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Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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

Blue Heron Farm Waterfront Chalet
Farm stay · 6 guests · 4 beds · 2 baths

Blue Heron Farm Waterfront ChaletRelax and unwind at the Chalet on Blue Heron Farm, a waterfront rustic retreat on the upper reaches of the Chester River. Tucked away on a 126 acre fourth-generation organic farm, the River Chalet is a peaceful and private getaway situated just 15 minutes from historic Chestertown. This recently restored 3-bedroom, 2 bath home features a giant wrap-around deck overlooking the river and floor-to-ceiling windows with serene waterfront views.

Basement living space w/bedroom
SUPERHOST
Entire house · 3 guests · 2 beds · 1 bath

Basement living space w/bedroomWalk out basement with a separate entrance and patio area. Sleeps three total; King size bed in one room and twin bed in living area. 30" TV includes Comcast/Xfinity - you can log into your own streaming service, Netflix, etc. Free internet. The space includes a mini fridge, microwave, small sink, (it is not a full kitchen). Private bathroom. Washer and Dryer access is also included. We have two dogs who live upstairs with us. They like to wake up early, go outside, then eat their food.

Persimmon Pastures
SUPERHOST
Entire cottage · 5 guests · 3 beds · 1 bath

Persimmon PasturesA quiet country setting in North East MD....located on a 7 acre horse farm with easy access to I95. Enjoy all the serenity of the country yet close to the shopping, marinas, and within 50 mile access to Baltimore, Wilmington and Philadelphia. The property is also within 30 minutes of Fair Hill Natural Resources Area with 5,500+acres and 80+ miles of trails for hiking, biking, and horseback riding. Pets are allowed. A pet (dog/cat) fee of $10/night/pet will be requested.

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Popular amenities for Middletown vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Middletown

  1. Entire house
  2. Dover
The Honeycomb Hideout
SUPERHOST
  1. Private room
  2. Millington
Guest Suite in a Victorian on the Chester River
SUPERHOST
  1. Entire house
  2. Chestertown
Entire River Front Home - 4 Bedrooms 4.5 Baths
SUPERHOST
  1. Private room
  2. Newark
Partage: Pastor & wife open home near UD
  1. Entire house
  2. Elkton
Fair Hill Nature Retreat
SUPERHOST
  1. Entire guest suite
  2. Chesapeake City
Benson House on Bohemia Ave (Back Deck)
SUPERHOST
  1. Entire house
  2. North East
cooper/mitchell house
SUPERHOST
  1. Entire guest suite
  2. North East
The Cozy Studio of North East MD
SUPERHOST
  1. Entire cottage
  2. North East
Cottage Just Off North East's Main Street
SUPERHOST
  1. Entire house
  2. Chesapeake City
Summer Wedding, Winery season Chesapeake City MD
SUPERHOST
  1. Entire guesthouse
  2. Chesapeake City
High-End Cottage, Water View, Chesapeake City, MD
SUPERHOST
  1. Entire house
  2. Elkton
Serene Hideaway

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