Anne Arundel Area Rentals
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 $385 per night (USD)Expedia
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Discover the enchanting allure of Safe Harbor at Herring Bay – an impeccably renovated haven tailored for group adventur ...
From $385 per night (USD)Expedia
From $365 per night (USD)VRBO
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)VRBO
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)VRBO
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)VRBO
From $386 per night (USD)Expedia
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
This home is located 17 miles from both Annapolis and Ellicott City, 38 miles from Washington DC, and 15 miles from Balt ...
From $386 per night (USD)Expedia
From $1191 per night (USD)VRBO
Walk to Downtown Annapolis & Spa Creek from Stunning Craftsman with Game Room, Parking and Backyard
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Experience the Difference: Professionally Managed by iTrip Annapolis Walk to Everything Ideal for Families & Groups ...
From $1191 per night (USD)VRBO
From $617 per night (USD)Expedia
Liberty Call has multiple gathering spaces, screened-in porch and parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Experience the Difference: Professionally Managed by iTrip Annapolis Located less than 15 minutes from Downtown Annapol ...
From $617 per night (USD)Expedia
From $426 per night (USD)VRBO
Spacious Home w/ Tranquil Patio ~ 29 Mi to DC!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Visit vibrant downtown Baltimore attractions or Washington, D.C. when you stay at this elegant 5-bedroom, 3-bathroom vac ...
From $426 per night (USD)VRBO
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)VRBO
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)VRBO
From $518 per night (USD)Expedia
Annapolis Spacious Family Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Just minutes from Sandy Point Beach and a short 15 minute drive to the US Naval Academy, this 4 story home has ...
From $518 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 $1141 per night (USD)VRBO
Historic Luxury Steps to USNA + Vibrant Waterfront
- 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 $1141 per night (USD)VRBO
From $424 per night (USD)Expedia
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)Expedia
From $790 per night (USD)VRBO
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)VRBO
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)VRBO
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)VRBO
From $420 per night (USD)Expedia
Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.
- 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 $420 per night (USD)Expedia
From $485 per night (USD)VRBO
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 $485 per night (USD)VRBO
From $718 per night (USD)Expedia
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)Expedia
From $564 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 $564 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 $143 per night (USD)VRBO
Experience Historical Annapolis + Complimentary Breakfast! Outdoor Pool!
- 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 $143 per night (USD)VRBO
From $1007 per night (USD)VRBO
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)VRBO
From $883 per night (USD)VRBO
Waterfront 5 Bedroom Near BWI/Annapolis/Baltimore
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Escape to paradise in this stunning 5-bedroom private waterfront oasis, only 20 minutes from BWI airport, US Naval Acade ...
From $883 per night (USD)VRBO
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 $642 per night (USD)VRBO
Enchanting West River Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our charming waterfront cottage nestled on the serene shores of the West River! Perfectly positioned with a 3 ...
From $642 per night (USD)VRBO
From $522 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 $522 per night (USD)Expedia
From $603 per night (USD)VRBO
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)VRBO
From $824 per night (USD)Expedia
Steps to USNA Gate 3, On-Site Parking & Private Patio at Historic Gatehouse
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Experience the Difference: Professionally Managed by iTrip Annapolis Historic Charm Across from the Naval Academy Nes ...
From $824 per night (USD)Expedia
From $189 per night (USD)VRBO
Governor Calvert King | Historic Inns | 0.3 Mi to City Dock | Dogs Allowed
- 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 $530 per night (USD)Expedia
Walk to Shops & Dining from Dog-Friendly Apartment w Parking & Private Backyard
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the Difference: Professionally Managed by iTrip Annapolis This beautifully-restored 1 bedroom apartment is o ...
From $530 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 $574 per night (USD)VRBO
Historic dog-friendly home 2 blocks to Main St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the Difference: Professionally Managed by iTrip Annapolis Stay right in the heart of Historic Annapolis, jus ...
From $574 per night (USD)VRBO
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
Click For PricingVRBO
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 PricingVRBO
From $276 per night (USD)VRBO
Minutes from History: 2 Relaxing Units w/ Free Breakfast Near Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Dive into Annapolis's rich heritage, just minutes from the US Naval Academy and historic downtown. Discover state landma ...
From $276 per night (USD)VRBO
From $275 per night (USD)VRBO
Annapolis Adventure: 2 Cozy Units, Outdoor Pool + Easy Access to Historic Sites!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Dive into Annapolis's rich heritage, just minutes from the US Naval Academy and historic downtown. Discover state landma ...
From $275 per night (USD)VRBO
From $846 per night (USD)Expedia
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)Expedia
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 $425 per night (USD)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 ...
From $425 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 $1056 per night (USD)Expedia
Luxury Home w Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to your Eastport escape! This newly ...
From $1056 per night (USD)Expedia
From $692 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 $692 per night (USD)VRBO
From $2525 per night (USD)Expedia
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 Ann ...
From $2525 per night (USD)Expedia
From $804 per night (USD)VRBO
Multi-unit Waterfront Home with Private Pool, Pier & Parking Mins to Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to this beautiful waterfront home in the q ...
From $804 per night (USD)VRBO
From $376 per night (USD)Expedia
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)Expedia
From $304 per night (USD)VRBO
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)VRBO
From $585 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 $585 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 $384 per night (USD)Expedia
Naval Academy Gate 1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This 2-bed, 1.5-bath townhome mixes modern renovations with 1900 classic charm. It's been lovingly decorated to accommod ...
From $384 per night (USD)Expedia
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)VRBO
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)VRBO
From $555 per night (USD)Expedia
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)Expedia
From $1198 per night (USD)VRBO
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)VRBO
From $459 per night (USD)Expedia
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)Expedia
From $321 per night (USD)VRBO
Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This home is located approximately 17 miles from both Annapolis and Ellicott City, 38 miles from Washington DC, and 15 m ...
From $321 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
From $514 per night (USD)VRBO
5-Star BWI Hanover 3-Level With Bonus Living Space
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
🚗 Prime Location: * BWI Airport: 15 minutes * Fort Meade: 10 minutes * Baltimore Inner Harbor: 25 minutes * Downtown D ...
From $514 per night (USD)VRBO
From $814 per night (USD)VRBO
Charming 4-bedroom house 2 blocks from the Navel Academy Stadium
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This 4-bedroom house in Annapolis is perfect for your escape to relaxation. With 4 queen beds and 3 bathrooms equipped w ...
From $814 per night (USD)VRBO
From $616 per night (USD)VRBO
Pet Friendly-newly built house in peaceful beach community, located in Riva MD.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy all that Annapolis has to offer in this stylish house located in Riva MD, just ten mins from downtown Annapolis, ...
From $616 per night (USD)VRBO
From $774 per night (USD)Expedia
Londontowne Home | Beach | 3BR
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Community beach access and a gated playground - all included with this 3-bedroom Edgewater home. The Londontow ...
From $774 per night (USD)Expedia
From $638 per night (USD)VRBO
Walk to Lake & Boat Ramp: Central Gem in Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Pet Friendly w/ Fee | Home Office Space | 7 Mi to United States Naval Academy Experience the best of Maryland when you ...
From $638 per night (USD)VRBO
From $578 per night (USD)Expedia
Cozy apartment in Historic Annapolis with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This Annapolis apartment is located within walking distance of everything Annapolis has to offer. Located just outside ...
From $578 per night (USD)Expedia
From $205 per night (USD)VRBO
Spacious 3-Bedroom, 1.5-Bath Home in Central Maryland with Screened Porch & More
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
This charming 3-bedroom, 1.5-bathroom home in central Maryland offers comfort and convenience for every guest. The fully ...
From $205 per night (USD)VRBO
From $578 per night (USD)Expedia
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Our 1700s home offers a perfect blend of luxury and comfort. With three beautiful bedrooms, three bathrooms, and a sleek ...
From $578 per night (USD)Expedia
From $153 per night (USD)VRBO
Quiet Apt w/ Private Deck, Near DC & Baltimore
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: Enjoy a stylish experience at this centrally-located place. 1BD 1BA APT is attached to the main home. Totall ...
From $153 per night (USD)VRBO
From $479 per night (USD)Expedia
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 15
Summary: This charming 5 BR (3x true bedrooms and 2x basement rooms with bunk beds) home is conveniently located in Ann ...
From $479 per night (USD)Expedia
From $475 per night (USD)VRBO
Charming Historic Row House in The Heart of Eastport's Horn Point
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this stunning historic rowhouse located in the charming and highly sought-after neighborhood of Horn Point Ea ...
From $475 per night (USD)VRBO
From $194 per night (USD)Expedia
Charming Lower Level Guest Unit, Fully Equipped Kitchen, WiFi, Free onsite park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Charming One Bedroom apartment on the Lower Level in a serene setting just minutes from Downs Park, trail, and the sceni ...
From $194 per night (USD)Expedia
From $952 per night (USD)VRBO
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Walk to Navy-Marine Corps Memorial Stadium from this 2,400 sq ft renovated home with a finished 930 sq ft base ...
From $952 per night (USD)VRBO
From $544 per night (USD)Expedia
Newly renovated in DTA w parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom, 2.5-bath single-family home mixes modern renovations with 1896 classic charm. It's been decorated with u ...
From $544 per night (USD)Expedia