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Vacation rentals in Essex

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Top-rated vacation rentals in Essex

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

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Guest favorite
A cozy sleeping area is featured, with a comfortable bed dressed in a plaid blanket. Soft lighting from two bedside lamps creates a warm glow. Artwork hangs above the headboard, adding a touch of modern design to the space.
Apartment in Dundalk
4.91 out of 5 average rating, 138 reviews

Modern Independent Private Apartment#1 And Parking

Kick back and relax in this calm, stylish space. You will be close to everything when you stay at this centrally-located home. But far enough from the hustle and bustle to enjoy some peaceful "you-time". Right off of the 695 beltway and Interstate 95..minutes away from the inner harbor of Baltimore City,20 minutes away from BWI airport,10 minutes away from Dundalk terminal port, lots of entertainment nearby movie theater, sports bars, restaurants malls, pools, zoo, bay area, state parks and more

Guest favorite
A sunroom features a yellow door leading outside, with a comfortable seating area adorned with floral patterns and yellow cushions. Lush greenery hangs from the ceiling and sits on various surfaces, creating a vibrant and fresh environment, illuminated by natural light from the nearby windows.
Home in Baltimore
4.95 out of 5 average rating, 207 reviews

RetroLux Guest Suite 20 min to Downtown Baltimore

Retro-Lux Suite has the feel of a luxurious separate apartment with all the necessities you may need during your stay; from a warm and cozy bedroom, a clean and airy bathroom, to an inviting bright living room/kitchenette combo well stocked for your needs. The icing on the cake is a fantastic zen-like sunroom to enjoy your morning coffee/tea, or a glass of wine in the evening. Best of all, it's on the first floor, easy to get in and out; you can't go wrong staying at this unique guest suite.

Top guest favorite
The single-story ranch home is set on a spacious lot adorned with a mix of grass and fallen leaves. Blue shutters frame the windows, and a welcoming front porch is furnished with several chairs. A two-car garage is visible to the left.
Home in Rock Hall
4.98 out of 5 average rating, 100 reviews

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

Top guest favorite
A charming cottage is nestled among lush trees, featuring a spacious yard of green grass. Ample sunlight filters through the leaves, casting playful shadows. The exterior showcases a combination of windows and porch areas, offering a welcoming appearance in a serene environment.
Cottage in Pasadena
4.97 out of 5 average rating, 187 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Top guest favorite
The exterior of a large, historic house is viewed from the river, surrounded by leafless trees and greenery. A deck is visible, along with a patio area featuring white chairs. The structure showcases multiple levels and a traditional architectural style.
Apartment in Chestertown
5 out of 5 average rating, 135 reviews

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

Top guest favorite
The living room features a high, wooden ceiling with large windows allowing natural light to fill the space. A comfortable arrangement of sofas and chairs offers ample seating, complemented by a stylish area rug. A modern fireplace adds warmth to the inviting design.
Home in Perry Hall
4.99 out of 5 average rating, 128 reviews

Gunpowder Retreat

Unwind and relax with friends & family at this peaceful mid-century modern home. Nestled along the Gunpowder Falls State Park you can enjoy long summer days lounging in the pool under a canopy of trees or take an adventure along the hiking trails easily accessible from the back yard. Although there is no reason to leave this oasis, shopping and restaurants are only a five-minute drive away. Enjoy the beauty of nature without giving up modern comforts in this 4 bedroom, 3 bath home.

Guest favorite
A wooden dock extends into a calm body of water, reflecting the blue sky and surrounding trees. The serene scene is framed by lush green foliage, enhancing the tranquil atmosphere of the creek.
Cabin in Worton
4.94 out of 5 average rating, 105 reviews

Cabin on the Creek ~ Kayaks and Fire Pit

Unwind in our cabin tucked away on a private lane mins from Chestertown. We are situated on 6.5 wooded acres, perched up on 100’ bluff overlooking Churn Creek, a tributary off the Chesapeake Bay. Idyllic water views framed by a canopy of oak trees. Enjoy nature as you relax outside by the fire pit or stroll down to the ‘point’ to take in wildlife, or take a kayak out to explore the creek and water fowl. Deer come up through the woods and are often spotted on the property.

Guest favorite
The living area features a spacious layout with large windows allowing natural light to fill the room. Two patterned armchairs are positioned around a central console with a television. A light fixture hangs from the ceiling, complementing the hardwood flooring and neutral wall colors.
Bungalow in Sparrows Point
4.94 out of 5 average rating, 155 reviews

Boatyard Bungalow, 6 beds; 2 Full Baths-Waterfront

The original schoolhouse for Edgemere that was built in 1898 and converted to a residential home/marina in the 1950s. With over 2,200 sq. ft., it's a perfect environment for wedding venue preparations, family and friend reunions. Please don't exceed maximum number of twelve (12) guests at any one time in the house, during the day; or ten (10) staying the night in the house. Additional Pirate & Mermaid Bath House on property will be available by end of May 2024.

Top guest favorite
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, 662 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 favorite
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, 172 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.

Guest favorite
Home in Dundalk
4.95 out of 5 average rating, 106 reviews

B’more Restful 3 Bedroom 2.5 Bath, Townhouse

🚫 IMPORTANT – PLEASE READ BEFORE BOOKING This is a quiet, residential property intended for registered guests only. We have a strict NO EVENTS, PARTIES, OR GATHERINGS policy. Enjoy a quiet, clean, and comfortable stay with easy access from the highway. Our space is well maintained, peaceful, and designed for a restful night’s sleep. Pet and child friendly. Perfect for travelers looking for convenience without sacrificing comfort or calm.

Top guest favorite
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.
Apartment in Essex
4.97 out of 5 average rating, 292 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.

Popular amenities for Essex vacation rentals

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