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Results: 484 Rentals

  • Maryland Inn Queen at Historic Inns of Annapolis, Pets Allowed
    From $290 per night (USD)

    VRBO

    Maryland Inn Queen at Historic Inns of Annapolis, Pets Allowed

    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 $290 per night (USD)

    VRBO

    Details
  • Maryland Inn Suite at Historic Inns of Annapolis, Pet-friendly
    From $856 per night (USD)

    VRBO

    Maryland Inn Suite at Historic Inns of 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 $856 per night (USD)

    VRBO

    Details
  • Top Location! Accommodation Close to Annapolis Historic Sites!
    From $440 per night (USD)

    VRBO

    Top Location! Accommodation Close to Annapolis Historic Sites!

    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 $440 per night (USD)

    VRBO

    Details
  • Governor Calvert King Balcony at Historic Inns of Annapolis
    From $341 per night (USD)

    VRBO

    Governor Calvert King Balcony at Historic Inns of Annapolis

    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 $341 per night (USD)

    VRBO

    Details
  • Governor Calvert Suite at Historic Inns of Annapolis
    From $586 per night (USD)

    VRBO

    Governor Calvert Suite at Historic Inns of Annapolis

    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 $586 per night (USD)

    VRBO

    Details
  • Right Where History Is! Just Across Maryland State House
    From $499 per night (USD)

    VRBO

    Right Where History Is! Just Across Maryland 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 $499 per night (USD)

    VRBO

    Details
  • Governor Calvert Historic King at Historic Inns of Annapolis
    From $377 per night (USD)

    VRBO

    Governor Calvert Historic King at Historic Inns of Annapolis

    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 $377 per night (USD)

    VRBO

    Details
  • Historic Architecture In and Out, Memorable Stay
    From $641 per night (USD)

    VRBO

    Historic Architecture In and Out, Memorable Stay

    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 $641 per night (USD)

    VRBO

    Details
  • Oasis by the Bay - Waterfront Heated Pool Hot Tub!
    From $2113 per night (USD)

    VRBO

    Oasis by the Bay - Waterfront Heated Pool Hot Tub!

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    18

    Summary: Located only 5 miles from Annapolis, this newly updated, 3-story home with great views of the Chesapeake Bay is ...

    From $2113 per night (USD)

    VRBO

    Details
  • New Eastport home with parking, dog-friendly & steps to shops with backyard
    From $566 per night (USD)

    Expedia

    New Eastport home with parking, dog-friendly & steps to shops with backyard

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    New listing available for Commissioning Week 2025! Charming 1905 Eastport Duplex: Historic Character Meets Modern Comfo ...

    From $566 per night (USD)

    Expedia

    Details
  • Timeless Charm Meets Modern Comfort
    From $417 per night (USD)

    VRBO

    Timeless Charm Meets Modern Comfort

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This charming 3-bedroom, 2.5 bath historic duplex in downtown Annapolis offers a perfect blend of timeless character and ...

    From $417 per night (USD)

    VRBO

    Details
  • Charming Annapolis Townhome
    From $691 per night (USD)

    Expedia

    Charming Annapolis Townhome

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Summary: Historic Annapolis Living! Welcome to your captivating 2-bedroom, 1.5-bath home. This stunning retreat offers a ...

    From $691 per night (USD)

    Expedia

    Details
  • Historic Row Home 1 Block from Gate 1 at USNA!
    From $744 per night (USD)

    VRBO

    Historic Row Home 1 Block from Gate 1 at USNA!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Steps away from the Naval Academy, St. John's College, State House, City Dock, Yacht Club, St. Mary's Church an ...

    From $744 per night (USD)

    VRBO

    Details
  • Dean Street's Lower Deck House!
    From $449 per night (USD)

    Expedia

    Dean Street's Lower Deck House!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Welcome to our charming 1-bedroom retreat in the heart of Annapolis’ Historic District! Just steps from shops, ...

    From $449 per night (USD)

    Expedia

    Details
  • Annapolis Gem: Stylish and Cozy
    From $475 per night (USD)

    VRBO

    Annapolis Gem: Stylish and Cozy

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Gather your loved ones and experience the charm of this comfortable, stylish apartment, designed for pleasure a ...

    From $475 per night (USD)

    VRBO

    Details
  • Modern condo in the heart of DTA with garage parking!
    From $491 per night (USD)

    Expedia

    Modern condo in the heart of DTA with garage parking!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Stay in the heart of downtown Annapolis in this bright, modern 2 bed, 2 bath condo with your own private balcony—just st ...

    From $491 per night (USD)

    Expedia

    Details
  • Walking distance to Navy Stadium! No cleaning fees!
    From $505 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 $505 per night (USD)

    VRBO

    Details
  • Walk to the stadium! - Lighthouse on Glenwood
    From $377 per night (USD)

    Expedia

    Walk to the stadium! - Lighthouse on Glenwood

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to your Annapolis retreat! This fully renovated Homewood colonial is ideal for Commissioning Week, Navy games, t ...

    From $377 per night (USD)

    Expedia

    Details
  • Charming Annapolis Retreat with Hidden Wine Room
    From $580 per night (USD)

    VRBO

    Charming Annapolis Retreat with Hidden Wine Room

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Discover charm in our 2BR, 1BA Eastport home, just a stroll away from downtown Eastport (under 1 mile), Downtow ...

    From $580 per night (USD)

    VRBO

    Details
  • Historic Downtown Annapolis Gem
    From $343 per night (USD)

    VRBO

    Historic Downtown Annapolis Gem

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Summary: Experience historic charm with modern upgrades in this 2-bed, 2.5-bath home in the heart of Downtown Annapolis. ...

    From $343 per night (USD)

    VRBO

    Details
  • Pet-Friendly Home Near USNA Stadium with Parking
    From $828 per night (USD)

    VRBO

    Pet-Friendly Home Near USNA Stadium with Parking

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Summary: Discover the charm of West Annapolis in our 4 bed, 2 bath home. Just steps away from dining, shops, and the new ...

    From $828 per night (USD)

    VRBO

    Details
  • Charming Rental in the Heart of Annapolis
    From $268 per night (USD)

    Expedia

    Charming Rental in the Heart of Annapolis

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Summary: Charming studio guest house in the heart of Eastport, just half a mile from downtown Annapolis and steps away f ...

    From $268 per night (USD)

    Expedia

    Details
  • Charming Annapolis Waterfront Condo
    From $463 per night (USD)

    VRBO

    Charming Annapolis Waterfront Condo

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Discover the charm of CAPTAINS QUARTERS, your exclusive waterfront retreat in the prestigious Yacht Club Condom ...

    From $463 per night (USD)

    VRBO

    Details
  • Charming Annapolis Home with Cozy Outdoor Hangout
    From $359 per night (USD)

    VRBO

    Charming Annapolis Home with Cozy Outdoor Hangout

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Freshly renovated 2BR/2BA home in Eastport, Annapolis. Sleeps 6 with brand-new furniture. Enjoy the spacious fe ...

    From $359 per night (USD)

    VRBO

    Details
  • DTA 2 bdrm w/parking, pet friendly, great location with all of the amenities!
    From $480 per night (USD)

    VRBO

    DTA 2 bdrm w/parking, pet friendly, great location with all of the amenities!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This 2-bedroom non-investor house has everything you need for a great stay! We live there part time so it’s not an empty ...

    From $480 per night (USD)

    VRBO

    Details
  • Boat-N-Breakfast! Luxurious Accommodations Aboard a 44' Catamaran
    From $484 per night (USD)

    VRBO

    Boat-N-Breakfast! Luxurious Accommodations Aboard a 44' Catamaran

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The most fun way to visit America's Sailing Capital, on the water accommodations aboard the sailcat Zep Tepi! Our cata ...

    From $484 per night (USD)

    VRBO

    Details
  • \The Studio\ Apartment in Colonial Historic District, Annapolis
    From $227 per night (USD)

    VRBO

    \"The Studio\" Apartment in Colonial Historic District, Annapolis

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    19th Century Coastal charm with modern comfort! Located in the quiet and beautiful Colonial Historic District, The Condu ...

    From $227 per night (USD)

    VRBO

    Details
  • \The Flat\ Apartment in Colonial Historic District, Annapolis.
    From $367 per night (USD)

    VRBO

    \"The Flat\" Apartment in Colonial Historic District, Annapolis.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    19th Century Coastal charm with modern comfort! Located in the quiet and beautiful Colonial Historic District, The Condu ...

    From $367 per night (USD)

    VRBO

    Details
  • The Penthouse
    From $380 per night (USD)

    VRBO

    The Penthouse

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    19th Century Coastal charm with modern comfort! Located in the quiet and beautiful Colonial Historic District, The Condu ...

    From $380 per night (USD)

    VRBO

    Details
  • Charming 2-bedroom apartment with WiFi, AC, kitchen, wash/dryer in Annapolis.
    From $305 per night (USD)

    VRBO

    Charming 2-bedroom apartment with WiFi, AC, kitchen, wash/dryer in Annapolis.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    Unwind in Annapolis at this charming 2 bedroom apartment. Master bedroom includes a queen bed and second smaller fits a ...

    From $305 per night (USD)

    VRBO

    Details
  • Spacious home in historic Annapolis, near USNA
    From $484 per night (USD)

    VRBO

    Spacious home in historic Annapolis, near USNA

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    Located in Annapolis, enjoy what this 3-bedroom house has to offer. With 2 queen beds and 2 twin bed, guests can relax i ...

    From $484 per night (USD)

    VRBO

    Details
  •  Beautiful 7BR home minutes from downtown Annapolis
    From $1276 per night (USD)

    Expedia

    Beautiful 7BR home minutes from downtown Annapolis

    Bedrooms:
    6
    Bathrooms:
    7
    Sleeps:
    14

    Newly renovated modern colonial on several acres just minutes from downtown Annapolis and the Naval Academy. Chefs kitch ...

    From $1276 per night (USD)

    Expedia

    Details
  • Upscale home in Eastport / Annapolis
    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

    Details
  • Cheerful 3-Bedroom House in Downtown Annapolis
    From $317 per night (USD)

    Expedia

    Cheerful 3-Bedroom House in Downtown Annapolis

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Private 3 floor house located at the edge of Annapolis historic district. You can be certain that you will have all the ...

    From $317 per night (USD)

    Expedia

    Details
  • Charming Historic Annapolis Home
    Click For Pricing

    VRBO

    Charming Historic Annapolis Home

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This delightful historic home is situated directly across the street from the Paca House, and only three blocks from the ...

    Click For Pricing

    VRBO

    Details
  • Waterfront 2BR Guest House on Cypress Creek - Severna Park
    From $560 per night (USD)

    Expedia

    Waterfront 2BR Guest House on Cypress Creek - Severna Park

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    3

    STR00626 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...

    From $560 per night (USD)

    Expedia

    Details
  • Elegant waterfront cottage and guest house,  garden setting, clubhouse and beach
    Click For Pricing

    VRBO

    Elegant waterfront cottage and guest house, garden setting, clubhouse and beach

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy waterfront views from every window, crabbing from the pier, sundowners on the wrap around porch, set in a private ...

    Click For Pricing

    VRBO

    Details
  • Perfect Eastport Location, walk everywhere, Annapolis
    From $335 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 $335 per night (USD)

    VRBO

    Details
  • Water taxi just mins to Downtown Annapolis from waterfront home with a beach, dog-friendly
    From $928 per night (USD)

    VRBO

    Water taxi just mins to Downtown Annapolis from waterfront home with a beach, dog-friendly

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Watch the sunrise on the private beach at Oh Happy Bay. The quaint two-story, cottage has a private beach on historic Be ...

    From $928 per night (USD)

    VRBO

    Details
  • Newly renovated historic Annapolis house.  walking distance to navy stadium, DTA
    From $1102 per night (USD)

    Expedia

    Newly renovated historic Annapolis house. walking distance to navy stadium, DTA

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    A perfect harmony of classic and modern, this newly renovated property has a quintessential Annapolis feel. Nestled in t ...

    From $1102 per night (USD)

    Expedia

    Details
  • Chesapeake Comfort, Annapolis.
    From $497 per night (USD)

    VRBO

    Chesapeake Comfort, Annapolis.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Annapolis Bungalow Home that is professionally cleaned and is a full time short-term rental. I have been a Superhost wit ...

    From $497 per night (USD)

    VRBO

    Details
  • Luxury Waterfront Annapolis home with your very own Private Beach & Dock
    From $1203 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 $1203 per night (USD)

    VRBO

    Details
  • Charming  Annapolis home in Eastport, Now available Commissioning Week!
    Click For Pricing

    VRBO

    Charming Annapolis home in Eastport, Now available Commissioning Week!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    This delightful restored home is just 3 blocks away from the Eastport Bridge and 1.3 miles away from the Naval Academy ...

    Click For Pricing

    VRBO

    Details
  • Cottage for Rent
    From $896 per night (USD)

    Expedia

    Cottage for Rent

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Cottage for Rent xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx ...

    From $896 per night (USD)

    Expedia

    Details
  • Historic Annapolis With Parking
    From $1077 per night (USD)

    VRBO

    Historic Annapolis With Parking

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Historic home with off-street parking for three cars and three blocks from the USNA. Across the Street from St. John Co ...

    From $1077 per night (USD)

    VRBO

    Details
  • Peaceful Home in Annapolis
    Click For Pricing

    Expedia

    Peaceful Home in Annapolis

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    11

    Relax with the whole family at this peaceful place to stay. A quaint 4-bedroom home tucked away on 2.2 acres. Enjoy the ...

    Click For Pricing

    Expedia

    Details
  • Charming Home located minutes from the Naval Academy and Downtown Annapolis
    From $618 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 $618 per night (USD)

    VRBO

    Details
  • Private yard and screened porch at Historic happy home, steps to Main Street with parking
    From $637 per night (USD)

    Expedia

    Private yard and screened porch at Historic happy home, steps to Main Street with parking

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic ...

    From $637 per night (USD)

    Expedia

    Details
  • Cozy Bungalow w/ Ample Outdoor Space Near Downtown
    From $247 per night (USD)

    VRBO

    Cozy Bungalow w/ Ample Outdoor Space Near Downtown

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to my charming Annapolis home in Eastport! My cozy 1 bed/1 bath house features a versatile spare room perfect fo ...

    From $247 per night (USD)

    VRBO

    Details
  • BY THE BAY
    From $792 per night (USD)

    Expedia

    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 $792 per night (USD)

    Expedia

    Details
  • BAY RIDGE MODERN HOME WITH VINTAGE CHARM
    From $896 per night (USD)

    VRBO

    BAY RIDGE MODERN HOME WITH VINTAGE CHARM

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Beautiful spacious modern family home with vintage charm. A great gathering spot for family or just wanting to spend som ...

    From $896 per night (USD)

    VRBO

    Details
  • 3 bdrm close to city center, great yard & parking!
    From $615 per night (USD)

    VRBO

    3 bdrm close to city center, great yard & parking!

    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 $615 per night (USD)

    VRBO

    Details
  • Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard
    From $822 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

    Welcome to this mid-century modern, Cape Cod in West Annapolis. This "Ralph-Lauren Cottage" exudes that "Annapolitan fee ...

    From $822 per night (USD)

    VRBO

    Details
  • Luxe Houseboat: Breathtaking Skyline 360 Views
    From $740 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 $740 per night (USD)

    Expedia

    Details
  • Beautiful colonial only 3 miles to the Naval Academy!
    From $1264 per night (USD)

    VRBO

    Beautiful colonial only 3 miles to the Naval Academy!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    11

    Beautiful colonial perfect for Naval Academy commissioning week! Bedrooms 6 - Baths: 2.5 Sleeps 11 comfortably. Finish ...

    From $1264 per night (USD)

    VRBO

    Details
  • Historic Home with Parking Steps From Capital & USNA
    From $344 per night (USD)

    Expedia

    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 $344 per night (USD)

    Expedia

    Details
  • Charming West Annapolis Cottage home
    From $516 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 $516 per night (USD)

    VRBO

    Details
  • Eastport Charmer Summ
    From $450 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 Eastpor ...

    From $450 per night (USD)

    Expedia

    Details
  • Belle By The Bay Summ
    From $340 per night (USD)

    VRBO

    Belle By The Bay Summ

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Summary: This lovely home has 3 bedrooms, 2.5 bathrooms, fully equipped kitchen with large island that seats 4 and an ou ...

    From $340 per night (USD)

    VRBO

    Details
  • Waterfront home with scenic porches, yard, grill, jetted tub, central AC, & W/D
    From $1030 per night (USD)

    Expedia

    Waterfront home with scenic porches, yard, grill, jetted tub, central AC, & W/D

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    The Salty Crab Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...

    From $1030 per night (USD)

    Expedia

    Details
  • Luxury Home with Private Backyard, Parking and Easy Walk to Restaurants, Shops and Stadium
    From $812 per night (USD)

    VRBO

    Luxury Home with Private Backyard, Parking and Easy Walk to Restaurants, Shops and Stadium

    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 $812 per night (USD)

    VRBO

    Details
  • Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1/2 bathrooms.
    Click For Pricing

    Expedia

    Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1/2 bathrooms.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Cozy cottage in a serene setting. A week spent in this cottage will decompress, reset, and rejuvenate. 100 year old Cott ...

    Click For Pricing

    Expedia

    Details
  • The Crabby Patty Summ
    From $736 per night (USD)

    VRBO

    The Crabby Patty Summ

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Nestled in the heart of historic downtown Annapolis, this three-bedroom home offers a perfect blend of modern c ...

    From $736 per night (USD)

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  • Mulberry's Gem
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    Mulberry's Gem

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    This is your home away from home. All the comforts you could need. The open concept living space is the perfect spot to ...

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  • Walk Everywhere! Your Ultimate Annapolis Retreat on Horn Point
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    Walk Everywhere! Your Ultimate Annapolis Retreat on Horn Point

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Escape to your ideal rental property at 125 Chester Avenue, located in the desirable neighborhood of Horn Point in Annap ...

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  • Beautiful 6 BR home on quiet, secluded lot, overlooking the Severn River
    From $2513 per night (USD)

    VRBO

    Beautiful 6 BR home on quiet, secluded lot, overlooking the Severn River

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    STR00749 - Heaven on the Severn � THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED ...

    From $2513 per night (USD)

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  • Pet Friendly - Stone's throw from City Dock w private back patio
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    Pet Friendly - Stone's throw from City Dock w private back patio

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    This well-appointed recently-renovated home in the heart of Annapolis is located just steps from both the Capitol and Ci ...

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  • Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit
    From $451 per night (USD)

    Expedia

    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 $451 per night (USD)

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  • Annapolis Retreat - 7 mins from downtown Annapolis!
    From $636 per night (USD)

    VRBO

    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 $636 per night (USD)

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  • Home Away From Home S
    From $296 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 $296 per night (USD)

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  • Cozy Annapolis Abode: 507 Schley Rd Vacation Rental, Minutes from Downtown!
    From $855 per night (USD)

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    Cozy Annapolis Abode: 507 Schley Rd Vacation Rental, Minutes from Downtown!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Property Highlights: This lovely 4-bedroom home boasts 3 full bathrooms and room to comfortably sleep up to 12 people. ...

    From $855 per night (USD)

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  • Serene, riverfront home with deck, balcony, kitchen & fireplace - dog-friendly
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    Expedia

    Serene, riverfront home with deck, balcony, kitchen & fireplace - dog-friendly

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Severn View of Serenity Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...

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  • Modern studio apartment 5 minute walk to downtown Annapolis
    From $357 per night (USD)

    VRBO

    Modern studio apartment 5 minute walk to downtown Annapolis

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Modern efficiency apartment with king bed, seating area with 2 recliner chairs for watching TV. Set up for remote work ...

    From $357 per night (USD)

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  • Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!
    From $1220 per night (USD)

    Expedia

    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 $1220 per night (USD)

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  • Hideaway in the middle of everything
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    Hideaway in the middle of everything

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Clean, spacious Eastport cottage in a prime location to downtown Annapolis and the United States Naval Academy. Both are ...

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  • Free Parking at Townhome 1 Block to Capital Bldg with Multiple Gathering Spaces & Private Backyard
    From $628 per night (USD)

    Expedia

    Free Parking at Townhome 1 Block to Capital Bldg with Multiple Gathering Spaces & Private Backyard

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Naptown Nook, conveniently located in downtown Annapolis, just steps from all the shops and restaurants in th ...

    From $628 per night (USD)

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  • MODERN 2022 NEWLY BUILT TOWNHOME
    From $846 per night (USD)

    VRBO

    MODERN 2022 NEWLY BUILT TOWNHOME

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy a stylish experience at this centrally-located and newly-built (2022) Eastport Annapolis townhome. Spacious two li ...

    From $846 per night (USD)

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  • Pristine Downtown 1-Bedroom Steps from State House
    From $269 per night (USD)

    Expedia

    Pristine Downtown 1-Bedroom Steps from State House

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Enjoy your stay in the heart of Annapolis's historic district, steps away from the Maryland State House and a few minute ...

    From $269 per night (USD)

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    Details
  • Annapolis Vacation Home: 2 Mi to Quiet Waters Park
    From $489 per night (USD)

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    Annapolis Vacation Home: 2 Mi to Quiet Waters Park

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    The Chesapeake Bay awaits you at this Annapolis vacation rental! 'Admiral's Post' is situated under 4 miles from the cit ...

    From $489 per night (USD)

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  • Beautiful waterfront home on The Chesapeake Bay with private dock & beach access
    From $1326 per night (USD)

    Expedia

    Beautiful waterfront home on The Chesapeake Bay with private dock & beach access

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Annapolis Bay Ridge Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...

    From $1326 per night (USD)

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  • Beautiful Cottage Style Home in Quiet Downtown Neighborhood
    From $634 per night (USD)

    VRBO

    Beautiful Cottage Style Home in Quiet Downtown Neighborhood

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    This is a beautiful house for your stay in Annapolis! This large fully renovated house is just off West Street, 1.5 mil ...

    From $634 per night (USD)

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  • 2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace
    From $909 per night (USD)

    Expedia

    2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Harrison Hall Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...

    From $909 per night (USD)

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  • Annapolis 4 BR w/ Gameroom & fire pits-walk everywhere!
    From $954 per night (USD)

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    Annapolis 4 BR w/ Gameroom & fire pits-walk everywhere!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    13

    This is the perfect house for your family friendly visit to Annapolis, MD Enjoy everything the sought after Eastport ne ...

    From $954 per night (USD)

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  • Huge deck overlooking water
    From $1059 per night (USD)

    Expedia

    Huge deck overlooking water

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Renovated, charming Annapolis home on half-acre lot fronting Burley Creek. Just a short paddle to Whitehall Bay and expa ...

    From $1059 per night (USD)

    Expedia

    Details
  • Lakefront home with private dock, deck, hot tub, firepit, Ping-Pong, large yard
    From $4463 per night (USD)

    VRBO

    Lakefront home with private dock, deck, hot tub, firepit, Ping-Pong, large yard

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    16

    Base Camp on the Lake Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...

    From $4463 per night (USD)

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  • Lakefront dog-friendly home with private outdoor pool, pool spa, dock & grill
    From $1739 per night (USD)

    Expedia

    Lakefront dog-friendly home with private outdoor pool, pool spa, dock & grill

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    The Morning Watch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...

    From $1739 per night (USD)

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  • Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D
    From $1652 per night (USD)

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    Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    The Admiral's Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...

    From $1652 per night (USD)

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  • Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill
    From $1533 per night (USD)

    Expedia

    Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    The Master Shipwright Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...

    From $1533 per night (USD)

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  • Cozy Home in Beautiful Annapolis
    From $209 per night (USD)

    VRBO

    Cozy Home in Beautiful Annapolis

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Keep it simple at this peaceful and centrally located Annapolis home. It has all the amenities and essentials of a home ...

    From $209 per night (USD)

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  • Charming brick home with patio, WiFi, AC, & W/D - walk to everything
    From $400 per night (USD)

    Expedia

    Charming brick home with patio, WiFi, AC, & W/D - walk to everything

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    The Little House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...

    From $400 per night (USD)

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  • Downtown furnished apartment - walking distance to restaurants
    From $299 per night (USD)

    VRBO

    Downtown furnished apartment - walking distance to restaurants

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Church owned 2nd Floor apartment in historic house - fully furnished - eat-in kitchen, dining room and living room - has ...

    From $299 per night (USD)

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  • NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
    From $521 per night (USD)

    Expedia

    NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Come enjoy a relaxing stay in our coastal waterfront cottage in Epping Forest! Just steps from a community pier perfec ...

    From $521 per night (USD)

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  • Indoor Soft Hot Tub - Family Stay @ The Cape!
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    Indoor Soft Hot Tub - Family Stay @ The Cape!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Make some memories at this unique and family-friendly place. Family Friendly Staycation fully outfitted to accommodate ...

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  • COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
    From $359 per night (USD)

    Expedia

    COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Located in the heart of Annapolis' historic district sits this one bedroom, 1.5 bath cozy apartment. A mere stone's thr ...

    From $359 per night (USD)

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  • Quiet Home Close to Downtown Annapolis and Parks
    From $377 per night (USD)

    VRBO

    Quiet Home Close to Downtown Annapolis and Parks

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Summary: This private single family home is located on a quarter acre and is just minutes to everything Annapolis has to ...

    From $377 per night (USD)

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  • West Annapolis Cottage
    From $1086 per night (USD)

    Expedia

    West Annapolis Cottage

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    14

    Summary: Recently renovated, this is the perfect location for your family & friends to enjoy Naval Academy events, boat ...

    From $1086 per night (USD)

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  • Annapolis Garden Suite
    From $319 per night (USD)

    VRBO

    Annapolis Garden Suite

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to our little oasis! We're tucked away on a beautiful residential street yet 7 minutes away from restaurants, co ...

    From $319 per night (USD)

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    Details
  • Historic Downtown House with Off Street Parking
    From $406 per night (USD)

    Expedia

    Historic Downtown House with Off Street Parking

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    Spacious living with all the modern amenities. Prime location - 1 block from the water, restaurants, and shops. Park you ...

    From $406 per night (USD)

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  • Cheerful 1 bedroom w pool
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    Cheerful 1 bedroom w pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Cozy one bedroom with pool outdoor eating space and expansive yard for the kids to play in. Private bedroom, bathroom, a ...

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  • Charming Historic Townhouse Steps From USNA
    From $287 per night (USD)

    Expedia

    Charming Historic Townhouse Steps From USNA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to our charming home nestled next to the prestigious Naval Academy in Annapolis. This inviting 1-bedroom, 1-bath ...

    From $287 per night (USD)

    Expedia

    Details