Annapolis, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Annapolis, Maryland on RentalSaver.com!

Annapolis Rentals

From $409 per night (USD)
VRBO
Charming West Annapolis Cottage home
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: This two-bedroom home in West Annapolis is a charming residence that boasts a spacious back yard, providing amp ...
From $409 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Charming Charles Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history ...
From $399 per night (USD)
Expedia
From $317 per night (USD)
VRBO
Downtwn Stylish 3BR/2BA with Exclusive Parking in Annapolis-USNA Stadium
Bedrooms:
1
Bathrooms:
4
Sleeps:
7
Welcome to this Annapolis gem located in the historic city of Annapolis. Enjoy living walking distance from all of the b ...
From $317 per night (USD)
VRBO
$Restful and Charming Home in Eastport\n$
From $384 per night (USD)
Expedia
Restful and Charming Home in Eastport\n
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
We offer a 10% military discount upon request! A cozy home away from home in Eastport located within 1.5 Miles of Histor ...
From $384 per night (USD)
Expedia
From $155 per night (USD)
VRBO
Adjacent to Quiet Waters Park and close to Eastport and Downtown Annapolis
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Plenty of off-street parking and a separate, secure entrance. Full lower unit with living room/kitchen/dining area, sep ...
From $155 per night (USD)
VRBO
Click For Pricing
Expedia
Beautiful Victorian in Great Eastport Location
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Available for Annapolis Boat Shows. Large historic Victorian in desirable Eastport, close to restaurants and short walk ...
Click For Pricing
Expedia
From $579 per night (USD)
VRBO
Historic downtown townhome with brick courtyard, sunroom & parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Corner Courtyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $579 per night (USD)
VRBO
From $779 per night (USD)
Expedia
Walk to Navy Stadium, Restaurants, Shops from Luxury Home with Private Backyard, Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Your Luxury West Annapolis Retreat! Nestled in the heart of West Annapolis, this beautifully remodeled crafts ...
From $779 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to my home! I hope that you love it as much as I do. It is an open concept 3 bedroom (two queens and a king) 1 ...
From $344 per night (USD)
VRBO
From $438 per night (USD)
Expedia
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Corner House – Quaint and Cozy 2 Bedroom Suite with Parking The Corner House is a hidden gem located in the quaint P ...
From $438 per night (USD)
Expedia
From $482 per night (USD)
VRBO
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Your family will be close to everything when you stay at this centrally-located place. Two blocks to Main Street, the Na ...
From $482 per night (USD)
VRBO
From $940 per night (USD)
Expedia
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Located on one of the most coveted streets in downtown Annapolis, walk to Main St. and City Dock. The Thomas Hyde House ...
From $940 per night (USD)
Expedia
From $341 per night (USD)
VRBO
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Anchors Away Abode Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $341 per night (USD)
VRBO
From $420 per night (USD)
Expedia
Annapolis Retreat - 7 mins from downtown Annapolis!
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Welcome to this charming five-bedroom, two-bathroom escape nestled in the Hillsmere Shores neighborhood of Annapolis. Ju ...
From $420 per night (USD)
Expedia
From $568 per night (USD)
VRBO
Annapolis Downtown - Historic Home - Brand New Furnishings. Walk to attractions
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We’re a Navy + Army Family with deep ties to the Naval Academy (and West Point…sorry, Navy fans). We love Annapolis and ...
From $568 per night (USD)
VRBO
From $300 per night (USD)
VRBO
Annapolis Escape, Steps to Harbor backs to Gate 1
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This ground floor, private entrance condo has been fully renovated w/ new paint, floors, bath & kitchen. Queen Bed & sle ...
From $300 per night (USD)
VRBO
From $779 per night (USD)
VRBO
Spacious Annapolis Abode: 507 Schley Rd Vacation Rental, Minutes from Downtown!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This lovely 4-bedroom home boasts 3 full bathrooms and room to comfortably sleep up to 12 people. With its spacious and ...
From $779 per night (USD)
VRBO
From $1070 per night (USD)
Expedia
Historic Annapolis Charmer <1Mile to NMC Stadium
Bedrooms:
4
Bathrooms:
6
Sleeps:
20
IMMACULATE SPACE AND RARE FIND IN DOWNTOWN ANNAPOLIS SLEEPING UP TO 12! Beautifully maintained 1930's home in the middl ...
From $1070 per night (USD)
Expedia
From $430 per night (USD)
VRBO
Gorgeous & bright retreat with patio, firepit, W/D, & stunning rooftop views
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Skyline Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $430 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Home Away From Home S
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Conveniently located to restaurants, shopping and other fun activities in the area. This is an ideal rental for ...
From $349 per night (USD)
Expedia
From $554 per night (USD)
VRBO
Cute bungalow blocks to Stadium
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: This stylish two bedroom home is conveniently located in Annapolis' Germantown neighborhood off West Street, ne ...
From $554 per night (USD)
VRBO
From $1535 per night (USD)
VRBO
Stately Brick Ranch On Corner Lot with Private Backyard for Entertaining
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
STR00803 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $1535 per night (USD)
VRBO
From $1583 per night (USD)
VRBO
Marvelous Home with Backyard Living Room in Murray Hill
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
NBS23-145336 Welcome to our charming vacation rental house nestled in the picturesque Murray Hill neighborhood of Annapo ...
From $1583 per night (USD)
VRBO
From $651 per night (USD)
VRBO
Eastport Oasis 4 BR 2 BA fully renovated home on quiet street with parking and gorgeous outdoor space
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $651 per night (USD)
VRBO
From $695 per night (USD)
VRBO
Fisher House: Steps From USNA + Covered Parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Summary: Welcome to our beautifully renovated historic home in the heart of Annapolis! The Fisher House, built in 1885, ...
From $695 per night (USD)
VRBO
From $626 per night (USD)
VRBO
Restriction Retreat - Relax & walk to Main St
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to the Restriction Retreat, where trouble checks in. Treat yourself and your family to five-star amenities, an u ...
From $626 per night (USD)
VRBO
From $531 per night (USD)
VRBO
Coastal Chesapeake cottage in Eastport
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Welcome to our newest listing - The Coastal Cottage on Chesapeake located in the Maritime community of Eastport . This b ...
From $531 per night (USD)
VRBO
From $909 per night (USD)
Expedia
Steps to USNA with Large Private Patio & Free Off-Site Parking
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Stay in this restored historic Annapolis home, located just steps from both USNA Gates 1 and 3. The proud Navy graduate ...
From $909 per night (USD)
Expedia
From $278 per night (USD)
VRBO
Bay Ridge house by Quiet Waters Park, Thomas Point Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Brand new home with comfortable beds, open floor plan with kitchen excellent for entertaining, and fully equipped. All f ...
From $278 per night (USD)
VRBO
From $469 per night (USD)
Expedia
Luxury Gourmet Kitchen with Backyard and Parking at 1st floor Eastport Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This beautifully upgraded one-bedroom apartment on the 1st floor of a two-flat is just steps from local popular restaura ...
From $469 per night (USD)
Expedia
From $278 per night (USD)
VRBO
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Property is 2 bedrooms and 1 bathroom furnished with brand new furniture. Bedrooms have fitted with comfortable queen si ...
From $278 per night (USD)
VRBO
From $1240 per night (USD)
Expedia
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
The Oaks Inn is an exceptional well-kept home, nestled in the heart of Historic Downtown Annapolis, that seamlessly comb ...
From $1240 per night (USD)
Expedia
Click For Pricing
VRBO
Stunning Waterfront Home with Incredible Views
Bedrooms:
5
Bathrooms:
5
Sleeps:
15
Perfect home for a family getaway, Commissioning Week or Boat Show event. Room for all to sleep, gather and play in thi ...
Click For Pricing
VRBO
From $1099 per night (USD)
VRBO
New home in historic Eastport! Steps from restaurants, retail, and more.
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Virtual tour: https://cquh.short.gy/eastportretreat Welcome to our charming Eastport retreat in Annapolis, Maryland – w ...
From $1099 per night (USD)
VRBO
From $174 per night (USD)
VRBO
2 BR home on quiet street in Eastport with lovely screened porch.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
RENT-004550-2024 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE B ...
From $174 per night (USD)
VRBO
From $238 per night (USD)
Expedia
Summer Special in Annapolis! Pristine, Peaceful, Walkable 1B/1B Apt. Sleeps 4.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Fox Haven, a bright, pristine 1 Bed/1 Bath apartment that sleeps 3-4 adults comfortably and has its own separ ...
From $238 per night (USD)
Expedia
From $482 per night (USD)
VRBO
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover this delightful three-bedroom getaway nestled within the ancient Annapolis historical area! Nestled just a 17-m ...
From $482 per night (USD)
VRBO
From $1141 per night (USD)
Expedia
Stunning Craftsman Steps to Downtown Annapolis & Spa Creek with Game Room, Parking and Backyard
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Walk to Everything Ideal for Families & Groups Welcome to your Eastport escape! Stay in this stunning, professionally d ...
From $1141 per night (USD)
Expedia
Click For Pricing
VRBO
Large House Downtown Annapolis with 2 Hot Tubs and 4 parking places
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
This Navy Themed house is located jn downtown annapolis, walking distance to all the shops and restaurants in annapolis ...
Click For Pricing
VRBO
From $1364 per night (USD)
VRBO
Fabulous Waterfront Contemporary with Rooftop Hot Tub!
Bedrooms:
3
Bathrooms:
5
Sleeps:
15
RENT-000856-2025 THIS PROPERTY IS MANAGED BY ANNAPOLIS ACOCMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL A TEAM M ...
From $1364 per night (USD)
VRBO
From $251 per night (USD)
VRBO
Newly Updated EV Charger Ready Peaceful Home in Annapolis
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Welcome to our stylish and modern home, where comfort meets convenience! Here's what you can expect during your stay: ✔ ...
From $251 per night (USD)
VRBO
Click For Pricing
Expedia
Downtown Annapolis Luxury House
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Our downtown luxury cottage is located 1.4 miles from Church Circle, which is the heart of downtown Annapolis. We are wa ...
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Expedia
Click For Pricing
VRBO
Beautifully Furnished Home, Steps to USNA Stadium, Walk to Downtown Annapolis!
Bedrooms:
2
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 ...
Click For Pricing
VRBO
From $1375 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 $1375 per night (USD)
VRBO
From $717 per night (USD)
VRBO
Charming 3-bedroom house with AC and WiFi in enchanting Annapolis/Eastport
Bedrooms:
2
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 $717 per night (USD)
VRBO
From $460 per night (USD)
Expedia
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 $460 per night (USD)
Expedia
Click For Pricing
VRBO
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 Pricing
VRBO
From $543 per night (USD)
Expedia
Ahoy! Game Room, Screened Porch, Yard Mins to DTA
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 $543 per night (USD)
Expedia
From $3306 per night (USD)
VRBO
Stunning remodel in Murray Hill
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to 9th wing (USNA reference for the boat schoolers out there!) We just completed renovations on this spacious h ...
From $3306 per night (USD)
VRBO
From $590 per night (USD)
VRBO
Darling 2 BR home with parking in the sought after Murray Hill section of Historic Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STR22-145187 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $590 per night (USD)
VRBO
From $787 per night (USD)
VRBO
Brand New Spacious Luxury Home
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
This brand-new build luxury home in Eastport close to downtown Annapolis has everything you and your guests (up to 16 to ...
From $787 per night (USD)
VRBO
From $136 per night (USD)
VRBO
Minutes from History: Room w/ Free Breakfast Near Downtown Annapolis
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $136 per night (USD)
VRBO
From $156 per night (USD)
VRBO
Our Welcoming Suite in Annapolis Near Historic Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $156 per night (USD)
VRBO
From $139 per night (USD)
VRBO
Annapolis Adventure: Room w/ Outdoor Pool + Easy Access to Historic Sites
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $139 per night (USD)
VRBO
From $472 per night (USD)
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 ...
From $472 per night (USD)
VRBO
From $513 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 $513 per night (USD)
Expedia
$Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.\n$
From $328 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 $328 per night (USD)
VRBO
From $461 per night (USD)
Expedia
Downtown Pinkney House w/Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: The Pinkney house is a 2 bedroom, 2.5 bath town home boasts an unparalleled location within close proximity to ...
From $461 per night (USD)
Expedia
From $404 per night (USD)
VRBO
Historic Annapolis Home!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
🌟 Discover the Allure of Historic Annapolis Living! 🌟 Welcome to your captivating 2-bedroom, 1.5-bath home nestled in ...
From $404 per night (USD)
VRBO
Click For Pricing
Expedia
Murray Hill beauty with short walk to Main Street
Bedrooms:
2
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 ...
Click For Pricing
Expedia
From $114 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 $114 per night (USD)
VRBO
From $114 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 $114 per night (USD)
VRBO
From $231 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 $231 per night (USD)
VRBO
From $114 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 $114 per night (USD)
VRBO
From $231 per night (USD)
VRBO
Maryland Inn 2 Doubles, Pet-Friendly, 2 Units
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 $231 per night (USD)
VRBO
From $231 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 $231 per night (USD)
VRBO
From $124 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 $124 per night (USD)
VRBO
From $121 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 $121 per night (USD)
VRBO
From $272 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 $272 per night (USD)
VRBO
From $116 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 $116 per night (USD)
VRBO
From $114 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 $114 per night (USD)
VRBO
From $121 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 $121 per night (USD)
VRBO
From $271 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 $271 per night (USD)
VRBO
From $124 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 $124 per night (USD)
VRBO
From $116 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 $116 per night (USD)
VRBO
From $112 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 $112 per night (USD)
VRBO
From $231 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 $231 per night (USD)
VRBO
From $295 per night (USD)
Expedia
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Bedrooms:
1
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 $295 per night (USD)
Expedia
From $142 per night (USD)
VRBO
Experience Historical Annapolis + Complimentary Breakfast! Outdoor Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $142 per night (USD)
VRBO
Click For Pricing
Expedia
Gorgeous House in the Heart of Annapolis, Walk to Everything!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located within walking distance of everything Annapolis has to offer, this 3BR/2.5 Bath historic Craftsman home is beaut ...
Click For Pricing
Expedia
From $1378 per night (USD)
VRBO
Eastport Classic Charm
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Welcome to our Eastport home where hardwood floors, large windows that allow ample natural light, and a cozy fi ...
From $1378 per night (USD)
VRBO
From $426 per night (USD)
Expedia
Walk to Everything - Historic Art’s District
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
HISTORIC ANNAPOLIS/ART’S DISTRICT Built in 1898, “John Stevens House” in sought-after neighborhood of President’s Hill ...
From $426 per night (USD)
Expedia
From $504 per night (USD)
VRBO
Mins to Downtown in Waterfront community at Pet-friendly Pinecrest Bungalow
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Just minutes from Downtown Annapolis, this charming Cape is located in a quiet water-privileged neighborhood with easy a ...
From $504 per night (USD)
VRBO
From $1085 per night (USD)
Expedia
On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Historic Charm Across from the Naval Academy Nestled in the heart of Downtown Annapolis, this spacious 5-bedroom, 4.5-ba ...
From $1085 per night (USD)
Expedia
From $112 per night (USD)
VRBO
Governor Calvert King, Historic Inns, Four-Poster Bed, Dining, Steps from State House
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 $112 per night (USD)
VRBO
From $484 per night (USD)
Expedia
Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This beautifully-restored 1 bedroom apartment is on the lower level of a 2-unit building in the charming Eastport neighb ...
From $484 per night (USD)
Expedia
From $1790 per night (USD)
VRBO
Spacious Converted Carriage House in Historic District near USNA
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Relax in this updated and sophisticated house near the USNA in Annapolis with the largest garden in downtown. This tranq ...
From $1790 per night (USD)
VRBO
From $483 per night (USD)
Expedia
Stay in Historic apartment 2 blocks from Main St with parking - dog-friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Still available for Commissioning Week 2025! Stay right in the heart of Historic Annapolis, just 2 blocks from Main Str ...
From $483 per night (USD)
Expedia
From $312 per night (USD)
VRBO
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
In the heart of Annapolis, where the bay breeze blows, Stands a small cottage, the Captain's Quarters, a peaceful repos ...
From $312 per night (USD)
VRBO
From $437 per night (USD)
Expedia
Historic dog-friendly home 2 blocks to Main St
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay right in the heart of Historic Annapolis, just 2 blocks from Main Street, and feel like you’re in a hotel suite wit ...
From $437 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Minutes from History: 2 Relaxing Units w/ Free Breakfast Near Downtown Annapolis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $268 per night (USD)
VRBO
From $277 per night (USD)
VRBO
Annapolis Adventure: 2 Cozy Units, Outdoor Pool + Easy Access to Historic Sites!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $277 per night (USD)
VRBO
Click For Pricing
VRBO
Amazing townhome in Annapolis, near Restaurants, USNA, Shopping centers, & more
Bedrooms:
3
Bathrooms:
3
Sleeps:
3
Amazing three bedroom townhome with Masters suite(with full bathroom), and 2 additional bedrooms with access to one full ...
Click For Pricing
VRBO
From $1180 per night (USD)
Expedia
All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to your Eastport escape! This newly decorated custom home has everything—Severn River views, a huge private ya ...
From $1180 per night (USD)
Expedia
From $612 per night (USD)
VRBO
Mins to DTA - King Beds - Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect Springtime getaway in the heart of Annapolis! This open-concept home is designed with family gat ...
From $612 per night (USD)
VRBO
From $342 per night (USD)
VRBO
2-bedroom waterfront Cottage in Annapolis, MD. Cove of Cork, view of the Severn.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Consider this charming cottage your home away from home while you visit Annapolis. Located on Cove of Cork, adjacent to ...
From $342 per night (USD)
VRBO
From $1340 per night (USD)
VRBO
Downtown Annapolis Duke's House
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: This newly renovated 4-bedroom, 3.5 bathroom home is perfectly situated in the heart of historic downtown Anna ...
From $1340 per night (USD)
VRBO
From $613 per night (USD)
VRBO
Main Street 4BR Gem – Steps to Waterfront, USNA, Shops & Dining
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Above it All - Downtown Historic Annapolis Vacation Rental on Main Street - Downtown Annapolis Retreat | 4BR Apartment ...
From $613 per night (USD)
VRBO
Click For Pricing
VRBO
Townhome steps from Main St. with private backyard patio & parking
Bedrooms:
3
Bathrooms:
2
Sleeps:
7
Welcome to City Gate, conveniently located in downtown Annapolis, just steps from all the shops and restaurants in the H ...
Click For Pricing
VRBO
From $499 per night (USD)
Expedia
Five Star Charmer! Great Location Downtown & Stadium! Parking too!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
New to the market and just in time for Navy Football. Located at the five star Corner House. Conveniently located on th ...
From $499 per night (USD)
Expedia

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