Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

An outdoor seating area is set on a wooden deck, featuring a large table surrounded by light blue chairs. A fire pit is visible in the foreground, with lush greenery and a sandy beach in the background, along with the home and upper deck partially shown.

Home in Middle River

4.95 out of 5 average rating, 39 reviews

Waterfront Home with Private Beach, Stunning Views

EvanRating, 5 stars6 days ago

Great place, we had a family get together and we had a very peaceful weekend. There were so many places to hang out between the porches and dock-side area, big living room and huge dining room table. Very tranquil, I was thoroughly pleased with the home!

Guest favorite

A breathtaking sunrise is captured over calm waters, creating a stunning reflection of vibrant hues of orange, pink, and purple. The private pier is visible on the right, complementing the serene landscape of trees on the distant shore and a tranquil island in the background.

Cottage in Edgewater

4.99 out of 5 average rating, 153 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

IsabelRating, 5 stars3 weeks ago

Heather’s place is a little paradise on the water. Peaceful, quiet, and perfect for some real rest and relaxation. The house was exactly as described—spotless, all new, and super comfortable inside, with beautiful outdoor spaces to enjoy. Annapolis is just a short 25-minute drive away if you’re looking for great food and things to do. Communication with Heather was easy and fast. I’d come back anytime I’m in the area again!

Top guest favorite

A tranquil view of a sandy beach along a calm river, framed by green grass and gentle waves lapping at the shore. The scene is dotted with trees and overlooks a distant white house, creating a serene atmosphere.

Cottage in Charlestown

4.98 out of 5 average rating, 101 reviews

Blue on the Bay

AndrewRating, 5 stars6 days ago

We loved staying here. The location is beautiful and just a few doors down from the beach. The place was perfectly sized and clean. As a plus, Monica surprised us with a birthday bottle of wine and balloons as a gift. I highly recommend staying here!

Guest favorite

A new wood pier extends over still waters towards a green, tree-lined shore. The pier is flanked by posts, leading to a rocky bank, with a clear view of a nearby cottage among the trees. Sunshine reflects gently off the water.

Cottage in Pasadena

4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

JulieRating, 5 stars4 months ago

The place is wonderful. We were down for Thanksgiving with my family and were travelling with our 2 dogs, Wally & Dolly. The location was perfect, close to Riviera Beach where our Family Thanksgiving Dinner was, very private, no noise or distractions for the dogs (that was great). The property was surrounded by water on three sides, great views! It is right next to Ft. Smallwood Park where we took the dogs for walks every day, they loved it. As for the house it was perfect for us, just about the size of our home, so that made it very comfortable for us. All one level, which made it great for us older people. It was furnished with very comfortable furniture. Lots of information about the local surroundings, things to do, and restaurants. Keith was wonderful to work with, very easy to communicate with which made the whole process very easy for us. We even had a conversation over the phone once we were in the house to make sure everything was to our liking, and we were happy !

Top guest favorite

Place to stay in Annapolis

4.94 out of 5 average rating, 119 reviews

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

GregRating, 5 stars4 days ago

Very Peaceful neighborhood Pauls house is very close to the water end of the road with nearly no traffic when we were there. neighborhood is extremely walkable loved having the porch, large gas grill and hot tub next to the home with view of the bay. All 3 rooms had large comfortable beds. house was clean. well kept. There is a retail center about 2. 5 miles away with a GIant" Grocery store and a few doors down a quality wine and spirit shop. My family loved the city of Annapolis and Very Happy we chose to stay at Pauls home.

Guest favorite

Home in Annapolis

4.92 out of 5 average rating, 113 reviews

Historic Downtown House with Off Street Parking

JenniferRating, 5 stars1 month ago

Perfect location to go exploring. Beds were comfortably. Disappointed I couldn't use the parking space. I didn't realize there was a height requirement to ho through a Gate to get to the parking spot. Found a parking garage that was 8'5" and parked there for $25 a day. Plenty of towels and toilet paper.

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Popular amenities for Middletown vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Middletown's top sights

Texas Roadhouse11 locals recommend

Crooked Hammock Brewery8 locals recommend

Cantwell's Tavern6 locals recommend

Everett Theatre5 locals recommend

Westown Movies5 locals recommend

1861 Bar3 locals recommend

Other great vacation rentals in Middletown

Guest favorite

The kitchen is designed with modern white cabinetry and natural wood accents. New appliances include a refrigerator, stove, and dishwasher. A central island with seating is complemented by large windows, allowing ample natural light to brighten the space.

Home in Quarryville

4.96 out of 5 average rating, 56 reviews

Charming 3-Bed Single Level Cottage

Maria & DanRating, 5 stars1 month ago

Perfect for our family of 4. Spacious but cozy. Had everything we needed. Loved the quiet, relaxing location that was still close to family we were visiting. The fresh, individual carrot cakes on arrival was a wonderfully, delicious touch. Would definitely stay here again when we visit our PA family.

Superhost

A spacious living area features elegant armchairs in soft hues, accompanied by a round wooden coffee table. A traditional area rug adds texture, while large windows dressed in blue curtains allow natural light to fill the room. A fireplace and decorative furnishings enhance the atmosphere.

Home in Wye Mills

4.91 out of 5 average rating, 11 reviews

⇚Family Getaway⇛| Lakeside + A Nature View |

LisaRating, 5 stars11 months ago

Kevin is a great host to us year after year! we love staying at his place!

Superhost

A spacious living area features a large sectional sofa positioned around a coffee table, with a geometric area rug beneath. A flat-screen TV is mounted on the wall, and natural light streams in through large windows, enhancing the open layout that flows to the dining area.

Home in Pasadena

4.86 out of 5 average rating, 58 reviews

Beautiful Home Near Beach and Patapsco River

EvaRating, 5 stars3 weeks ago

This home is really nice! We stayed there because our daughter was getting married at a venue about 5 minutes away from the home. It was perfect! Plenty of space for our family and was great for the bridal party to get ready! Nice open floor plan. The beds a bedrooms were very large with comfortable beds. The home was well equipped. The outdoor area was nice and I’m sure the pool is nice in the summertime. Thank you for sharing your home with us on this very special occasion.

Superhost

A unique a-frame cabin is situated among tall trees, with a pathway leading up from a snow-covered ground. The clear blue sky provides a bright backdrop to the scene, enhancing the rustic charm of the cabin and surrounding landscape.

Cabin in Airville

4.92 out of 5 average rating, 12 reviews

AFrame Cabin at Mill Creek

KathrynRating, 5 stars8 months ago

We had a fantistic time getting away at Kelly's A-Frame. Beautiful surroundings, and a rustic lot were just what we needed for a retreat. Thanks for a great stay!

Guest favorite

A modern kitchen features a central island with bar seating for three. Light fixtures illuminate the space, highlighting white cabinets and stainless steel appliances. A countertop with a subtle pattern complements the tiled floor, while decorative items are arranged on the island.

Townhouse in Elkton

4.92 out of 5 average rating, 61 reviews

Bright and airy townhome with outdoor seating

JaredRating, 5 stars2 months ago

Cozy stay - passed through for work and was able to recharge by staying here. Carrie was responsive and the place was super comfy. Would definitely stay here again next time I’m in Newark.

Superhost

A spacious, modern home is nestled amidst lush greenery, featuring a combination of outdoor patios and terraces. Trees and well-maintained shrubs surround the property, with a gentle slope leading to a vibrant green lawn, offering a serene and inviting atmosphere.

Home in Queenstown

5 out of 5 average rating, 9 reviews

The Perfect Waterfront Escape!

AnnRating, 5 stars4 months ago

As others have said, beautiful and spacious house with stunning views on the water! The house was clean, kitchen filled with all the tools for cooking (even things like wax paper, aluminum foil, all the spices you could think of, etc.), and we loved the ping pong table in the garage. The grounds were super peaceful and fun to walk around. We came in November so the pool was covered, but it was great to go out on the dock and kayak on the water. Not sure if it was the cold or not, but on some of the doors, the deadbolt was a little sticky and difficult to turn, so we just avoided these doors throughout our stay. We would love to come back in the summer time/when the weather is warmer to enjoy the pool! Also very much appreciated that we could bring our dog.

Superhost

Home in Stevensville

4.96 out of 5 average rating, 84 reviews

Kent Island Beach House II by the Kentmorr Marina

GregRating, 5 stars10 months ago

Great place! Really cool location that makes you feel part of this unique community. We were in town for a family wedding and it was perfect. Our host Donna was exceptional (and friendly). We need to find a reason to go back soon!

Superhost