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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.

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Spacious 3 Bedrooms House+Patio

Spacious 3 bedrooms house with functional patio, located in Edgewater, only 15 mins drive to downtown Annapolis. The house is 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. You can easily fit 2 cars in our private driveway. Very quiet neighborhood with proximity to everything!

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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!

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Across from stadium - walk to downtown Annapolis!

Across the street from the Navy and Marine Corps Stadium and walking distance to historic downtown Annapolis - you will be in the heart of it all! Our home is a warm and welcoming space in a park-like setting with plenty of parking and gathering spaces to enjoy with family and friends. Bringing kids? They are sure to enjoy the kid space with games, toys and art. Entertaining? Use the large yard, decks, & multiple living areas. Multiple families? Enjoy two master suites and plenty of room.

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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.

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Sophisticated & Spacious Historic Home w/ Parking!

Located in the Historic District, our home is a unique blend of vintage charm and modern comforts. Off-street parking in a driveway is a rare find, & additional parking spaces in the rear are available with permission. We are 2 blocks to USNA Gate 1, and 1 mile to the Navy Stadium. A shady and quiet backyard is a peaceful respite, with retail shops, restaurants and coffee houses just steps away. It doesn't get better than this!

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Charming house; walk to everywhere in Annapolis

Charming historic house, private and upscale, tucked away in the quiet President’s Hill neighborhood, located off West Street (Annapolis Arts District) where many restaurants and shops are located. City Dock and the Navy Stadium within walking distance. Free shuttle bus to downtown. Enjoy entire house, including front porch and back yard garden. Fully stocked for cooking including all basics (spices, oil/vinegar), coffee/tea.

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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!

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7 mins away from Downtown Annapolis, Vega's Home

Welcome to our home! There are six bedrooms and two full bathrooms. We can accommodate 10 people. It's about a 7 minutes drive from Downtown Annapolis and the Naval Academy. Where you can enjoy the beautiful historic attractions and explore countless restaurants. A short drive to the Mall and grocery stores ( Giants, Trader Joes, Whole Foods, Target,). Its also about a 30-35 minutes drive from BWI airport.

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Cozy Annapolis Cottage.

Stay in the heart of Annapolis! 1 Gig Internet speeds. 220v outlet for EV charging (bring your own cable).Walk to downtown, the Naval Academy and Navy Stadium. Meticulously kept home and newly renovated. Professional cleaning team with every turnover of the house. Stay in the comforts of your own home and experience all that Annapolis has to offer. Art throughout home by local artist Amy Holt Cline.

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Modern Waterfront: Quiet but close to Everything.

Welcome to your Annapolis waterfront retreat. Perched high above your private dock on Weems Creek the freshly remodeled modern home blends the tranquility of a leafy wooded neighborhood with the luxury and accessibility of a 5-star resort. Located just 1 mile from the Navy Stadium and 2 miles from the Historic District, our home offers easy access to everything Annapolis offers.

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Historic & sunny home steps from USNA/downtown

This beautiful and cozy 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City Dock and Gate 1 (main gate) of the US Naval Academy. Filled with sunlit, spacious rooms and equipped with numerous amenities (incl. gas fireplace), this home can sleep up to 7 and offers a combination of location and charm that is hard to beat!

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Bay Breeze Retreat

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Waterfront, Fabulous Home for Families with Pool!

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Large Home with Pool & 7 bedrooms; sleeps 21

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Cattail Landing- Photographer's Waterfront Retreat

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5 BEDR, Inground Pool+Billiard Table, Close To D.C

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Spacious/Unique in Heart of DC Designer Rowhome

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Chesapeake Bay Waterfront ARTectural Home w/ Pool!

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The Little Gypsy BoHome

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Nautical Retreat! 6 Guests • 3 BDR • 2 Baths

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Downtown Annapolis Luxury House

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4 bedrooms, 7 beds, 3 bath completely updated

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The General's House

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Downtown Annapolis Home

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Sunset Corner House

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Nautical - and SO nice! Park Free Walk to Stadium

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Harbor’s Edge Retreat: Walk to Main St & Academy

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West street historic home

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1 level 1 mile to Stadium 4 King Beds dog-friendly

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Elegant & Authentic Annapolis

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Annapolis 2025 - Visit Fox Haven, 1 Bed/1 Bath Apt

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Dog friendly! Next to Navy Stadium & DTA Shuttle!

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West Annapolis cottage, walk to USNA, City Dock

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Annapolis Cottage at Bay Ridge, Renovated 2022

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Cozy 2BR Row House near Naval Academy

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