This vacation home includes a garden and laundry facilities.
Kitchen
Washer
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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.

The Best Way to Find Vacation Rentals in Caroline County 

How cheap is a vacation rental in Caroline County?


You can find Caroline County vacation rentals from just $159 per night. 


How do you look for the best vacation rental deals in Caroline County with Travelocity?


Simply enter your travel dates and filter by price, property type, bedrooms, amenities, and more. We put all the best deals in one place, so it’s easy to find your perfect stay. You’ll always find incredible deals on Caroline County vacation rentals with Travelocity. 


Are cancellations free on vacation rentals with Travelocity?


You may be able to cancel your Caroline County vacation rental for free. Cancellation policies differ between properties so check the terms of your stay before you book. Travelocity offers many flexible cancellation options as well as book now, pay later deals for peace of mind.


What types of vacation rentals are available in Caroline County?


Whether you’re in search of adventure, planning a romantic getaway, or booking a trip for the whole family, you’re sure to find the perfect Caroline County vacation rental. Check out our tempting selection of resorts, apartments, vacation homes, condos and more and start building a trip to really look forward to, whatever your budget and your wish list.


What are the benefits of booking a short-term rental in Caroline County?


Whether you’re a winter wanderer or planning a summer sojourn, Caroline County vacation rentals make for a great trip—find one at Travelocity for a fantastic price. With a range of amenities on offer, like swimming-pools, free WiFi, breakfast included, pet-friendly options and many more, it’s easy to book a vacation rental that checks all the boxes. And with Travelocity’s easy filtering system, you’ll find yours in no time. 


Where can I find vacation rentals in Caroline County?


Take your pick from the excitement of the big Caroline County cities. Or escape to nature in the miles of greenery that are waiting for you. Browse a selection of the best deals with Travelocity, enter your travel dates, or check out the map view to find a hidden gem. 


How do I find a family-friendly vacation rental in Caroline County?


Simply enter your travel dates and hit search. From here, you can filter to find your family-friendly stay, as well as a range of other amenities, such as hot tubs, pools, and even waterparks. 


Why is Travelocity the best site to find your Caroline County rentals?


Travelocity takes care of everything, bringing incredible deals on an impressive selection of accommodation into one simple-to-use portal. And because we always source incredible deals, you can make a saving on many bookings. Travelocity makes it easy.


How do I cancel my vacation rental with Travelocity?


It’s simple. Just contact the property manager. You’ll find their contact information in the itinerary section of your Travelocity account. In many cases, you may be able to get a full refund if you cancel before the cancellation deadline. Deadlines differ between properties, so it’s always best to check before you book. To find out more, visit the Customer Service PortalOpens in a new window.