Annapolis, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Annapolis, Maryland on RentalSaver.com!

Annapolis Rentals

From $396 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 $396 per night (USD)
VRBO
From $320 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 $320 per night (USD)
VRBO
From $285 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 $285 per night (USD)
VRBO
From $396 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 $396 per night (USD)
VRBO
From $1633 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 $1633 per night (USD)
VRBO
From $728 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 $728 per night (USD)
Expedia
From $367 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 $367 per night (USD)
VRBO
From $364 per night (USD)
Expedia
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 $364 per night (USD)
Expedia
From $152 per night (USD)
VRBO
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 $152 per night (USD)
VRBO
From $759 per night (USD)
Expedia
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 ...
From $759 per night (USD)
Expedia
From $570 per night (USD)
VRBO
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 $570 per night (USD)
VRBO
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 $700 per night (USD)
VRBO
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 $700 per night (USD)
VRBO
From $422 per night (USD)
Expedia
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 $422 per night (USD)
Expedia
From $604 per night (USD)
VRBO
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 $604 per night (USD)
VRBO
From $720 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 $720 per night (USD)
VRBO
From $390 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 $390 per night (USD)
VRBO
From $416 per night (USD)
Expedia
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 $416 per night (USD)
Expedia
From $520 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 $520 per night (USD)
VRBO
From $509 per night (USD)
Expedia
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 $509 per night (USD)
Expedia
From $268 per night (USD)
VRBO
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)
VRBO
From $423 per night (USD)
Expedia
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 $423 per night (USD)
Expedia
From $366 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 $366 per night (USD)
VRBO
From $437 per night (USD)
Expedia
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 $437 per night (USD)
Expedia
From $585 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 $585 per night (USD)
VRBO
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
From $759 per night (USD)
VRBO
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 $759 per night (USD)
VRBO
From $552 per night (USD)
Expedia
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 $552 per night (USD)
Expedia
From $229 per night (USD)
VRBO
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 $229 per night (USD)
VRBO
From $249 per night (USD)
Expedia
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 $249 per night (USD)
Expedia
From $456 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 $456 per night (USD)
VRBO
From $365 per night (USD)
Expedia
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 $365 per night (USD)
Expedia
From $794 per night (USD)
VRBO
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 $794 per night (USD)
VRBO
From $993 per night (USD)
Expedia
Spacious Historic Home with Private Parking in the Heart of Downtown Annapolis
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Elegant Historic Home with Private Parking in the Heart of Downtown Annapolis Welcome to your beautifully restored retr ...
From $993 per night (USD)
Expedia
From $510 per night (USD)
VRBO
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 $510 per night (USD)
VRBO
From $299 per night (USD)
Expedia
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 $299 per night (USD)
Expedia
From $671 per night (USD)
VRBO
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 $671 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $1059 per night (USD)
VRBO
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)
VRBO
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 $722 per night (USD)
VRBO
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 $722 per night (USD)
VRBO
From $980 per night (USD)
Expedia
Heart of Downtown Annapolis -- History In Style Next to City Dock, Main Street
Bedrooms:
3
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 $980 per night (USD)
Expedia
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 $685 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 $685 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $434 per night (USD)
Expedia
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our 2BR, 1BA Boutique Brick Beauty located in historic Eastport. This beauty is steps from downtown, the U.S ...
From $434 per night (USD)
Expedia

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Annapolis Rentals

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Results: 446 Rentals