Middletown Cottage Rentals
House
9.6(14 Reviews)
2 Bedrooms
1 Bath
6 Guests
1550 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $193/Night
7 Nights - US $1,353
Bed & Breakfast
10.0(20 Reviews)
1 Bedroom
1 Bath
2 Guests
269.1 ft²
Oceanfront
Breakfast- Parking
Ocean View
US $244/Night
7 Nights - US $1,707
Bed & Breakfast
10.0(88 Reviews)
1 Bedroom
1 Bath
- Breakfast
Pool- Balcony/Terrace
- Air Conditioner
US $247/Night
7 Nights - US $1,726
House
9.6(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $300/Night
7 Nights - US $2,100
House
10.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
2949.31 ft²
- Parking
- Balcony/Terrace
View- Air Conditioner
US $309/Night
7 Nights - US $2,160
House
9.4(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $428/Night
7 Nights - US $2,996
House
9.8(7 Reviews)
2 Bedrooms
2 Baths
6 Guests
1399.31 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $731/Night
7 Nights - US $5,115
New
House
4 Bedrooms
3 Baths
10 Guests
2950 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
Internet
US $468/Night
7 Nights - US $3,278
New
Apartment
1 Bedroom
1 Bath
2 Guests
1399.31 ft²
- Parking
- Pool
Child Friendly
Wellness Facilities
US $186/Night
7 Nights - US $1,303
US $381/Night
7 Nights - US $2,665
Apartment
4 Bedrooms
2 Baths
8 Guests
1700.7 ft²
- Parking
- Pool
- Child Friendly
Security/Safety
US $325/Night
7 Nights - US $2,276
US $415/Night
7 Nights - US $2,906
Why Choose Rent By Owner for your Middletown Cottage Rentals?
What makes our Cottage Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Middletown
How to Book Your Middletown Cottage Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cottage rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Middletown
Common Cottage Rentals Amenities
What amenities can you expect?
Our Cottage Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Middletown, DE
Port Penn
Frog Hollow Golf Club
Back Creek Golf Club
Frightland
Dutch Country Farmers Market
Your Creation Station
Middletown Cottage Rentals Frequently Asked Questions
1. What are the top Cottages in Middletown?
There are a lot of options in Middletown. If you plan on staying in the Middletown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in Middletown:
- Holiday Inn Express & Suites Middletown by IHG
- Fairfield Inn & Suites by Marriott Middletown
- Fairfield by Marriott Inn & Suites Middletown
- Hampton Inn Middletown
- Pleasant Hill Motel
- Pleasant Hill Motel
- 3-bedroom house in charming Middletown with AC
- Hampton Inn Middletown
- Secluded serenity. Perfect Holiday Get Away. Located near Historic Odessa DE.
2. How many Cottages are available in Middletown?
Currently, the total number of properties listed by RBO in 2026 is over 33 in the Middletown area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Middletown.
More Rentals You May Like Near Middletown
Hotel
9.0(189 Reviews)
10 Baths
333.68 ft²
Private Pool- Parking
- Pool
- Air Conditioner
US $152/Night
7 Nights - US $1,062
New
House
3 Bedrooms
3 Baths
6 Guests
- Air Conditioner
- Child Friendly
Laundry
Bedding/Linens
US $373/Night
7 Nights - US $2,613
US $287/Night
7 Nights - US $2,008
US $223/Night
7 Nights - US $1,560
New
House
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $169/Night
7 Nights - US $1,184
Apartment
4.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $101/Night
7 Nights - US $709
House
9.6(11 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $190/Night
7 Nights - US $1,329
House
9.4(3 Reviews)
4 Bedrooms
3 Baths
7 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $406/Night
7 Nights - US $2,840
Apartment
9.0(2 Reviews)
8 Bedrooms
2 Baths
2 Guests
1 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $175/Night
7 Nights - US $1,226
House
3 Bedrooms
2 Baths
6 Guests
3200 ft²
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $617/Night
7 Nights - US $4,322
House
4 Bedrooms
3 Baths
8 Guests
3240 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $393/Night
7 Nights - US $2,753
House
5.0(1 Review)
2 Bedrooms
1 Bath
3 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $78/Night
7 Nights - US $546
