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

Holiday Homes in Middletown

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Middletown holiday homes

A bedroom with a single bed, a wooden wardrobe, and a ceiling light.

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

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.2 out of 10, Wonderful, (5 reviews)
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A two-story residential building with a stone facade, a large front lawn, and a driveway.

2. 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.
Elegant Family Stay • Quiet Neighborhood • Comfort
A bunk bed room with white bedding and blue throw blankets.

3. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
Bohemia Manor Farm
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

4. 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.
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A home theater room with a curved seating area, a large flat-screen TV, and a carpeted floor.

5. 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.
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
A modern kitchen with stainless steel appliances, white cabinetry, and a large window providing a view of greenery.

6. Welcome to the secluded waterfront oasis

Welcome to the secluded waterfront oasis
Millington
8.0 out of 10, Very good, (3 reviews)
"We really enjoyed our stay here! The house was clean, cozy, and had everything we needed. The host was so nice and easy to communicate with, which made everything really easy. We felt right at home and would definitely stay here again!"
United States
Destiny H.
Welcome to the secluded waterfront oasis
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

7. 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, (163 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
5-bedroom vacation home 5 minutes from historic Charlestown
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.

8. 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)
"This property was amazing! The perfect spot to relax and recharge. It has such a cozy feel. The decor was perfection. We’ll definitely be back. And Dave was super quick to respond to all questions. Thank you!"
United States
Sandy B.
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
A garden with a fountain, surrounded by lush greenery and flowering plants.

9. 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.
New Construction townhome close to everything downtown w/transparent pricing
A living room with a dark grey sectional sofa, a round wooden coffee table, and a small side table.

10. Cozy, Comfortable, Pet Friendly Home with a fenced in private yard

Cozy, Comfortable, Pet Friendly Home with a fenced in private yard
Wilmington
10.0 out of 10, Exceptional, (1 review)
"Spotless and so cozy. It was like coming home. Our host was communicative and kind. We’d love to come back."
United States
Chris D.
Cozy, Comfortable, Pet Friendly Home with a fenced in private yard
A rural landscape with open fields, a barn, and a large tree.

11. Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
9.0 out of 10, Wonderful, (4 reviews)
"Property was close enough to stores and restaurants if needed. House is located in the rural area of the county (very peaceful). Property had all of the necessary kitchen utensil, pots, pans, and dishes that was needed for this trip. "
United States
jckglss6 G.
Amish Countryside Escape at Forest Edge Farm
A living room with a fireplace, two sofas, a zebra rug, and a ceiling fan.

12. Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group

Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
Wilmington
9.2 out of 10, Wonderful, (9 reviews)
"Comfy cozy… home away from home. Location was perfectly centered for the activities we did and the restaurants we chose. Beds and sheets were great and plenty of hot water. We had a nice relaxing stay."
United States
carla k.
Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
A kitchen with white cabinets, a dishwasher, a window with a view of greenery, and a door with a glass panel.

13. Entire Private Wilmington Home | Sleeps 6 | 2 Baths & Parking

Entire Private Wilmington Home | Sleeps 6 | 2 Baths & Parking
Wilmington
10.0 out of 10, Exceptional, (5 reviews)
"The property is very clean, recently updated and had more than enough room for the four of us staying. There was even an extra bedroom with 2 twin beds we didn't need. The neighborhood was super quiet and perfect to come back to after long days of adventure in the area."
United States
Grant S.
Entire Private Wilmington Home | Sleeps 6 | 2 Baths & Parking
A modern living room with a grey sofa, a round coffee table, and a large horse painting on the wall.

14. New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi

New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
Hilltop
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful stay , comfortable and very warm welcoming"
United States
Shyaniece S.
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
A spacious living area with a large gray sofa, a coffee table, and a bar area with stools.

15. Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court

Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
Elkton
10.0 out of 10, Exceptional, (15 reviews)
"Everything was as advertised, clean, neat & spacious. Great communicators and readily available to answer questions."
United States
Gary S.
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
A house with a covered porch, a grill, and a propane tank in the yard.

16. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
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
"The hotel is in downtown Wilmington. Great location and close by to the Christiana Care Hospital. Which is why I chose it since I was having surgery. The hotel was very well maintained, the rooms were clean and spacious. When we checked in they were having happy hour with snacks and drinks. My husband enjoyed breakfast the next morning. We didn’t get to use any of the amenities. But I still gave a 5 star rating. You will not be disappointed booking a room here. A ha what was funny when we got there was we didn’t know you had to use your room key for the elevator. We thought it was broken. We got off the elevator to use another one and the same thing happened talk about feeling like idiots. We laughed about it most of the night."
Virginia 1-night trip
Posted 4 hours ago
Staybridge Suites Wilmington Downtown by IHG

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
Accommodation
182 Holiday Homes
Lowest Price
AU$476
Highest Price
AU$476