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Holiday rentals in Essex

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Top-rated holiday rentals in Essex

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

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Top guest favourite
The historic brick building features a classic architectural style, with several evenly spaced windows and two prominent blue doors at the entrance. A pathway leads to the doorway, with a flag displayed on the left side. Lush greenery surrounds the property, creating a serene outdoor setting.
Flat in Monkton
4.95 out of 5 average rating, 185 reviews

The Fisherman's Lodge at the 1858 Monkton Hotel

Love the outdoors? Love to fish, hike, bike, kayak? All of the above? The Monkton Hotel is a registered landmark that sits on the NCR trail, which runs along the Gunpowder River, home for some of the best trout fly fishing in the country. This fully renovated apartment, themed the "Fisherman's Lodge", is on the second floor and has the latest amenities. Nothing in the area matches the charm, convenience and history. An electric bike store, tube rental and great cafe are all in the same building.

Top guest favourite
A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.
Cottage in Annapolis
4.96 out of 5 average rating, 456 reviews

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Top guest favourite
A wooden deck overlooks the Chesapeake Bay, furnished with lounge chairs and potted plants. Sturdy steps lead down to the water, where a lower deck and dock are visible. The scene captures a serene water view under a partly cloudy sky.
Cottage in Essex
5 out of 5 average rating, 53 reviews

The Little House of Rockaway Beach, Maryland

Unwind at this new home in a quiet, safe neighborhood on the Chesapeake Bay. Designed by the host, the house is decorated with a mix of vintage and new items lovingly chosen to create an eclectic coastal cottage. Four adults (no pets) will sleep comfortably on a queen bed and a sleep sofa w/queen mattress. The clean and modern kitchen is fully equipped. Enjoy water views from the attached deck or walk a short distance to the waterfront where a designated deck offers seating and water sport gear.

Top guest favourite
A wooden pier extends over calm waters, featuring three light blue adirondack chairs arranged for relaxation. Lush green trees line the shore, and various homes are visible in the background, contributing to a scenic view of the waterway.
Home in Essex
5 out of 5 average rating, 31 reviews

Sue Creek Waterfront Cottage

Kick back & relax on the water in a fully renovated private 2 story home w/ a dedicated pier located on Sue Creek on the Chesapeake Bay! Includes 2 master bedrooms each with a queen size bed and dedicated bathroom with large shower stall. Kitchen & Great room are fully equipped with all amenities for a comfortable stay. Outside includes a large patio with furniture and charcoal grill, a pier w/ 2 Kayaks & private parking area. Convenient to many water & land establishments! No Pets or smokin

Top guest favourite
Flat in Baltimore
4.98 out of 5 average rating, 521 reviews

Butchershill- Clean, Fireplace, King Bed, Parking!

My name is John S Marsiglia. Always clean, very comfortable new King Mattress, Warm & Cozy Fireplace, Self checkin , Historic 2207 E Baltimore St. Search online. 900 Sq Ft. 12 ft ceilings,Fully equipped kitchen/kitchenette,Coffee,Tea,Cream,Brita filtered water pitcher,50" 4K smart TV, streaming only, Free Netflix, Prime,top speed WiFi, surround sound, comfortable clean furniture, antiques, oriental rugs, workspace w/desk, modern beautiful bathroom, dual shower heads&seats, private full size W&D

Top guest favourite
Flat in Dundalk
4.98 out of 5 average rating, 50 reviews

Waterfront Romantic Studio

Unwind at our private studio getaway-featuring an updated kitchen & bathroom, and cozy sleeping area. Separate entrance for complete privacy. Step out onto the shared deck and take in stunning water views, perfect for your morning coffee or a relaxing evening drink enjoy the waterfront vibe. Make memories around the fire pit or explore nearby state parks with scenic hiking trails and beaches. Whether you’re here for a show, a convention, or just some sightseeing, only 20 minutes from Baltimore.

Guest favourite
The exterior of the home is framed by a colorful landscape of blooming azaleas in vibrant reds and pinks. A driveway leads up to the house, which is nestled among green trees, providing a serene and inviting ambiance.
Bungalow in Baltimore
4.97 out of 5 average rating, 285 reviews

Cozy Retreat Bungalow 20 min to downtown Baltimore

Welcome home! Whether you are in town for business or leisure, this home will meet your needs at a very competitive price, and we are only 20 minutes from downtown Baltimore. If you're looking for a clean, comfortable, airy, and memorable home for your trip, congratulations, you just found it! No more worries about finding parking, handling the noise from neighbors above or below you, or sharing the house with anybody else. The entire house is all yours to enjoy. You will enjoy your stay here!

Top guest favourite
A spacious living area features a large sectional sofa arranged around a central area rug. The open layout includes a kitchen with modern appliances visible in the background. Ambient lighting and ceiling fans enhance the room's comfort and functionality.
Flat in Sparrows Point
4.97 out of 5 average rating, 103 reviews

Safe, quiet neighborhood close to downtown!

Private, clean, spacious studio apartment in a safe, quiet community located on the Chesapeake Bay. Walk out the yard to a walking/bike path leading you to the North Point State Park. Bikes available upon request. *6-14 miles from most major hospitals and great for traveling professionals. *9 miles from Camden yards and M&T Bank to attend sports events. *12 miles from BWI airport. Will decorate for special occasions Free, convenient parking Hot tub

Top guest favourite
A serene riverfront scene features a reflecting water surface, with the sky painted in soft pinks and purples at sunset. Lush greenery borders the water's edge, and silhouettes of trees frame the tranquil landscape.
Guest suite in Pasadena
4.98 out of 5 average rating, 671 reviews

Sea Dreamer

Tranquil TIDAL, riverfront, split-level home. Rent the spacious lower level with 2 bedrooms, full custom kitchen, large living room (TVs, sleeper sofas, massage chair), dining/office space, and full bath with luxury shower. Includes soaps, towels, hairdryer. Kitchen equipped for cooking, includes full fridge. Patio with grill/fire-pit, lounging and kayaks. Convenient: 25 min to BWI, 45min to Annapolis, 60min to DC. Ideal for relaxing and exploring!

Guest favourite
A wooden dock extends into a body of water, framed by vibrant colors of an evening sunset. Shades of orange, pink, and purple blend across the sky, reflecting on the water's surface, creating a serene atmosphere.
Farm stay in Essex
4.94 out of 5 average rating, 174 reviews

Studio Apartment at historic Walnut Grove

Apartment in the wing of the historic Walnut Grove farmhouse with its own central heating and cooling and spa tub. Our farmette has 10 free range hens outside your window, and pets. Beautiful sunsets, bald eagles, osprey, and water fowl viewed from the dock across the street. Close to Baltimore and 5 miles from 95. Local dining, shopping, parks, and golf course, tennis court at the school. No smoking , vaping or pot allowed inside or outside.

Top guest favourite
A serene view showcases the landscaped yard, featuring blooming pink flower clusters in the foreground. A large tree stands in the center with a backdrop of greenery and a peaceful waterway. The two nearby structures are connected by a deck, reflecting the tranquil surroundings.
Flat in Essex
4.97 out of 5 average rating, 304 reviews

A unique place on sue creek

Enjoy your private apartment and deck on the water or come sit down by the waterfront and watch the Ospreys, herons, ducks and the occasional eagle. Fishing off the pier and possible small boat docking available. We are close to Rocky Point golf club, Baltimore yacht club, 20 minutes from Camden Yards and M&T stadium. We are 38 minutes from BWI. You will have private parking in a quiet safe neighborhood. Sorry, no pets allowed.

Guest favourite
The exterior of the waterfront home showcases a spacious wooden deck with a ramp leading to double glass doors. The structure is framed by large windows, and the surrounding greenery adds a natural touch to the entryway.
Home in Essex
4.88 out of 5 average rating, 91 reviews

Waterfront getaway Essex, MD

Take it easy at this unique and tranquil getaway. 2 Bedroom, 1 Bath recently renovated Waterfront home in Essex, MD. Modern and fully equipped Kitchen, dining room, and living room. Cozzy bedrooms, High-speed internet & WIFI, 77” smart TV. Outdoor gas grill. Washer and dryer available. Ample parking space. Over 100 feet of Waterfront will allow you to fish, crab, paddleboard, kayak, and enjoy the waterfront dream.

Popular amenities for Essex holiday rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Baltimore County
  5. Essex