Anne Arundel Area Rentals
From $735 per night (USD)VRBO
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Summary: This is a gorgeous home with in ground *heated* "6 month" pool & "9 month" hot tub - less than a mile walk fro ...
From $735 per night (USD)VRBO
From $982 per night (USD)VRBO
Cottage for Rent
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Cottage for Rent xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx ...
From $982 per night (USD)VRBO
From $1724 per night (USD)VRBO
Beautiful colonial only 3 miles to the Naval Academy!
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
Beautiful colonial perfect for Naval Academy commissioning week! Bedrooms 6 - Baths: 2.5 Sleeps 11 comfortably. Finish ...
From $1724 per night (USD)VRBO
From $957 per night (USD)VRBO
Annapolis gem with beautiful outdoor dining! Near U.S. Naval Academy
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
In Annapolis this charming 3-bedroom home is moments away from USNA Stadium, and the Naval Academy, and picturesque Cit ...
From $957 per night (USD)VRBO
From $442 per night (USD)VRBO
Historic district home, View of the Capital, WALK Downtown, w/ Outdoor Dining!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
*** WE ARE COMPLIANT WITH THE CITY OF ANNAPOLIS!!! Strict short term rental rules are in place for this area. We are pro ...
From $442 per night (USD)VRBO
From $511 per night (USD)Expedia
Belle By The Bay Summ
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Escape to Annapolis in this stylish home, perfect for large groups! Enjoy a private brick patio with a fire pi ...
From $511 per night (USD)Expedia
From $369 per night (USD)VRBO
Cool Spring waterfront apartment with pier mins to Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the Difference: Professionally Managed by iTrip Annapolis The charming, newly-furnished waterfront Suite is ...
From $369 per night (USD)VRBO
From $808 per night (USD)VRBO
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully renovated home in the heart of West Annapolis. The main level has been updated to an open floor plan to acco ...
From $808 per night (USD)VRBO
From $441 per night (USD)VRBO
Welcome to our newly built house
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This is a brand new house (built in June of 2022) Located in hearth of the beautiful city of Glen Burnie. Minutes from B ...
From $441 per night (USD)VRBO
From $542 per night (USD)Expedia
Eastport Charmer Summ
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Your family will be close to everything when you stay at this charming 2-bedroom cottage nestled in the Eastpo ...
From $542 per night (USD)Expedia
From $1372 per night (USD)VRBO
Luxury Waterfront Annapolis home with your very own Private Beach & Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Stunning Contemporary Home with private beach! House has been listed on another site receiving five st ...
From $1372 per night (USD)VRBO
From $295 per night (USD)Expedia
Pet Friendly Water View Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Escape to our updated 2-bed, 2-bath cottage in a charming Pasadena water privileged neighborhood. Comfortably ...
From $295 per night (USD)Expedia
From $411 per night (USD)VRBO
Charming Charles -Walkable Downtown Annapolis Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Escape to your private oasis in this stylish 2-bed, 2.5-bath townhome in the heart of Downtown Annapolis. This ...
From $411 per night (USD)VRBO
From $802 per night (USD)Expedia
A Private Luxury Spa Retreat in Severn, MD.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Step into a Private Luxury Spa Retreat in Severn, MD, centrally located between Washington DC, Columbia, Baltimore, and ...
From $802 per night (USD)Expedia
From $167 per night (USD)VRBO
Cheerful 2 Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to this relaxing home for your getaway. It is perfect for vacations, retreats, meetings, family visits, and BUSI ...
From $167 per night (USD)VRBO
From $300 per night (USD)Expedia
Waterfront Unit | Dock, Kayaks & SUPs Included
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Wake up on the water in this brand-new guest unit between Casa Rio Marina and West River Yacht Club. Dock your ...
From $300 per night (USD)Expedia
From $130 per night (USD)VRBO
Indulge in Home Like Comfort! Full Kitchen, Pet-Friendly Property
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Comfortable rooms near Baltimore attractions with a free airport shuttle service This listing is for a room within a ho ...
From $130 per night (USD)VRBO
From $438 per night (USD)Expedia
Restful and Charming Home in Eastport
- 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 $438 per night (USD)Expedia
From $511 per night (USD)VRBO
Cozy Private Family Palace near BWI, Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Have fun with the whole family at this stylish place curated by ImmaBe Real Estates. Conveniently located close to diver ...
From $511 per night (USD)VRBO
From $246 per night (USD)Expedia
Waterfront CHeerful 2 with Private Pier
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to this relaxing home by the water for your getaway. It is perfect for vacations, retreats, meetings, family vis ...
From $246 per night (USD)Expedia
From $855 per night (USD)VRBO
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Discover 'The Crabby Patty,' a spacious 3-BR, 2.5-BA home in the heart of downtown Annapolis. Blending modern ...
From $855 per night (USD)VRBO
From $470 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 $470 per night (USD)Expedia
From $578 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 $578 per night (USD)VRBO
From $3127 per night (USD)VRBO
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Why rent a hotel when you can be in a Floatel on a Fountaine Pajot Saba luxurious 50 foot catamaran six Cabin six head l ...
From $3127 per night (USD)VRBO
From $654 per night (USD)VRBO
Downtown Fleet St home with garage parking EV Walk to USNA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
Friends! We are a USNA family (‘92) and love this town! Walk to bottom of Fleet Street and you are at the docks. Walk to ...
From $654 per night (USD)VRBO
From $362 per night (USD)Expedia
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
| OVERVIEW | Welcome aboard FLOHOM 3 | Bung-a-flo, a Bohemian-inspired floating tiny home docked at the scenic Ferry P ...
From $362 per night (USD)Expedia
From $593 per night (USD)VRBO
13 Mi to Annapolis: Dog-Friendly Home w/ Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Furnished Deck | Fenced Backyard | In-Unit Laundry | 25 Mi to Washington, D.C. Book this Crofton home-away-from-home! W ...
From $593 per night (USD)VRBO
From $684 per night (USD)VRBO
Charming Eastport CapeCod
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful Cape Code made for entertaining, this Eastport home is perfect for your next trip to Annapolis! Newly renovate ...
From $684 per night (USD)VRBO
From $1758 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 $1758 per night (USD)VRBO
From $1386 per night (USD)Expedia
Historic Annapolis Charmer <1Mile to NMC Stadium
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 20
IMMACULATE SPACE AND RARE FIND IN DOWNTOWN ANNAPOLIS SLEEPING UP TO 12! Beautifully maintained 1930's home in the middl ...
From $1386 per night (USD)Expedia
From $113 per night (USD)VRBO
Baltimore Adventure Awaits! Prime Location, Pets Allowed, Fully Kitchen!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Comfortable rooms near Baltimore attractions with a free airport shuttle service This listing is for a room within a ho ...
From $113 per night (USD)VRBO
From $130 per night (USD)VRBO
Central Baltimore Gem, Kitchen, Pet-Friendly Property, Explore Inner Harbor!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Comfortable rooms near Baltimore attractions with a free airport shuttle service This listing is for a room within a ho ...
From $130 per night (USD)VRBO
From $714 per night (USD)VRBO
Historic Annapolis Home | 2 Blocks to Main St
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Summary: Historic 1885 row home two blocks from Main Street and steps from the U.S. Naval Academy. Three bedrooms acros ...
From $714 per night (USD)VRBO
From $566 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 $566 per night (USD)VRBO
From $636 per night (USD)VRBO
Coastal Chesapeake cottage in Eastport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our newest listing - The Coastal Cottage on Chesapeake located in the Maritime community of Eastport . This b ...
From $636 per night (USD)VRBO
From $1977 per night (USD)VRBO
Welcoming Waterfront Luxury Estate for Family, Friends, and Pets in Annapolis
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Large Waterfront Family Estate House in an Old Oak Forest at the end of a private gated Community in Annapolis. Architec ...
From $1977 per night (USD)VRBO
From $596 per night (USD)VRBO
Steps to USNA with Large Private Patio & Free Off-Site Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Stay in this restored historic Annapolis home, loc ...
From $596 per night (USD)VRBO
From $279 per night (USD)Expedia
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 $279 per night (USD)Expedia
From $1738 per night (USD)VRBO
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
The Oaks Inn is a well-kept home, built in 1860 with original hardwood floors. It is nestled in the heart of Historic Do ...
From $1738 per night (USD)VRBO
From $502 per night (USD)VRBO
Winter Retreat Near Naval Academy+ Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
◉ 5-min stroll to private beach ◉ Dock access for your boat ◉ Gourmet kitchen + private chef (by request) ◉ Stunning ...
From $502 per night (USD)VRBO
From $515 per night (USD)VRBO
Peaceful home overlooking a quiet cove--perfect getaway!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Visiting the Kayak Cove is all you could want for a relaxing stay. Our cottage is located on a peaceful cove where you ...
From $515 per night (USD)VRBO
From $365 per night (USD)Expedia
Arts District - Peaceful, Sparkling, 1 Bed/1 Bath, Walk to Navy Stadium and Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Fox Haven, a bright, pristine 1 Bed/1 Bath apartment that sleeps 3 adults comfortably and has its own separat ...
From $365 per night (USD)Expedia
From $373 per night (USD)VRBO
Relaxing Waterfront Apartment!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Welcome to our Bayhouse StayApartment! Our waterfront getaway features a large dock where you can relax on Adirondack ch ...
From $373 per night (USD)VRBO
From $596 per night (USD)Expedia
Creek-Side Bliss: Unwind and Create Lasting Memories at Our Beautiful Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to our little slice of tranquility by the creek! Picture this: you wake up to the gentle murmur of the nearby cr ...
From $596 per night (USD)Expedia
From $943 per night (USD)VRBO
Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 13
Welcome to our waterfront oasis on Parish’s Creek just off of the Chesapeake Bay! Our spacious house is the perfect retr ...
From $943 per night (USD)VRBO
From $274 per night (USD)Expedia
Sailboat Experience in Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Choosingthis C and C 33 sailboat for your stay is opting for an experience over extravagance. It's about immersing yours ...
From $274 per night (USD)Expedia
From $514 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 $514 per night (USD)VRBO
From $1259 per night (USD)Expedia
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 18
Turning Point on the Little Magothy is a wonderful and private Estate that sleeps 18 comfortably! Turning Point on the ...
From $1259 per night (USD)Expedia
From $580 per night (USD)VRBO
Ahoy! Game Room, Screened Porch, Yard Mins to DTA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to The Buccaneer, a family-friendly home l ...
From $580 per night (USD)VRBO
From $233 per night (USD)VRBO
Water view studio. 20 minutes from Annapolis.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This property is an efficiency that sits on top of a garage in a quiet neighborhood. The perfect place to stay while ta ...
From $233 per night (USD)VRBO
From $424 per night (USD)VRBO
Bayfront Maryland Retreat w/ Deck, Near Beaches!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Days spent relaxing on the sandy shores, exploring the local shops and eateries along The Boardwalk, or visiting The Wal ...
From $424 per night (USD)VRBO
From $790 per night (USD)Expedia
The General's House-Spacious Home w/Pool & Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: Look no further for your next vacation home in Annapolis! Relax, unwind or entertain friends and family in thi ...
From $790 per night (USD)Expedia
From $138 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 $138 per night (USD)VRBO
From $158 per night (USD)VRBO
Our Welcoming Suite in Annapolis Near Historic Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This listing is for a room within a hotel. ✦ Your room is 957 sq. ft, equipped with complimentary toiletries, standard ...
From $158 per night (USD)VRBO
From $138 per night (USD)VRBO
Annapolis Adventure: Room w/ Outdoor Pool + Easy Access to Historic Sites
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 484 sq. ft, equipped with complimentary toiletries, standard ...
From $138 per night (USD)VRBO
From $547 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 $547 per night (USD)Expedia
From $718 per night (USD)VRBO
Stay Mins from Annapolis in Luxury Waterfront Home on Deep Water w Private Pier & Gourmet Kitchen
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Experience the Difference: Professionally Managed by iTrip Annapolis Prepare to be spoiled at this custom-renovated lux ...
From $718 per night (USD)VRBO
From $189 per night (USD)VRBO
Maryland Inn 2 Double Beds | Historic Inns | 0.3 Mi to Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $189 per night (USD)VRBO
Real Maryland Unit | 0.3 Mi to Banneker-Douglass Museum | Steps to State Capitol
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $370 per night (USD)VRBO
2 Maryland Units | Perfect for Historic Getaways | Pets are Allowed
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $370 per night (USD)VRBO
From $189 per night (USD)VRBO
Authentic 18th Century Hotel Near US Naval Academy - Walking Distance
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $367 per night (USD)VRBO
Maryland Inn 2 Doubles | Pet-Friendly | 2 Units
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $367 per night (USD)VRBO
From $370 per night (USD)VRBO
2 Maryland Inn Units at Historic Inns of Annapolis | Waterfront Vicinity
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $370 per night (USD)VRBO
From $197 per night (USD)VRBO
Just Steps from Waterfront | Robert Johnson King | 0.3mi to US Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $197 per night (USD)VRBO
From $197 per night (USD)VRBO
Unique Victorian Stay | Steps from Waterfront | 0.1mi to State House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $197 per night (USD)VRBO
From $325 per night (USD)VRBO
Robert Johnson Townhouse | 0.1mi State House | 0.3mi Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $325 per night (USD)VRBO
From $189 per night (USD)VRBO
Governor Calvert 2 Double Beds | Historic Inns | Near Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $189 per night (USD)VRBO
Maryland Inn King, Historic Inns, Elegant Dining, Waterfront Proximity
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $197 per night (USD)VRBO
Robert Johnson 2 Double Beds | Historic Inns | 0.8 miles to Cheston Avenue Wharf
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $197 per night (USD)VRBO
From $329 per night (USD)VRBO
Robert Johnson Townhouse | 0.2mi to Main Street Shops & 0.3mi to Waterfront
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $329 per night (USD)VRBO
From $197 per night (USD)VRBO
Robert Johnson King | Historic Inns | Near Top Dining & City Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $197 per night (USD)VRBO
From $189 per night (USD)VRBO
Charming Downtown Hotel Room w/ Vintage Character + Historic Site
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $189 per night (USD)VRBO
Elegant Boutique Hotel Near Maryland State House - Short Walk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $367 per night (USD)VRBO
2 Historic Ambiance Stays for Perfect Getaways | Pets Are Allowed
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $367 per night (USD)VRBO
From $354 per night (USD)VRBO
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 $354 per night (USD)VRBO
From $1007 per night (USD)Expedia
Waterfront Sanctuary only 50 Min. From DC/Balt.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
New listing on VRBO!! Please see other sites for 50+ reviews on this property. New full home renovation with gourmet ki ...
From $1007 per night (USD)Expedia
From $842 per night (USD)VRBO
Family Home on Mayo Peninsula | Deck | Sleeps 10
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Renovated home on the Mayo Peninsula sleeping 10 - ideal for large families and groups. Master bedroom with tw ...
From $842 per night (USD)VRBO
From $219 per night (USD)Expedia
Wright's Cottage- Pet's Welcome & EV Charging
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: We offer a very tiny, mostly original, cottage built in the 1940’s. Located in the community of Bon Haven, larg ...
From $219 per night (USD)Expedia
From $522 per night (USD)VRBO
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 $522 per night (USD)VRBO
From $603 per night (USD)Expedia
Mins to Downtown in Waterfront community at Pet-Friendly Pinecrest Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Just minutes from Downtown Annapolis, this charmin ...
From $603 per night (USD)Expedia
From $659 per night (USD)VRBO
Stay at Waterfront Home with Pier & Community Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Discover the perfect waterfront escape near Annapo ...
From $659 per night (USD)VRBO
From $1943 per night (USD)Expedia
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 $1943 per night (USD)Expedia
From $625 per night (USD)VRBO
Historic Suite 2 Blocks from Main St with On-Site Parking & Dog-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Still available for Commissioning Week 2025! ...
From $625 per night (USD)VRBO
From $428 per night (USD)Expedia
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 $428 per night (USD)Expedia
From $1394 per night (USD)VRBO
6 bedroom waterfront home minutes from Downtown Annapolis!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Nestled on the Magothy River with a plunge pool and hot tub. Large outdoor patio with bar, grill, and gas fire pit. We a ...
From $1394 per night (USD)VRBO
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Rock Creek Cottage, Waterfront, Serene Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Rock Creek Cottage. Serene views from the deck and dock of deep water Rock Creek, by the Patapsco River and C ...
Click For PricingExpedia
From $846 per night (USD)VRBO
Charming 3-bedroom house in Annapolis two blocks from the Navy Stadium
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Peaceful house on a quiet street two blocks from the Navy Stadium with easy access to downtown Annapolis via the stadium ...
From $846 per night (USD)VRBO
From $936 per night (USD)VRBO
Private 4-bedroom house in Annapolis, great location!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Your home away from home in Annapolis with 4 bedrooms. Under 2 miles to the Naval Academy! This spacious home is located ...
From $936 per night (USD)VRBO
From $129 per night (USD)VRBO
Charming 1-bedroom house in wonderful Severn with office, WiFi, fitness room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Escape to this brilliant house in picturesque Severn. This welcoming property features a cozy bedroom with a king bed, a ...
From $129 per night (USD)VRBO
From $692 per night (USD)Expedia
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 $692 per night (USD)Expedia
From $376 per night (USD)VRBO
Charming 3-bedroom house in Hanover with WiFi and AC
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
This pleasant house in Hanover offers 3 cozy bedrooms - 2 with queen beds and 1 with a twin bed. With 2 bathrooms equipp ...
From $376 per night (USD)VRBO
From $304 per night (USD)Expedia
Secluded Tiny Pool House -Private Pool -Self Check in
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Secluded Tiny Guest House Retreat with Private Pool – Near Baltimore & Annapolis As you pull into the driveway, the city ...
From $304 per night (USD)Expedia
From $595 per night (USD)VRBO
Steps to Marinas & Shops w Parking in Eastport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Eastport's Third Time's the Charm – Steps from Mar ...
From $595 per night (USD)VRBO
From $840 per night (USD)VRBO
South River Retreat- Go Navy!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Located across the bridge from Annapolis. This home is located in a beautiful water privileged neighborhood on the South ...
From $840 per night (USD)VRBO
From $438 per night (USD)VRBO
Charming on Charles Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our elegant stand alone charming home on Charles Street in Historic Annapolis. This 3 bedroom 2.5 bath is jus ...
From $438 per night (USD)VRBO
From $362 per night (USD)Expedia
Cozy Cottage with Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Perfect for groups of 4 wanting to be near Annapolis and the Chesapeake Bay, but far enough away for peace, quiet, and e ...
From $362 per night (USD)Expedia
From $555 per night (USD)VRBO
Edgewater's Shelby on the Bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to our newly updated 4 bedroom, 3.5 bath coastal beauty w/beautiful views of the South River! Situate ...
From $555 per night (USD)VRBO
From $1198 per night (USD)Expedia
Waterfront- 5-bedroom house with dock in charming North Beach
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 18
Experience an unforgettable vacation in this newly listed waterfront 5-bedroom house. This beautiful property offers ple ...
From $1198 per night (USD)Expedia
From $459 per night (USD)VRBO
Walking distance to Navy Stadium! No cleaning fees!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This centrally located 3-story rental is steps away from everything Annapolis offers! Whether you're in town to explore ...
From $459 per night (USD)VRBO
From $331 per night (USD)VRBO
Cozy & Modern Getaway Upper Level Suite in Arnold
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your home away from home! Located in the charming town of Arnold, MD, this beautifully designed, modern retre ...
From $331 per night (USD)VRBO