A steel arch bridge over a river with surrounding trees and buildings.

Middletown Vacation Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Middletown vacation rentals

A wooden cabin with a porch, surrounded by dense forest.

1. 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.
The price is SAR 263
SAR 417 total
includes taxes & fees
29 Oct - 30 Oct
Country Get Away Studio Apartment
A riverside dock with boats, a covered seating area, and a bridge in the background.

2. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (31 reviews)
"This is a great place, to feel comfortable. Exactly as advertised Just around the corner from Schaeffers."
United States
Janice H.
The price is SAR 405
SAR 1,046 total
includes taxes & fees
25 Oct - 26 Oct
Historic Chesapeake City Stay
A bedroom with a single bed, a wooden wardrobe, and a ceiling light.

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
9.4 out of 10, Exceptional, (6 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
The price is SAR 540
SAR 1,093 total
includes taxes & fees
5 Nov - 6 Nov
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

4. 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
The price is SAR 255
SAR 469 total
includes taxes & fees
28 Oct - 29 Oct
Guest Suite for up to 2 in a Victorian on the Chester River
A covered deck area with a grill and outdoor seating.

5. 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
The price is SAR 709
SAR 876 total
includes taxes & fees
25 Oct - 26 Oct
Nature's Haven Tiny Home
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)
"The host was great and easy to communicate with. It was a first time experience staying on a boat for my family and I and we really enjoyed it. Perfect for a few nights to visit family nearby."
United States
Jessica
The price is SAR 938
SAR 1,111 total
includes taxes & fees
25 Oct - 26 Oct
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Terrace/patio

7. 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.
The price is SAR 709
SAR 996 total
includes taxes & fees
25 Oct - 26 Oct
Tiny Home Tranquil Oasis
A two-story residential building with a stone facade, a large front lawn, and a driveway.

8. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
The price is SAR 945
SAR 1,322 total
includes taxes & fees
26 Oct - 27 Oct
Elegant Family Stay • Quiet Neighborhood • Comfort
A brick house with a front porch, a chimney, and a well-maintained lawn.

9. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is SAR 1,187
SAR 1,258 total
includes taxes & fees
25 Oct - 26 Oct
Bohemia Manor Farm
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

10. 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)
"Nothing fancy but extremely functional! House was clean, had what we needed in kitchen, beds were comfy. Would highly recommend!"
United States
Shana G.
The price is SAR 641
SAR 1,439 total
includes taxes & fees
27 Oct - 28 Oct
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A bedroom with a bed, a ceiling fan, a wall decal with the Eiffel Tower, and a window.

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
8.2 out of 10, Very good, (21 reviews)
"I’ve stayed in much better locations."
United States
Grant H.
The price is SAR 709
SAR 1,469 total
includes taxes & fees
25 Oct - 26 Oct
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

12. 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.
The price is SAR 450
SAR 699 total
includes taxes & fees
2 Nov - 3 Nov
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.

13. 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, (7 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is SAR 527
SAR 1,314 total
includes taxes & fees
1 Nov - 2 Nov
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
A beach with a water tower, beach umbrellas, and a hotel in the background.

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

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
The price is SAR 553
SAR 692 total
includes taxes & fees
1 Nov - 2 Nov
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
A residential house with a brick exterior, a dark roof, and a front porch with a bench.

15. 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
The price is SAR 521
SAR 680 total
includes taxes & fees
23 Oct - 24 Oct
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
A garden with a fountain, surrounded by lush greenery and flowering plants.

16. New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.6 out of 10, Exceptional, (30 reviews)
"We love this townhouse, close to everything!"
United States
Judy P.
The price is SAR 429
SAR 722 total
includes taxes & fees
25 Oct - 26 Oct
New Construction townhome close to everything downtown w/transparent pricing
A compact kitchen with dark cabinets, a stainless steel refrigerator, a microwave, and a stove.

17. Cozy 1-bedroom apartment in Lincoln University

Cozy 1-bedroom apartment in Lincoln University
Lincoln University
10.0 out of 10, Exceptional, (2 reviews)
"My girlfriend and I were in town for a wedding and the VRBO was perfect. Great privacy, lovely decor, and comfortable bed. A full use kitchen was great to have. Cheech (the pig!!) was so friendly and the host even dropped off carrots for us to feed him. The host responded to every question in a timely manner and check in and check out were painless."
United States
Zachary Z.
The price is SAR 525
SAR 770 total
includes taxes & fees
3 Nov - 4 Nov
Cozy 1-bedroom apartment in Lincoln University
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

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.
The price is SAR 878
SAR 1,869 total
includes taxes & fees
27 Oct - 28 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

19. Turtle Cove Room

Turtle Cove Room
Kent County
The price is SAR 653
SAR 807 total
includes taxes & fees
3 Nov - 4 Nov
Turtle Cove Room
A covered pavilion with a brick floor and benches, surrounded by greenery and a body of water.

20. Entire place with private parking

Entire place with private parking
Hilltop
8.0 out of 10, Very good, (11 reviews)
"great place very clean. Will stay again loved private parking "
United States
kennya J.
The price is SAR 375
SAR 598 total
includes taxes & fees
25 Oct - 26 Oct
Entire place with private parking
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

Red Roof Inn & Suites Newark - University

Red Roof Inn & Suites Newark - University

10/10 Excellent
"Great"
Misty 1-night trip
Posted 17 hours ago
Red Roof Inn & Suites Newark - University

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.