5 star hotels in Middletown, DE

1. Ship Watch Inn

  • Address: 401 1st St, Chesapeake City, MD 21915
  • Phone: (410) 885-5300
  • Ratings: 4.6 (114 reviews) Excellent
  • Website : Ship Watch Inn
  • Check-in time: 2:00 PM
  • Check-out time: 11:00 AM
  • Quick Summary: Quaint waterfront B&B with balconies & canal views, plus gourmet breakfast & an outdoor hot tub.

About this hotel

Overlooking Back Creek, this romantic waterfront B&B is 8 miles from Lums Pond State Park and 7 miles from Elk Forest Wildlife Management Area.Elegant rooms are furnished with antiques in a traditional style and come with private bathrooms (some with whirlpool tubs), hardwood floors, and shared balconies with canal views, as well as minifridges, ceiling fans, cable TV and free Wi-Fi.Gourmet breakfast is served either in the dining room or on the waterside deck. Other amenities include an outdoor hot tub, and complimentary drinks and baked goods.

Things You Need to Know

  • 13 min walk to C & D Canal Museum
  • Guests praised the service
  • Guests mentioned “canals” 15 times
  • Guests liked “a deck”, mentioned 10 times in reviews
  • Guests praised the breakfast
  • One of the few hotels in the area with a hot tub

Feedback From Real Customers

Nichole Marie Perry

My husband and I came for a few days and it was Amazing! We parked the car and it never moved We walked around the town, shopping and very nice restaurants The Inn was beautiful inside, the room was so clean and nicely decorated, and we loved the breakfast

An abundant amount of delicious foods The innkeepers were kind, friendly, and extremely hospitable! Having the deck right on the canal was a wonderful surprise Thank you Ship Watch Inn for a wonderful few days We will be back for sure

Tori Falkenstein

I cannot say enough good things about the Ship Watch Inn We booked the entire Inn for our wedding weekend All the rooms have been updated and look like something out of a magazine

The staff were very friendly and went above and beyond for us The views from each room are absolutely stunning Breakfast was provided to us every morning and it was delicious The Inn is definitely worth booking for whatever occasion you have coming up We absolutely loved our experience and will be booking many more stays in the future

Anthony R

I was a little put back by the word innThis place was clean, spacious and had amazing scenery you really donsee ships passing by)

They baked cookies or muffins everyday They gave tips on what they enjoyed doing in the area A local family with experience of how to truly host The area and scenery was amazing Only 1 hour from Philly so a must do

2. Crow Vineyard & Winery

About this hotel

Set on 365 acres of land, this family owned farm and bed-and-breakfast is 6.7 miles from Turner Creek Park and 30.6 miles from Bombay Hook National Wildlife Refuge.Rustic rooms in a 1847 farmhouse are furnished with family heirlooms and offer views of the pasture, vineyard or barn. A 2-bedroom cottage adds a full kitchen, a sitting room and a laundry room.Amenities in the farmhouse include free hot breakfast featuring regional fare, plus a common living area; continental breakfast is an option for cottage guests. There’s a pond, multiple vineyards and a wine tasting room. Picnic meals and in-room massage services are available upon request (fee).

Things You Need to Know

  • 9 min drive to Hopkins Game Farm
  • Guests praised the service
  • Guests praised the bar

Feedback From Real Customers

Denise Howell

We came here as a Harvest Host stop on our way down south It’s a beautiful setting on a working farm and winery The wines are excellent and you can sample 3 – 5 different ones in 3 different flights

My favorite was the Chocolate Pairing Flight, with 4 different chocolates and 3 different wineswe ended up getting a bottle of one them to go! Plus another! This is a great stop for the wine enthusiast I highly recommend this place!

3. Inn at the Canal (3-star hotel)

  • Address: 104 Bohemia Ave, Chesapeake City, MD 21915
  • Phone: (410) 885-5995
  • Ratings: 4.8 (88 reviews) Excellent
  • Website : Inn at the Canal
  • Check-in time: 3:00 PM
  • Check-out time: 11:00 AM
  • Quick Summary: 19th-century inn with antiques-filled private-bath rooms, water views & gourmet breakfast.

About this hotel

This 19th-century waterfront B&B sits between the Chesapeake and Delaware Canal and Ferryslip Road Park. Elk Neck State Forest is 16.9 miles away.Quaint rooms have antiques including 4-poster beds, water views and are furnished in a Victorian style. All come with private baths (some with soaking tubs), cable TV, DVD players and free WiFi. There’s a 3-room suite that comes with a kitchenette, a private balcony and a fireplace.Guests are served gourmet breakfasts, and meeting rooms can be arranged.

Things You Need to Know

  • One of the few hotels in the area with air conditioning
  • The rooms have kitchenettes and minibars
  • 12 min walk to C & D Canal Museum
  • Guests mentioned “rum” 12 times
  • The hotel has breakfast
  • The hotel has a boutique store
  • The hotel has Wi-Fi

Feedback From Real Customers

Jennifer Stowell

A lot of positive to say about this lovely place; It’s decorated nicely; bed comfortable; upbeat, helpful service team all around at the ready to accomodate your every need Loved the backyard vibes with the food and beverage availability; beautiful all around; great location near unique shopping and water views; i strolled around and loved every minute

Bryan Schoell

Have never stayed overnight as a guest, but have patronized their bar numerous times The staff is friendly and very good at what they do The drinks are great, the food is amazing and they update the menu every few weeks

The owners are warm and welcoming, very interactive with guests and even pitch in helping the staff with anything from bussing tables, to serving drinks and food Overall, one of my favorite places I have ever been Love this establishment

4. Sutton Inn (1-star hotel)

  • Address: 405 E Pulaski Hwy, Elkton, MD 21921
  • Phone: (410) 398-3830
  • Ratings: 4.4 (90 reviews) Very good
  • Website : Sutton Inn
  • Check-in time: 2:00 PM
  • Check-out time: 12:00 PM
  • Quick Summary: Unfussy rooms & suites in a 1950s low-rise lodging with free cooked breakfast, WiFi & parking.

About this hotel

Set in a 1950s low-rise building just off Highway 40, this family-run lodging is a 10-minute walk from the Big Elk Mall Shopping Center, 1.4 miles from downtown Elkton and 7.2 miles from Lums Pond State Park.The simply furnished rooms have free WiFi and cable TV; some also include microwaves and minifridges. Suites sleep up to 4 and add extra living space.A complimentary cooked breakfast is served in the functional dining room, and there’s also free parking.

Things You Need to Know

  • Guests praised the clean rooms, which have kitchenettes
  • Guests praised the bathrooms
  • 10 min drive to Iron Hill Park
  • Guests praised the service

Feedback From Real Customers

Lee Carver

We just stayed at the Sutton Inn for 9 nights We were suppose to stay 3 originally and since location was centered between my family we stayed the entire trip Room was always clean, Chuck and his daughter were very friendly and accommodating and the bed and pillows were the best we have ever had in a hotel

We will stay there again if in the area

5. Relax Inn Smyrna (2-star hotel)

About this hotel

Sitting in a south Smyrna retail area at the junction of US Highway 13 and Korean War Veterans Memorial Hwy, this basic hotel is 8 minutes’ drive from Delaware Technical Community College plus 14 minutes’ drive from downtown Dover and Dover Air Force Base.Standard rooms offer air-conditioning, flat-screen with cable channels and free WiFi, as well as minifridges and microwaves.Free off-street parking is provided.

Things You Need to Know

  • The rooms have refrigerators
  • 4 min drive to Big Oak County Park
  • Guests praised the service, which has a concierge

Feedback From Real Customers

Amarjit Kumari

Great location in terms of distance to Dover and the local universities Grocery stores and coffee shops within walking distance There is a new drive-thru Starbucks being built very close by so you don’t have to drive to Dover! Shopping complexes are within a 15 minute drive

Rooms are exceptionally clean and great customer service! Free parking onsite!

BabyGirlJSH0321 Halter

The manager and his family are great people and are always friendly and polite I stay at the Relax Inn quite a bit, the rooms are always clean and I’ve never had a problem getting clean linens or towels when I need them Also, the rates are very reasonable

The only thing that they should change is check-out time, instead of 10:00 AM it should be 11:00 AM like all other motels12/5/17 I stayed here lastnight and it was very quiet and cozy, the bed was so comfortable that as soon as I laid down on it I was ready to go to sleep and it was only 3:30 in the afternoon, instead of going to sleep I took a walk to the shopping center next door and got myself dinner and also went to the Dollar Store over there and got some things I had forgotten to bring for the shower, once I ate my dinner and showered I gave in to that big, comfy bed and slept like a baby all night! The Relax Inn is the best you will find in the area and don’t let the looks from the outside fool youthe rooms have been remodeled and are really nice inside!

6. Motel 6 Elkton, MD (2-star hotel)

  • Address: 223 Belle Hill Rd, Elkton, MD 21921
  • Phone: (410) 392-5020
  • Ratings: 3.2 (1142 reviews) Fair
  • Website : Motel 6 Elkton, MD
  • Check-in time: 3:00 PM
  • Check-out time: 11:00 AM
  • Quick Summary: Straightforward budget property offering modern rooms with cable TV & free morning coffee.

About this hotel

Located just off Interstate 95, this unpretentious budget lodging is 2.9 miles from Elkton’s main street and 4.2 miles from the University of Delaware.The modern rooms include flat-screen TVs with expanded cable channels, plus wood floors, granite countertops and WiFi (fee). Kids 17 and under stay free with an adult family member.Free morning coffee is also available.

Things You Need to Know

  • 6 min drive to Milburn Orchards
  • Guests liked the service
  • Some guests complained about the unclean bathrooms

Feedback From Real Customers

Michael Mayer

Very easy location from the highway and convenient to travel services The low cost is justified Front desk staff was very nice

The room needs dedicated cleaning and rehab Broken locks, broken TV stand bolted to the table, box springs that are heavily damaged No bed bugs detectedThe parking lot is WELL illuminated at night


The Good: Decent location, quite, dog friendly, easy check-in/out, room was fairly cleanThe Bad: I question the cleanliness of the tub, bathroom floor was wavy (most likely not properly installed and water damaged), the grass was quite long, no shampoo/conditioner (I bring my own anyway), room was smaller than other hotels of this price range, AC could have been a little cooler, no fridge/microwave, bed may not be the best option if you need support, you may or may not be able to park in font of your room Oh, and watch your car getting out of the parking lot

it’s a bit steepSummary: If you’re looking for a 5 star hotel at a one star price, this is not it If you’re not too picky and need a place to stay for a night or two that won’t hurt your wallet, well, here you go

Jona Rodriguez

Dead bugs everywhere, looked like the floor hasn’t been swept in days The bathroom door was broken so bad we couldn’t shut it to use it Huge blood stain next to were we rest our head! The spring mattress was so uncomfortable, couldn’t even sleep

The thinnest blanket in the world to cover up We were freezing! Never going back again Do better people!

7. The Inn at Salem Country Club

About this hotel

91 Salem Country Club Rd, Salem, NJ 08079(609) 420-8190

Things You Need to Know

  • 7 min drive to Salem County Historical Society
  • Guests liked the service
  • Guests mentioned rooms 11 times
  • Guests mentioned “the sunset” 13 times

Feedback From Real Customers

Dana Melton

I was lucky enough to get to stay at the Inn and meet the owner and her staff this weekend – and I can’t express how welcoming they were They made what can be such a stressful time so much easier than we ever expected – and what’s more, they made sure our Bride enjoyed her entire weekendTop marks on quality service and quality people


John Ensslen

Uniquely different The food was catered by Restruate in Penns Grove,NJI was 300th Church Anniversary celebration I haven’t seen these folks in yearsI very thankful to meet with them Plus it has been at least 23 years since I haven’t been in this place which was High School class Reunion

I did not stay overnight It was just gathering It was wonderousIt great host

Reta Rios

Beautiful venue Private and intimate setting No other weddings and no other people coming on and off grounds

We got married under their tree and started our ceremony and took pictures in their garden area then moved the party to their deck where our guests enjoyed the beautiful sunset while we took more pictures Yvonne the owner is fantastic at working with you and getting you organized before the big day Be sure to hire Caroline as your wedding planner because she helped us find vendors and set up our ceremony and the venue better than how I envisioned it Highly recommended!!

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