Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Middletown vacation rentals

A modern living room with a flat-screen TV, a brown sofa, a dining table with placemats, wicker chairs, and a kitchen area with a microwave and stove.

1. Bohemia Hideaway. Escape to a 14 acre peaceful retreat.

Bohemia Hideaway. Escape to a 14 acre peaceful retreat.
Middletown
$274 nightly
The price is $285
Nov 11 - Nov 12
Total with taxes and fees
Bohemia Hideaway. Escape to a 14 acre peaceful retreat.
A house with a paved walkway leading to the front door, surrounded by a landscaped garden with mulch and plants.

2. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (52 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
$97 nightly
The price is $103
Nov 11 - Nov 12
Total with taxes and fees
Country Get Away Studio Apartment
A wooden deck with outdoor furniture, a small shed, and a view of a body of water.

3. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.6 out of 10, Exceptional, (7 reviews)
"Everything was as advertised. Property is not new, but everything was clean and well cared for. Evenings on the water were peaceful and relaxing. We enjoyed our stay and definitely intend to return."
United States
John
$253 nightly
The price is $268
Nov 8 - Nov 9
Total with taxes and fees
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A living room with a sofa, a coffee table, and a patterned rug. There is a window with curtains, a door, and a small table with chairs.

4. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (31 reviews)
"Cute place. Clean, comfortable, and convenient to the soccer complex. I wasn’t familiar with Chesapeake City but we had a great time at the waterfront restaurants."
United States
John P.
$280 nightly
The price is $297
Nov 5 - Nov 6
Total with taxes and fees
Historic Chesapeake City Stay
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

5. Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
$110 nightly
The price is $117
Nov 5 - Nov 6
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

6. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
9.8 out of 10, Exceptional, (7 reviews)
"Great stay. Awesome owner. Nice restaurant right up the ramp. Would def recommend and do again if in the area!!!"
United States
Justin M.
$272 nightly
The price is $283
Nov 7 - Nov 8
Total with taxes and fees
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
A covered deck area with a grill and outdoor seating.

7. Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
$215 nightly
The price is $224
Nov 5 - Nov 6
Total with taxes and fees
Nature's Haven Tiny Home
Terrace/patio

8. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
$244 nightly
The price is $253
Nov 5 - Nov 6
Total with taxes and fees
Tiny Home Tranquil Oasis
A two-story residential building with a stone facade, a large front lawn, and a driveway.

9. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
$375 nightly
The price is $388
Dec 1 - Dec 2
Total with taxes and fees
Elegant Family Stay • Quiet Neighborhood • Comfort
Restaurant

10. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
$587 nightly
The price is $622
Nov 11 - Nov 12
Total with taxes and fees
Bohemia Manor Farm
A modern kitchen with dark cabinets, a white refrigerator, a microwave, an oven, and a bar area with stools.

11. Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
New Castle
8.4 out of 10, Very good, (24 reviews)
"I’ve stayed in much better locations."
United States
Grant H.
$355 nightly
The price is $363
Nov 8 - Nov 9
Total with taxes and fees
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

12. Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
9.8 out of 10, Exceptional, (6 reviews)
"Wonderful spot for five ladies to enjoy an evening away close to Chesapeake City"
United States
Rebecca G.
$343 nightly
The price is $363
Nov 9 - Nov 10
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

13. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
$138 nightly
The price is $141
Nov 5 - Nov 6
Total with taxes and fees
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A covered outdoor seating area with a fire pit, wicker furniture, and a Netflix sign.

14. Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Newark
9.8 out of 10, Exceptional, (8 reviews)
"Enjoyed our stay."
United States
Erik H.
$372 nightly
The price is $372
Dec 2 - Dec 3
Total with taxes and fees
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
A courtyard with wicker furniture, a fire pit, and a pool area.

15. Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
$176 nightly
The price is $193
Nov 30 - Dec 1
Total with taxes and fees
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
A living room with a white sofa, a clock, a dining area with a table and chairs, and a kitchen in the background.

16. 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
Elkton
10.0 out of 10, Exceptional, (15 reviews)
"It is in a lovely neighborhood and the hosts were very welcoming of us and my 2 dogs. We were all very comfortable."
United States
Barb
$163 nightly
The price is $173
Nov 5 - Nov 6
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
A spacious room with a large sliding glass door leading to a deck, a dining area with a white table, and a cozy seating area with a view of the water.

17. Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Charlestown
10.0 out of 10, Exceptional, (5 reviews)
"Had a wonderful stay. They really thought of everything. Had everything we could have possibly needed. It's a beautiful place and it was very clean and cared for."
United States
Laura K.
$401 nightly
The price is $419
Nov 9 - Nov 10
Total with taxes and fees
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
A bedroom with a bed, a nightstand, and a window overlooking a deck with outdoor furniture.

18. 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, (165 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
$476 nightly
The price is $505
Nov 17 - Nov 18
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
A wooden deck with lounge chairs and a dock extending into calm water.

19. 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, (115 reviews)
"Matt was a wonderful host whi responded to my texts very quickly. The house was perfect for a quick getaway celebrating my dad's retirement. Fishing from the dock was a plus, and everyone caught fish, even some "keepers"."
United States
Joe M.
$485 nightly
The price is $514
Nov 5 - Nov 6
Total with taxes and fees
Waterfront house with amazing views. Top of the Chesapeake
A room with a large sliding glass door leading to a balcony with a view of the sea and a wooden deck.

20. Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (8 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
$442 nightly
The price is $463
Nov 9 - Nov 10
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
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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Find vacation rentals that suit your style

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Top Middletown Hotel Reviews

A sunroom with white wicker furniture, large windows, and a ceiling fan.
Miller-Dunham House Bed & Breakfast

Miller-Dunham House Bed & Breakfast

Miller-Dunham House Bed & Breakfast
Odessa

10/10 Excellent

Private, friendly atmosphere, beautiful grounds, breakfast made by owners, "chef" absolutely incredible. Must stay..
United States
Kelly
Reviewed April 29, 2024
Miller-Dunham House Bed & Breakfast

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 $102 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.

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?

Sailor's Sunrise Cottage - Chesapeake Bay: This vacation home rental near Middletown is located on a lake and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals are there in Middletown?

With 3 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 Historic District and Middletown Town Hall 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.

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