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Middletown Vacation Rentals

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Vacation Rentals in Middletown

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
Historic home in the heart of Main Street- walkable to shops and restaurants
10.0 out of 10, Exceptional, (7)
"Way to make us feel welcome. From the accommodations to the amenities this property is a vrbo treasure. The owners exceeded our expectations in every way."
Historic home in the heart of Main Street- walkable to shops and restaurants
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
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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!
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 CA $354
CA $768 total
includes taxes & fees
May 19 - May 20
Thunder Hill Retreat - Peaceful - sleeps 12
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
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (18)
"Was very warm and cozy home and right on the water with beach you can easily access"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
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 CA $285
CA $414 total
includes taxes & fees
Jun 9 - Jun 10
Quarry Landing - Center of Town & River View - 3 Bedroom
Stunning waterfront villa with indoor pool and kids swing set and play area.
10.0 out of 10, Exceptional, (3)
"Great weekend with friends in this beautiful home. Plenty of space for the 14 of us. Indoor pool/bar area was the perfect space for us to hang out together."
Stunning waterfront villa with indoor pool and kids swing set and play area.
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
10.0 out of 10, Exceptional, (3)
"Lark’s Nest was a cute little place! Very clean! The view from the patio was stunning, and if you’re a bird lover you will be in your glory! Bring your binoculars and sit on the deck and wait! House was well equipped with most everything you would need! Host was very quick to write back when asked a question! First time in this area and hopefully be back again in the future!"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Private townhouse near downtown and state park
10.0 out of 10, Exceptional, (3)
"Property was extremely clean!"
The price is CA $244
CA $472 total
includes taxes & fees
May 16 - May 17
Private townhouse near downtown and state park
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (89)
"Our Family decided to take a last minute Spring Break trip and had a fantastic time. Matt was a great host and easy to communicate with. We were pleasantly surprised by all of the local dining options. Despite terrible weather that we experienced, we made the best of our trip and had a great time."
Waterfront house with amazing views. Top of the Chesapeake
Private Carriage House Retreat on a 33 Acre Historic Working Estate
10.0 out of 10, Exceptional, (8)
"It was me, my son and my sister staying. The grounds were beautiful, and we fed the goats too! It was late season, so no pool or any relaxing outdoors. Brrr. Traffic is light in the area so it was easy to get in a 2+ mile walk and see the local neighborhoods. As it was mentioned in the listing (but not obvious in the photos), you have to walk through the bunk room to get to the master bedroom, and the door to the upstairs bath doesn't offer total privacy. No place is perfect, and we would...
Private Carriage House Retreat on a 33 Acre Historic Working Estate
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
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.
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.
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
Two-story condo in luxury townhouse. Free parking.
9.8 out of 10, Exceptional, (8)
"The property was beautiful and the host was helpful"
The price is CA $328
CA $513 total
includes taxes & fees
May 19 - May 20
Two-story condo in luxury townhouse. Free parking.
A cottage on the shore of the Delaware River
9.8 out of 10, Exceptional, (54)
"Although weather was unsettled there was still much to do. Home clean and safe."
A cottage on the shore of the Delaware River
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
9.8 out of 10, Exceptional, (34)
"Great view awesome living space and easy access. Thank you."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
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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

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 CA $167
CA $185 total
includes taxes & fees
May 19 - May 20
Holiday Inn Express And Suites Middletown, an IHG Hotel
Fairfield Inn & Suites by Marriott Middletown
2.5 star property
9.2 out of 10, Wonderful, (102)
"."
The price is CA $146
CA $162 total
includes taxes & fees
May 29 - May 30
Fairfield Inn & Suites by Marriott Middletown
Hampton Inn Middletown
2.5 star property
8.8 out of 10, Excellent, (677)
"Great"
The price is CA $172
CA $191 total
includes taxes & fees
May 30 - May 31
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.