
Condo holiday rentals in Annapolis
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Top-rated condo rentals in Annapolis
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HEART of OLD TOWN! Historic 2 BR! Walk to KING ST
Step into our historic 2-bedroom loft in the heart of Old Town Alexandria, set in a charming 1790 building. This desired location offers a unique stay with a cozy loft area and modern amenities. Nearby public parking and less than a block from King St, you're surrounded by local cafes, bars, and shops. The perfect blend of historical ambiance and urban convenience awaits you. Explore, unwind, and enjoy the best of Alexandria from this prime spot. Ready for an amazing stay? Book with us today!

Newly Renovated & Modern 1BR Condo - Unit 4
Completely renovated, stylishly furnished condo unit in Arlington, VA just one stoplight from Washington DC, the Pentagon, Clarendon, Crystal City & National Airport. Spacious unit with free cable TV, secure Internet/Wi-Fi, FREE reserved PARKING space in private lot, in-unit Washer/Dryer, Full Kitchen. Steps away from public transit buses that route to multiple Orange/Blue/Silver line Metro trains. Comfortably accommodates the traveling professional, those on vacation and is kid friendly.

Historic Schoolhouse Condo
Perched on a hill in Historic Ellicott City, this charming 1800s schoolhouse condo is perfect for long-term stays (30+ nights). Bright, spacious, and thoughtfully designed, it features a fully equipped kitchen, in-unit laundry, high-speed internet, and a dedicated workspace. Walk to Main Street, explore Trolley Trail #9 and Patapsco State Park, or easily access Columbia (10 min), Baltimore (20 min), and Washington D.C. (40 min) - historic charm meets modern comfort for an ideal extended stay.

1 bedroom -king in Annapolis- low cleaning fee
Brand New Vacation Rental – Prime Annapolis Location! 1 bedroom. Experience the best of Annapolis in this newly renovated, beautifully furnished 1-bedroom condo with a king bed and NO chore list! This open-concept retreat offers a bright, modern interior and a private balcony to unwind. Start your day with a scenic walk through Truxton Park trails or head to the boat ramp to catch a water taxi to downtown Annapolis! Whether you're here for relaxation or adventure, this is the perfect spot.

Annapolis Waterfront Condo - Unit #: A-203
Cozy, comfortable condo. Great views - 2nd flr. Fireplace 1 bed/bath condo, sleeps 4 max, covered, water front deck, reserved parking! .5 mile walk to dwnt Annapolis and the Naval Academy, 1.9mi to the Navy stadium. Book NOW for the Summer! Easy access to Spring/Fall boatshows. 12 stairs, no elevator. Pool Memorial to Labor Day: MWTh 4pm-8 Tues: Closed FSS and Holidays: 12pm-8 The pool is one of the best places to be on a hot summer day. If hours are unacceptable, pls select another

Annapolis @Gate 1 steps to the Harbor Free parking
Parking included. The heart of Annapolis 1 street from the harbor, fun restaurants & backs to the Naval Academy. This 1st floor 2 bed / 1 ba condo has been fully renovated with new paint, floors, bath & kitchen. 1 Parking space included & additional paid parking on street. Queen Bed & sleeper couch is a full size. Linens included. Kitchen includes refrigerator, stove/oven, microwave, keurig, dishes silverware, pots and pans. High speed internet included & separate work area.

Sun House in Hampden Private Apartment no stairs
Artists and creatives are welcomed! Stay at our 1920 rowhouse with its mix of 70's era textiles and contemporary style. Only two steps to a welcoming porch and keyless entry to our foyer/Shared hall. Straight ahead is Sun Apartment, private studio with stocked kitchen, comfiest 5 star bed, private bath, laundry and back yard access. Yoga room/ office located in shared hall. No need for a car in the heart of Hampden's Avenue just a block away. LGBTQ+ friendly

Renovated Apt In Historic Dist w/2 Parking Spots
Renovated upstairs unit two bedroom with TWO parking spots in the Historic District. Everything is high end and used exclusively as a short term rental. Private entrance, cute small custom kitchen, ceiling fans, mini split AC/ heat in every room for year round comfort. Hardwood floors, quality linens , lucid mattresses, Keurig coffee bar, toiletries. Walk to town in 10 min or less or take the free trolley to Main St, USNA, Churches, AYC. No children under 12.

Modern, spotless 1br for families or work
Bright and unique basement gem in the heart of DC! This thoughtfully renovated private space gets sunlight in the front and rear through real windows and glass doors. Enjoy your morning coffee on your own private patio. Come and go easily with your dedicated gated parking spot (free parking, off street!). Enjoy a full kitchen. Working during your stay? We have fast wi-fi. Live like a local in a (relatively) quiet residential neighborhood.

1st Floor Condo in Annapolis
This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in Eastport. Within easy walking distance of restaurants (3 min), Main Street/City Dock (10 min) & USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high-speed wifi, free onsite parking lot, a secure building entrance, dock and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

Cozy Old Town Apartment
Welcome to our charming condo in the heart of historic Old Town Alexandria! Enjoy a fully equipped kitchen, cozy living room with a 55” smart TV, and a peaceful master bedroom with en-suite bathroom. With two private entrances, dedicated parking, and easy access to King Street’s dining, shopping, and metro, this home offers comfort and convenience. Perfect for relaxing after exploring D.C., or enjoying the charm of Old Town on foot!

Stylish Condo, DC Views, Free Parking
Chic 1-BR apt with private balcony & stunning views of the DC skyline, including the Washington Monument. Perfect for 2 guests. Features a queen bed, dedicated workspace, full kitchen & fast WiFi. Enjoy building amenities like free parking, a gym & club room. Prime location, steps from the Metro, Pentagon Row & Fashion Center Mall, offering easy access to DC & DCA. Your home base for exploring the capital region!
Popular amenities for Annapolis condo rentals
Weekly condo rentals

Charming Capitol Hill/Union stCondo/PerfectGetaway

Nava 1-Bed Bsmt-Apartment | Near DC

NEW Hilltop Hideaway |Chic Stay Near H Street

Sojourn in DuPont Circle: Modern Meets Historic

Downtown Bethesda | 2 Bedrooms + Parking

Trendy retreat in Bloomingdale with free parking

THE ROYAL: Nostalgic Go-Go Theme Suite w/Fireplace

Cherry Blossoms, Capitol Hill 2BR, Sleeps 6
Pet-friendly condo rentals

Spacious Bloomingdale 1BR; garage parking included

Best Location EVER! 2BR/2BA, Pet friendly

Bright, large zen studio on historic Logan Circle

New 2BR - Cherry Blossom Suite - walk everywhere!

Bright 2br w amazing loc and view

Hill East BnB - Modern Style and Comfort 3BR/3BA

Lux in heart of DC social scene, free parking!

New, Sunny, 2BR - Parking, Patio, Firepit
Condo rentals with a pool

1 BR National Harbor near D.C.

Stylish 1BR Condo in Vibrant National Harbor, MD

Wyndham National Harbor | 1BR/1BA King Bed Suite

Wyndham National Harbor | 3BR/2BA King Bed Suite

Wyndham National Harbor | 1BR/1BA King Bed Suite

DC Views/Walk to Metro jr 1 bedroom

Club Wyndham National Harbor, 2 BR Deluxe

Wyndham National Harbor- 3 bedroom
When is the best time to visit Annapolis?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $245 AUD | $221 AUD | $229 AUD | $241 AUD | $283 AUD | $258 AUD | $262 AUD | $273 AUD | $269 AUD | $284 AUD | $303 AUD | $287 AUD |
| Avg. temp | 1°C | 3°C | 7°C | 13°C | 18°C | 23°C | 26°C | 25°C | 21°C | 14°C | 8°C | 4°C |
Quick stats about condo rentals in Annapolis

Total holiday rentals
Explore 20 holiday rentals in Annapolis

Nightly prices starting at
Annapolis holiday rentals start at $85 AUD per night before taxes and fees

Verified guest reviews
Over 2,070 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Annapolis holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Annapolis rentals

4.8 Average rating
Annapolis stays are highly rated by guests—averaging 4.8 out of 5!
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- Georgetown University
- Walter E Washington Convention Center
- National Mall
- M&T Bank Stadium
- Nationals Park
- The White House
- District Wharf
- National Museum of Natural History
- Capital One Arena
- Baltimore Convention Center
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Arlington National Cemetery
- Howard University
- Betterton Beach
- Sandy Point State Park
- Georgetown Waterfront Park
- Washington Monument
- Patterson Park
- National Harbor
- Smithsonian American Art Museum
- Great Falls Park
- Six Flags America
- The Pentagon




