Cottages in Annapolis

October 2026
November 2026

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Cottages in Annapolis

1. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
Marley
$258
$308 total
includes taxes & fees
Sep 28 - Sep 29
Lakefront Home Firepit BWI Marleycreek River

2. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
Green Haven
$224
$485 total
includes taxes & fees
Oct 8 - Oct 9
Idyllic Pasadena Retreat With Garden + Hot Tub!
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Top neighborhoods in Annapolis

Historic District

Discover a well-preserved historic district with elements of the original town plan, featuring landmarks like the Maryland State House, St. Ann's Church, and Paca House and Gardens. The neighborhood features prestigious educational institutions like St. John's College and the U.S. Naval Academy.

Eastport

Eastport's maritime soul comes alive through its scenic waterfront promenades along the Severn River and Back Creek. The Annapolis Maritime Museum showcases local nautical heritage while the peninsula's "Restaurant Row" buzzes with seafood spots and live music. Explore charming streets lined with historic homes or watch sailboats glide through Annapolis Harbor from public piers. Waterfront dining dominates the food scene with fresh Chesapeake Bay blue crabs and oysters taking center stage. Most visitors stay in boutique inns or bed & breakfasts housed in converted historic buildings. The neighborhood is best explored on foot, with easy access to downtown Annapolis via the Eastport Bridge.

West Annapolis

West Annapolis gives you a front-row seat to authentic Maryland living without the tourist crowds. Tree-lined streets and well-maintained colonial homes create a peaceful retreat just minutes from downtown attractions. Navy-Marine Corps Memorial Stadium sits nearby, while the neighborhood's proximity to the Severn River and College Creek offers scenic waterfront walks for nature lovers. Getting around is best done by car or on foot through this residential haven. While dining options are limited within the neighborhood itself, downtown Annapolis restaurants are just a short drive away. Travelers can find charming bed & breakfasts and vacation rentals that provide a genuine taste of local life.

Murray Hill

Murray Hill offers a peaceful retreat from downtown Annapolis with its tree-lined streets and historic charm. Colonial and Federal-style homes create a living museum of early American architecture just steps from the water. Take a leisurely stroll to nearby Spa Creek or catch a performance at the Ballet Theater of Maryland. Dining requires a quick walk to downtown's seafood spots and Chesapeake Bay specialties. Most visitors stay in charming bed & breakfasts housed in converted colonial homes with period furnishings. The neighborhood's proximity to marinas and waterfront promenades makes it perfect for travelers seeking authentic maritime history without the tourist crowds.

Hillsmere

Hillsmere offers a slice of authentic waterfront living just outside Annapolis's busy core. The community beach and marina invite you to kayak, swim, or just watch the Chesapeake Bay waters lap against the shore. Maryland Quiet Waters Park provides peaceful trails through nature, while the Great Frogs Winery offers tastings with local flavor. Tree-lined streets create a calm retreat from tourist crowds, with comfortable vacation rentals replacing typical hotels. Downtown Annapolis is just a 15-minute drive away, making this neighborhood perfect for travelers who want suburban tranquility with easy access to city attractions.

Top landmarks in Annapolis

A large building with ornate architecture, a cannon, and a sign reading "Bancroft Hall".

U.S. Naval Academy

9.4/10 (1,474 reviews)
If you'd like to get a taste of Naval Academy student life, check out U.S. Naval Academy, in the heart of the town. Why not take a stroll along the port and watch the sunset while you're here?
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A park with a walking path, picnic tables, and a large tree. In the background, there is a bridge over a body of water.

Sandy Point State Park

8.6/10 (221 reviews)
Sandy Point State Park is 5.4 mi (8.8 km) from central Annapolis, why not stop by during your stay. Why not take a stroll along the port and watch the sunset while you're here?
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A beach with two people, a large suspension bridge in the background.

Chesapeake Bay Bridge

8.8/10 (1,066 reviews)
If seeing the sights is on your list of things to do, head to Chesapeake Bay Bridge— just one of the landmarks located 5.2 mi (8.3 km) from central Annapolis. Why not take a stroll along the port and watch the sunset while you're here?
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Annapolis City Dock

9.4/10 (1,099 reviews)
If you want to give your credit card some exercise, head out to Annapolis City Dock in Historic District. Why not take a stroll along the port and watch the sunset while you're here?
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Navy-Marine Corps Memorial Stadium

9.2/10 (287 reviews)
You can catch an event at Navy-Marine Corps Memorial Stadium, located 0.8 mi (1.3 km) from central Annapolis. Why not take a stroll along the port and watch the sunset while you're here? If you think Navy-Marine Corps Memorial Stadium is cool, you also might like Alumni Hall and Tose Family Tennis Center, both located nearby.
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Westfield Annapolis Mall

8.8/10 (394 reviews)
If you like shopping, take time out to go to Westfield Annapolis Mall when in Parole. Why not take a stroll along the port and watch the sunset while you're here? Splash some more cash at Annapolis Mall Shopping Center.
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Annapolis Mall Shopping Center

9.0/10 (23 reviews)
If you like shopping, take time out to go to Annapolis Mall Shopping Center when in Parole. Why not take a stroll along the port and watch the sunset while you're here? Splash some more cash at Westfield Annapolis Mall.
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Maryland Renaissance Festival

10.0/10 (1 review)
If thrills are what you're after, head to Maryland Renaissance Festival, located 5.4 mi (8.6 km) from central Annapolis. If you have fun at Maryland Renaissance Festival, you'll love Maryland Hall for Creative Arts and Annapolis Bowl, both located nearby.
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Annapolis and related destinations

Brick-lined streets wind past Georgian mansions where American history feels less like homework and more like gossip among neighbors. The Naval Academy campus welcomes visitors with military precision and surprising artistic touches. After watching midshipmen drill, head to City Dock where 'Ego Alley' earned its nickname from boaters showing off their vessels. Maryland State House still flaunts the dome where Washington resigned his commission, making it America's oldest capitol in continuous use. Chesapeake Bay beckons sailors while downtown restaurants transform the bay's blue crabs into cakes that ruin you for imitations elsewhere. When evening falls, historic pubs fill with a lively mix of midshipmen, politicians, and sailors swapping tales across three centuries.

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A historic town street at dusk with a prominent church dome, brick buildings, and a yellow fire hydrant.

About the destination

There's a lot visitors like about Annapolis, especially its restaurants and historical sites. Simply book a local tour to enjoy your stay a little more. You might find the perfect souvenir at Annapolis City Dock or Annapolis Harbor Center Shopping Center. While you're in town, don't miss a chance to see sights like Maryland State House and William Paca House.