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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

Compare 59 Cottages in Orchard Beach with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (207)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
Exterior

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

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

9.8 out of 10, Exceptional, (23)
"Perfect place for a family, centrally located to everything you need for a fun vacation."
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Peaceful getaway convenient to local amenities including beach, boating & food
Beach towels

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

9.8 out of 10, Exceptional, (110)
"Great location and local restaurants. Perfect side for small group to do paper crafting. Would definitely book this place again. "
Peaceful getaway convenient to local amenities including beach, boating & food
Amazing views, short walks to great dining!
Iron/ironing board, travel crib, free WiFi, bed sheets

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (80)
"We had a wonderful stay! Very cozy with beautiful views. Our host was very helpful and made sure our stay was great! Will definitely be back! "
Amazing views, short walks to great dining!
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Terrace/patio

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

10.0 out of 10, Exceptional, (26)
"Amazing house! perfect for my family and our stay in Annapolis. Perfect location to everything. We had all of the amenities we needed and everything was easy to use. If I had one thing negative to say, I wish I could have had my dogs with us, I would have gladly paid a cleaning fee to have them there. Luckily I was able to make other arrangements. Thank you for sharing your house with my family!"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
The Heron's Nest at Atlantic Marina
Exterior

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (287)
"It was definitely a trip to remember thank God for the AC and heat conditioner it really helped because of the water of course it's cold at night but it's understanding I do wanna say the sheets on the Queen bed and blanket was very itchy when laying down so I didn't sleep as good but my kids was fine so that was good maybe the detergent not sure but that was my only issue the blanket didn't smell as clean as it should so I use my blanket in the car which was good for the nights"
The Heron's Nest at Atlantic Marina
Eastern Shore beach cottage get-away
Fridge, microwave, oven, stovetop

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
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring
Exterior

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring

10.0 out of 10, Exceptional, (85)
"Our eighth stay at this property was just as good as ever. It is our home-away-from-home when visiting family in Annapolis. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Property grounds

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

10.0 out of 10, Exceptional, (7)
"We really enjoyed our long weekend at The Oyster Cottage. We needed some rest and relaxation and this cottage was perfect. Very well maintained and stocked! "
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Waterfront River Cottage for 2, dog-friendly
Exterior

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
Pet-friendly Annapolis Home: Walk to Beach!
Interior

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
Chic Baltimore Retreat - 6 Mi to Downtown!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Chic Baltimore Retreat - 6 Mi to Downtown!

3.0 star property
Chic Baltimore Retreat - 6 Mi to Downtown!
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Outdoor dining

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

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Secluded Cozy Cottage in Historic Downtown
Terrace/patio

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (8)
"Perfect location for family visit at USNA! House was super clean and cozy with easy access to all downtown and academy events."
The price is AED 1,469
AED 2,470 total
includes taxes & fees
5 May - 6 May
Secluded Cozy Cottage in Historic Downtown
The Yellow Cottage on Harness Creek
Exterior

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (157)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Property grounds

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"The place has a wonderful view of the bay & a cabin-like look. The exterior (deck) is fantastic with lots of lawn chairs, bbq grills, & tables and the view of the bay. The main kitchen in the 1st house (you enter into from parking) is good with 2 ovens, 1 big stove, and 1 big refrigerator. Kuerig machines in the main & small kitchen are a nice bonus. The small kitchen in the 2nd house is also nice & functional. The 2 bedrooms & 1 bathroom in the 2nd house are in good condition (except the...
The price is AED 1,469
AED 2,634 total
includes taxes & fees
16 Apr - 17 Apr
Chesapeake Cottages- 2 Quaint Waterfront Retreats
House w/Water Views of Rock Creek 2BA 2BA Cottage
Terrace/patio

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

10.0 out of 10, Exceptional, (26)
"The house is nice, open & very clean. The host is great with communication & very responsive. The street is really quiet which was great for us, we were just hanging out for the weekend & checking out Annapolis for something to do. Great place for two couples or a small friend group!!"
House w/Water Views of Rock Creek 2BA 2BA Cottage
Cozy Cottage
Terrace/patio

Cozy Cottage

10.0 out of 10, Exceptional, (1)
"Lovely home with everything you need."
Cozy Cottage
Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach
Living area

Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach

The price is AED 2,204
AED 3,827 total
includes taxes & fees
30 Apr - 1 May
Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach
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
Studio Apartment | Private kitchen | Fridge, microwave, oven, stovetop

WhyHotel by Placemakr Columbia

4.0 star property
9.0 out of 10, Wonderful, (684)
"My kids loved this place. They didn’t want to leave and see any of the area. I guess that means it was an absolute hit."
The price is AED 437
AED 494 total
includes taxes & fees
20 Apr - 21 Apr
WhyHotel by Placemakr Columbia
Luxe Houseboat: Breathtaking Skyline 360 Views
Terrace/patio

Luxe Houseboat: Breathtaking Skyline 360 Views

10.0 out of 10, Exceptional, (14)
"My wife and I like to try different type of getaway experiences and this was that. "
The price is AED 1,242
AED 2,524 total
includes taxes & fees
24 Apr - 25 Apr
Luxe Houseboat: Breathtaking Skyline 360 Views
Fantastic 2 bedrooms apt. Harbor
Lobby

Fantastic 2 bedrooms apt. Harbor

4.0 star property
10.0 out of 10, Exceptional, (1)
"It was a nice place"
Fantastic 2 bedrooms apt. Harbor
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.