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Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Nov 21 - Nov 23
In two months
Jan 2 - Jan 4
In three months
Jan 30 - Feb 1
In four months
Feb 27 - Mar 1

Vacation Rentals in Middletown

Exterior
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
9.6 out of 10, Exceptional, (19)
"It was very clean and cozy! My partner and I loved staying here! "
United States
Tyaunna W.
The price is ￥10,433
￥19,190 total
includes taxes & fees
Nov 12 - Nov 13
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds
Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment

Elkton
9.8 out of 10, Exceptional, (40)
"The hosts were amazing and enjoyed talking with them. We look forward to coming back soon. Sean and Paula "
United States
Michael B.
The price is ￥10,739
￥17,075 total
includes taxes & fees
Nov 17 - Nov 18
Country Get Away 1 Bedroom Apartment
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.
The price is ￥20,436
￥32,232 total
includes taxes & fees
Nov 13 - Nov 14
Quarry Landing - Center of Town & River View - 3 Bedroom
Iron/ironing board, WiFi, bed sheets
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

2.0 star property
Elkton
9.8 out of 10, Exceptional, (6)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is ￥18,410
￥24,719 total
includes taxes & fees
Nov 10 - Nov 11
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Marina
Historic Chesapeake City Stay

Historic Chesapeake City Stay

Chesapeake City
9.0 out of 10, Wonderful, (15)
"Perfect little place for 2. Quiet Very close to Schaefers. "
United States
Karen H.
The price is ￥16,569
￥42,770 total
includes taxes & fees
Nov 12 - Nov 13
Historic Chesapeake City Stay
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.
The price is ￥16,876
￥28,682 total
includes taxes & fees
Nov 17 - Nov 18
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
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.
The price is ￥13,938
￥26,396 total
includes taxes & fees
Nov 11 - Nov 12
Summer Rustic Camping with AC and King Bed
Dining
The Loft at Gilpin Place*King Bed*Trolley Square! by RedAwning

The Loft at Gilpin Place*King Bed*Trolley Square! by RedAwning

2.0 star property
Wilmington
8.0 out of 10, Very Good, (1)
"I'm local to Wilmington and stayed here with my husband while our bathroom was being renovated. The apartment is adorable and in a great location, Trolley Square. Walkable to restaurants and bars. Parking can be tough, but it's a safe neighborhood, so to park a block away isn't a problem. This would be a good place to stay for someone who needed to be in Wilmington for business (there's a desk in the living room, and the wifi seemed reliable) or a couple coming here for an event or to check out...
United States
Bridget E.
The price is ￥15,403
￥46,854 total
includes taxes & fees
Nov 10 - Nov 11
The Loft at Gilpin Place*King Bed*Trolley Square! by RedAwning
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.
The price is ￥24,716
￥43,472 total
includes taxes & fees
Nov 10 - Nov 11
Private townhouse near downtown and state park
Apartment, 1 Bedroom | Private kitchen | Fridge, coffee/tea maker
Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning

Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning

3.0 star property
Wilmington
6.0 out of 10, (1)
"Be aware that there is on street parking that requires a permit from the city of Wilmington. Red Awni ng worked with me to resolve the issue but it took some time and a few texts to make it work.The on street parking placed me a block and half from the propery. No cost but need proof of renting the space. The GPS sent you down a one way street that does not bring by the front of the property. This was a problem finding the property after dark. No climate control of the rental unit. The bed was...
United States
Clifford
The price is ￥12,838
￥42,417 total
includes taxes & fees
Nov 11 - Nov 12
Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning
Interior
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Newark
9.8 out of 10, Exceptional, (19)
"This place is beautiful in a quiet neighborhood. The kitchen is well stocked, the bed are so comfortable and the bathrooms are very nice, especially the master bath!!! I'd definitely stay here again."
United States
Lisa Y.
The price is ￥29,687
￥51,121 total
includes taxes & fees
Nov 10 - Nov 11
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Fridge, microwave, oven, stovetop
Cozy loft above ink shop

Cozy loft above ink shop

Bear
9.0 out of 10, Wonderful, (2)
"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."
United States
Krystle M.
The price is ￥12,703
￥16,344 total
includes taxes & fees
Nov 10 - Nov 11
Cozy loft above ink shop
Fridge, microwave, oven, stovetop
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Elkton
8.0 out of 10, Very Good, (9)
"Although it was just for a late overnight stay, the house was perfect for our needs. Clean, with hospitable, accommodating host!"
United States
Wendy Z.
The price is ￥20,712
￥43,421 total
includes taxes & fees
Nov 10 - Nov 11
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Outdoor spa tub
Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub

Lincoln University
10.0 out of 10, Exceptional, (16)
"Great property, space and location for the boys and dad to have there own space, big elk creek for fishing and grill was fabulous to do chicken and burgers for a large group"
United States
Richard F.
The price is ￥29,618
￥72,674 total
includes taxes & fees
Nov 12 - Nov 13
Thunder Hill Retreat - Spacious/Deck/Hot tub
Fridge, microwave, oven, stovetop
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

2.0 star property
Chesapeake City
9.4 out of 10, Exceptional, (3)
"Cozy and very suitable. No issues, quiet and clean. "
United States
Rich D.
The price is ￥27,616
￥51,390 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Terrace/patio
Nature's Haven Tiny Home

Nature's Haven Tiny Home

Bear
10.0 out of 10, Exceptional, (4)
"Nature’s Haven Tiny Home worked great for us. Karin was a great communicator and we really enjoyed ourselves. "
United States
James S.
The price is ￥28,996
￥36,285 total
includes taxes & fees
Nov 10 - Nov 11
Nature's Haven Tiny Home
Fridge, microwave, oven, stovetop
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
10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is ￥20,712
￥52,691 total
includes taxes & fees
Nov 10 - Nov 11
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Interior
Room #2 in Elkton, MD – Easy Access to I-95

Room #2 in Elkton, MD – Easy Access to I-95

2.0 star property
Elkton
The price is ￥12,120
￥17,726 total
includes taxes & fees
Nov 10 - Nov 11
Room #2 in Elkton, MD – Easy Access to I-95
Private kitchen
High tech 1BR Condo with Basement Lounge

High tech 1BR Condo with Basement Lounge

Downtown Wilmington
The price is ￥21,402
￥41,236 total
includes taxes & fees
Nov 11 - Nov 12
High tech 1BR Condo with Basement Lounge
Outdoor dining
Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm

2.0 star property
Nottingham
The price is ￥15,495
￥28,720 total
includes taxes & fees
Nov 11 - Nov 12
Amish Countryside Escape at Forest Edge Farm
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

Ramada by Wyndham Newark/Wilmington

Ramada by Wyndham Newark/Wilmington

10/10 Excellent
"Breakfast"
Wayne 1-night trip
Posted 3 days ago
Ramada by Wyndham Newark/Wilmington

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

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.