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Middletown Vacation Rentals

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Find properties with these dates

Tonight
May 13 - May 14
Tomorrow
May 14 - May 15
This weekend
May 17 - May 19
Next weekend
May 24 - May 26

Vacation Rentals in Middletown

1 bedroom, WiFi, bed sheets
Oaxaca, a private room with private entrance
9.0 out of 10, Wonderful, (7)
"I hope to stay again!"
The price is ￥11,684
per night
May 15 - May 16
Oaxaca, a private room with private entrance
Pool | Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (50)
"Had an excellent time at this beautiful and secluded property on the Chester River. Although very private and a lot of outside space to roam, we were still very close to all that Chestertown has to offer. So, it was the best of both worlds. Plenty of amazing scenery and wildlife to enjoy around the property, and Beth is an excellent communicator. If you're a wine drinker, check out a number of close-by wineries like: Casa Carmen, Bu-De, Broken Spoke and Crow Vineyards. Would highly recommend...
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Beach nearby, sun loungers
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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Pool
Historic Chesapeake City Stay
8.0 out of 10, Very Good, (1)
"The place overall is very simple and nice. The bed was a little uncomfortable And decided to not stay the extra night and come home and use my own bed. Overall, very clean very nice."
The price is ￥17,966
per night
May 15 - May 16
Historic Chesapeake City Stay
Property grounds
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, (80)
"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Property grounds
Entire place with private parking
8.0 out of 10, Very Good, (5)
"Overall great location, space and with secure parking."
The price is ￥12,307
per night
May 21 - May 22
Entire place with private parking
Exterior
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
9.8 out of 10, Exceptional, (85)
"Such a comfortable place to stay! Fully stocked kitchen, big rooms with comfortable beds and linens. Everything is clean and the appliances are new. Sweet welcome gift of pastries and water. Quiet neighborhood. Easy to access and property host was very responsive."
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Interior
Historic home in the heart of Main Street- walkable to shops and restaurants
10.0 out of 10, Exceptional, (7)
"Minutes from our job site. Thank you for your hospitality."
Historic home in the heart of Main Street- walkable to shops and restaurants
Property grounds
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
10.0 out of 10, Exceptional, (65)
"We had a great get-away for a few days with our friends. The cabin was in a quiet neighborhood with amazing views. We especially enjoyed using the fire pit while sitting in the comfortable Adirondack chairs overlooking the Chesapeake Bay. The owners were friendly and great to work with. Highly recommend!"
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Property grounds
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.2 out of 10, Wonderful, (9)
"Clean, great location. Had a very relaxing weekend that was greatly needed. There was plenty of things to see and do in the beautiful town. Had a small problem but the host took care of it immediately. He was great. Thank you for a wonderful time."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
9.6 out of 10, Exceptional, (42)
"Suzanne's place was very comfortable and she supplied everything you'd need. It was fun cooking in her kitchen and I was also able to work remotely as well."
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
Fridge, microwave, oven, stovetop
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.8 out of 10, Exceptional, (27)
"This location was perfect for our stay during a bass tournament on the upper bay. boa parking was great and very secure compared to hotels. SAhelly was very accomadating"
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Dining
Family-Friendly Cottage, Walk to the Beach!
10.0 out of 10, Exceptional, (13)
"The cottage exceeded our expectations. Everything is as pictured. The place is sparkling clean and stocked with everything you need and more. Communication was excellent. Loved the location and the private beach access was a real plus. Great location to use as home base and take day trips in the area."
Family-Friendly Cottage, Walk to the Beach!
Property grounds
Two bedroom luxury apartment! Amenities included!
The price is ￥23,367
per night
May 15 - May 16
Two bedroom luxury apartment! Amenities included!
Aerial view
Thunder Hill Retreat - Peaceful - sleeps 12
10.0 out of 10, Exceptional, (4)
"Fantastic property, one the the best hosts we have ever had. I would recommend this house and this host to anyone. Above and beyond, we appreciate everything our host did in order for us to enjoy our stay."
The price is ￥40,326
per night
May 20 - May 21
Thunder Hill Retreat - Peaceful - sleeps 12
Fridge, microwave, oven, stovetop
Two-story condo in luxury townhouse. Free parking.
9.8 out of 10, Exceptional, (8)
"I booked this property for my bridesmaids during my wedding weekend. It was beautiful, comfortable, and very conveniently located! The host was very responsive with any questions as well."
The price is ￥37,387
per night
May 15 - May 16
Two-story condo in luxury townhouse. Free parking.
Property grounds
Beachfront Sunsets on the Water at Oakwood Beach
10.0 out of 10, Exceptional, (19)
"The location was great for us because it was relatively close to Newark, DE and Philadelphia. Water views were great from so much of the house and owners had thought of every possible touch to make people feel at home. There were plenty of outlets, chargers, TVs, tables & chairs, hooks in bathrooms, nightlights, etc. The fridge was free of all sorts of open condiments that are probably supposed to be helpful for guests but that drive my husband crazy as they've taken up half the fridge in the...
Beachfront Sunsets on the Water at Oakwood Beach
Fridge, microwave, oven, stovetop
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (18)
"Betty Ann’s property was exactly as described. The personal touches of full ice trays, cooler, a well-stocked kitchen and welcome snacks really show the care and thought Betty Ann takes in her rental. The sunsets are even more gorgeous than described- and literally 20 steps away. We loved our stay so much, we booked our next stay while we were there :) Keep in mind you are above the owners garage, so you make hear their use of it at any time!"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom
10.0 out of 10, Exceptional, (5)
"What a beautiful home. The host was attentive to the small details in the house, and my friend and I greatly enjoyed our stay."
The price is ￥32,558
per night
May 28 - May 29
Quarry Landing - Center of Town & River View - 3 Bedroom
Pool | Outdoor pool, a heated pool
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
9.6 out of 10, Exceptional, (154)
"The property was beautiful and just as described. The property managers were quick to respond and very helpful. We truly enjoyed our stay."
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
Don't see what you're looking for?
See all available properties in Middletown
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.

Other types of properties in Middletown you may be interested in

Exterior
Holiday Inn Express And Suites Middletown, an IHG Hotel
2.5 star property
9.2 out of 10, Wonderful, (433)
"Very nice hotel. Great breakfast. Friendly and easy check in!"
The price is ￥19,110
per night
May 19 - May 20
Holiday Inn Express And Suites Middletown, an IHG Hotel
Lobby
Fairfield Inn & Suites by Marriott Middletown
2.5 star property
9.2 out of 10, Wonderful, (101)
"Great place to stay. "
The price is ￥17,342
per night
May 20 - May 21
Fairfield Inn & Suites by Marriott Middletown
Indoor pool
Hampton Inn Middletown
2.5 star property
8.8 out of 10, Excellent, (676)
"Was .05 miles from friends we were visiting. Plenty of places to eat at. Hotel staff were helpful and friendly. Will stay here again."
The price is ￥19,719
per night
May 27 - May 28
Hampton Inn Middletown
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.

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?

Oaxaca, a private room with private entrance: This vacation home rental near Middletown is located in the city center and offers a garden, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

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?

Explore the area and family-friendly sights such as Frightland, or get out into nature at a spot like Lums Pond State Park. While here, Dutch Country Farmers Market 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.