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Compare 532 Vacation Homes in Essex with updated reviews, rates, and availability.

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.0 out of 10, Wonderful, (2)
"no kettle no cutting board"
Pet-Friendly Home on Chester River w/ Dock!

House on the Gwynns Falls

8.4 out of 10, Very Good, (5)
"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 SAR 635
SAR 820 total
includes taxes & fees
30 Dec - 31 Dec
House on the Gwynns Falls

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

9.6 out of 10, Exceptional, (19)
"This property meets all expectations! The host was very easy to communicate with. I loved the quaintness of the area and the ease of access to the highways was so nice! I would highly recommend this property to anyone visiting the Baltimore area!"
⭐️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, (205)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

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

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, (73)
"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

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.

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

9.8 out of 10, Exceptional, (50)
" We ( a group of 16 women) enjoyed having our annual retreat at Nauti or Knot. We stayed for a weekend and the accommodations could not have been better! The bedrooms and bathrooms were wonderful. The living room was able to sit 16 comfortably and the dining room table was big enough for all of us to have dinner together. This is an excellent house!! Our only complaint and it’s minor is that the freezer door was really hard to open."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

9.8 out of 10, Exceptional, (27)
"Felt like home as soon as we walked in...except it was CLEANER than home :-) Comfortable, spacious, well-stocked. Hosts were attentive & quick to answer messages. Great experience!"
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

* Lovely Gem w/ Perfect Combo of Flair & Class *

10.0 out of 10, Exceptional, (47)
"This place suited our needs, clean and roomy!"
The price is SAR 559
SAR 997 total
includes taxes & fees
12 Jan - 13 January 2025
* Lovely Gem w/ Perfect Combo of Flair & Class *

* Stunning New Bungalow Perfect for Everyone *

9.8 out of 10, Exceptional, (90)
"Owners were responsive. House was immaculate and beds were so comfortable!"
The price is SAR 563
SAR 1,028 total
includes taxes & fees
2 Jan - 3 January 2025
* Stunning New Bungalow Perfect for Everyone *

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

10.0 out of 10, Exceptional, (62)
"Bigger, nicer and newer than it looks in the pics; a pleasant surprise. Great location, we’d go again. "
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

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 SAR 567
SAR 1,570 total
includes taxes & fees
30 Dec - 31 Dec
Welcome to the Charm City Getaway!

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!

10.0 out of 10, Exceptional, (16)
"We had an annual girls trip at this property last weekend and it was perfect and as described! The local food recommendations were on point and the house was clean and well stocked with all we needed. Thank you for opening your home to us!"
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!

Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

10.0 out of 10, Exceptional, (11)
"We came for the annual sailboat Race to Rock Hall. We had two sailing teams sharing the house and everyone enjoyed themselves. We’ll be back next year"
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

7.4 out of 10, Good, (3)
"About a 10 minute walk to main street, 15-20 to the Marinas. The house is cute, has a nice common room, and the bed was comfy."
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

Experience Elevated Comfort: Luxe Breeze Townhouse.

9.0 out of 10, Wonderful, (2)
"This place was perfect for us. Very clean and comfortable in a nice neighborhood. It was only 25 minutes from the homecoming event we attended on Saturday at McDaniel College so the location was perfect. We would highly recommend to anyone staying in the area."
The price is SAR 342
SAR 1,791 total
includes taxes & fees
7 Jan - 8 January 2025
Experience Elevated Comfort: Luxe Breeze Townhouse.

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

10.0 out of 10, Exceptional, (23)
"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

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 SAR 428
SAR 1,050 total
includes taxes & fees
12 Jan - 13 January 2025
Rooftop Deck Escape! Free 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

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

9.6 out of 10, Exceptional, (19)
"This property meets all expectations! The host was very easy to communicate with. I loved the quaintness of the area and the ease of access to the highways was so nice! I would highly recommend this property to anyone visiting the Baltimore area!"
⭐️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, (205)
"A great experience all around"
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, (23)
"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"
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.