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Compare 534 Vacation Homes in Essex with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Canton’s Finest Luxury Stay: Walk to Park, Bars!

9.8 out of 10, Exceptional, (11)
"Really great location, the park nearby was great, especially for our dog. The kitchen and bathrooms were not as clean as expected, but linens were clean. Overall, very nice apartment and would stay here again."
The price is AED 400
AED 1,032 total
includes taxes & fees
25 Nov - 26 Nov
Canton’s Finest Luxury Stay: Walk to Park, Bars!

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

House on the Gwynns Falls

10.0 out of 10, Exceptional, (4)
"Mary's home is lovely! She is welcoming and kind and the check-in process is simple. I would stay at the home in the future."
The price is AED 621
AED 802 total
includes taxes & fees
25 Nov - 26 Nov
House on the Gwynns Falls

Modern Farmhouse 3Br/3.5Bth Home ☆☆Close to Johns Hopkins University &Downtown☆☆

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great thank you "
Modern Farmhouse 3Br/3.5Bth Home ☆☆Close to Johns Hopkins University &Downtown☆☆

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

10.0 out of 10, Exceptional, (20)
"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Luxurious, Inner Harbor Federal Hill Townhome

9.0 out of 10, Wonderful, (18)
"Fantastic location convenient for walking to stadiums, inner harbor, and many restaurants. Owner was friendly and very responsive, and house was just as described. Would definitely consider staying here again!"
The price is AED 856
AED 1,727 total
includes taxes & fees
24 Nov - 25 Nov
Luxurious, Inner Harbor Federal Hill Townhome

Charming garden row home, easy 4 block walk to the heart of Annapolis.

10.0 out of 10, Exceptional, (108)
"We have stayed at this property multiple times since we have a son at the Naval Academy. This place is beautiful, well appointed and comfortable. The hosts are very responsive and they go out of their way to make their guests feel extra special- we will be back. "
Charming garden row home, easy 4 block walk to the heart of Annapolis.

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

10.0 out of 10, Exceptional, (71)
"House is exceptionally clean. Hosts are very responsive to questions. House is very well supplied and convenient to most of Annapolis. House is as advertised. "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (20)
"We had the best time at this rental — it was accessible, cozy, stocked with things like good toilet paper (silly, but we noticed and appreciated!), and in an amazing location! Absolutely recommend! "
Charming Historic Townhouse Steps From USNA

Idyllic Pasadena Retreat with Garden + Hot Tub!

9.8 out of 10, Exceptional, (21)
"This place was a wonderful little getaway for my partner and I! It's even more lovely than in the photos! Spacious and very comfortable and cozy. Immaculately clean and well stocked with the essentials. The king bed was very very comfy. The hot tub was amazing and super relaxing! The patio is beautiful and the fountain in the back yard is adorable and added a lovely bit of scenery and ambiance as well. It's also in a great location, just a couple minutes away from anything you might need, like...
Idyllic Pasadena Retreat with Garden + Hot Tub!

Fox Cottage *Pet Friendly*

10.0 out of 10, Exceptional, (32)
"Great stay at this property. Comfortable bed and couch and great shower. Nearby to Baltimore and Columbia. The dogs loved staying here. The host was super responsive and flexible with our stay. Would stay here again!"
The price is AED 496
AED 1,020 total
includes taxes & fees
7 Dec - 8 Dec
Fox Cottage *Pet Friendly*

Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard

10.0 out of 10, Exceptional, (16)
"Very clean, great location - easily walkable for a USNA reunion to stadium and alumni center!"
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard

Federal Hill & Inner Harbor Lux Retreat: Sleeps 6

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great house for a fun weekend. Super clean and comfortable. Withing walking distance of good restaurants and stadiums. Will definately look to book this location again when we are back in Baltimore."
Federal Hill & Inner Harbor Lux Retreat: Sleeps 6

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

10.0 out of 10, Exceptional, (1)
"What a wonderful home, spacious just beautiful! But the view of the bay was everyone’s favorite, we spent 98% of the time outside only inside for eating and sleeping. The grandkids didn’t pick up and electronic device the entire time, they played basketball, fished, cornhole, counting boats. The only time a TV was turned on was to watch Big Blue Madness and the Kentucky/Vandy game (we’re from Kentucky). But if you like TV there is one in every room! This home is very well stocked with everything...
Charming Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Near JHU & Downtown - Luxury Modern 4bd/3.5bath Rowhome w/ Outdoor Lounge

2.0 star property
10.0 out of 10, Exceptional, (17)
"We were in town for a family’s wedding and this place did not let down! We all had our own space and bathroom so getting ready was a breeze. The place was clean and well taken care of. Decor was adorable. It was a great location for us since the ceremony was held at the art museum. They gave us great recommendations for places to eat. They also were great at responding quickly to any questions we had! Loved this place would definitely stay again!!"
Near JHU & Downtown - Luxury Modern 4bd/3.5bath Rowhome w/ Outdoor Lounge

Rooftop Deck Escape! Free Parking!

9.0 out of 10, Wonderful, (23)
"Good location, close to Light Street. House was nice, enjoyed the rooftop deck with fire table. "
The price is AED 419
AED 1,027 total
includes taxes & fees
26 Nov - 27 Nov
Rooftop Deck Escape! Free Parking!

Cozy & Luxury 4 bedroom Baltimore downtown home

7.8 out of 10, Good, (28)
"Very nice place. Easy access to major amenities. No complaints at all. Highly recommend. "
Cozy & Luxury 4 bedroom Baltimore downtown home

Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.

9.4 out of 10, Exceptional, (26)
"I rented this property as part of a surprise weekend getaway for my son's 16th birthday. Our party included 2 adults, 4 teenage boys, and 2 small pups. To start, communication with the host, Ray, was superb! He has a great personality and is very easy to talk to. Prior to our trip, he gave me a complete overview of the property, its location and better driving directions than any of the map apps. Our set up was a little complicated because I was surprising my son and we had the majority of our...
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.

Lovely colonial-style home with pool access, firepit & large yard - dog-friendly

9.2 out of 10, Wonderful, (44)
"The stay was good. The guest bedroom mattress was not to comfortable and the pool was closed but everything was fine."
Lovely colonial-style home with pool access, firepit & large yard - dog-friendly
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

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

10.0 out of 10, Exceptional, (16)
"Perfect place for Ravens Game. Walking distance to stadium. Super clean. Nice neighbors. Responsive host. "
⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

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

10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

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

10.0 out of 10, Exceptional, (20)
"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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.