Annapolis Rentals
From $944 per night (USD)VRBO
Historic Annapolis Treasure
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Entire Home in Historic Downtown Annapolis Forget your worries in this spacious and serene enchanting Victorian home in ...
From $944 per night (USD)VRBO
From $457 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 $457 per night (USD)Expedia
From $540 per night (USD)VRBO
Darling on Dean Street- Nautical home w parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Ideally located between the vibrant West Street and the historic Main Street, our downtown Annapolis home offers easy ac ...
From $540 per night (USD)VRBO
From $554 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 $554 per night (USD)VRBO
From $479 per night (USD)VRBO
Marymont Cottage in awesome Annapolis walking distance to local pub!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Discover this adorable 3-bedroom gem in Annapolis, just across the creek from sought after West Annapolis. This charming ...
From $479 per night (USD)VRBO
From $381 per night (USD)Expedia
Newly Renovated Downtown Annapolis Charm - Game Room, Patio
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Home in the Historic District! You will be in the heart of downtown Annapolis. Walk to USNA, St. John's College, the St ...
From $381 per night (USD)Expedia
From $665 per night (USD)VRBO
Admiral's Abode - Charming Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Charming 4-bedroom, 3-bath home in the heart of downtown Annapolis! This beautifully updated property is steps from the ...
From $665 per night (USD)VRBO
From $535 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 Anna ...
From $535 per night (USD)Expedia
From $482 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 $482 per night (USD)VRBO
From $533 per night (USD)Expedia
All Star Annapolis Retreat - Walk to Stadium
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Welcome to our Town- House in Annapolis Maryland. This charming 1.5-story retreat offers 2,400 square feet of ...
From $533 per night (USD)Expedia
From $468 per night (USD)VRBO
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 $468 per night (USD)VRBO
From $602 per night (USD)Expedia
Less than 1 mile to Navy Stadium, Fenced-in Yard and Dog-Friendly Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
A new home but managed by experienced hosts, iTrip Annapolis, dedicated to exceptional hospitality. Discover the perfect ...
From $602 per night (USD)Expedia
From $583 per night (USD)VRBO
Stay in the Heart of Annapolis on King George Street Steps to USNA Gate 1 & Main Street
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Your Historic Annapolis Retreat! Discover this newly-renovated and professionally-decorated gem on the presti ...
From $583 per night (USD)VRBO
From $505 per night (USD)Expedia
Family/Group Retreat Near USNA stadium & Downtown Annapolis; Private yard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
ALL NEW! Just minutes from USNA Stadium, downtown Annapolis and US Naval Academy, MBA Homes' Nautical Oasis is perfect f ...
From $505 per night (USD)Expedia
From $1413 per night (USD)VRBO
Waterfront Oasis with pool! 4 BR home minutes from downtown Annapolis!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
STR259 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1413 per night (USD)VRBO
From $541 per night (USD)Expedia
Unique 2-Bedroom Condo in Renovated Parish House
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Step into a truly exceptional condo nestled in a beautifully preserved historic church, just two blocks from the U.S. Na ...
From $541 per night (USD)Expedia
From $396 per night (USD)VRBO
Annapolis Blue and Gold Haven
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Nestled in the heart of Annapolis, this charming 2-bedroom townhome offers the perfect blend of comfort and con ...
From $396 per night (USD)VRBO
From $213 per night (USD)VRBO
Studio Apartment in Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
19th Century Coastal charm with modern comfort! Located in the quiet and beautiful Colonial Historic District, This stud ...
From $213 per night (USD)VRBO
From $360 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 $360 per night (USD)VRBO
From $365 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, within wa ...
From $365 per night (USD)VRBO
From $370 per night (USD)VRBO
Charming apt in the heart of Eastport & Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Start your Annapolis adventure in this charming 1-bedroom apartment, comfortably accommodating up to 7 guests. Located i ...
From $370 per night (USD)VRBO
From $138 per night (USD)VRBO
Robert Johnson Queen 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 $138 per night (USD)VRBO
From $138 per night (USD)VRBO
Explore Local Attractions, 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 $138 per night (USD)VRBO
From $292 per night (USD)VRBO
Robert Johnson 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 $292 per night (USD)VRBO
From $292 per night (USD)VRBO
Experience History in Annapolis, Near Chesapeake Bay & Beaches!
- 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 $292 per night (USD)VRBO
From $136 per night (USD)VRBO
Worry-free Stay, Allergy-friendly Room, Exceeds HEPA Standards
- 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 $136 per night (USD)VRBO
From $136 per night (USD)VRBO
Robert Johnson 2 Double Beds Pure Wellness Room 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 $136 per night (USD)VRBO
From $145 per night (USD)VRBO
Robert Johnson 1 King Bed Pure Wellness Room 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 $145 per night (USD)VRBO
From $150 per night (USD)VRBO
Robert Johnson 1 Queen Bed Pure Wellness Room 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 $150 per night (USD)VRBO
From $145 per night (USD)VRBO
Prime Location! Close to Chesapeake Bay & Beaches
- 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 $145 per night (USD)VRBO
From $150 per night (USD)VRBO
Allergy-friendly Unit, Short Drive to Annapolis Westfield Mall
- 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 $150 per night (USD)VRBO
From $125 per night (USD)VRBO
Surrounded with History! Pet-friendly Accommodation
- 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 $125 per night (USD)VRBO
From $308 per night (USD)VRBO
Pet-friendly Accommodation at Historic Inns of Annapolis! Enjoy Historic Views!
- 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 $308 per night (USD)VRBO
From $125 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 $125 per night (USD)VRBO
From $308 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 $308 per night (USD)VRBO
From $198 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 $198 per night (USD)VRBO
From $197 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 $197 per night (USD)VRBO
From $280 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 $280 per night (USD)VRBO
From $197 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 $197 per night (USD)VRBO
From $198 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 $198 per night (USD)VRBO
From $280 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 $280 per night (USD)VRBO
From $1245 per night (USD)Expedia
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 $1245 per night (USD)Expedia
From $690 per night (USD)VRBO
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 $690 per night (USD)VRBO
From $383 per night (USD)Expedia
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 $383 per night (USD)Expedia
From $437 per night (USD)VRBO
Unique and central in Eastport
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Take it easy at this unique and tranquil getaway in historic Eastport. This 4-bedroom, 3-bathroom home has plenty of spa ...
From $437 per night (USD)VRBO
From $131 per night (USD)Expedia
Charming townhome with AC and WiFi in delightful Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Property is near naval Acedemy and downtown and harbourit is connected by bus route 70 and green bus and free downtown s ...
From $131 per night (USD)Expedia
Click For PricingVRBO
New Home w Luxe King Suite, Porch Vibes & Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New Beautiful Home in Downtown Annapolis’ Murray Hill Walk to Downtown with Gourmet Kitchen Welcome to your home-away-f ...
Click For PricingVRBO
From $528 per night (USD)Expedia
Modern Styled Home in Historic Annapolis Eastport Neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Built in 2021 and freshly styled in 2025 with a unique modern European touch, our family-friendly retreat offers the per ...
From $528 per night (USD)Expedia
From $375 per night (USD)VRBO
Charming 3-bedroom house in Annapolis Eastport! Beautiful fully furnished home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful fully furnished 3 bedroom, 2 bath home, available for short term rental in Eastport Annapolis! 4 minutes uber ...
From $375 per night (USD)VRBO
From $857 per night (USD)Expedia
Stunning 4 BR Home - Walking Distance to Stadium
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: This charming 4 BR home is conveniently located in Annapolis' Germantown neighborhood; within walking distance ...
From $857 per night (USD)Expedia
From $434 per night (USD)VRBO
Beautiful Historic Flat next to City Dock + USNA
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Just steps from Main Street, City Dock, and the USNA (300 ft), you'll be in the perfect location for exploring Annapolis ...
From $434 per night (USD)VRBO
From $624 per night (USD)Expedia
Annapolis Home Near Beach & Quiet Waters Park!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
Discover your next peaceful escape in our charming retreat! Nestled in a warm, inviting space, this cozy home offers bri ...
From $624 per night (USD)Expedia
From $803 per night (USD)VRBO
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 $803 per night (USD)VRBO
From $424 per night (USD)VRBO
Annapolis Academy Holiday Home
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our Academy Holiday Home, where we invite you to visit, relax, and spend time with family and friends (and yo ...
From $424 per night (USD)VRBO
From $358 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 $358 per night (USD)VRBO
From $343 per night (USD)VRBO
Historic Downtown Annapolis Gem
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
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
From $500 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 $500 per night (USD)VRBO
Click For PricingExpedia
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 ...
Click For PricingExpedia
From $421 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 $421 per night (USD)VRBO
From $343 per night (USD)Expedia
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 $343 per night (USD)Expedia
From $427 per night (USD)VRBO
Cozy Stay in Downtown Naptown -Located in the heart of Annapolis - 3BR, 2 BA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to 17 Lafayette Ave—your charming retreat in the heart of historic Annapolis! Just steps from downtown, the U.S. ...
From $427 per night (USD)VRBO
From $566 per night (USD)VRBO
Pet-Friendly & Spacious Home in Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Spacious 4BR/2.5BA home roughly 10 mins from Downtown Annapolis - close to the action, yet tucked in a quiet ne ...
From $566 per night (USD)VRBO
From $707 per night (USD)VRBO
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 $707 per night (USD)VRBO
From $625 per night (USD)Expedia
Sing Second Stays—Spacious Annapolis Home Near USNA & Navy Stadium
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Sing Second Stays, a comfortable and spacious retreat in the heart of Annapolis. Just 1.4 miles from Navy-Mar ...
From $625 per night (USD)Expedia
From $701 per night (USD)VRBO
Historic Row Home 1 Block from Gate 1 at USNA!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Summary: Steps away from the Naval Academy, St. John's College, State House, City Dock, Yacht Club, St. Mary's Church an ...
From $701 per night (USD)VRBO
From $457 per night (USD)Expedia
Dean Street's Lower Deck House!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: Welcome to our charming 1-bedroom retreat in the heart of Annapolis’ Historic District! Just steps from shops, ...
From $457 per night (USD)Expedia
From $485 per night (USD)VRBO
Annapolis Gem: Stylish and Cozy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Summary: Gather your loved ones and experience the charm of this comfortable, stylish apartment, designed for pleasure a ...
From $485 per night (USD)VRBO
From $449 per night (USD)VRBO
DTA 2 bdrm w/parking, pet friendly, great location with all of the amenities!
- Bedrooms:
- 1
- 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 $449 per night (USD)VRBO
From $407 per night (USD)VRBO
Walk to the stadium! - Lighthouse on Glenwood
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your Annapolis retreat! This fully renovated Homewood colonial is ideal for Commissioning Week, Navy games, t ...
From $407 per night (USD)VRBO
From $776 per night (USD)Expedia
Stay in the Heart of Historic Annapolis in this unique two-unit home with parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Stay right in the heart of Historic Annapolis, just 2 blocks from Main Street. This 2-unit property offers the opportun ...
From $776 per night (USD)Expedia
From $1076 per night (USD)VRBO
Spacious Historic Home with Private Parking in the Heart of Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Elegant Historic Home with Private Parking in the Heart of Downtown Annapolis Welcome to your beautifully restored retr ...
From $1076 per night (USD)VRBO
From $390 per night (USD)Expedia
Historic 3 BR Home - 15 Min Walk to N-MC Stadium
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Enjoy a true Annapolis experience at this centrally-located place close to downtown, Navy Stadium and US Naval ...
From $390 per night (USD)Expedia
From $316 per night (USD)VRBO
Annapolis Town Center Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Our charming, newly updated 2-bedroom, 2 bath cottage house in the heart of the Annapolis Town Center area is p ...
From $316 per night (USD)VRBO
From $447 per night (USD)Expedia
Historic Row Home in Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Steps away from the Naval Academy, St. John's College, State House, City Dock, Yacht Club, St. Mary's Church an ...
From $447 per night (USD)Expedia
From $452 per night (USD)VRBO
Upscale Condo in Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
See the best of Annapolis effortlessly when you book this 2-bed, 2-bath vacation rental! Equipped with all the essential ...
From $452 per night (USD)VRBO
From $1059 per night (USD)Expedia
Modern Style Meets Eastport Charm, 2BR Walkable to Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in Annapolis, this beautifully renovated house offers 2 cozy bedrooms with queen beds, 2 bathrooms with showers, ...
From $1059 per night (USD)Expedia
From $532 per night (USD)VRBO
The 1845 Outpost in Historic Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The 1845 Outpost, a comfortable, well-equipped home in the heart of Annapolis. Built in 1845, the same year ...
From $532 per night (USD)VRBO
From $688 per night (USD)Expedia
Historic Charm Meets Walkable Convenience in the Heart of Annapolis with Parking
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to your Annapolis getaway! Situated on an expansive and rare 1/2 acre homesite, this beautifully preserved home ...
From $688 per night (USD)Expedia
From $1015 per night (USD)VRBO
Downtown Annapolis History In Style Next to City Dock with Street Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the historic Strohm House, just half a block from Main Street and the City Dock, with the U.S. Naval Academy ...
From $1015 per night (USD)VRBO
From $1164 per night (USD)VRBO
2-bedroom apartment in Annapolis
- Bedrooms:
- 0
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Annapolis, this charming apartment offers a pleasant stay for guests. One bedroom and a sunroom that closes o ...
From $1164 per night (USD)VRBO
From $795 per night (USD)VRBO
Clay Street Summary:
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: This 100 year old row home is close to everything Annapolis making it easy to plan your visit. Walk to downtown ...
From $795 per night (USD)VRBO
From $645 per night (USD)Expedia
Quiet Waters Family Home 4BR Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to this charming Hillsmere Shores retreat, in one of Annapolis’ top waterfront neighborhoods. Just min ...
From $645 per night (USD)Expedia
From $698 per night (USD)VRBO
3 Bedroom/2.5 bathroom close to Naval Academy, NMCM Stadium, and downtown.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Close to US Naval Academy (1.6 mi.), Navy-Marine Corps Memorial Stadium (1.1mi), and Anne Arundel Medical Center (less t ...
From $698 per night (USD)VRBO
From $303 per night (USD)Expedia
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our 2BR, 1BA Boutique Brick Beauty located in historic Eastport. This beauty is steps from downtown, the U.S ...
From $303 per night (USD)Expedia
From $597 per night (USD)VRBO
Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Perfect home for families traveling to Annapolis! Your family will be close to everything when you stay at this central ...
From $597 per night (USD)VRBO
From $255 per night (USD)VRBO
Waterfront 2-bedroom condo in Eastport, Annapolis with private parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located just half a block from Spa Creek Draw Bridge, this first-floor condo offers water views and a relaxed, upscale a ...
From $255 per night (USD)VRBO
From $978 per night (USD)VRBO
Annapolis Halloween Escape!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Come visit The GOAT Getaway...... • walk to Navy Memorial Stadium - less than 1/2 mile • short 1 1/2 mile drive or walk ...
From $978 per night (USD)VRBO
From $673 per night (USD)Expedia
Boutique Historic Cedar Home 2 blocks from the Waterfront, USNA and Main Street
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Step into Annapolis history at this beautifully restored three-story cedar home. Built in the late 18th century, this pr ...
From $673 per night (USD)Expedia
From $896 per night (USD)VRBO
Steps from the Waterfront with Private Backyard at Historic Philip Clayton House
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Historic Philip Clayton House – Downtown Annapolis Retreat Step into Annapolis history at the Philip Clayton House, a l ...
From $896 per night (USD)VRBO
From $1396 per night (USD)Expedia
3-bedroom boat in amazing Annapolis with AC
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a soothing stay on this boat in Annapolis. This superb 3-bedroom boat features 3 queen beds, heating, and AC. Each ...
From $1396 per night (USD)Expedia
From $562 per night (USD)VRBO
Newly Renovated Eastport Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Located in Annapolis, this lovely house features 2 queen bedrooms, 2 bathrooms with showers, and a cozy living room with ...
From $562 per night (USD)VRBO
From $402 per night (USD)Expedia
Serene Boutique Home near Annapolis Downtown/USNA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
10 mins Annapolis | United States Naval Academy A Serene, Family-Friendly Retreat Near the Water. 3BR, 2BA haven nestled ...
From $402 per night (USD)Expedia
From $762 per night (USD)VRBO
Walk Everywhere From New Eastport Cape Cod with High-End finishes and Gourmet Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Eastport Cape Cod – Walk to Downtown Annapolis Welcome to your Annapolis retreat! This all-new Cape Cod in the heart of ...
From $762 per night (USD)VRBO
From $677 per night (USD)Expedia
Historic Annapolis Retreat – Steps from the Statehouse & City Dock with Parking and Private Patio
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
In the shade of the Maryland Statehouse, this historic home has welcomed family, friends, and travelers for more than 17 ...
From $677 per night (USD)Expedia
From $353 per night (USD)VRBO
Pet Friendly Annapolis Stay Walk to DTA & Stadium
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Enjoy the best of Annapolis from this centrally located, pet-friendly home. Walk to Downtown Annapolis, Navy ta ...
From $353 per night (USD)VRBO
From $320 per night (USD)VRBO
1 Block to USNA Stadium: Modern Annapolis Home!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Central Location | New Build | In-Unit Laundry | Fire Pit | 2 Mi to USNA Settle into this Annapolis vacation rental tha ...
From $320 per night (USD)VRBO
From $380 per night (USD)VRBO
Eastport Private Suite – 1 mi to USNA & Downtown, Near Boat Shows & Comm Week
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Goat House, a secure and modern private suite in Eastport, just 1 mile from the U.S. Naval Academy and mi ...
From $380 per night (USD)VRBO
From $509 per night (USD)Expedia
Waterfront Condo with Views of Annapolis, Pool & Prime Eastport Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Wake up to sparkling water views and the charm of historic Annapolis right outside your window. This 3rd-floor waterfron ...
From $509 per night (USD)Expedia
From $655 per night (USD)VRBO
Fabulous 5-bedroom house with AC in charming Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Looking to explore Annapolis and live comfortably on a budget? This cozy square house will be just right for you! The si ...
From $655 per night (USD)VRBO
From $1142 per night (USD)Expedia
Spacious Waterfront 5-bedroom house in charming Annapolis with Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Your Fun Filled getaway awaits in Annapolis at this Phenomenal Waterfront House with Hot Tub! With 5 bedrooms including ...
From $1142 per night (USD)Expedia