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Featured Cottages in Orchard Beach and around

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (73)
"Perfect for a romantic weekend away!"
Amazing views, short walks to great dining!

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

10.0 out of 10, Exceptional, (80)
"My husband and son really loved their stay at Pat & Ken's VRBO house! They enjoyed going on walks around the neighborhood, visiting the local restaurants, and sitting in the hot tub. It was perfect for our family. Pat & Ken are such gracious hosts, and we will definitely stay here again!"
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,

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

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

9.2 out of 10, Wonderful, (7)
"It's a beautiful location and we enjoyed our visit."
Waterfront River Cottage for 2, dog-friendly

Chic Baltimore Retreat - 6 Mi to Downtown!

3.0 star property
Chic Baltimore Retreat - 6 Mi to Downtown!

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (2)
"We stayed at this gem with family for a auSNA event. The cottage was clean, well appointed and a perfect location. Jennifer was responsive and helpful throughout. We loved our stay!"
The price is €628
includes taxes & fees
27 Nov - 28 Nov
Secluded Cozy Cottage in Historic Downtown

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (204)
"Very cozy and clean. Beautiful surroundings with direct view of the water. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (132)
"This house was the cutest little place right across the street from the beach with a beautiful view. The house was clean and had all the amenities needed for our stay. We would definitely stay there again!"
Eastern Shore beach cottage get-away

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

10.0 out of 10, Exceptional, (24)
"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,

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

9.8 out of 10, Exceptional, (29)
"My stay was wonderful, listing just as described. Beautiful water views and enjoyed the local area. Highly recommend and plan to return. Thank you so much for a lovely stay!"
Waterfront dog-friendly home with beach just mins to Downtown Annapolis

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

House w/Water Views of Rock Creek 2BA 2BA Cottage

10.0 out of 10, Exceptional, (22)
"Very quiet street, our stay was relaxing and just what we needed! "
House w/Water Views of Rock Creek 2BA 2BA 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!

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

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier

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!

3.0 star property
6 Mi to Dtwn Baltimore: Home w/ Fire Pit!
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 Orchard Beach

WhyHotel by Placemakr Columbia

4.0 star property
9.0 out of 10, Wonderful, (567)
"clean, easy, affordable "
The price is €118
includes taxes & fees
1 Dec - 2 Dec
WhyHotel by Placemakr Columbia

⭐️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

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.