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Vacation Homes in Essex

Our top choices for Essex vacation homes

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (32)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Affordable Luxury Town Home in Federal Hill Baltimore.

9.4 out of 10, Exceptional, (56)
"Home was in a great location convenient to many restaurants and bars. Listing stated they had a grill but unfortunately did not. There was a fire pit in the back yard but no propane tank so we couldn’t use it. Parking was a challenge every night we came back from the family we were there visiting. House is decorated nicely but living room furniture was super uncomfortable but beds were very comfortable."
Affordable Luxury Town Home in Federal Hill Baltimore.

Rooftop Deck Escape! Free Parking!

8.6 out of 10, Excellent, (30)
"Fun family stay"
$245 nightly
The price is $283
Aug 25 - Aug 26
Total with taxes and fees
Rooftop Deck Escape! Free Parking!

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.4 out of 10, Exceptional, (34)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA

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

10.0 out of 10, Exceptional, (229)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

1 Mi to Dtwn: Townhome w/ Patio in Baltimore!

8.8 out of 10, Excellent, (9)
"This place was very beautiful and I really enjoyed my stay. When they said first come, first serve for parking it was definitely true. For anyone who doesn’t know the area (like my family) there’s barely parking available as none of the cars moved the entire weekend. Once we found parking we spent a lot using the Lyft app to move around, if not we would not have found parking for blocks upon returning from some of the planned destinations of our trip. Other than that the stay really was...
1 Mi to Dtwn: Townhome w/ Patio in Baltimore!

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (73)
"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Affordable Furnished LuxuryTownhouse near Stadiums In Baltimore Pig Town.

9.0 out of 10, Wonderful, (31)
"Nice place close to everything neighborhood decent for Baltimore. Would stay here with my family "
Affordable Furnished LuxuryTownhouse near Stadiums In Baltimore Pig Town.

Large 2 bedroom house with private parking in a nice neighborhood

9.6 out of 10, Exceptional, (26)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
$333 nightly
The price is $380
Aug 24 - Aug 25
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood

Charming Baltimore Townhome w/ Scenic Views

9.4 out of 10, Exceptional, (8)
"Great neighborhood! Lots to walk to, friendly people everywhere!"
Charming Baltimore Townhome w/ Scenic Views

Luxury Federal Hill Home w/Rooftop & 4 Parking Spots

9.6 out of 10, Exceptional, (23)
"Last minute family trip to Baltimore. House was perfect for our family. Location was great, walking diatance to camden Yards for a baseball game (25 minutes) and to the Inner Harbor (15 minutes). Awesome rooftop deck woth panoramic views of downtown that we didnt take advantage of enough. Thanks for letting us stay!"
$523 nightly
The price is $604
Aug 28 - Aug 29
Total with taxes and fees
Luxury Federal Hill Home w/Rooftop & 4 Parking Spots

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (30)
"Exactly what we expected. What wasn’t expected is how quiet and serene that entire town is. "
Entire Townhouse in Rock Hall

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (27)
"It was great!"
Charming Historic Townhouse Steps From USNA

Cozy Baltimore Townhome

9.6 out of 10, Exceptional, (14)
"Great Place"
$268 nightly
The price is $309
Aug 27 - Aug 28
Total with taxes and fees
Cozy Baltimore Townhome

Large Home with Pool & 7 bedrooms; sleeps 21

9.8 out of 10, Exceptional, (24)
"We did a guys golf trip hitting courses around both Baltimore and Washington DC. We didn’t spend much time at the property but plenty of rooms and beds and perfect to get a few families together and meet up for a vacation"
$847 nightly
The price is $970
Sep 2 - Sep 3
Total with taxes and fees
Large Home with Pool & 7 bedrooms; sleeps 21

Orioles, Ravens, Baltimore Inner Harbor, Towson

8.8 out of 10, Excellent, (9)
"very comfortable home, extra plus with an xbox included!"
Orioles, Ravens, Baltimore Inner Harbor, Towson

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (38)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.

Luxury Waterfront Executive Family Home Annapolis with All Amenities

10.0 out of 10, Exceptional, (2)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Waterfront Annapolis Home: Fire Pit & Fishing Pier

9.2 out of 10, Wonderful, (37)
"Great location"
Waterfront Annapolis Home: Fire Pit & Fishing Pier

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (6)
"The property is everything it claims to be & more. Awesome location on the bay. Great accommodations. So peaceful. We had a wonderful time. Would highly recommend! "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
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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Top Essex Hotel Reviews