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Compare 39 Cottages in Essex with updated reviews, rates, and availability.

Amazing views, short walks to great dining!
"The cottage is lovely—vintage charm in perfect combination with the best modern updates. I was comfortable every minute I spent there..." Darcy - June 2021

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (76)
"Very well-maintained property in a quiet neighborhood. Although we didn't need anything, host was always available."
Amazing views, short walks to great dining!
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
Exterior detail

Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,

10.0 out of 10, Exceptional, (82)
"A very nice and well-maintained cottage in the Cape St. Clair neighborhood where family members live. The owners have done a great job of provisioning the cottage both inside and outside, for recreational opportunities and enjoyment (barbecuing and relaxing). The backyard is very large and great for games provided with the property, like corn hole. There is also a hot tub. The owners have found the right balance for being responsive when you need them, while leaving you in peace otherwise....
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
The Heron's Nest at Atlantic Marina
Family Room with Water View

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (286)
"We booked this property, along with the other property at the marina for our wedding weekend and WOW - we LOVED our stay. The views from this cute little cottage are phenomenal. We woke up each morning to watch the sunrise. The hosts were extremely accommodating and even helped secure our cake topper that we accidentally left behind in the whirlwind of check-out. This was the perfect spot for our first look as well. I would highly recommend booking this place for a cute romantic stay!"
The Heron's Nest at Atlantic Marina
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Regularly cleaned and maintained hot tub perfect for cool nights

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

9.8 out of 10, Exceptional, (22)
"My husband and I stayed here for 3 nights while I recovered from a surgery. It was a perfect, peaceful cottage and beautiful neighborhood. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Waterfront River Cottage for 2, dog-friendly
Welcome to the waterfront cozy River Cottage!

Waterfront River Cottage for 2, dog-friendly

9.2 out of 10, Wonderful, (7)
"It's a beautiful location and we enjoyed our visit."
Waterfront River Cottage for 2, dog-friendly
Eastern Shore beach cottage get-away
Early morning crabbing with Bay Bridge 12 miles away over the water.

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (133)
"Perfect location for watching the sunsets as the house is located right across the street from the beach. Also, an easy bike ride to restaurants and shops on Main St. The house is clean and comfortable. Highly recommend to other guests!"
Eastern Shore beach cottage get-away
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Room

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

10.0 out of 10, Exceptional, (25)
"Property as described. Very clean. Appreciated having shampoo/linens. Check out easy as well. Would recommend!"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Peaceful getaway convenient to local amenities including beach, boating & food
Cottage In Town

Peaceful getaway convenient to local amenities including beach, boating & food

9.8 out of 10, Exceptional, (109)
"We were in town for the local triathlon and had a great stay! My kids (3&4) and I were able to walk to the finish line from the location. The house was clean and large enough that we were all comfortable. If you have kids, it’s across the street from a cool boat playground. Diane was very responsive to my questions and provided plenty of towels, blankets, etc. Overall, a great stay! "
Peaceful getaway convenient to local amenities including beach, boating & food
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Welcome to the Coastie Cottage!

Rare find! Chic cottage, salt water heated pool May 15-Oct15.

10.0 out of 10, Exceptional, (50)
"The house was even nicer than in photos or descriptions. The house very spacious, the pool and pool area were perfect for our needs. The hosts were very gracious, communicative, and easy to work with. I would definitely recommend this property."
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Outdoor seating area just off the kitchen.

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

10.0 out of 10, Exceptional, (5)
"My friend and I wanted to meet up part way between our two cities, and when we decided on the Chesapeake Bay, Rock Hall seemed a good option, and we were right! What a great little town, and the house was just perfect for us. She brought her two little ones (6 and 2), and I was on my own. I think with just 1 bathroom, many more than that would really not be ideal. The whole stay was great, we both agreed we'd love to come back again. The only hiccup (and I am sure it will be fixed), was that...
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Terrace/patio

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Waterfront and Wonderful! Welcome to the Bayburst Lodge.
Exterior

Waterfront and Wonderful! Welcome to the Bayburst Lodge.

8.0 out of 10, Very Good, (11)
"This was our second visit to Bayburst Lodge and it was even better than our first! We spent an entire week this time and it really was relaxing and quite enjoyable. We did a lot of fishing this trip. We caught huge catfish off the beach behind the house, and also did a 4 hour charter in which we caught our limit in Striped Bass. The weather was incredible and we spent a lot of time walking, shopping, and sitting on the screened porch. We tried a new restaurant called Ark and Dove this trip....
Waterfront and Wonderful! Welcome to the Bayburst Lodge.
6 Mi to Dtwn Baltimore: Home w/ Fire Pit!
Outdoor dining

6 Mi to Dtwn Baltimore: Home w/ Fire Pit!

3.0 star property
6 Mi to Dtwn Baltimore: Home w/ Fire Pit!
Sunny Glen Burnie Home - On-site Water Access
Exterior

Sunny Glen Burnie Home - On-site Water Access

3.0 star property
Sunny Glen Burnie Home - On-site Water Access
Spacious Home w/ Tranquil Patio ~ 29 Mi to DC!
Living area

Spacious Home w/ Tranquil Patio ~ 29 Mi to DC!

3.0 star property
Spacious Home w/ Tranquil Patio ~ 29 Mi to DC!
Baltimore Area Vacation Rental w/ Deck!
Living area

Baltimore Area Vacation Rental w/ Deck!

3.0 star property
Baltimore Area Vacation Rental w/ Deck!
Eastern Shore Getaway: Walk to Tolchester Marina!
Exterior

Eastern Shore Getaway: Walk to Tolchester Marina!

3.0 star property
Eastern Shore Getaway: Walk to Tolchester Marina!
Private cottage
Interior

Private cottage

Private cottage
Cozy Nautical Cottage in Annapolis w/ Beautiful Outdoor Space
Terrace/patio

Cozy Nautical Cottage in Annapolis w/ Beautiful Outdoor Space

8.8 out of 10, Excellent, (3)
"The most lovely and completely outfitted and furnished with the latest tech and very nice amenities. The owner William answers any and all questions within minutes. The perfect spot to get away from it all yet near the Naval Academy very close by. Our first trip to this region and will not be our last."
Cozy Nautical Cottage in Annapolis w/ Beautiful Outdoor Space
Near Top Attractions: Deck Dining at Severn Home!
Living area

Near Top Attractions: Deck Dining at Severn Home!

3.0 star property
Near Top Attractions: Deck Dining at Severn Home!
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
Interior overview

⭐️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!
Private rear courtyard

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
Miscellaneous

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.