Vacation rentals in Chesapeake City

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Top vacation rentals in Chesapeake City

Historic Chesapeake City Stay

Historic Chesapeake City Stay

0.18 mi from city center
$263 nightly
The price is $279 total per night
$279 total
Sep 14 - Sep 15
Total with taxes and fees
Stay at this cabin in Chesapeake City. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Chesapeake City Bridge and The Pell Gardens are located nearby.
Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

0.5 mi from city center
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This vacation home features a gym and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

0.42 mi from city center
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This vacation home features laundry facilities.
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

6.08 mi from city center
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This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Tip Of The Town Fresh and New 3 Bedroom Nest

Tip Of The Town Fresh and New 3 Bedroom Nest

8.5 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.
Charming 2-bedroom cabin close to Fair Hill on horse farm

Charming 2-bedroom cabin close to Fair Hill on horse farm

3.92 mi from city center
$297 nightly
The price is $315 total per night
$315 total
Sep 11 - Sep 12
Total with taxes and fees
This cabin featured laundry facilities and barbecue grills.
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

15.33 mi from city center
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This vacation home features a water park, a garden, and laundry facilities.
Sailor's Sunrise Cottage - Chesapeake Bay

Sailor's Sunrise Cottage - Chesapeake Bay

10.58 mi from city center
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A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

18.21 mi from city center
$199 nightly
The price is $210 total per night
$210 total
Sep 11 - Sep 12
Total with taxes and fees
Stay at this cottage in Cecil County. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Steppingstone Museum and Susquehanna State Park are located nearby.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

8.07 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

19.61 mi from city center
$148 nightly
The price is $154 total per night
$154 total
Sep 24 - Sep 25
Total with taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills.
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

2 out of 5
12.5 mi from city center
$152 nightly
The price is $161 total per night
$161 total
Sep 11 - Sep 12
Total with taxes and fees
This apartment features laundry facilities.
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

14.94 mi from city center
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This houseboat featured laundry facilities and barbecue grills.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

10.93 mi from city center
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This cottage features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Chesapeake Point | Waterfront w/ HOT TUB + Beach!

Chesapeake Point | Waterfront w/ HOT TUB + Beach!

3.71 mi from city center
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A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
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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 your Vacation Rentals in Chesapeake City

How cheap can a vacation rental in Chesapeake City be?

You can find vacation rentals in Chesapeake City for as low as $154 per night.

How do you look for the best vacation rental deals in Chesapeake City with Travelocity?

Travelocity provides the best vacation rental deals in various locations throughout Chesapeake City so you can create the perfect plan for you. You can search and filter by type of property, amenities, neighborhood, price range, number of bedrooms, and more.

Are cancellations free on vacation rentals with Travelocity?

Each vacation rental has its own cancellation policy. It’s essential to understand the terms of your agreement before booking. Most rentals in Chesapeake City can be canceled for free when notifying the property before the cancellation deadline.

What types of vacation rentals are available in Chesapeake City?

Short term rentals come in all shapes and sizes. Choose from properties for a wide range of budgets and types of holidays. Families, couples, outdoor adventurers, and leisure travelers alike will find the perfect place for them. Check out our Chesapeake City vacation apartments to get started building your trip.

What are the benefits of booking a short-term rental in Chesapeake City?

Whether it’s for a summer getaway, a winter excursion, or a routine business trip, Chesapeake City vacation homes are often an excellent choice. You can enjoy group vacations with short term rentals to fit your party size. You might take a romantic weekend for two or plan a family reunion, and all stay under one roof. The options are endless, and you can find them on Travelocity.

Why is Travelocity the best site to find your vacation rental in Chesapeake City?

With Travelocity, all your travel needs are taken care of in one convenient platform. We offer fantastic deals on our large selection of vacation rentals to get you the most savings and rewards back on every booking. Save more when you bundle bookings together, including car rentals, flights, and activities. Here, you can build custom Chesapeake City vacations.

How to cancel your vacation rental with Travelocity?

To cancel your vacation rental, contact the property manager. You can find their contact information in the ‘Itinerary’ section of your Travelocity account. Most properties receive a full refund when you cancel before the cancellation deadline. Policies vary by property, so it’s important to understand the terms before booking. For more information, visit our customer service portal.