Severn River Rentals
- From $339 per night (USD)
VRBO
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Amongst the allure of downtown living, lies this quant Annapolis home. This two bedroom, one and a half bath has a spaci ...
From $339 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Stunning Waterfront Cottage with Breathtaking Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A Gorgeous, Waterfront setting in the Sailing Capital of the World! Charm, Detail, and Hospitality were not spared in t ...
From $400 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Historic Annapolis Home And Garden
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This delightful two bedroom, two full bath duplex occupies the second and third floors of a lovely home built in 1900, u ...
From $350 per night (USD)VRBO
- From $383 per night (USD)
VRBO
Large Luxury Apartment In Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bed/2 Bath Apartment in Historic Downtown Annapolis steps away from the main entrance of the Naval Academy. Upstairs ...
From $383 per night (USD)VRBO
- From $645 per night (USD)
VRBO
Waterfront Oasis in Eastport - Walk to Downtown and USNA
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our newest listing in listing in the Maritime section of Annapolis . This upscale , fully renovated waterfron ...
From $645 per night (USD)VRBO
- From $375 per night (USD)
VRBO
PERFECT LOCATION in the heart of history
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Be our guest at Historic 19 East Street, in the heart of the Annapolis national landmark district. Walk out the front d ...
From $375 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Walk everywhere . . .just minutes to historic Annapolis, Updated.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A modern historic gem in a 10 unit building in Eastport or as the locals call it the Maritime Republic of Eastport or "M ...
From $300 per night (USD)VRBO
- From $480 per night (USD)
VRBO
Large Contemporary in Wooded Privacy
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Lovely, contemporary sitting on three and-a-half acres of wooded beauty. Lots of glass and cedar. Open and airy floor pl ...
From $480 per night (USD)VRBO
- From $886 per night (USD)
VRBO
USNA Stay w\/ Private Pool, Indoor Soft Hot Tub, King Beds, & CHILD FRIENDLY GEAR
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
USNA Family Stay w/Pool - Infant/Toddler Friendly! Enjoy the newest addition to my “Family Friendly Staycation” home ho ...
From $886 per night (USD)VRBO
- From $198 per night (USD)
VRBO
Ideal Eastport\/ Annapolis Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This spacious, fully furnished one bedroom1st floor apartment is perfectly located and has everything you need for your ...
From $198 per night (USD)VRBO
- From $290 per night (USD)
VRBO
Your Annapolis Adventure Starts Here!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your charming Annapolis getaway! This beautifully furnished home is the perfect retreat for your stay in this ...
From $290 per night (USD)VRBO
- From $717 per night (USD)
VRBO
Beautiful Blend of Restoration and Renovation in this Downtown Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this newly updated rental home, a stunning blend of renovation and restoration located in the heart of the Hi ...
From $717 per night (USD)VRBO
- From $574 per night (USD)
VRBO
Restriction Retreat - Relax & walk to Main St
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Restriction Retreat, where trouble checks in. Treat yourself and your family to five-star amenities, an u ...
From $574 per night (USD)VRBO
- From $674 per night (USD)
VRBO
Private Waterfront Woods | Dock, Kayaks, Views
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 19
Welcome to The Compass Rose, a serene haven with backyard shoreline surrounded by 4+ acres of pristine woods. Enjoy excl ...
From $674 per night (USD)VRBO
- From $524 per night (USD)
VRBO
Annapolis Downtown - Historic Home - Brand New Furnishings. Walk to attractions
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We’re a Navy + Army Family with deep ties to the Naval Academy (and West Point…sorry, Navy fans). We love Annapolis and ...
From $524 per night (USD)VRBO
- From $299 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 $299 per night (USD)Expedia
- From $250 per night (USD)
VRBO
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 $250 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 $934 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 $934 per night (USD)VRBO
- From $643 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 $643 per night (USD)Expedia
- From $432 per night (USD)
VRBO
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 $432 per night (USD)VRBO
- From $2500 per night (USD)
Expedia
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)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 $225 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 $225 per night (USD)Expedia
- From $180 per night (USD)
VRBO
USNA home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
You won't find a better location than this for your Annapolis getaway! Situated near Arundel Center, our home is conven ...
From $180 per night (USD)VRBO
- From $582 per night (USD)
Expedia
Riverfront home with kayaks, woodstove, firepit, & central AC - walk to downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Dreams Upon Weems Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $582 per night (USD)Expedia
- From $421 per night (USD)
VRBO
Gracie's Garden in Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come stay in a Heavenly Bed in the heart of Annapolis. Located 1 mile from downtown this garden apartment is completely ...
From $421 per night (USD)VRBO
- From $390 per night (USD)
Expedia
Charming 1926 renovated home in quite neighborhood perfectly situated
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A centrally located home that exceeds all needs and comfort or your family. Both cozy and spacious from well thought out ...
From $390 per night (USD)Expedia
- From $800 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 $800 per night (USD)VRBO
- Click For Pricing
Expedia
USNA Commissioning Week - 2 Blocks Away
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Host the perfect USNA Commissioning week family get together - just two blocks from the Naval Academy! Modern convenienc ...
Click For PricingExpedia
- From $374 per night (USD)
VRBO
Available 2024 Commissioning Week 20 mins to USNA
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
**Still available for 2024 Commissioning Week** Enjoy the magnificent waterfront views from this custom-built home with ...
From $374 per night (USD)VRBO
- Click For Pricing
Expedia
Newly-renovated waterfront home with private pier and all the bells and whistles
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Stay in this exceptional newly-renovated waterfront home with phenomenal views of the Severn River. Nestled in the desir ...
Click For PricingExpedia
- From $809 per night (USD)
VRBO
Annapolis Villa Aquamarine
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Annapolis and its very own Villa Aquamarine: your exclusive oasis awaits in this exceptional five bedroom hom ...
From $809 per night (USD)VRBO
- From $422 per night (USD)
Expedia
Coastal Cabins.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming & cozy, 2- level Victorian style home built in the 1920s. Well stocked w/ modern conveniences for your home awa ...
From $422 per night (USD)Expedia
- 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 $841 per night (USD)
Expedia
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)Expedia
- From $500 per night (USD)
VRBO
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)VRBO
- 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 $205 per night (USD)
VRBO
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 $205 per night (USD)VRBO
- From $540 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 $540 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 $208 per night (USD)
Expedia
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 $208 per night (USD)Expedia
- From $357 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 $357 per night (USD)VRBO
- From $343 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 $343 per night (USD)Expedia
- From $434 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 $434 per night (USD)VRBO
- From $198 per night (USD)
Expedia
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 $198 per night (USD)Expedia
- 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 $536 per night (USD)
VRBO
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 $536 per night (USD)VRBO
- From $382 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 $382 per night (USD)VRBO
- From $220 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 $220 per night (USD)VRBO
- From $807 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 $807 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 $272 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 $272 per night (USD)Expedia
- From $474 per night (USD)
VRBO
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 $474 per night (USD)VRBO
- 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 $441 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 $441 per night (USD)VRBO
- From $188 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 $188 per night (USD)VRBO
- From $180 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 $180 per night (USD)VRBO
- From $1033 per night (USD)
VRBO
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 $1033 per night (USD)VRBO
- From $800 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 $800 per night (USD)VRBO
- From $1370 per night (USD)
Expedia
3-story home near river with patio, firepit, Ping-Pong, grill and wood fireplace
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
Ensign's Ridge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $1370 per night (USD)Expedia
- From $375 per night (USD)
VRBO
Quiet Neighborhood 2.3 miles from Downtown w\/FREE parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Spinnakers Run, nestled just 2.3 miles from Historic Downtown Annapolis and Eastport with plenty of free park ...
From $375 per night (USD)VRBO
- From $145 per night (USD)
Expedia
Freshly renovated 3-story home 1 block from USNA!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Welcome to The Wardroom! Originally built in 1902 and completely renovated in 2014, this 3 story home is the p ...
From $145 per night (USD)Expedia
- From $582 per night (USD)
VRBO
Lovely home with a deck, gas grill, AC, firepit, & washer\/dryer
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Portside Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $582 per night (USD)VRBO
- From $265 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 $265 per night (USD)Expedia
- From $1400 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 $1400 per night (USD)VRBO
- From $456 per night (USD)
VRBO
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 $456 per night (USD)VRBO
- Click For Pricing
VRBO
Eastport Hideaway - Perfect little guesthouse for 2
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
Welcome to our newest listing in Annapolis . Tucked away is this sweet little guesthouse that has been newly renovated . ...
Click For PricingVRBO
- 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 $921 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 $921 per night (USD)VRBO
- 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
VRBO
Cottage for Rent
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Cottage for Rent xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx ...
Click For PricingVRBO
- From $1043 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 $1043 per night (USD)VRBO
- 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 $633 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 $633 per night (USD)VRBO
- Click For Pricing
VRBO
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 PricingVRBO
- From $1400 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 $1400 per night (USD)VRBO
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
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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 ...
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- 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
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VRBO
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 $1733 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 $1733 per night (USD)VRBO
- From $170 per night (USD)
VRBO
Cozy Bungalow w\/ Ample Outdoor Space Near Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to my charming Annapolis home in Eastport! My cozy 1 bed/1 bath house features a versatile spare room perfect fo ...
From $170 per night (USD)VRBO
- From $1103 per night (USD)
VRBO
Treasure Trove on Thompson
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
NBS22-145199 - PLEASE NOTE: IF YOU BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS TO FINALIZE A ...
From $1103 per night (USD)VRBO
- From $860 per night (USD)
VRBO
The place to be together! Linstead on the Severn River
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Two main floor bedrooms& baths and three bedrooms and one bath upstairs. Open and meandering decorator’s home full of en ...
From $860 per night (USD)VRBO
- From $785 per night (USD)
VRBO
Elegant waterfront cottage and guest house, garden setting, clubhouse and beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy waterfront views from every window, crabbing from the pier, sundowners on the wrap around porch, set in a private ...
From $785 per night (USD)VRBO
- From $750 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 $750 per night (USD)VRBO
- 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 $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 $313 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 $313 per night (USD)VRBO
- From $751 per night (USD)
VRBO
Parking at Stunning On Cloud 9 with private patio pet-friendly
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to this stunning home in downtown Annapolis with all the things you will ever need: parking for 2 cars (1 on-sit ...
From $751 per night (USD)VRBO
- From $655 per night (USD)
VRBO
Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
*Still available for 2024 Commissioning Week - 5-night minimum! Watch the sunrise on the private beach at Oh Happy Bay. ...
From $655 per night (USD)VRBO
- From $404 per night (USD)
VRBO
Cozy private home 3 min walk to downtown, elevator, private driveway
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy a short walk to the center of Annapolis and harbor, this home includes a private driveway for 1 large vehicle (a r ...
From $404 per night (USD)VRBO
- From $299 per night (USD)
VRBO
Perfect Eastport Location, walk everywhere, Annapolis NO CLEANING FEE
- 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 $299 per night (USD)VRBO
- From $695 per night (USD)
VRBO
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)VRBO
- From $785 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 $785 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
- From $295 per night (USD)
VRBO
Annapolis Retreat - 7 mins from downtown Annapolis!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Welcome to this charming five-bedroom, two-bathroom escape in Annapolis. Located in the Hillsmere Shores neighborhood, t ...
From $295 per night (USD)VRBO
- From $508 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 $508 per night (USD)Expedia