Photo by Elizabeth Csanady

Search Vacation Homes in Essex

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Compare 560 Vacation Homes in Essex with updated reviews, rates, and availability.

"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"

"We had a great time, plenty of space for family of 8 with close distance to the aquarium. "

AED 1,035 total

includes taxes & fees

2 Feb - 3 Feb

"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. "

"Great property and location to everything is ideal. Would definitely book this place again. "

Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier

"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."

"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. "

AED 2,342 total

includes taxes & fees

2 Feb - 3 Feb

"Heron house was perfect for our family weekend getaway. Doug and Kris are great hosts and made our stay as easy as could be! "

Chestertown Vacation Rental | 4BR | 4.5BA | 6 Steps Required | 3,232 Sq Ft

"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!!!"

Annapolis Vacation Rental | 4BR | 3.5BA | 2,900 Sq Ft | Stairs Required

"I love this property and host! Incredible place to stay close to museums the Naval Academy, local shopping, excellent restaurants and the airport. I will highly recommend this property to friends & family. "

"Clean, comfortable home with lovely rooftop patio! "

AED 1,413 total

includes taxes & fees

3 Feb - 4 Feb

"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."

AED 1,319 total

includes taxes & fees

3 Feb - 4 Feb

"A great place to stay with homie accommodations.Would definitely use again if traveling through Baltimore."

"We needed a getaway near Baltimore so we could visit some family and attractions. The location was easy to navigate to and is nestled in a historic village. We enjoyed the ambiance of the house and the host made sure we were comfortable. We highly recommend this stay to anyone who enjoys a unique and quiet getaway. We particularly enjoyed listening to the nearby waterfall from the upstairs balcony. The house was clean and stocked with necessities. We would love to return as we found many places...

AED 810 total

includes taxes & fees

3 Feb - 4 Feb

Waterfront with private pier and great views

"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "

"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."

AED 1,548 total

includes taxes & fees

2 Feb - 3 Feb

Baltimore Vacation Rental | 3BR | 2.5BA | Stairs Required | 1,480 Sq Ft

"Outstanding rental in a great location. The place was clean and check-in/out was no issue. Will stay again!"

"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."

Save an average of 15% on thousands of hotels when you're signed in

Other property types in Essex

"I highly recommend this property if you’re visiting the Baltimore area. Very spacious for myself, my husband and our 4 kids. Lorraine checked in on us every other day and Mr. Derrick made sure everything was in order upon our arrival."

AED 1,883 total

includes taxes & fees

1 Mar - 2 Mar