Annapolis Rentals
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Beautifully Furnished Home, Steps to USNA Stadium, Walk to Downtown Annapolis!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3 BR/3 Bath home is literally steps from the USNA Stadium (graduation) and within walking distance of downtown Anna ...
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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
From $717 per night (USD)VRBO
Charming 3-bedroom house with AC and WiFi in enchanting Annapolis/Eastport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay comfortably in Annapolis at this 3-bedroom house. With 1 king bed, 1 queen bed, and 1 full bed, this tremendous pro ...
From $717 per night (USD)VRBO
From $460 per night (USD)Expedia
Waterfront 2-Bedroom Condo on Spa Creek
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your home away from home in Annapolis! Nestled in the charming neighborhood of Eastport, this beautifully app ...
From $460 per night (USD)Expedia
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Anchor Drop
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful modern single-family home with heated pool. Located in Eastport, Annapolis, Maryland. Totally renovated in 2 ...
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From $543 per night (USD)Expedia
Ahoy! Game Room, Screened Porch, Yard Mins to DTA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to The Buccaneer, a family-friendly home located just 3 miles from Historic Downtown Annapolis and Eastport. Thi ...
From $543 per night (USD)Expedia
From $3306 per night (USD)VRBO
Stunning remodel in Murray Hill
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to 9th wing (USNA reference for the boat schoolers out there!) We just completed renovations on this spacious h ...
From $3306 per night (USD)VRBO
From $590 per night (USD)VRBO
Darling 2 BR home with parking in the sought after Murray Hill section of Historic Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STR22-145187 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $590 per night (USD)VRBO
From $787 per night (USD)VRBO
Brand New Spacious Luxury Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
This brand-new build luxury home in Eastport close to downtown Annapolis has everything you and your guests (up to 16 to ...
From $787 per night (USD)VRBO
From $472 per night (USD)Expedia
Stylish & New, Pet Friendly Fenced Yard, Walkable Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This stunning detached home, designed by Stylish Stays, is the perfect place for a stay in THE HEART of Annapolis. This ...
From $472 per night (USD)Expedia
From $328 per night (USD)VRBO
Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Immerse yourself in the rich history of Annapolis at our century-old home in Presidents Hill. With 3 bedrooms, 2 baths, ...
From $328 per night (USD)VRBO
From $461 per night (USD)Expedia
Downtown Pinkney House w/Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: The Pinkney house is a 2 bedroom, 2.5 bath town home boasts an unparalleled location within close proximity to ...
From $461 per night (USD)Expedia
From $114 per night (USD)VRBO
Maryland Inn King, Historic Inns, Fireplace, Elegant Dining, Waterfront Proximity
- 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 $114 per night (USD)VRBO
From $295 per night (USD)Expedia
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the close proximity to all Annapolis has to offer at this row house located next to college creek. Nicely decorat ...
From $295 per night (USD)Expedia
From $426 per night (USD)VRBO
Walk to Everything - Historic Art’s District
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
HISTORIC ANNAPOLIS/ART’S DISTRICT Built in 1898, “John Stevens House” in sought-after neighborhood of President’s Hill ...
From $426 per night (USD)VRBO
From $504 per night (USD)Expedia
Mins to Downtown in Waterfront community at Pet-friendly Pinecrest Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Just minutes from Downtown Annapolis, this charming Cape is located in a quiet water-privileged neighborhood with easy a ...
From $504 per night (USD)Expedia
From $1085 per night (USD)VRBO
On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Historic Charm Across from the Naval Academy Nestled in the heart of Downtown Annapolis, this spacious 5-bedroom, 4.5-ba ...
From $1085 per night (USD)VRBO
From $484 per night (USD)Expedia
Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This beautifully-restored 1 bedroom apartment is on the lower level of a 2-unit building in the charming Eastport neighb ...
From $484 per night (USD)Expedia
From $1790 per night (USD)VRBO
Spacious Converted Carriage House in Historic District near USNA
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Relax in this updated and sophisticated house near the USNA in Annapolis with the largest garden in downtown. This tranq ...
From $1790 per night (USD)VRBO
From $483 per night (USD)Expedia
Stay in Historic apartment 2 blocks from Main St with parking - dog-friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Still available for Commissioning Week 2025! Stay right in the heart of Historic Annapolis, just 2 blocks from Main Str ...
From $483 per night (USD)Expedia
From $312 per night (USD)VRBO
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
In the heart of Annapolis, where the bay breeze blows, Stands a small cottage, the Captain's Quarters, a peaceful repos ...
From $312 per night (USD)VRBO
From $437 per night (USD)Expedia
Historic dog-friendly home 2 blocks to Main St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay right in the heart of Historic Annapolis, just 2 blocks from Main Street, and feel like you’re in a hotel suite wit ...
From $437 per night (USD)Expedia
From $1180 per night (USD)VRBO
All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to your Eastport escape! This newly decorated custom home has everything—Severn River views, a huge private ya ...
From $1180 per night (USD)VRBO
From $612 per night (USD)Expedia
Mins to DTA - King Beds - Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect Springtime getaway in the heart of Annapolis! This open-concept home is designed with family gat ...
From $612 per night (USD)Expedia
From $1340 per night (USD)VRBO
Downtown Annapolis Duke's House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: This newly renovated 4-bedroom, 3.5 bathroom home is perfectly situated in the heart of historic downtown Anna ...
From $1340 per night (USD)VRBO
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Townhome steps from Main St. with private backyard patio & parking
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to City Gate, conveniently located in downtown Annapolis, just steps from all the shops and restaurants in the H ...
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From $461 per night (USD)VRBO
Steps to Marinas & Shops w Parking in Eastport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Eastport's Third Time's the Charm – Steps from Marinas, Dining, and Historic Annapolis This beautiful home is located in ...
From $461 per night (USD)VRBO
From $531 per night (USD)VRBO
Charming on Charles
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our elegant stand alone charming home on Charles Street in Historic Annapolis . This 3 bedroom 2.5 bath is ju ...
From $531 per night (USD)VRBO
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 $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 $690 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 $690 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
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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 ...
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From $528 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 $528 per night (USD)VRBO
From $434 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 $434 per night (USD)Expedia
From $624 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 $624 per night (USD)VRBO
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 $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
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)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 $343 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 $452 per night (USD)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 ...
From $452 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 $645 per night (USD)VRBO
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)VRBO
From $698 per night (USD)Expedia
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)Expedia
From $303 per night (USD)VRBO
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)VRBO
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)Expedia
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)Expedia
From $673 per night (USD)VRBO
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)VRBO
From $896 per night (USD)Expedia
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)Expedia
From $1396 per night (USD)VRBO
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)VRBO
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)VRBO
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)VRBO
From $762 per night (USD)Expedia
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)Expedia
From $677 per night (USD)VRBO
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)VRBO
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)Expedia
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)Expedia
From $509 per night (USD)VRBO
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)VRBO
From $655 per night (USD)Expedia
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)Expedia
From $1142 per night (USD)VRBO
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)VRBO
From $288 per night (USD)Expedia
The Red Door Cottage in Eastport - Pet-Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This stylish, pet-friendly boho retreat is just 1 mile from downtown Annapolis and Eastport’s restaurants—your perfect h ...
From $288 per night (USD)Expedia
From $378 per night (USD)VRBO
Modern Gem Near Historic Annapolis & Naval Academy
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Built in August 2025 | Group-Friendly Layout w/ 4 En-Suite Bedrooms | 1 Mi to Shopping, Dining & Hospitals Spacious and ...
From $378 per night (USD)VRBO