Chesapeake City Holiday Rentals

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Holiday Rentals in Chesapeake City

Historic Chesapeake City Stay

Chesapeake City
9.0 out of 10, Wonderful, (18)
"Perfect little place for 2. Quiet Very close to Schaefers. "
United States
Karen H.
The price is NZ$493
includes taxes & fees
18 Nov - 19 Nov
Historic Chesapeake City Stay

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

Chesapeake City
9.8 out of 10, Exceptional, (6)
"Exactly as advertised and Brad was very helpful/responsive!"
United States
Gregory M.
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

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

Chesapeake City
10.0 out of 10, Exceptional, (57)
"Dennis’s property was everything we needed. We had plenty of room for our 14 people. The separate houses were nice to give the infants and their parents a place to retreat to. The older kids loved the great room with the juke box where they could look out for boats. The house was well stocked which made it perfect for preparing our Thanksgiving dinner! Thanks Dennis!!"
United States
Kay C.
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

Chesapeake City Quiet Overlook

Chesapeake City
10.0 out of 10, Exceptional, (24)
"We attended a wedding across the canal from this house at the Chesapeake Inn. It was very cool to see these really large ships go by as we sat on the deck. Very nice accommodations here! Jane was a great host!"
United States
Gary C.
Chesapeake City Quiet Overlook

Chesapeake Bay House with Dock & Private Beach

Elkton
10.0 out of 10, Exceptional, (177)
"Absolutely love this property! This is my family’s second stay here, we will definitely be coming back. Great hosts, clean house, wonderful location!"
United States
Katie H.
Chesapeake Bay House with Dock & Private Beach

Beachfront Sunsets on the Water at Oakwood Beach

Salem
10.0 out of 10, Exceptional, (43)
"House was well maintained and very clean. Fantastic view."
United States
Paul P.
Beachfront Sunsets on the Water at Oakwood Beach

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville
9.8 out of 10, Exceptional, (146)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
United States
Ashlee S.
The price is NZ$1,063
includes taxes & fees
17 Nov - 18 Nov
5-bedroom vacation home 5 minutes from historic Charlestown

Waterfront house with amazing views. Top of the Chesapeake

Perryville
10.0 out of 10, Exceptional, (102)
"Great accommodation overall - would visit again! Calm, great view, perfect spot for a private getaway."
United States
Jörg
Waterfront house with amazing views. Top of the Chesapeake

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

Wilmington
2.0 out of 10, (2)
"The neighborhood was creepy. Mail was on the doorstep unopened, the owner never communicated the code to get in. I sent a text/email and never got a response. The neighbors were doing drugs. … some sort of sniffing, smoking?!? We felt totally unsafe and went to an Embassy Suites. I would expect a full refund and have contacted my credit card company to enter a complaint. I would never recommend this place to anyone !!!"
United States
marsha k.
The price is NZ$220
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

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

Elkton
9.6 out of 10, Exceptional, (12)
"Good experience"
United States
Thomas Z.
Charming 2-bedroom cabin close to Fair Hill on horse farm

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

Port Deposit
10.0 out of 10, Exceptional, (30)
"This was our second time staying at this site. Always very clean, quiet and enjoyable."
United States
Chris S.
The price is NZ$372
includes taxes & fees
16 Nov - 17 Nov
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville
9.8 out of 10, Exceptional, (59)
"Wonderful house in a welcoming, friendly community. "
United States
Benjamin A.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Elkton
9.8 out of 10, Exceptional, (14)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
United States
Deborah M.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Perryville
9.2 out of 10, Wonderful, (181)
"Perfect spot for a relaxing weekend on the water, even if the kids are playing in a sports tournament."
United States
Donald R.
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Chestertown
10.0 out of 10, Exceptional, (10)
"Check-in was very easy. House was clean and well supplied with everything we needed. Peaceful and quiet. Mowed and cleared trails to enjoy. "
United States
Carol B.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Luxury Waterfront Home Built for Entertaining!

Abingdon
8.0 out of 10, Very good, (5)
The price is NZ$1,469
includes taxes & fees
16 Nov - 17 Nov
Luxury Waterfront Home Built for Entertaining!

Tiny Home Tranquil Oasis

Bear
The price is NZ$427
includes taxes & fees
14 Nov - 15 Nov
Tiny Home Tranquil Oasis

Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Havre de Grace
9.8 out of 10, Exceptional, (6)
"Beautiful house with lots of space for a family gathering. After a couple very hot days at Ripken (only 15 minute drive) the kids enjoyed cooling off in the pool and playing in the large yard. Would definitely stay again! "
United States
melissa d.
The price is NZ$2,355
includes taxes & fees
20 Nov - 21 Nov
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Summer Rustic Camping with AC and King Bed

Elkton
9.6 out of 10, Exceptional, (5)
"The dome and surrounding areas looks like it does in the photos, and using the compost toilet, shower, etc were pretty easy even for a camping novice like myself. The farm is beautiful and quiet. Good opportunities for birding too. I never saw or heard the gentlemen who live in the farmhouse, I only saw their cars come and go. I came here for rest and a connection to nature, and that’s what I got. I’d love to come back in the future! I think it would be even nicer later in the spring."
United States
Lady N.
The price is NZ$300
includes taxes & fees
17 Nov - 18 Nov
Summer Rustic Camping with AC and King Bed

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Elkton
9.8 out of 10, Exceptional, (42)
"We stayed for my Birthday! It was definitely a great place to stay. The house was decorated beyond my expectation. We are planing to book again for Girls Weekend."
United States
Billie W.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
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 Chesapeake City Hotel Reviews

Find out more about Chesapeake City

Everything you need to know about Chesapeake City holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake City holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake City holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesapeake City holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake City. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake City holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake City holiday rentals we have selected for you start as low as NZ$220 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesapeake City rentals

At Expedia, we put the best Chesapeake City holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesapeake City rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake City holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake City. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Chesapeake City?

Yes, there are holiday rentals close to the most popular sights in Chesapeake City, or you can select a more secluded option if you're looking for a relaxing stay. Chesapeake City is known for its restaurants and waterfront. Make sure you have time to check out the museums while you're in the area.

What are some of the best holiday rentals that Chesapeake City has to offer?

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Chesapeake City is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Chesapeake City?

With 10 Expedia holiday rentals, you're guaranteed to find just the right place for your Chesapeake City stay.

What can I see and do in Chesapeake City?

Cultural attractions include C and D Canal Museum, whereas Canal Wildlife Management Area is a spot to enjoy nature. While here, Chesapeake Inn Marina and Chesapeake City Docks are other places worth a visit.

What are holiday rentals like in Chesapeake City?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesapeake City. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip.