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Crab Cakes and Football Historic District

Soak up the vintage charm of this restored property. The house features a private master suite balcony, an open-plan living space, chic eclectic furnishings, exposed brick, a wood burning fireplace, a front garden, and an outdoor back BBQ area. STR# 143754 When we decided to convert to a short term rental I looked at other properties in the area and how they described them. I could tell you the house was built in 1901 and is located in one of the most sought after neighborhoods in historic Annapolis. That's all well and good but to be honest there's a book on the coffee table that will tell you all the history (if you really want to know). I might not know a lot about writing a great summary but after almost 3 decades of living in Annapolis I think I know what people want: 1) Great food and drink! 2) Great location for walking to everything and.. 3) An outdoor area to enjoy the mornings and evenings during any down time. Unfortunately the one thing that can really ruin the fun is PARKING! Well guess what, we've got all the things I listed above and not one parking spot, but TWO (right at your back door!). Don't be fooled when other properties offer you a parking pass. That does not mean you'll be parking near your rental! Enjoy full access to our home. We do not live there so it is not cluttered with "stuff". Consider it a hotel with all the amenities of home! We live 5-10 minutes from the property so you'll have your privacy but we are nearby if you need assistance. We are available by text or calling for any questions or help you may need. The home is in the Art District of Annapolis right in the middle of all the fun. Enjoy the hustle and bustle of the city center during the day and evening, but return to a quiet neighborhood to recharge. Free designated parking for 2 cars. Park upon arrival and you my never need your car again until your departure! No parties. Dogs welcome on a case by case basis.

Rachel's BnB

A well outfitted home away from home! A fully stocked kitchen with everything you need to cook for yourselves and your guests. Close to historic downtown Annapolis, the US Naval Academy, St. John's College and MD Statehouse are less than 10 minutes away There are king and queen beds in the rooms, and the 3rd bed is a comfortable pullout couch in the living room. All linens are Egyptian cotton and the beds have real down duvets. Additional cot beds and linens (up to 4) can be provided ($20 each)

Elegant & Authentic Annapolis

Enjoy comfortable elegance in this historic beauty on one of the prettiest streets in Downtown Annapolis--Main Street and the Water only 2 blocks away. This private unit is the full main level with its own eat-in kitchen, living room, front porch and back patio. Bedroom features queen size bed, dresser and walk-in closet. Bathroom has shower/tub and counterspace for your comfort. Street parking is available or public garage parking is a short stroll away. Relish this quiet & convenient location.

Charming Eastport Getaway – Near Downtown & USNA

Bright and comfortable Eastport retreat just 3 minutes by car or a 20–25 minute walk to Downtown Annapolis and the Naval Academy. Eastport dining is even closer, with favorites like Vin 909, Boatyard Bar & Grill, and Bread & Butter Kitchen only 8–17 minutes on foot. Enjoy nearby waterfront restaurants, marinas, and shops. Perfect for family getaways, remote work, or weekend escapes, the home features a chef’s kitchen, patio with fire pit, fast Wi-Fi, Smart TV, laundry, workspace and free parking

Annapolis Area Waterside Retreat

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

Quaint in the Heart of Annapolis

Quaint 2 bedroom, 1 bath home located in the heart of historic Annapolis. Completely remodeled with free off-street parking. Located towards the end of a safe, quiet, dead end road, less than 3 miles from downtown Annapolis, the Naval Academy, the Annapolis Mall, St. John’s College, and the Navy-Marine Corps Memorial Stadium. Walk downtown or to the Annapolis Town Center, restaurants, shops, and so much more! -Wi-Fi -2 free parking spaces -Keurig Coffee -TV -Toothbrushes/Paste -Shampoo/Soaps

"Hilltop Hideaway"- Private basement suite

Location, location! "Hilltop Hideaway" is a private basement apartment just 16 miles from BWI airport, 10 miles from Fort Meade and Annapolis, and less than 30 miles to Baltimore and Washington, DC! Nestled in a wooded setting on 2 acres, it is perfect for 1-2 adults (25yrs old or older). Not suited for children. Offers living space, bathroom, kitchenette w/microwave, toaster oven, coffee maker, crock pot, apartment size fridge and separate dining nook. Private key code entrance and parking.

4 bedrooms, 7 beds, 3 bath completely updated

Not your typical Airbnb. This is our vacation house too and we have it stocked so you can enjoy all of the amenities of home, without having to bring them yourself. Full kitchen with fresh coffee beans, K cups, and tea provided for starters. Breakfast starters provided too. Everything you need if you want to cook. Games for inside (including PS5), and backyard games too. 3 bedrooms on ground floor so no constantly having to go up and down steps. We love our place and know you will too.

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

Spacious 3 Bedrooms House+Patio+Playground

Spacious 3 bedrooms house with functional patio + private playround located in Edgewater, only 15 mins drive to downtown Annapolis. Fully equipped with designer furnitures, with a sense of home! Huge dining room and fully functional kitchen, perfect to enjoy a great evening with your friends and family! Bedrooms are equipped with your own desks if you want to do some works even in your vacation. Easily fit 2 cars in private driveway. Very quiet neighborhood with proximity to everything!

3BR/2BA Annapolis Cottage

Our cottage is located a little over a mile from downtown Annapolis, on a quiet peninsula close to the water. It is a short car ride to the heart of downtown and we have plenty of off-street parking. The trail can be used to walk/bike downtown and to Navy Stadium. The home recently had a complete renovation with an all-new kitchen, bathrooms, and hardwood floors throughout. Enjoy a tree-lined backyard with deck and gas grill. A clean comfortable space to relax while you enjoy Annapolis.

The Navy House-Walk or Shuttle Downtown! 3 bd

Your family will be close to everything when you stay at this centrally-located home. 3 blocks from the Navy stadium and walking distance to amazing restaurants! Here is your Annapolis home away from home. Our 3 bedroom 2.5 bath bungalow retreat is perfect for 6-7 people wanting to relax and see all that beautiful Annapolis has to offer. There’s also a free shuttle that takes you downtown to the water. Come, enjoy!