Annapolis Rentals
- From $355 per night (USD)
VRBO
Nautical charmer near the City Dock with open layout, W\/D, & AC
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Plebe's Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $355 per night (USD)VRBO
- From $1000 per night (USD)
Expedia
Beautifully Furnished Home, Steps to USNA Stadium, Walk to Downtown Annapolis!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This 3 BR/3 Bath home is literally steps from the USNA Stadium (graduation) and within walking distance of downtown Anna ...
From $1000 per night (USD)Expedia
- From $1200 per night (USD)
VRBO
Upscale home in Eastport \/ Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
Ideal location in the heart of Eastport, walking distance to everything Annapolis offers. Only 3 blocks to the Spa Creek ...
From $1200 per night (USD)VRBO
- From $675 per night (USD)
Expedia
Charming 3-bedroom house with AC and WiFi in enchanting Annapolis\/Eastport
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stay comfortably in Annapolis at this 3-bedroom house. With 1 king bed, 1 queen bed, and 1 full bed, this tremendous pro ...
From $675 per night (USD)Expedia
- From $357 per night (USD)
VRBO
Waterfront 2-Bedroom Condo on Spa Creek
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your home away from home in Annapolis! Nestled in the charming neighborhood of Eastport, this beautifully app ...
From $357 per night (USD)VRBO
- Click For Pricing
Expedia
Anchor Drop
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful modern single-family home with heated pool. Located in Eastport, Annapolis, Maryland. Totally renovated in 2 ...
Click For PricingExpedia
- From $392 per night (USD)
VRBO
Ahoy! The Buccaneer awaits you just outside Annapolis - fenced-in yard and rec room
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to The Buccaneer, a family-friendly home located just 3 miles from Historic Downtown Annapolis and Eastport. Thi ...
From $392 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Downtown Annapolis, steps from Main Street, City Dock, and Naval Academy - Apt 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This apartment is centrally located and on one of the loveliest streets in Historic Downtown Annapolis. You will be ste ...
From $250 per night (USD)VRBO
- From $375 per night (USD)
VRBO
Fox Hollow House- The perfect Annapolis Getaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Get ready for an awesome family gathering in our spacious 4 bedroom home with the perfect back yard for entertaining! N ...
From $375 per night (USD)VRBO
- From $145 per night (USD)
VRBO
Downtown Annapolis, steps from Main Street, City Dock, and Naval Academy - Apt 3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This apartment is centrally located and on one of the loveliest streets in Historic Downtown Annapolis. You will be ste ...
From $145 per night (USD)VRBO
- From $145 per night (USD)
VRBO
Downtown Annapolis, steps from Main Street, City Dock, and Naval Academy - Apt 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This apartment is centrally located and on one of the loveliest streets in Historic Downtown Annapolis. You will be ste ...
From $145 per night (USD)VRBO
- From $964 per night (USD)
Expedia
Stunning 5-bedroom remodel in the heart of Murray Hill.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to 9th wing (USNA reference for the boat schoolers out there!) We are nearing the end of renovations on this sp ...
From $964 per night (USD)Expedia
- From $466 per night (USD)
VRBO
Darling 2 BR home with parking in the sought after Murray Hill section of Historic Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
STR22-145187 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $466 per night (USD)VRBO
- From $825 per night (USD)
VRBO
Historic Luxury Steps to USNA + Vibrant Waterfront\n
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Fair Winds, a beautiful, spacious and sunlit historic home on gorgeous Prince George Street in the heart of d ...
From $825 per night (USD)VRBO
- From $704 per night (USD)
VRBO
5 Min to Downtown Annapolis
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
This brand-new build Eastport luxury home has everything you and your guests need for an upgraded stay in Annapolis. Eac ...
From $704 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Minutes from History: Room w\/ Free Breakfast Near Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dive into Annapolis's rich heritage, just minutes from the US Naval Academy and historic downtown. Discover state landma ...
From $150 per night (USD)VRBO
- From $182 per night (USD)
VRBO
Enjoy Complimentary Breakfast at Our Welcoming Suite in Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Dive into Annapolis's rich heritage, just minutes from the US Naval Academy and historic downtown. Discover state landma ...
From $182 per night (USD)VRBO
- From $156 per night (USD)
VRBO
Annapolis Adventure: Room w\/ Outdoor Pool + Easy Access to Historic Sites
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Dive into Annapolis's rich heritage, just minutes from the US Naval Academy and historic downtown. Discover state landma ...
From $156 per night (USD)VRBO
- Click For Pricing
VRBO
Stylish & New, Pet Friendly Fenced Yard, Walkable Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This stunning detached home, designed by Stylish Stays, is the perfect place for a stay in THE HEART of Annapolis. This ...
Click For PricingVRBO
- From $390 per night (USD)
Expedia
Dog friendly! Next to Navy Stadium and DTA Shuttle!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your stay in our charming home centrally located directly across from Navy-Marine Corps Memorial Stadium on Taylor ...
From $390 per night (USD)Expedia
- From $258 per night (USD)
VRBO
Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Immerse yourself in the rich history of Annapolis at our century-old home in Presidents Hill. With 3 bedrooms, 2 baths, ...
From $258 per night (USD)VRBO
- From $242 per night (USD)
Expedia
The Annapolis Pinkney House- complete with parking!
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 4
The Pinkney house is a 2 bedroom, 2.5 bath town home boasts an unparalleled location within close proximity to the Naval ...
From $242 per night (USD)Expedia
- From $744 per night (USD)
VRBO
Walk everywhere with multiple suites, dining spaces, parking
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Naptown Villa! This charming fully-renovated home in downtown Annapolis has all the finishes of a luxury rent ...
From $744 per night (USD)VRBO
- From $185 per night (USD)
Expedia
Discover Historic Annapolis living in a captivating 2-bedroom, 1.5-bath home!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
🌟 Discover the Allure of Historic Annapolis Living! 🌟 Welcome to your captivating 2-bedroom, 1.5-bath home nestled in ...
From $185 per night (USD)Expedia
- From $1800 per night (USD)
VRBO
Murray Hill beauty with short walk to Main Street
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
A perfect place to celebrate your Midshipmen's commissioning in a 1900 built home! Fabulous patio and back yard to enjo ...
From $1800 per night (USD)VRBO
- From $264 per night (USD)
VRBO
Maryland Inn 2 Double Beds, Historic Inns, Modern Amenities, Event Space, City Center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $264 per night (USD)VRBO
- From $238 per night (USD)
VRBO
Enjoy Stepping Back in Time at Charming Hotel in Annapolis - Pet-Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $238 per night (USD)VRBO
- From $407 per night (USD)
VRBO
2 Historic Ambiance Stays Perfect for Romantic Getaways - Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $407 per night (USD)VRBO
- From $237 per night (USD)
VRBO
Authentic 18th Century Hotel Near US Naval Academy - Walking Distance
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $237 per night (USD)VRBO
- From $527 per night (USD)
VRBO
2 Historic Ambiance Stays Perfect for Romantic Getaways - Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $527 per night (USD)VRBO
- From $366 per night (USD)
VRBO
2 Maryland Inn 2DBeds, Historic Inns of Annapolis, Waterfront Vicinity
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $366 per night (USD)VRBO
- From $235 per night (USD)
VRBO
Elegant Stay Perfect for Romantic Getaway, Just Steps from Waterfront
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $235 per night (USD)VRBO
- Click For Pricing
VRBO
2 Robert Johnson Townhouse, Historic Inns of Annapolis, Annapolis Heart
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
Click For PricingVRBO
- From $230 per night (USD)
VRBO
Unique Victorian Stay w\/ Modern Amenities + Steps from Waterfront
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $230 per night (USD)VRBO
- From $343 per night (USD)
VRBO
Robert Johnson Townhouse, Historic Inns, Fireplace, Downtown Locale
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $343 per night (USD)VRBO
- From $187 per night (USD)
VRBO
Governor Calvert 2 Double Beds, Historic Inns, Gym Access, Near Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $187 per night (USD)VRBO
- From $264 per night (USD)
VRBO
Maryland Inn King, Historic Inns, Fireplace, Elegant Dining, Waterfront Proximity
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $264 per night (USD)VRBO
- From $256 per night (USD)
VRBO
Robert Johnson 2 Double Beds, Historic Inns, Antique Style, Near Chesapeake Bay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $256 per night (USD)VRBO
- Click For Pricing
VRBO
2 Historic Boutique Rooms Near Sailing in Annapolis – Short Stroll
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
Click For PricingVRBO
- From $309 per night (USD)
VRBO
Elegant Stay Perfect for Exploring Annapolis' Shops and Boutiques.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $309 per night (USD)VRBO
- From $261 per night (USD)
VRBO
Robert Johnson King, Historic Inns, Near Top Dining & City Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $261 per night (USD)VRBO
- From $243 per night (USD)
VRBO
Charming Downtown Hotel w\/ Vintage Character + Modern Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $243 per night (USD)VRBO
- From $234 per night (USD)
VRBO
Elegant Boutique Hotel Near Maryland State House - Short Walk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $234 per night (USD)VRBO
- From $474 per night (USD)
VRBO
2 Historic Ambiance Stays Perfect for Romantic Getaways - Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $474 per night (USD)VRBO
- From $832 per night (USD)
VRBO
Stunning Home Nestled on the Peninsula of Eastport
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 bedroom home is an absolute gem! The Craftsman style architecture adds character and warmth, while the detailed t ...
From $832 per night (USD)VRBO
- From $239 per night (USD)
Expedia
Cute and Close to Downtown! Off street parking w\/ short walk to Academy\/Stadium
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the close proximity to all Annapolis has to offer at this row house located next to college creek. Nicely decorat ...
From $239 per night (USD)Expedia
- From $329 per night (USD)
VRBO
Art's Dist
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Built circa 1890, “John Stevens House” in the sought-after neighborhood of “President’s Hill”, aka the “Arts District”. ...
From $329 per night (USD)VRBO
- From $167 per night (USD)
VRBO
Enticing Suite w\/ Pet Friendly Options + Complimentary Breakfast! Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Annapolis's rich heritage, just minutes from the US Naval Academy and historic downtown. Discover state landma ...
From $167 per night (USD)VRBO
- From $360 per night (USD)
VRBO
Gorgeous House in the Heart of Annapolis, Walk to Everything!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located within walking distance of everything Annapolis has to offer, this 3BR/2.5 Bath historic Craftsman home is beaut ...
From $360 per night (USD)VRBO