Anne Arundel Area Rentals
- From $822 per night (USD)
VRBO
Unique Listing! Entire Downtown Triplex w\/Private Parking. Sleeps 12-18. Pets ok
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
*** Commissioning Wk 2024 AVAILABLE*** Unique opportunity to rent an entire triplex Downtown Annapolis! One property wi ...
From $822 per night (USD)VRBO
- From $118 per night (USD)
Expedia
Comfort and Convenience! Pet-friendly Unit with Fully equipped Kitchen!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Experience wonderful conveniences that you should take advantage of including free Wi-Fi, onsite parking, fully function ...
From $118 per night (USD)Expedia
- From $700 per night (USD)
VRBO
Chesapeake Spectacular Waterfront- Kayaks, Spa, Pier
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Wonderful Chesapeake waterfront with private pier, large yard, kayaks, stand up paddleboards provided. Try fishing or cr ...
From $700 per night (USD)VRBO
- Click For Pricing
VRBO
Charming furnished colonial in Cape St. Clare available for rent!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Charming colonial in Cape St. Clare furnished and ready for rent! Weekend and weekly availability over the Summer of 202 ...
Click For PricingVRBO
- From $120 per night (USD)
VRBO
Modern Coastal Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
PERSONAL RESERVATION SPECIALIST AVAILABLE 24/7 FREE LINENS & TOWELS PROVIDED! Welcome to our newly renovated home in t ...
From $120 per night (USD)VRBO
- From $250 per night (USD)
VRBO
'Newer Cottage Incredibly and Comfortably Furnished.'
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come Join Us In Our Lushiously Appointed Cottage! We are located in the Private Beach Community of Oyster Harbor, Md. F ...
From $250 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Serene waterfront home with kayaks, paddle board, grill, firepit, W\/D, and AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Valentine Creek Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $295 per night (USD)VRBO
- From $338 per night (USD)
Expedia
Cozy suite Located in Presidents Hill
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Corner House – Quaint and Cozy 2 Bedroom Suite with Parking The Corner House is a hidden gem located in the quaint P ...
From $338 per night (USD)Expedia
- From $120 per night (USD)
VRBO
Peaceful private wooded setting. FURNISHED! Kitchenware & linens etc. provided
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Breathe easy. This is a fine house for a poet! or a sailor! or any nature lover. Easy access to the City of Annapolis an ...
From $120 per night (USD)VRBO
- From $187 per night (USD)
Expedia
The Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
A beautifully furnished quiet oasis to kick back and relax or if you are fast paced, you can visit many of the attractio ...
From $187 per night (USD)Expedia
- From $375 per night (USD)
VRBO
Beautiful New Renovated Home on 3 Acres Between Annapolis\/DC\/Balt
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Brand new renovated farmhouse centrally located between Annapolis, Baltimore and DC. Tour the sights and then return hom ...
From $375 per night (USD)VRBO
- From $441 per night (USD)
Expedia
Annapolis Family Haven
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is a fantastic place for your family to stay while exploring all that Annapolis has to offer! Nestled in the quiet ...
From $441 per night (USD)Expedia
- From $172 per night (USD)
VRBO
Waterfront CHeerful 2 with Private Pier\n
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to this relaxing home by the water for your getaway. It is perfect for vacations, retreats, meetings, family vis ...
From $172 per night (USD)VRBO
- From $575 per night (USD)
Expedia
Charming 2 BR Rancher w\/ parking and EV charger! Main floor living and just steps to the stadium
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
NBS23-145253 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $575 per night (USD)Expedia
- From $964 per night (USD)
VRBO
The View | Elegant house in Annapolis overlooking the river and Naval Academy
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
The View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $964 per night (USD)VRBO
- From $607 per night (USD)
Expedia
Historic downtown townhome with brick courtyard, sunroom & parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Corner Courtyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $607 per night (USD)Expedia
- From $134 per night (USD)
VRBO
(ALL TO YOURSELF, NOT SHARED) Free Complimentary Breakfast!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
You'll stay in (1) lower level bedroom with bunkbed and Murphy beds and will have access to kitchen, living room, and 1. ...
From $134 per night (USD)VRBO
- From $373 per night (USD)
VRBO
Glen Burnie Haven: Your Tranquil Home Away from Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to our charming 4-bedroom, 2-bathroom rambler-style retreat in Glen Burnie, MD! Nestled in a quiet neighborhood ...
From $373 per night (USD)VRBO
- From $370 per night (USD)
VRBO
Welcome to our newly built house
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This is a brand new house (built in June of 2022) Located in hearth of the beautiful city of Glen Burnie. Minutes from B ...
From $370 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully renovated home in the heart of West Annapolis. The main level has been updated to an open floor plan to acco ...
From $500 per night (USD)VRBO
- From $188 per night (USD)
VRBO
House w\/Water Views of Rock Creek 2BA 2BA Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come experience a water community getaway in Pasadena Maryland. Renovated cottage in a waterfront neighborhood with full ...
From $188 per night (USD)VRBO
- From $389 per night (USD)
Expedia
Walk to Main Street from Waterfront Condo with pool and parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
This beautifully-renovated and designed 2-bedroom/2-bath condo feels like a luxury hotel suite with views of Spa Creek a ...
From $389 per night (USD)Expedia
- From $410 per night (USD)
VRBO
History & Charm Near the Annapolis City Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
This charming 3-BR, 2.5-BA townhome is just a 1/2-block from the city dock and is a luxurious vacation getaway in the he ...
From $410 per night (USD)VRBO
- From $1826 per night (USD)
Expedia
Stay On the Waterfront in Edgewater custom-built chalet w private pier and hot tub
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 15
Stay at On The Waterfront in Edgewater, MD at this amazing custom-built estate resembling a ski chalet. Located on almos ...
From $1826 per night (USD)Expedia
- From $264 per night (USD)
VRBO
3 Story Stunner in Murray Hill <1 mile from USNA!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Summary: This is an *amazing* 3 story / 5 bedroom house with a finished basement! This is the perfect house for a large ...
From $264 per night (USD)VRBO
- From $1050 per night (USD)
VRBO
Hidden Treasure on Weems Creek
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
STR00704 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $1050 per night (USD)VRBO
- From $850 per night (USD)
VRBO
Bay Ridge Beauty with Wooded Serenity and Community Water Views
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
STR00711 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $850 per night (USD)VRBO
- From $318 per night (USD)
Expedia
Dog-friendly house with yard, deck, firepit, washer\/dryer & AC - near golf
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Seas The Bay Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $318 per night (USD)Expedia
- From $841 per night (USD)
VRBO
Riverfront home with private dock, foosball table, fireplace, river views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Taids Inn Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $841 per night (USD)VRBO
- From $500 per night (USD)
Expedia
Historic district home, View of the Capital, WALK Downtown, w\/ Outdoor Dining!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy Annapolis, MD in this charming Federal-style home nestled in the heart of the historic district. Newly renovated w ...
From $500 per night (USD)Expedia
- Click For Pricing
Expedia
Waterfront Oasis w Boat Dock & Backyard BBQ
- Bedrooms:
- 3
- Bathrooms:
- 0
- Sleeps:
- 12
Experience the epitome of waterfront living at our exquisite 4-bedroom home, nestled just moments away from the serene M ...
Click For PricingExpedia
- From $195 per night (USD)
Expedia
Cozy Maryland Retreat Near Sandy Pointe State Park
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Discover the best of Annapolis with ease from this updated 3-bedroom, 1-bathroom home! The vacation rental has all the e ...
From $195 per night (USD)Expedia
- Click For Pricing
VRBO
Upscaled Efficiency Apartment in Private Community
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
800 sq ft of newly designed apartment with full size kitchen, full size bathroom, lots of storage space, laundry room wi ...
Click For PricingVRBO
- From $202 per night (USD)
Expedia
Special Rates. Close to Annapolis. Justin Beach Cottage Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
About this space This 2-bedroom, 2-full bathroom home is perfect for those looking to enjoy a relaxing Getaway. Solo or ...
From $202 per night (USD)Expedia
- Click For Pricing
Expedia
3 Bedroom Fully Fenced Nautical Themed Home only 6 Minutes from DT Annapolis\n
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Nautical Nest! You'll enjoy comfort and relaxation in this clean, family friendly entire home with a ful ...
Click For PricingExpedia
- From $396 per night (USD)
Expedia
New! Steps from USNA Gates 1 & 3 with large private patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*Still available for 2024 Commissioning Week - 5-night minimum! Stay in this restored historic Annapolis home, located ...
From $396 per night (USD)Expedia
- From $185 per night (USD)
VRBO
Comfortable home with a work desk, washer\/dryer, streaming, & internet
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 9
Perch Between Cities Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $185 per night (USD)VRBO
- From $239 per night (USD)
Expedia
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 $239 per night (USD)Expedia
- From $1500 per night (USD)
VRBO
Serene and Sophisticated 4 BR Waterfront Contemporary just outside of Annapolis.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
STR00841 - PLEASE NOTE, IF YOU REQUEST TO BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS TO FINAL ...
From $1500 per night (USD)VRBO
- From $262 per night (USD)
Expedia
Shiloh Acres Farmhouse Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Location, Location, Location! Welcome to our charming 3-bedroom, 2-bath modern farmhouse nestled on a serene 2.5-acre f ...
From $262 per night (USD)Expedia
- From $2500 per night (USD)
VRBO
Stunning Waterfront Home with Incredible Views
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 15
Perfect home for a family getaway, Commissioning Week or Boat Show event. Room for all to sleep, gather and play in thi ...
From $2500 per night (USD)VRBO
- From $205 per night (USD)
Expedia
USNA home Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for the perfect location for your Annapolis getaway? Look no further than our home, situated near Arundel Center ...
From $205 per night (USD)Expedia
- From $483 per night (USD)
VRBO
Hillbottom Hideaway Beachhouse - Severna Park pet friendly! With hot tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience living by the water in our beautifully renovated 3-bedroom, 2-bathroom three level home. With stunning water ...
From $483 per night (USD)VRBO
- From $603 per night (USD)
Expedia
The General's House- The Ideal Annapolis Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Nestled in a serene neighborhood, this exquisite 4-bedroom, 4-bathroom home offers the epitome of luxury living and ente ...
From $603 per night (USD)Expedia
- From $974 per night (USD)
VRBO
4BR Home with Pool on the Magothy River Pasadena
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Waterfront vacationing awaits you behind the doors of this stunning 5BR/3.5BA brick home which sits on over an acre of l ...
From $974 per night (USD)VRBO
- From $392 per night (USD)
Expedia
Bayfront Maryland Retreat w\/ Deck, Near Beaches!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Days spent relaxing on the sandy shores, exploring the local shops and eateries along The Boardwalk, or visiting The Wal ...
From $392 per night (USD)Expedia
- From $629 per night (USD)
VRBO
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 18
Turning Point on the Little Magothy is a wonderful and private Estate that sleeps 18 comfortably! Turning Point on the ...
From $629 per night (USD)VRBO
- From $392 per night (USD)
Expedia
Ahoy! The Buccaneer awaits you just outside Annapolis - fenced-in yard and rec room
- 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 $392 per night (USD)Expedia
- From $250 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 $250 per night (USD)VRBO
- From $375 per night (USD)
Expedia
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 $375 per night (USD)Expedia
- From $150 per night (USD)
VRBO
Water view studio. Cozy but mighty! 20 minutes from Annapolis.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This property is an efficiency that sits on top of a garage in a quiet neighborhood. The perfect place to stay while ta ...
From $150 per night (USD)VRBO
- From $145 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 $145 per night (USD)VRBO
- From $145 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 $145 per night (USD)VRBO
- From $964 per night (USD)
Expedia
Stunning 5-bedroom remodel in the heart of Murray Hill.
- 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 $964 per night (USD)Expedia
- From $290 per night (USD)
VRBO
Lakehouse: private pier, fireplace and huge backyard, 5min from navel academy
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Huge lakehouse with massive backyard and private pier onto the peaceful lake! 5min to navel academy This gorgeous, air ...
From $290 per night (USD)VRBO
- From $753 per night (USD)
Expedia
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 $753 per night (USD)Expedia
- From $1325 per night (USD)
VRBO
Sailor's Caribbean FantaSea -5 BR Creekside Contemporary with Private Dock 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 $1325 per night (USD)VRBO
- From $234 per night (USD)
Expedia
Water-view condo with rooftop pool & balcony - minutes from downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
USNA Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $234 per night (USD)Expedia
- From $225 per night (USD)
VRBO
10 Minutes from BWI Airport - Cozy, Aesthetic Home, kid-friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located only minutes from the BWI airport, this home is close to just about any convenience you could need. 25 minutes f ...
From $225 per night (USD)VRBO
- From $429 per night (USD)
Expedia
Spacious Home w\/ Tranquil Patio ~ 29 Mi to DC!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Visit vibrant downtown Baltimore attractions or Washington, D.C. when you stay at this elegant 5-bedroom, 3-bathroom vac ...
From $429 per night (USD)Expedia
- From $321 per night (USD)
VRBO
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 $321 per night (USD)VRBO
- From $900 per night (USD)
VRBO
Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 13
Welcome to our waterfront oasis on Parish’s Creek just off of the Chesapeake Bay! Our spacious house is the perfect retr ...
From $900 per night (USD)VRBO
- From $355 per night (USD)
VRBO
Nautical charmer near the City Dock with open layout, W\/D, & AC
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Plebe's Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $355 per night (USD)VRBO
- From $272 per night (USD)
Expedia
Perfect Home near Chesapeake Bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to this bright home nestled on a quiet cul-de-sac in Eastport. Our home offers proximity to local attractions, pa ...
From $272 per night (USD)Expedia
- From $675 per night (USD)
VRBO
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 $675 per night (USD)VRBO
- From $418 per night (USD)
Expedia
The State Rooms
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this stately home in the water privileged community of Cape St Claire just a short 10 minute drive to downtow ...
From $418 per night (USD)Expedia
- From $1200 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 $1200 per night (USD)VRBO
- From $165 per night (USD)
VRBO
Charming 3-bedroom 3.5 bath townhome in delightful Gambrills
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
This memorable townhome is the perfect home base for your trip to Gambrills. With 3 bedrooms, including 2 queen beds and ...
From $165 per night (USD)VRBO
- From $825 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 $825 per night (USD)VRBO
- From $75 per night (USD)
Expedia
Cozy Basement with Private Entrance
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Kick back and relax in this calm, stylish space. Very cozy and spacious in a friendly, safe and quiet neighborhood. You ...
From $75 per night (USD)Expedia
- From $550 per night (USD)
VRBO
Come Seize the Bay! 4 miles from the Navy Campus
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Relax with the whole family at this peaceful place to stay. This neighborhood has sidewalks, water access, and a playgro ...
From $550 per night (USD)VRBO
- From $90 per night (USD)
Expedia
Modern gateway near BWI\/DC
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 14
During this time, it is very important to provide a clean and safe space for all of our guests while away from home. Our ...
From $90 per night (USD)Expedia
- From $700 per night (USD)
VRBO
Walk to everything! Downtown Historic Annapolis “Arts District”
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Built in 1920, the “Norfolk-Sheets House” at 39 Madison Place is a historic home, c.1904, located in the sought-after ne ...
From $700 per night (USD)VRBO
- Click For Pricing
Expedia
Cottage for Rent
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Cottage for Rent xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx ...
Click For PricingExpedia
- From $1045 per night (USD)
VRBO
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 $1045 per night (USD)VRBO
- From $325 per night (USD)
Expedia
Entire house on quiet street w\/fenced yard—1 block from river, 3 from bay
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 6
Arundel-on-the-Bay is a private community on Annapolis Neck peninsula, and this home sits right in the middle. Ideal sp ...
From $325 per night (USD)Expedia
- Click For Pricing
VRBO
Charming Annapolis home in Eastport, Now available Commissioning Week!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This delightful restored home is just 3 blocks away from the Eastport Bridge and 1.3 miles away from the Naval Academy ...
Click For PricingVRBO
- From $700 per night (USD)
Expedia
Cozy Coastal Waterfront Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
WATERFRONT HOME on Meredith Creek in Annapolis! This beautiful 3 bedroom, 2 bathroom home is the perfect cozy coastal re ...
From $700 per night (USD)Expedia
- From $408 per night (USD)
VRBO
Luxe Modern Chesapeake Waterfront Oasis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts ...
From $408 per night (USD)VRBO
- From $1429 per night (USD)
VRBO
Luxury Waterfront Annapolis\/ Private Beach & Dock
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Stunning Contemporary Home with private beach! House has been listed on another site receiving five st ...
From $1429 per night (USD)VRBO
- From $263 per night (USD)
VRBO
Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to my home! This open concept 3 bedroom (all queens) 1.5 bath cottage has a large, fenced yard and backs up to ...
From $263 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Charming Family Home in Blackwalnut Cove!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A beautiful family home located in the heart of Annapolis. Our property has a large yard for hosting and communal areas ...
From $500 per night (USD)VRBO
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VRBO
Tranquil Waterfront Cottage in Shady Side - 50 minutes to DC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
About this space Escape to our peaceful, riverside cottage. Enjoy sweeping views of the West River with 390 feet of priv ...
Click For PricingVRBO
- From $455 per night (USD)
VRBO
Charming Home located minutes from the Naval Academy and Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Private 4BR, 2.5BA luxurious Gem was recently upgraded, and tastefully decorated awaits your arrival. The ranch style ho ...
From $455 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Waterfront 2BR Guest House on Cypress Creek - Severna Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
STR00626 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $350 per night (USD)VRBO
- Click For Pricing
Expedia
Peaceful Home in Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Relax with the whole family at this peaceful place to stay. A quaint 4-bedroom home tucked away on 2.2 acres. Enjoy the ...
Click For PricingExpedia
- From $1063 per night (USD)
VRBO
Waterfront Architectural Masterpiece with private dockage available.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 11
Heron Point House is an owner imagined home, designed by one of the region's leading architects and built to perfection. ...
From $1063 per night (USD)VRBO
- From $60 per night (USD)
Expedia
Private Cozy Basement Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Hey there, I have a private basement apartment in Arnold, Maryland (greater Annapolis) available to rent May 11th! My to ...
From $60 per night (USD)Expedia
- Click For Pricing
VRBO
Waterfront house with panoramic views from every room.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Windy Point. Wake up to breathtaking sun rises. Spend the day lounging by the water. Enjoy a paddle board rid ...
Click For PricingVRBO
- From $300 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 $300 per night (USD)VRBO
- From $219 per night (USD)
VRBO
Free Wi-Fi + Complimentary Breakfast + Outdoor Pool | Near the BWI Airport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Your next trip starts with a stay in our suite! The BWI Airport is just 2 miles away, and there is a complimentary 24-ho ...
From $219 per night (USD)VRBO
- From $695 per night (USD)
Expedia
BY THE BAY
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
WATER, WATER everywhere! Our home is centrally located to all the water Bay Ridge has to offer. Our home is located jus ...
From $695 per night (USD)Expedia
- From $786 per night (USD)
VRBO
BAY RIDGE MODERN HOME WITH VINTAGE CHARM
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful spacious modern family home with vintage charm. A great gathering spot for family or just wanting to spend som ...
From $786 per night (USD)VRBO
- From $466 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 $466 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Historic house in Annapolis Arts District
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Super host house rental in charming historic house, private and upscale, tucked away in the quiet President’s Hill neigh ...
From $250 per night (USD)VRBO
- From $471 per night (USD)
Expedia
Historic happy home, steps to Main Street, parking and lots of outdoor space
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic ...
From $471 per night (USD)Expedia
- Click For Pricing
VRBO
Fully renovated house in the heart of the Historic District!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fully updated 3 bed/1.5 bath in Historic Annapolis, less than a mile from the main gates of the Naval Academy! Main bedr ...
Click For PricingVRBO
- Click For Pricing
Expedia
Charming Historic Annapolis Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This delightful historic home is situated directly across the street from the Paca House, and only three blocks from the ...
Click For PricingExpedia
- From $1765 per night (USD)
VRBO
7BR\/ 5.5 Bath Home AVAILABLE CW 2024, 2025
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 16
USNA Commissioning Week Rentals welcome! Perfect location for easy access to USNA events! A convenient 5 min drive from ...
From $1765 per night (USD)VRBO
- From $782 per night (USD)
Expedia
Oyster Harbor Waterfront Vacation Home -- Private Dock and Backyard
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Spacious and luxurious vacation home in Oyster Harbor, Annapolis. Features 4 bedrooms (7 beds), 3 full baths. A lively o ...
From $782 per night (USD)Expedia