Photo by Elizabeth Csanady

Holiday Homes in Essex

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Featured Holiday Homes in Essex

⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

9.6 out of 10, Exceptional, (21)
"Couldn't ask for a better location for walking to The Bank. Parking pass good on game days. Had no problem parking right out front. Excellent communication with host and house was very nicely appointed! Stairs wider and safer than most in Pigtown"
⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

Rooftop Deck Escape! Free Parking!

8.8 out of 10, Excellent, (26)
"Overall place was great and was in perfect location for our family trip to a ravens game. However we were looking forward to the fire pit on the roof but there was no full propane tanks. There was multiple empty propane tank"
The price is AU$431
includes taxes & fees
23 Feb - 24 Feb
Rooftop Deck Escape! Free Parking!

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (206)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Freshly renovated 3-story home 1 block from USNA!

10.0 out of 10, Exceptional, (29)
"Best property we’ve stayed at in Annapolis by far. We look forward to our next stay. The property was spacious, well stocked, cozy and full of beautiful light! Central location to everything you need. Friendly neighborhood and great location. "
The price is AU$1,019
includes taxes & fees
23 Feb - 24 Feb
Freshly renovated 3-story home 1 block from USNA!

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

10.0 out of 10, Exceptional, (73)
"Heron house was perfect for our family weekend getaway. Doug and Kris are great hosts and made our stay as easy as could be! "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (4)
"An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!"
Pet-Friendly Home on Chester River w/ Dock!

Walk to Lake & Boat Ramp: Central Gem in Annapolis

Walk to Lake & Boat Ramp: Central Gem in Annapolis

Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning

3.0 star property
Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning

Luxury Federal Hill Home w/Rooftop & 4 Parking Spots

9.4 out of 10, Exceptional, (12)
"Clean, comfortable home with lovely rooftop patio! "
The price is AU$617
includes taxes & fees
6 Mar - 7 Mar
Luxury Federal Hill Home w/Rooftop & 4 Parking Spots

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

10.0 out of 10, Exceptional, (14)
"This property from website fit the beds and bathrooms we needed so everyone got their own bed. When we opened the front door it was better looking in person than on web.Would absolutely recommend this place and we will definitely be back."
The price is AU$560
includes taxes & fees
20 Mar - 21 Mar
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Charming Home: Parking, Sleeps 10, WFH Space

2.0 star property
10.0 out of 10, Exceptional, (2)
"A friend and I stayed for 3 nights and really enjoyed our time. The communication from the property management was prompt and the row house was spacious and well equipped. With only 2 adults we had more than enough room. We could have comfortably had 6 adults children. The location was great for us. Easy walks to the two stadiums, the casino, and 3 breweries (Wico, Checkerspot, and Pickett). Also, a short walk to the Philly Hoagie Factory. Excellent Cheese steaks and other sandwiches made by a...
Charming Home: Parking, Sleeps 10, WFH Space

Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite

House on the Gwynns Falls

8.6 out of 10, Excellent, (10)
"Mary was a very gracious host and very accommodating when we added a 6th person at the last minute. She was always very responsive when I messaged her and greeted us with a warm welcome when we arrived. The house is a beautiful historic home tucked away in quiet neighborhood "
The price is AU$353
includes taxes & fees
27 Feb - 28 Feb
House on the Gwynns Falls

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Welcome to the Charm City Getaway!

9.4 out of 10, Exceptional, (3)
"We had a pleasant stay in Mr. Farrow’s home. It’s spacious, clean, and felt like home. Doc made sure we had everything we needed. We barely noticed that he was sharing his home with us. He was very accommodating to our needs and responded to us within a reasonable time. We would definitely stay here again."
The price is AU$661
includes taxes & fees
23 Feb - 24 Feb
Welcome to the Charm City Getaway!

Quirky Baltimore Townhome ~ 2 Mi to Inner Harbor

9.2 out of 10, Wonderful, (10)
"Outstanding rental in a great location. The place was clean and check-in/out was no issue. Will stay again!"
Quirky Baltimore Townhome ~ 2 Mi to Inner Harbor

Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View

8.8 out of 10, Excellent, (11)
"The location is spectacular with expansive views of the Chesapeake Bay and the Bay Bridge. The house itself is immaculate and had lots of space for our family. I would imagine it's even better in the summer when the pool is available.One caution: the playhouse is really cool but not a place to let younger kids play unsupervised."
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View

Big 3 story house near stadiums, aquarium, museums, 5 bedrooms, parking

10.0 out of 10, Exceptional, (6)
"This was one of my favorite stays. The house is gorgeous, location is key, communication with the owner was impeccable. We will be coming back!"
The price is AU$939
includes taxes & fees
24 Feb - 25 Feb
Big 3 story house near stadiums, aquarium, museums, 5 bedrooms, parking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Essex

Fantastic 2 bedrooms apt. Harbor

4.0 star property
10.0 out of 10, Exceptional, (1)
"It was a nice place"
Fantastic 2 bedrooms apt. Harbor

Entire House 1BD King Bed near Downtown

2.0 star property
The price is AU$221
includes taxes & fees
23 Feb - 24 Feb
Entire House 1BD King Bed near Downtown

'At Fells Point' CitySide - 'Tons better than a hotel!'

9.8 out of 10, Exceptional, (185)
"The property is compact but cute. They have a door that slides across doorway between the bedroom and the living room that blocks noise from the outside. We did find the property chilly but when we contacted the owner, he had one of his staff come over, wait a few minutes for us outside, and provide us with space heaters that warmed the place up very effectively and quietly. We felt valued and cared for. I highly recommend this cozy little place and the people who manage it!"
The price is AU$323
includes taxes & fees
25 Feb - 26 Feb
'At Fells Point' CitySide - 'Tons better than a hotel!'
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.