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Middletown Vacation Rentals

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Nov 9 - Nov 10
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Nov 21 - Nov 23

Vacation Rentals in Middletown

Outdoor dining
Chesapeake Bay House with Dock & Private Beach

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
On the beach, sun loungers, beach towels
Beachfront Sunsets on the Water at Oakwood 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
Fridge, microwave, oven, stovetop
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

Wilmington
8.6 out of 10, Excellent, (12)
"Was in Wilmington to work a trade show at the Chase Center on the Riverfront. Everything was as described and the communications with the host were great. Only about a 12 minute drive to the venue and lots of restaurants within a 10 minute drive. It’s nothing fancy but for about the same price as a budget hotel room you get a kitchen, two comfy bedrooms and a living room. "
United States
Douglas R.
$182 nightly
The price is $187
Nov 11 - Nov 12
Total with taxes and fees
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Sun loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown

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.
$571 nightly
The price is $605
Nov 11 - Nov 12
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
Terrace/patio
Waterfront house with amazing views. Top of the Chesapeake

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
Fridge, microwave, oven, stovetop
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

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.
$120 nightly
The price is $125
Nov 11 - Nov 12
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Interior
Charming 2-bedroom cabin close to Fair Hill on horse farm

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
Smart TV, books
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville
9.8 out of 10, Exceptional, (58)
"Wonderful house in a welcoming, friendly community. "
United States
Benjamin A.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Property grounds
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

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

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

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!
Fridge, microwave, oven, stovetop
Two-story condo in luxury townhouse. Free parking.

Two-story condo in luxury townhouse. Free parking.

Downtown Wilmington
9.6 out of 10, Exceptional, (16)
"This is a great place and super conveniently located. We loved all the amenities! Special shout out for the lovely towels! We would definitely stay here again!"
United States
Shelly S.
$350 nightly
The price is $360
Nov 11 - Nov 12
Total with taxes and fees
Two-story condo in luxury townhouse. Free parking.
Marina
Historic Chesapeake City Stay

Historic Chesapeake City Stay

Chesapeake City
9.0 out of 10, Wonderful, (17)
"Perfect little place for 2. Quiet Very close to Schaefers. "
United States
Karen H.
$263 nightly
The price is $279
Nov 12 - Nov 13
Total with taxes and fees
Historic Chesapeake City Stay
Fridge, microwave, oven, stovetop
Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis

Bear
$233 nightly
The price is $242
Nov 11 - Nov 12
Total with taxes and fees
Tiny Home Tranquil Oasis
1 bedroom
Summer Rustic Camping with AC and King Bed

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.
$157 nightly
The price is $158
Nov 11 - Nov 12
Total with taxes and fees
Summer Rustic Camping with AC and King Bed
On the beach
A cottage on the shore of the Delaware River

A cottage on the shore of the Delaware River

Salem
9.8 out of 10, Exceptional, (68)
"We stayed in Beth’s cozy beachfront home while playing in local lax tournament and it was perfect. We loved the quaintness and seclusion of the property, its pricing, and the ability to walk out and immediately fish the river. Book it — you won’t be disappointed!"
United States
Michael M.
A cottage on the shore of the Delaware River
Fridge, microwave, oven, stovetop
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

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
Exterior detail
Luxury Condo + Free Garage Parking 402

Luxury Condo + Free Garage Parking 402

Downtown Wilmington
$203 nightly
The price is $207
Dec 1 - Dec 2
Total with taxes and fees
Luxury Condo + Free Garage Parking 402
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom

Port Deposit
9.8 out of 10, Exceptional, (10)
"Amy has a beautiful home, filled with character and special touches. We absolutely loved our stay and have zero complaints. The location was wonderful and we were extremely comfortable."
United States
Geoff F.
$200 nightly
The price is $212
Nov 13 - Nov 14
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
2 bedrooms, WiFi
Private townhouse near downtown and state park

Private townhouse near downtown and state park

Downtown Wilmington
9.4 out of 10, Exceptional, (11)
"Property was extremely clean!"
United States
margaret p.
$276 nightly
The price is $283
Nov 11 - Nov 12
Total with taxes and fees
Private townhouse near downtown and state park
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 Middletown Hotel Reviews

Staybridge Suites Wilmington Downtown by IHG

Staybridge Suites Wilmington Downtown by IHG

10/10 Excellent
"Broken bottle on sidewalk, area safety in question "
Chris 1-night trip
Posted 1 day ago
Staybridge Suites Wilmington Downtown by IHG

Find out more about Middletown

Everything you need to know about Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Middletown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $125 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation 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 Middletown 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 Middletown vacation.

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

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Middletown?

Yes, you can find vacation rentals in Middletown close to Frightland, or you can choose a secluded option if you're looking for extra privacy while you relax. Our travelers say Middletown has a good selection of restaurants. Make sure you have time to check out the festivals and churches during your trip.

What are some of the best vacation rentals that Middletown has to offer?

Chesapeake Bay House with Dock & Private Beach: This vacation home rental near Middletown is located on the beach and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Middletown?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Middletown stay.

What can I see and do in Middletown?

Cultural attractions include The Everett Annex and Everett Theatre, whereas Frightland is just one of the family-friendly sights. While here, Middletown Town Hall and Back Creek Golf Club are other places worth a visit.

What are vacation rentals like in Middletown?

Vacation rentals are private accommodations you can stay in for several days or more in Middletown. Vacation rentals provide amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.