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Next weekend
12 Sept - 14 Sept
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19 Sept - 21 Sept
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3 Oct - 5 Oct
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31 Oct - 2 Nov

Browse Select Essex Holiday Homes

Our top choices for Essex holiday homes

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (33)
"We had 14 family members join us to celebrate my son’s graduation from the Naval Academy. The house is clean, the rooms were great, the property was beautiful, and it was close to USNA. Our family loved the open concept. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (47)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is £227
includes taxes & fees
9 Sept - 10 Sept
BAYSIDE BUNGALOW
Large 2 bedroom house with private parking in a nice neighborhood
Smart TV, books

Large 2 bedroom house with private parking in a nice neighborhood

9.4 out of 10, Exceptional, (28)
"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."
The price is £266
includes taxes & fees
1 Oct - 2 Oct
Large 2 bedroom house with private parking in a nice neighborhood
Waterfront Oasis w/ Private Dock, 3BR/2BA
Marina

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

9.4 out of 10, Exceptional, (35)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA
Affordable Luxury Town Home in Federal Hill Baltimore.
Fridge, microwave, oven, stovetop

Affordable Luxury Town Home in Federal Hill Baltimore.

9.4 out of 10, Exceptional, (57)
"We stayed here for 2 nights. Place was as noted on VRBO site. It was clean and we slept well in the king bed. Just a suggestion to note on this property that the parking is street parking on your own. Also, not sure VRBO has this as a selection but to note if a place is ADA. The stairs in this place were a bit challenging for us. Others may not be so lucky. We managed but next time I will ask about this before booking. "
Affordable Luxury Town Home in Federal Hill Baltimore.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (192)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Rooftop Deck Escape! Free Parking!
Smart TV, stereo

Rooftop Deck Escape! Free Parking!

8.6 out of 10, Excellent, (30)
"Fun family stay"
The price is £224
includes taxes & fees
15 Sept - 16 Sept
Rooftop Deck Escape! Free Parking!
Charming 2-bedroom townhome in Baltimore with WiFi, AC
Exterior

Charming 2-bedroom townhome in Baltimore with WiFi, AC

10.0 out of 10, Exceptional, (4)
"Had an amazing stay "
Charming 2-bedroom townhome in Baltimore with WiFi, AC
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Outdoor dining

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
Orioles, Ravens, Baltimore Inner Harbor, Towson
Smart TV

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
Pet-Friendly Home on Chester River w/ Dock!
Interior

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (14)
"A large sprawling house that’s perfect for groups, this property offers stunning views of the Chester River. We spent every evening of our stay sitting along the water. "
Pet-Friendly Home on Chester River w/ Dock!
Charming Baltimore Townhome w/ Scenic Views
Terrace/patio

Charming Baltimore Townhome w/ Scenic Views

9.0 out of 10, Wonderful, (9)
"Great neighborhood! Lots to walk to, friendly people everywhere!"
Charming Baltimore Townhome w/ Scenic Views
Luxury Federal Hill Home w/Rooftop & 4 Parking Spots
Terrace/patio

Luxury Federal Hill Home w/Rooftop & 4 Parking Spots

9.6 out of 10, Exceptional, (23)
"We had a great experience. Everything was as described. House was in a great, safe neighborhood. We felt very safe walking around. Very close to the inner harbor area. Lots of restaurants within a short walk. Uber could easily locate the house. The owner was very prompt in responding to our questions. The decor was nice. Great experience all around. "
The price is £458
includes taxes & fees
10 Sept - 11 Sept
Luxury Federal Hill Home w/Rooftop & 4 Parking Spots
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Property grounds

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
Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (27)
"It was great!"
Charming Historic Townhouse Steps From USNA
Spacious 4-bedroom house in cool Woodlawn with AC, WiFi Baltimore DC area
Fridge, microwave, oven, stovetop

Spacious 4-bedroom house in cool Woodlawn with AC, WiFi Baltimore DC area

8.0 out of 10, Very good, (3)
"We had a pleasant stay with my family in MD, very homely and spacious, we had an incidence with the bathroom door locking behind my wife, but the owner responded promptly and helped open the door. Only negative thing is house is next to a main highway, so there was so much noise with the cars passing by day and night. Otherwise, it was clean and owner hospitable."
Spacious 4-bedroom house in cool Woodlawn with AC, WiFi Baltimore DC area
1900 Historic Fells Point Home
Fridge, microwave, oven, stovetop

1900 Historic Fells Point Home

10.0 out of 10, Exceptional, (11)
"Perfect location. Beautiful home."
1900 Historic Fells Point Home
Entire Townhouse in Rock Hall
Fridge, microwave, oven, stovetop

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (31)
"Exactly what we expected. What wasn’t expected is how quiet and serene that entire town is. "
Entire Townhouse in Rock Hall
Parkside Comfort & Spaciousness-Family Friendly
Fridge, microwave, oven, stovetop

Parkside Comfort & Spaciousness-Family Friendly

9.8 out of 10, Exceptional, (56)
"The house is clean, easy to get to and park, with lots of things to do in walkable distance. We had a great time exploring Baltimore."
Parkside Comfort & Spaciousness-Family Friendly
Beautiful, spacious, quiet waterfront house!
Fridge, microwave, oven, stovetop

Beautiful, spacious, quiet waterfront house!

10.0 out of 10, Exceptional, (55)
"The place is fantastic. Beautiful views of the water, and the house is well-stocked with everything one might need for a relaxing, comfortable stay. Gordon is a very responsive and accommodating host. We had a lovely stay and would love to come back in the future."
Beautiful, spacious, quiet waterfront house!
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

Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

10/10 Excellent
"Great "
Yedelyn 1-night trip
Posted 3 days ago
Renaissance Baltimore Harborplace Hotel
Kimpton Hotel Monaco Baltimore Inner Harbor by IHG

Kimpton Hotel Monaco Baltimore Inner Harbor by IHG

10/10 Excellent
"Very convenient to the concert we went to at the arena. We were able to get snacks in the lobby afterwards and order DoorDash late night. Dunkin' Donuts was across the street for morning breakfast. The wine happy hour is a huge bonus and coffee/tea in the morning. Our room was big and the bed was comfortable. It was easy to get to and easy to navigate leaving the city. Valet was quick and easy too, right out front. I would definitely recommend. "
Megan 1-night trip
Posted 5 days ago
Kimpton Hotel Monaco Baltimore Inner Harbor by IHG

Find out more about Essex

Find out more about Essex

Essex Holiday Homes information

Number of reviews
Accommodation
679 Holiday Homes
Lowest Price
£224
Highest Price
£458

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