
Family-friendly holiday rentals in Essex
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Top-rated family-friendly rentals in Essex
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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.

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.

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

Cozy, clean & spacious lower level of a new home
This is a spacious lower level of a newly built home. This private guest area has a lounge, dinning, and kitchenette in addition to a bedroom and a bathroom. Guests share only the main entrance of the townhouse with owners who live upstairs. This private decorated space includes a smart TV, comfortable seating, dining for 4, microwave, coffee maker, full refrigerator, toaster/air fryer, queen bed, wardrobe & dresser. Washer/dryer available upon request. Please review house rules before booking

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

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.

Scenic, private 2 room-guest suite, near Bel Air
Relax and enjoy the scenic view of the countryside in this spacious (3 room) guest suite. The sunset is gorgeous! Spend the weekend enjoying the local activities: Dance under the stars at Boordy Vineyard Taste the craft beers at local breweries Hiking at Rocks State Park Biking nearby at the old railroad trail Explore the shops and restaurants on Main Street in historic Bel Air Spend a work trip in this peaceful, quiet space, located close to Aberdeen Proving Grounds, Peach Bottom Plant.

Basement Guest Suite & Retreat - Waltherson
Enjoy historic Waltherson! A 15-minute drive to downtown Baltimore. Within walking distance of Walther Gardens, the neighborhood nursery, gift shop, and famous snowball stand. Fully furnished basement suite with queen cabinet bed, living room, bathroom, cable TV, Netflix, wifi, basic dishes/utensils, HVAC, and laundry room. The area has a mini fridge, microwave, coffee pot, kuerig, tea kettle, and bottled water. There is no cook top/stove or kitchen sink. Keyless entry. No smoking in unit.

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.

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.

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

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.
Popular amenities for Essex family-friendly rentals
Family-friendly home rentals with a hot tub

Beautiful, quiet waterfront house. Lots of room!

Cozy 3-bedroom home w/ Hot tub & firepit

Chesapeake Bay View 3BR/2BA Duplex*HOT TUB*

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Coastal Comfort Retreat near Annapolis, EV charger

Long Beach Cottage, Hot Tub, Beachfront

Gunpowder Retreat

Celebrate Summer In Your Private Pool & Hot Tub
Family- and pet-friendly home rentals

B’more Restful 3 Bedroom 2.5 Bath, Townhouse

Glen Burnie Escape

Fox Cottage *Pet Friendly*

Historic Hillside Cottage

Parkside Charm & Spaciousness-Family Friendly

Historic Gatehouse Master Suite

Cozy Waterfront Apartment Chester, MD

Stay in a Former Fells Point Bar! - Private Studio
Family-friendly home rentals with a pool

#2 Foggy Bottom/Georgetown Apartment

Rollingside: Two-Room Guest Suite

Annapolis Garden Suite

Luxury 4 Bedroom - Pool/HotTub/Fire Pit

A home away from home

Bright and Cozy 2nd floor apt

1st Floor Condo in Annapolis

Waterfront-View of Bay from your Bed
Destinations to explore
- Norfolk Holiday rentals
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Georgetown University
- Walter E Washington Convention Center
- The White House
- National Mall
- M&T Bank Stadium
- Nationals Park
- District Wharf
- Baltimore Convention Center
- National Museum of Natural History
- Capital One Arena
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Arlington National Cemetery
- Georgetown Waterfront Park
- Sandy Point State Park
- Howard University
- Betterton Beach
- Washington Monument
- National Harbor
- The Anthem
- Johns Hopkins University
- Patterson Park
- Smithsonian American Art Museum
- CFG Bank Arena





