Anne Arundel Area Rentals
From $695 per night (USD)VRBO
Escape Villa in Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Perfect getaway, a short stroll to West Street, the Naval Academy, Navy-Marine Corps Memorial Stadium, City Dock, and Do ...
From $695 per night (USD)VRBO
From $338 per night (USD)Expedia
Searenity Stays, a Cozy Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy 3 Bd, 2 Bth Near Chesapeake Bay, Parks & Playgrounds Currently decorated for Christmas! (Decor to be removed after ...
From $338 per night (USD)Expedia
From $1215 per night (USD)VRBO
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The location is ideal - one short block to USNA Gate 3, and just 4 blocks to the downtown waterfront. Home has a privat ...
From $1215 per night (USD)VRBO
From $336 per night (USD)Expedia
Annapolis Charm –Bright 3BR in Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to this spacious and fully furnished home, designed to be your comfortable home away from home. Spanning three l ...
From $336 per night (USD)Expedia
From $758 per night (USD)VRBO
4BR-Gameroom-Firepit-Gym-Walkable-Sleeps 13
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
This is the perfect house for your family friendly visit to Annapolis! *Please no bachelor/bachelorette parties Enjoy ...
From $758 per night (USD)VRBO
From $546 per night (USD)VRBO
Annapolis Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious three level home in water privileged community of Cape St. Claire Maryland. Perfect for traveling health profe ...
From $546 per night (USD)VRBO
From $444 per night (USD)VRBO
Charming 1926 Four Bedroom Home w Ample Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A centrally located home that exceeds all needs and comfort or your family. Both cozy and spacious from well thought ou ...
From $444 per night (USD)VRBO
From $996 per night (USD)Expedia
House near Patapsco River 2700 square feet
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Paradise Beach Retreat Whether you're planning to explore Pasadena, Annapolis, Baltimore, or Washington, DC, this stunn ...
From $996 per night (USD)Expedia
From $632 per night (USD)VRBO
Historic Happy Home Steps from Main Street w Private Yard, Screened-In Porch & Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Enjoy a piece of Annapolis history! Nestled at the ...
From $632 per night (USD)VRBO
From $467 per night (USD)Expedia
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Bring your boat, your fishing gear, and your appetite for coastal charm! This 3BR/2BA Annapolis cottage offers access to ...
From $467 per night (USD)Expedia
From $535 per night (USD)VRBO
HiddenParadise in Scenic community, mins to attractions & WaterFront. Sleeps 9
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
**Absolutely no parties allowed in the unit. Family unit celebrations ok but must be discussed with host ahead of time. ...
From $535 per night (USD)VRBO
From $651 per night (USD)Expedia
Waterfront home with private pier mins to Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Enjoy the magnificent waterfront views from this c ...
From $651 per night (USD)Expedia
From $495 per night (USD)VRBO
Brand-new Modern Pasadena Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This cozy new home is located in the heart of Pasadena on a quiet end in Rivera Beach, just a few houses away from publi ...
From $495 per night (USD)VRBO
From $142 per night (USD)Expedia
Spacious Private Basement
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
New to Vrbo!! Private basement w/entrance. Great for PCS season. Just few miles away from Baltimore downtown, Ft Meade, ...
From $142 per night (USD)Expedia
From $695 per night (USD)VRBO
Modern Bay Dream
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy the Chesapeake Bay in this brilliant 3-bedroom, 3-bathroom mid-century modern home nestled in the heart of Deale, ...
From $695 per night (USD)VRBO
From $150 per night (USD)VRBO
Stunning four-bedroom town home located in Millersville
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
This property is a Stunning four-bedroom town home that can accommodate up to 9 guests comfortably. The bedrooms are wel ...
From $150 per night (USD)VRBO
From $433 per night (USD)VRBO
Perfect Eastport Location, walk everywhere, Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Leave your car behind and walk to everything Annapolis, Eastport is full of charm, Restaurants, Museums, live music. Com ...
From $433 per night (USD)VRBO
From $662 per night (USD)Expedia
Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Watch the sunrise on the private beach at Oh Happy ...
From $662 per night (USD)Expedia
From $903 per night (USD)VRBO
A quiet, family retreat home on the Chesapeake Bay, south of Annapolis MD
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
A perfect spot for relaxing, reading, and writing, or as a home-base for visiting the many cultural and natural attracti ...
From $903 per night (USD)VRBO
From $936 per night (USD)VRBO
Pristine Waterfront Home with Expansive Views.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
**Monthly discounts only apply for Off-Season rentals (October-April) If relaxing in luxury on the water is what you a ...
From $936 per night (USD)VRBO
From $1038 per night (USD)VRBO
Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 18
Unique opportunity to rent an entire triplex Downtown Annapolis! One property with 3 nearly identical side-by-side uni ...
From $1038 per night (USD)VRBO
From $1136 per night (USD)VRBO
Beautiful Blend of Restoration and Renovation in this Downtown Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this newly updated rental home, a stunning blend of renovation and restoration located in the heart of the Hi ...
From $1136 per night (USD)VRBO
From $882 per night (USD)VRBO
BY THE BAY
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
WATER, WATER everywhere! Our home is centrally located to all the water Bay Ridge has to offer. Our home is located jus ...
From $882 per night (USD)VRBO
From $131 per night (USD)VRBO
Comfort and Convenience! Pet-friendly Unit with Fully equipped Kitchen!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Comfort and convenience. It’s like you never left home. This listing is for a room within a hotel. ✦ Your room is 505 ...
From $131 per night (USD)VRBO
From $651 per night (USD)VRBO
3 bdrm close to city center, great yard & parking! Perfect for cooks and pets!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Approx .7 mile to stadium, 1.4 to Naval Academy. Walk to free shuttle at Park Place and to great coffee every morning fr ...
From $651 per night (USD)VRBO
From $422 per night (USD)Expedia
18th Cent. Charm in Historic Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lower level furnished apartment, in one of Historic Annapolis's 10 oldest Private residences. Lovely wood, brick & ornam ...
From $422 per night (USD)Expedia
From $732 per night (USD)VRBO
Secluded Cozy Cottage in Historic Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Beautifully restored 1930s cottage w/ open floor plan & vaulted ceilings provide a homey vibe Enjoy having Historic Ann ...
From $732 per night (USD)VRBO
From $515 per night (USD)Expedia
Historic 3 Bedroom Downtown Annapolis Townhome
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Be close to everything when you stay at this centrally-located, historic townhome! Located steps from the Naval Academy, ...
From $515 per night (USD)Expedia
From $296 per night (USD)VRBO
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming 3 bedroom, 2 bathroom private cottage is situated in a friendly community along the beautiful Chesapeake Bay. ...
From $296 per night (USD)VRBO
From $387 per night (USD)Expedia
The Hideaway Spot- Waterfront w/ Dock on Long Cove
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Take a moment to unplug in nature with beautiful waterfront views! Perfect space for a family of four, two adult couples ...
From $387 per night (USD)Expedia
From $1684 per night (USD)VRBO
Waterfront Architectural Masterpiece with private dockage available.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Heron Point House is an owner imagined home, designed by one of the region's leading architects and built to perfection. ...
From $1684 per night (USD)VRBO
From $139 per night (USD)VRBO
Nautical Adventure Awaits in Annapolis Suites! Pets Allowed Here! Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Modern family units with private kitchens for the ultimate Annapolis experience This listing is for a room within a hot ...
From $139 per night (USD)VRBO
From $582 per night (USD)VRBO
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to this mid-century modern, Cape Cod in We ...
From $582 per night (USD)VRBO
From $113 per night (USD)VRBO
Your Home Base for Exploring Charm City! Fully-equipped Kitchen, Pets Allowed!
- 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 $1035 per night (USD)VRBO
Walk to the Naval Academy and Historic Annapolis. Private parking at the home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our favorite part of this home is its unbeatable location in downtown Annapolis (DTA)- with private parking. You can wa ...
From $1035 per night (USD)VRBO
From $736 per night (USD)VRBO
Charming Home located minutes from the Naval Academy and Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Private 4BR, 2.5BA luxurious Gem was recently upgraded, and tastefully decorated awaits your arrival. The ranch style ho ...
From $736 per night (USD)VRBO
From $508 per night (USD)VRBO
Prime Eastport Location - Waterfront Condo w Pool & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Experience the Difference: Professionally Managed by iTrip Annapolis Waterfront Condo with Spa Creek Views, Rooftop Poo ...
From $508 per night (USD)VRBO
From $608 per night (USD)Expedia
Walk to Main St, City Dock, USNA from Historic Catch 22 w Private Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Experience the Difference: Professionally Managed by iTrip Annapolis This charming 3-BR, 2.5-BA townhome is just a 1/2- ...
From $608 per night (USD)Expedia
From $1868 per night (USD)VRBO
On the Waterfront Luxury Chalet w Multiple Suites, Private Pier and Hot Tub in Edgewater
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 15
Experience the Difference: Professionally Managed by iTrip Annapolis Escape to this spectacular custom-built waterfront ...
From $1868 per night (USD)VRBO
From $624 per night (USD)Expedia
Luxe Houseboat: Breathtaking Skyline 360 Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
| OVERVIEW | Welcome to FLOHOM 1 | Bay Escape, your home away from shore! Our luxury houseboat is docked at the premie ...
From $624 per night (USD)Expedia
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 $1824 per night (USD)VRBO
LUXE Private Waterfront Retreat with Pool, Hot Tub and Game Room for Family Fun
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Experience the Difference: Professionally Managed by iTrip Annapolis Family Rental only! This brand new custom hom ...
From $1824 per night (USD)VRBO
From $442 per night (USD)Expedia
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)Expedia
From $511 per night (USD)VRBO
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)VRBO
From $369 per night (USD)Expedia
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)Expedia
From $546 per night (USD)VRBO
Entire contemporary, luxury 4 level Town House in Gorgeous, quiet neighborhood
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
This special place is close to everything, making it easy to plan your visit. Located in gorgeous quite neighborhood min ...
From $546 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 $190 per night (USD)VRBO
Enjoy a Hassle-Free Stay! Pet-Friendly, Close to William Paca Garden
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Modern family units with private kitchens for the ultimate Annapolis experience This listing is for a room within a hot ...
From $190 per night (USD)VRBO
From $542 per night (USD)VRBO
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)VRBO
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 $313 per night (USD)VRBO
Historic Home with Parking Steps From Capital & USNA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to this vibrant downtown Annapolis oasis—a unique purple parallelogram with a parking spot. From the front door, ...
From $313 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 $178 per night (USD)VRBO
Always a Great Idea To Unwind! Pet-Friendly, w/ Pool, Free Breakfast!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Comfort and convenience. It’s like you never left home. This listing is for a room within a hotel. ✦ Your room is 768 ...
From $178 per night (USD)VRBO
From $349 per night (USD)VRBO
Spacious Good-Value Accommodation! 2 Relaxing Units, w/ Pool, Free Breakfast!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
Comfort and convenience. It’s like you never left home. This listing is for 2 separate rooms within a hotel. The price ...
From $349 per night (USD)VRBO
From $531 per night (USD)VRBO
Indulge in Home Like Comfort! 3 Comfortable Units, w/ Pool, Free Breakfast!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 15
Comfort and convenience. It’s like you never left home. This listing is for 3 separate rooms within a hotel. The price ...
From $531 per night (USD)VRBO
From $141 per night (USD)VRBO
Best Value, Quality Stay! Free Breakfast, w/ Pool, Near M&T Bank Stadium!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Comfort and convenience. It’s like you never left home. This listing is for a room within a hotel. ✦ Your room is 538 ...
From $141 per night (USD)VRBO
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 $776 per night (USD)Expedia
Renovated Bungalow | Walk to Beach | Dog-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Walk to Edgewater Park and Historic London Town & Gardens from this fully renovated bungalow with a loft, new ...
From $776 per night (USD)Expedia
From $300 per night (USD)VRBO
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)VRBO
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)VRBO
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)VRBO
From $511 per night (USD)Expedia
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)Expedia
From $246 per night (USD)VRBO
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)VRBO
From $855 per night (USD)Expedia
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)Expedia
From $11327 per night (USD)VRBO
South River Waterfront | Pier, Hot Tub & Elevator
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Three-story waterfront home on the South River with a private pier, hot tub, elevator, and balconies on every ...
From $11327 per night (USD)VRBO
From $432 per night (USD)VRBO
Glen Burnie Haven: Your Tranquil Home Away from Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to our charming 4-bedroom, 2-bathroom rambler-style retreat in Glen Burnie, MD! Nestled in a quiet neighborhood ...
From $432 per night (USD)VRBO
From $666 per night (USD)VRBO
Navy Weekend Haven, Family-Friendly Luxury Home w Fenced-in Backyard & Parking
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to Your Luxury West Annapolis Retreat! N ...
From $666 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 $557 per night (USD)VRBO
Sunny and spacious water view/access home in Annapolis.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The property is all set up for boating and fishing with a drive-thru driveway. It is located one block from the boat ram ...
From $557 per night (USD)VRBO
From $578 per night (USD)Expedia
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)Expedia
From $426 per night (USD)VRBO
Glen Burnie Vacation Rental w/ Private Deck!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the best of the East Coast from this spacious 3-bed, 4-bath vacation rental in Glen Burnie. Located just a shor ...
From $426 per night (USD)VRBO
From $1276 per night (USD)VRBO
Six bedroom 2020 Fountaine Pajot catamaran
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Beautiful 6 bedroom 6 bathroom catamaran just miles from downtown Annapolis on the South River from June to November. Sa ...
From $1276 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)Expedia
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)Expedia
From $362 per night (USD)VRBO
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)VRBO
From $669 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 $669 per night (USD)Expedia
From $257 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 $257 per night (USD)VRBO
From $593 per night (USD)Expedia
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)Expedia
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)VRBO
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)VRBO
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 $526 per night (USD)Expedia
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, a ...
From $526 per night (USD)Expedia
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Mins to Annap; Luxury Townhome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Visiting the Annapolis area? Stay in style in this very spacious 3-bed, 3.5-bath 3-level townhouse. Sleeps 8 very comfor ...
Click For PricingVRBO
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)Expedia
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)Expedia
From $279 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 $279 per night (USD)VRBO
From $481 per night (USD)Expedia
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 $481 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