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Smyrna Holiday Rentals

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Holiday Rentals in Smyrna

JVA LUXURY HOUSING

The price is NZ$843
includes taxes & fees
6 Oct - 7 Oct
JVA LUXURY HOUSING

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

9.6 out of 10, Exceptional, (8)
"Good experience"
Charming 2-bedroom cabin close to Fair Hill on horse farm

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (172)
"Property was in good shape and had plenty of space. Our family loved the beach and the shallow water for the children to play in. Even though we didn’t have perfect weather, we had a wonderful trip."
Chesapeake Bay House with Dock & Private Beach

Eagles Nest

10.0 out of 10, Exceptional, (111)
"What an incredible stay! Every image was 100% accurate. The house was immaculate and the town was quaint and rustic-exactly the type of peace and quiet that we needed. Even the locals were so warm and friendly. Highly recommend the local restaurant at the end of the island, The Charlesworth!! I fully intend to stay here again soon!"
The price is NZ$390
includes taxes & fees
30 Sept - 1 Oct
Eagles Nest

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
The price is NZ$483
includes taxes & fees
30 Sept - 1 Oct
Historic Chesapeake City Stay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (57)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Peaceful living just outside of town

10.0 out of 10, Exceptional, (12)
"The house was very clean and the beds were extremely comfortable. "
Peaceful living just outside of town

Captain's Quarters

9.8 out of 10, Exceptional, (99)
"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "
Captain's Quarters

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (48)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Tiny Home Tranquil Oasis

The price is NZ$418
includes taxes & fees
30 Sept - 1 Oct
Tiny Home Tranquil Oasis

Cozy loft above ink shop

10.0 out of 10, Exceptional, (1)
"Cozy little place to stay that was fully stocked for a fair price compared to others in the area. Plenty of parking and quiet even with the tattoo shop below. The only thing that I would like to have had is a light on the front porch but I used my flashlight on my phone so it wasn’t too bad. I would definitely stay again."
The price is NZ$170
includes taxes & fees
9 Oct - 10 Oct
Cozy loft above ink shop

NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

10.0 out of 10, Exceptional, (25)
"Nice stay… good family home…. Lots of sleeping accommodations…. A few steps from the beach!!!!! Great host!!!!!"
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

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

9.8 out of 10, Exceptional, (6)
"We rented Hook, Wine & Sinker for our family to stay in during the weekend of our son's wedding in Chesapeake City, MD. The home is absolutely beautiful, very clean, spacious, and one of the best rentals that I've stayed in with VRBO. "
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

2.0 star property
8.6 out of 10, Excellent, (4)
"Would I stay here again? No. Would I recommend it to a friend? Also no.While the unit was clean, it felt quite tired and in need of a refresh. The kitchen was minimally equipped, with very few pots and pans, making it difficult to cook meals. Additionally, there were air fresheners and purifiers in every room, which made us wonder if they were masking an underlying issue. Overall, the space could benefit from some updates and better preparation for guests."
Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (22)
"Peaceful relaxing getaway with my family. The cottage was perfect in every way. The property outside was a dream. Every day we were outside on the deck or dock enjoying nature. This is exactly what we needed to recharge with life. Can’t wait to come back and enjoy this perfect retreat again! "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

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

10.0 out of 10, Exceptional, (9)
"Great, cozy, quiet little spot! Perfect for 4 adults and a baby. My 1.5 year old loved exploring the deck with an amazing water view, and gained lots of confidence navigating the little steps throughout the house and worked on her balance. Kitchen was well appointed and suited our needs. Would stay here again!"
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Luxurious and spacious townhome with all necessary amenities awaits your stay.

9.4 out of 10, Exceptional, (9)
"Great experience all around! "
Luxurious and spacious townhome with all necessary amenities awaits your stay.

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (3)
"Enjoyed"
The price is NZ$406
includes taxes & fees
30 Sept - 1 Oct
Nature's Haven Tiny Home

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

9.2 out of 10, Wonderful, (12)
"Great location right on the water. Great for fishing or just sitting and relaxing. The house is in a quiet secluded area but only 10 minutes from Chesapeake Bay. Pool was an awesome extra. My son enjoyed it. The home was clean and plenty of space. "
Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Fisherman's Dream- Delaware Bay Waterfront- Dog and kid friendly- 3br/1b- wifi

9.8 out of 10, Exceptional, (11)
"The house is situated just across the street from the bay. You can see the bay from the second floor.The second floor is accessible via a steep set of stairs. The shower is small, but great hot water and pressure. "
Fisherman's Dream- Delaware Bay Waterfront- Dog and kid friendly- 3br/1b- wifi
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 Smyrna Hotel Reviews

Find out more about Smyrna

Find out more about Smyrna

Everything you need to know about Smyrna 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 Smyrna 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 Smyrna holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Smyrna holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Smyrna. 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 Smyrna 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 Smyrna holiday rentals we have selected for you start as low as NZ$170 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Smyrna rentals

At Expedia, we put the best Smyrna 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 Smyrna 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 Smyrna 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 Smyrna. 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 a holiday rental in Smyrna?

Yes, there are holiday rentals close to the most popular sights in Smyrna, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Smyrna is known for its shops. Make sure you have time to check out the restaurants and coffee shops during your trip.

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

Captain's Quarters: This holiday home rental outside of Smyrna is located near the beach, and has a balcony, a garden 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 will I find in Smyrna?

Choose from 3 Expedia holiday rentals in Smyrna for a memorable holiday.

What’s there to see and do in Smyrna?

Explore the area and cultural attractions such as Delaware State Police Museum and Education Center, or visit one of the family-friendly sights such as Frightland. In the wider area, you’ll find Woodland Beach and Wheel of Fortune.

What’s a holiday rental in Smyrna like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Smyrna. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for small groups.