Annapolis Rentals
From $608 per night (USD)VRBO
Large House Downtown Annapolis with 2 Hot Tubs and 4 parking places
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
This Navy Themed house is located jn downtown annapolis, walking distance to all the shops and restaurants in annapolis ...
From $608 per night (USD)VRBO
From $1344 per night (USD)Expedia
5 BR Creekside Contemporary WATERFRONT HOME with Private Dock, ROOF TOP HOT TUB, and Water Taxi Service!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
STR23-145260 - THIS PROPERTY IS MANAGED BY ANNAPOLIS ACOCMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL A TEAM MEM ...
From $1344 per night (USD)Expedia
From $292 per night (USD)VRBO
Water-view condo with rooftop pool & balcony - minutes from downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
USNA Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $292 per night (USD)VRBO
From $243 per night (USD)Expedia
Newly Updated EV Charger Ready Peaceful Home in Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to our stylish and modern home, where comfort meets convenience! Here's what you can expect during your stay: ✔ ...
From $243 per night (USD)Expedia
From $417 per night (USD)VRBO
Nautical charmer near the City Dock with open layout, W\/D, & AC
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Plebe's Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $417 per night (USD)VRBO
From $466 per night (USD)Expedia
Steps from USNA Gates 1 & 3 with large private patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Visit the magic of Annapolis during the Holiday Season Stay in this restored historic Annapolis home, located just steps ...
From $466 per night (USD)Expedia
From $251 per night (USD)VRBO
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Property is 2 bedrooms and 1 bathroom furnished with brand new furniture. Bedrooms have fitted with comfortable queen si ...
From $251 per night (USD)VRBO
From $717 per night (USD)Expedia
Charming 3-bedroom house with AC and WiFi in enchanting Annapolis\/Eastport
- Bedrooms:
- 3
- 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)Expedia
From $447 per night (USD)VRBO
Ahoy! The Buccaneer awaits you mins from Annapolis w 3-seasons room, fenced-in yard and rec room
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Visit the magic of Annapolis during the Holiday Season Welcome to The Buccaneer, a family-friendly home located just 3 m ...
From $447 per night (USD)VRBO
From $234 per night (USD)VRBO
Downtown Annapolis, steps from Main Street, City Dock, and Naval Academy - Apt 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This apartment is centrally located and on one of the loveliest streets in Historic Downtown Annapolis. You will be ste ...
From $234 per night (USD)VRBO
From $666 per night (USD)VRBO
Fox Hollow House- The perfect Annapolis Getaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Get ready for an awesome family gathering in our spacious 4 bedroom home with the perfect back yard for entertaining! N ...
From $666 per night (USD)VRBO
From $200 per night (USD)VRBO
Downtown Annapolis, steps from Main Street, City Dock, and Naval Academy - Apt 3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This apartment is centrally located and on one of the loveliest streets in Historic Downtown Annapolis. You will be ste ...
From $200 per night (USD)VRBO
From $235 per night (USD)VRBO
Downtown Annapolis, steps from Main Street, City Dock, and Naval Academy - Apt 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This apartment is centrally located and on one of the loveliest streets in Historic Downtown Annapolis. You will be ste ...
From $235 per night (USD)VRBO
From $2907 per night (USD)Expedia
Stunning remodel in Murray Hill- Available Commissioning Week 2025, 2026
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to 9th wing (USNA reference for the boat schoolers out there!) We are nearing the end of renovations on this sp ...
From $2907 per night (USD)Expedia
From $240 per night (USD)VRBO
Governor Calvert King, Historic Inns, Four-Poster Bed, Dining, Steps from 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 $240 per night (USD)VRBO
From $496 per night (USD)Expedia
Walk everywhere from this 1st floor dog-friendly apartment with parking, private backyard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Visit the magic of Annapolis during the Holiday Season This beautifully-restored 1 bedroom apartment is on the lower lev ...
From $496 per night (USD)Expedia
From $625 per night (USD)VRBO
Eastport Classic Charm House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled in the charming neighborhood of Eastport, Annapolis, this spacious 4-bedroom, 3.5-bathroom home offers the perfe ...
From $625 per night (USD)VRBO
From $372 per night (USD)Expedia
Unbeatable Downtown Location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 2-bed, 1.5-bath townhome mixes modern renovations with 1900 classic charm. It's been lovingly decorated to accommod ...
From $372 per night (USD)Expedia
From $231 per night (USD)VRBO
Another Five Star Charmer! Great Location Downtown & Navy Football ! Parking too
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
New to the market and just in time for Navy Football. Located at the five star Corner House. Conveniently located on th ...
From $231 per night (USD)VRBO
From $969 per night (USD)Expedia
Perfect Townhouse for USNA Commissioning Week!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to the perfect townhouse for USNA Commissioning Week! As a former midshipman, I know how important it is to have ...
From $969 per night (USD)Expedia
From $409 per night (USD)VRBO
Charming on Charles - Stately 3 bedroom home in the Historic District
- Bedrooms:
- 3
- 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 $409 per night (USD)VRBO
From $437 per night (USD)Expedia
Charming home in Annapolis in walking distance to shops, restaurants, & the bay
- Bedrooms:
- 3
- 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 $437 per night (USD)Expedia
From $549 per night (USD)VRBO
Cozy apartment in Historic Annapolis with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This Annapolis apartment is located within walking distance of everything Annapolis has to offer. Located just outside ...
From $549 per night (USD)VRBO
From $329 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 $329 per night (USD)Expedia
From $114 per night (USD)VRBO
Waterfront condo in Eastport, ONLY available for the Legislative session
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
On Back Creek in Eastport, this delightful condo offers 2 bedrooms - one with a king bed and the other with a cozy murph ...
From $114 per night (USD)VRBO
From $436 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 $436 per night (USD)VRBO
From $402 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 $402 per night (USD)VRBO
From $1211 per night (USD)VRBO
Historic Luxury Steps to USNA + Vibrant Waterfront\n
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Fair Winds, a beautiful, spacious and sunlit historic home on gorgeous Prince George Street in the heart of d ...
From $1211 per night (USD)VRBO
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 $1077 per night (USD)Expedia
Historic Annapolis With Parking
- Bedrooms:
- 3
- 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)Expedia
Click For PricingVRBO
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 PricingVRBO
From $355 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 $355 per night (USD)VRBO
From $663 per night (USD)VRBO
Private patio, parking, dog and family-friendly at professionally-designed On Cloud 9
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Visit the magic of Annapolis during the Holiday Season Welcome to this stunning home in downtown Annapolis with all the ...
From $663 per night (USD)VRBO
From $682 per night (USD)Expedia
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Visit the magic of Annapolis during the Holiday Season Watch the sunrise on the private beach at Oh Happy Bay. The quain ...
From $682 per night (USD)Expedia
From $641 per night (USD)VRBO
Private yard and screened porch at Historic happy home, steps to Main Street, parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Visit the magic of Annapolis during the Holiday Season Enjoy a piece of Annapolis history! Nestled at the end of a row, ...
From $641 per night (USD)VRBO
From $342 per night (USD)VRBO
Comfortable Townhouse Minutes from City Dock and US Naval Academy!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Make this well-appointed townhouse your home away from home in the family-friendly Hunt Meadow community conveniently lo ...
From $342 per night (USD)VRBO
From $582 per night (USD)VRBO
3 bdrm close to city center, great yard & parking!
- Bedrooms:
- 3
- 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 $582 per night (USD)VRBO
From $1049 per night (USD)VRBO
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 $1049 per night (USD)VRBO
Click For PricingVRBO
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 ...
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From $303 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 $303 per night (USD)Expedia
From $2105 per night (USD)VRBO
Reno'd Home in West Annapolis: Great for Stadium Events, Boat Shows & Downtown
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
West Annapolis is a neighborhood close to everything, but with peace and quiet in mind. Shopping and food options are c ...
From $2105 per night (USD)VRBO
From $287 per night (USD)Expedia
Chesapeake Comfort, Annapolis.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Annapolis Bungalow Home that is professionally cleaned and is a full time Airbnb. I have been a Superhost with other lis ...
From $287 per night (USD)Expedia
Click For PricingVRBO
Picturesque home with yard, central AC, washer\/dryer & cable
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Stadium Gardens Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
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From $608 per night (USD)VRBO
Annapolis 4 BR House w\/ Cottage and Gameroom
- Bedrooms:
- 4
- 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 $608 per night (USD)VRBO
From $589 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 $589 per night (USD)VRBO
Click For PricingExpedia
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 ...
Click For PricingExpedia
From $492 per night (USD)VRBO
Townhouse with multiple gathering spaces, 1 block to Capital Bldg and free parking
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Visit the magic of Annapolis during the Holiday Season Welcome to Naptown Nook, conveniently located in downtown Annapol ...
From $492 per night (USD)VRBO
From $715 per night (USD)Expedia
MODERN 2022 NEWLY BUILT TOWNHOME
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a stylish experience at this centrally-located and newly-built (2022) Eastport Annapolis townhome. Spacious two li ...
From $715 per night (USD)Expedia
From $368 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 $368 per night (USD)VRBO
From $1013 per night (USD)Expedia
Stunning, Large Historic Annapolis Home, Steps to Academy and Downtown.
- 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. Enjoy the eleganc ...
From $1013 per night (USD)Expedia
From $250 per night (USD)VRBO
Pristine Downtown 1-Bedroom Steps from State House
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $250 per night (USD)VRBO
From $1349 per night (USD)VRBO
Gatehouse Annapolis
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy the beauty and convenience of Historic Downtown Annapolis and the U.S. Naval Academy. This 5 BR/ 4.5 baths home of ...
From $1349 per night (USD)VRBO
From $433 per night (USD)VRBO
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
The Chesapeake Bay awaits you at this Annapolis vacation rental! 'Admiral's Post' is situated under 4 miles from the cit ...
From $433 per night (USD)VRBO
Click For PricingExpedia
USNA Commissioning Week 2023 Downtown Annapolis House that sleeps 13 people
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 13
This 3 story half duplex is in the perfect location, situated in historical downtown Annapolis with a modern day feel, r ...
Click For PricingExpedia
From $286 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 $286 per night (USD)VRBO
From $324 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 $324 per night (USD)Expedia
From $834 per night (USD)VRBO
Updated historic home with parking; near Academy, college & harbor - central AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Anchors Aweigh Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $834 per night (USD)VRBO
From $1489 per night (USD)Expedia
Renovated historic home with courtyard, balcony, grill, great downtown location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Submariners Gate Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $1489 per night (USD)Expedia
From $411 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 $411 per night (USD)VRBO
From $412 per night (USD)Expedia
Beautiful Home close to it all.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
This cozy yet spacious home offers 3 queen beds, a twin over full bunk bed with a pull out trundle, 2 full baths, 2 kitc ...
From $412 per night (USD)Expedia
From $624 per night (USD)VRBO
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 $624 per night (USD)VRBO
From $1530 per night (USD)Expedia
Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
The Master Shipwright Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1530 per night (USD)Expedia
From $432 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
Visit the magic of Annapolis during the Holiday Season Welcome to this mid-century modern, Cape Cod in West Annapolis. T ...
From $432 per night (USD)VRBO
From $715 per night (USD)Expedia
Luxe Houseboat: Breathtaking Skyline 360 Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
| OVERVIEW | Welcome to FLOHOM 1 | Bay Escape, your home away from shore! Our luxury houseboat is docked at the premie ...
From $715 per night (USD)Expedia
From $333 per night (USD)VRBO
Belle By the Bay- Great location and parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
As soon as you enter this beautiful two-floor home, you'll be greeted by the modern yet very comfortable open-concept de ...
From $333 per night (USD)VRBO
From $402 per night (USD)Expedia
Quiet dog-friendly suburban home with patio, grill, yard, kitchen, & Pack-N-Play
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Admiral's Glen Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $402 per night (USD)Expedia
From $662 per night (USD)VRBO
The Crabby Patty- Your Downtown Annapolis getaway
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history and vibr ...
From $662 per night (USD)VRBO
From $1368 per night (USD)Expedia
Walk Everywhere! Your Ultimate Annapolis Retreat on Horn Point
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to your ideal rental property at 125 Chester Avenue, located in the desirable neighborhood of Horn Point in Annap ...
From $1368 per night (USD)Expedia
Click For PricingVRBO
Two-story retreat near the harbor with a washer\/dryer, patio, & gas fireplace
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Eastport Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
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From $432 per night (USD)Expedia
Eastport Cozy Charmer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our cottage home- the perfect location for your family & friends to enjoy Naval Academy events, boat shows, s ...
From $432 per night (USD)Expedia
From $292 per night (USD)VRBO
Historic Home with Parking Steps From Capital & USNA
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to this vibrant downtown Annapolis oasis—a unique purple parallelogram with a parking spot. From the front door, ...
From $292 per night (USD)VRBO
From $445 per night (USD)Expedia
Go Navy West Annapolis home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This two-bedroom home in West Annapolis is a charming residence that boasts a spacious back yard, providing ample outdoo ...
From $445 per night (USD)Expedia
From $736 per night (USD)VRBO
Nautical-themed home with four bedrooms, bright interior, deck, W\/D, and AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
The Robins Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $736 per night (USD)VRBO
From $414 per night (USD)Expedia
Pet Friendly - Stone's throw from City Dock w private back patio, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Visit the magic of Annapolis during the Holiday Season This well-appointed recently-renovated home in the heart of Annap ...
From $414 per night (USD)Expedia
From $670 per night (USD)VRBO
Walk to restaurants from large luxury home, shops and stadium in West Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Visit the magic of Annapolis during the Holiday Season Welcome to this luxury craftsman-style home in West Annapolis, on ...
From $670 per night (USD)VRBO
From $334 per night (USD)Expedia
The Carrollton Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy this charming 2 bedroom, 1.5 bathroom cottage home conveniently located within walking distance of Downtown Annapo ...
From $334 per night (USD)Expedia
From $721 per night (USD)VRBO
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 10 people. ...
From $721 per night (USD)VRBO
From $379 per night (USD)Expedia
Gorgeous dog-friendly retreat w\/ fireplace, patio, & firepit - centrally located
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Anchors Away Abode Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $379 per night (USD)Expedia
Click For PricingVRBO
Downtown Annapolis Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Two bedroom and two bathroom in Historic Annapolis, only 1 mile from arts district (west street), 2 miles from downtown ...
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From $361 per night (USD)Expedia
Historic Downtown House with Off Street Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious living with all the modern amenities. Prime location - 1 block from the water, restaurants, and shops. Park you ...
From $361 per night (USD)Expedia
From $435 per night (USD)VRBO
Historic & sunny home w\/ Fireplace steps from USNA & Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
This beautiful 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City ...
From $435 per night (USD)VRBO
From $327 per night (USD)Expedia
Historic Annapolis Home 1.5 blocks from center of town.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Historic home 1.5 blocks from center of town. Easy walk to the shops, food, harbor, Naval Academy and historic attractio ...
From $327 per night (USD)Expedia
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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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From $748 per night (USD)Expedia
West Annapolis Cottage
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
CONTACT OWNER FOR CW2024/2025 RATES/BOOKING! Recently renovated, this is the perfect location for your family & friends ...
From $748 per night (USD)Expedia
From $348 per night (USD)VRBO
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $348 per night (USD)VRBO
From $303 per night (USD)Expedia
Charming Historic Townhouse Steps From USNA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our charming home nestled next to the prestigious Naval Academy in Annapolis. This inviting 1-bedroom, 1-bath ...
From $303 per night (USD)Expedia
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New Private Bdrm & Bath in Eastport (walk to Downtown Annapolis)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A brand new, clean pied-a-terre just a walk away from downtown Annapolis! Enjoy Commissioning Week/Blue Angels, Boat Sho ...
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Historic Annapolis Home, Convenient to Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Historic Annapolis home convenient to downtown, restaurants, shopping, commuter routes and public transportation! -0.5 ...
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From $210 per night (USD)VRBO
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Five blocks to Naval Bagels, Agave, Chessie's Wharf, Evelyn's, Bean Rush Cafe, Rutabagas, Grauls Groceries and other sho ...
From $210 per night (USD)VRBO
From $755 per night (USD)Expedia
Newly renovated downtown home with patio, gas grill, and gas fireplace
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Blue Angel's Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $755 per night (USD)Expedia
From $370 per night (USD)VRBO
Adorable home steps from Navy Stadium!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Can’t beat the space and location of this property for your trip to Annapolis! Just a block away from Navy Stadium for a ...
From $370 per night (USD)VRBO
From $386 per night (USD)VRBO
NEW Eastport Bungalow walkable to USNA, Restaurants, & Historic Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your family will be 1mi. to Main Street & Downtown Annapolis home of the US Naval Academy (ask about our Navy family di ...
From $386 per night (USD)VRBO
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Beautifully Furnished Home, Steps to USNA Stadium, Walk to Downtown Annapolis!
- Bedrooms:
- 3
- 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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Downtown Annapolis Luxury House
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our downtown luxury cottage is located 1.4 miles from Church Circle, which is the heart of downtown Annapolis. We are wa ...
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From $232 per night (USD)VRBO
Visit Annapolis Spring\/Summer 2025, 1B\/1B Apt, Pristine, Peaceful, Walkable
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Fox Haven, a bright, pristine 1 Bed/1 Bath apartment with its own separate lower level entrance. This lovely ...
From $232 per night (USD)VRBO
From $356 per night (USD)Expedia
Eastport apartment with gourmet kitchen, backyard and parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Visit the magic of Annapolis during the Holiday Season This beautifully upgraded one-bedroom apartment on the 1st floor ...
From $356 per night (USD)Expedia
From $155 per night (USD)VRBO
2 BR home on quiet street in Eastport with lovely screened porch.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
STR-146397 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $155 per night (USD)VRBO
From $189 per night (USD)Expedia
House with 3 beds 2 bedrooms and backyard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
26 miles from US Capitol in Washington DC and 2 miles from Historic downtown of Annapolis; 2.3 miles from US Navy Academ ...
From $189 per night (USD)Expedia
From $1172 per night (USD)VRBO
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
The Oaks Inn is an exceptional home hjistoric nestled in the heart of Historic Downtown Annapolis that seamlessly combin ...
From $1172 per night (USD)VRBO
From $470 per night (USD)Expedia
Annapolis House Minutes from Downtown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
This Quiet peaceful location with Spacious 4 bedroom, 2 full and 1 half bath is just 3 miles from Downtown Annapolis. Pe ...
From $470 per night (USD)Expedia