Severn River Rentals
- From $221 per night (USD)
VRBO
Anchor's Away in the Heart of Eastport!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Downtown in the heart of Eastport Annapolis, this first floor studio condo boasts high ceilings with lots of natural lig ...
From $221 per night (USD)VRBO
- From $285 per night (USD)
VRBO
2-bedroom waterfront Cottage in Annapolis, MD. Cove of Cork, view of the Severn.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Consider this charming cottage your home away from home while you visit Annapolis. Located on Cove of Cork, adjacent to ...
From $285 per night (USD)VRBO
- From $384 per night (USD)
VRBO
Annapolis Coastal Gem w\/ Hot Tub, Dock, Close to Everything & Sleeps 5
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy the ultimate Annapolis experience! Make yourself at home in this coastal getaway, a ~2000 s/f apartment in the low ...
From $384 per night (USD)VRBO
- From $278 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 $278 per night (USD)Expedia
- Click For Pricing
VRBO
Waterfront Magic - 10 minutes from downtown Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
A peninsula on the Severn River located in the beautiful neighborhood of Linstead. This home is a waterfront playground ...
Click For PricingVRBO
- Click For Pricing
Expedia
Private Eastport Guest Suite in Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a clean, comfortable and private suite in the heart of Eastport. Steps away from Davis' Pub and Forward Brewing as ...
Click For PricingExpedia
- Click For Pricing
VRBO
USNA Commissioning Week 2023 Downtown Annapolis House that sleeps 13 people
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 PricingVRBO
- From $340 per night (USD)
Expedia
Historic Annapolis Home 1.5 blocks from center of town.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Historic home 1.5 blocks from center of town. Easy walk to the shops, food, harbor, Naval Academy and historic attractio ...
From $340 per night (USD)Expedia
- From $1767 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 $1767 per night (USD)VRBO
- From $763 per night (USD)
Expedia
Fisher House - Downtown Annapolis!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to our beautifully renovated historic home in the heart of Annapolis! The Fisher House was built in 1885 and nam ...
From $763 per night (USD)Expedia
- From $1772 per night (USD)
VRBO
Downtown Annapolis Duke's House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
This newly renovated 4-bedroom, 3.5 bathroom home is perfectly situated in the heart of historic downtown Annapolis, ma ...
From $1772 per night (USD)VRBO
- From $385 per night (USD)
VRBO
Stay on a boat while in annapolis for the shows.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Large 43' sailboat with 3 cabins, 2 bathrooms, a large cockpit and plenty of space on the deck. The boat is anchored in ...
From $385 per night (USD)VRBO
- Click For Pricing
VRBO
2003 Craftsman; Heart of Eastport!
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 0
Eastport Craftsman (2003). Short stroll to DT Historic Annapolis shops & Restaurants! Open floor plan! Stunning 2,464 sq ...
Click For PricingVRBO
- Click For Pricing
VRBO
Quaint Cottage is the perfect getaway retreat in Eastport.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by Annapol ...
Click For PricingVRBO
- From $273 per night (USD)
VRBO
Waterfront Condo- Eastport Annapolis- Next to Spa Creek Draw Bridge & AYC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Upscale renovated units on the first floor of Yacht Club Condos. Both units A1 and C1 are available. First floor walk o ...
From $273 per night (USD)VRBO
- Click For Pricing
Expedia
Condo Houseboat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This BRAND NEW condo house boat is nestled in Back Creek. The views of the Chesapeake Bay are amazing! This is the best ...
Click For PricingExpedia
- From $193 per night (USD)
VRBO
Beautiful Condo - Water View Near City Dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Newport Condominium has a beautiful water view of Spa Creek in Eastport. This condo is newly decorated with new ca ...
From $193 per night (USD)VRBO
- From $819 per night (USD)
Expedia
Steps to Gate 1 and onsite parking at Naval-Academy Themed Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to this gorgeous 1900's fully-renovated home, restored to a new modern grandeur, which includes coveted parking ...
From $819 per night (USD)Expedia
- From $448 per night (USD)
VRBO
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
421 Irie City Of Annapolis License Number 145052 Skip the lines!!! I offer personal chef services!!! NOTE: I ❤️ my n ...
From $448 per night (USD)VRBO
- From $709 per night (USD)
VRBO
Historic Annapolis Getaway - 45 steps to Downtown and 156 steps to USNA!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
45 steps from the Annapolis City Dock and 156 steps to the United States Naval Academy! Walk to all Shops, Restaurants, ...
From $709 per night (USD)VRBO
- From $603 per night (USD)
VRBO
Hanover House across from USNA Gate 3 with private back patio
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The fully-renovated 1800 historic home is just steps from USNA’s Gate 3. Located in the heart of historic downtown on a ...
From $603 per night (USD)VRBO
- From $314 per night (USD)
Expedia
Bay View Studio Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private ...
From $314 per night (USD)Expedia
- From $455 per night (USD)
VRBO
Quiet home with large yard, close to Navy Bridge.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Come relax at our spacious home and enjoy our quiet neighborhood! We are located near the greatest attractions in Annapo ...
From $455 per night (USD)VRBO
- From $389 per night (USD)
Expedia
ACROSS FROM STADIUM - walk to downtown Annapolis.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Across the street from the Navy and Marine Corps Stadium and walking distance to historic downtown Annapolis - you will ...
From $389 per night (USD)Expedia
- Click For Pricing
VRBO
Historic Annapolis Home Convenient to Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Historic Annapolis home convenient to downtown, restaurants, shopping, commuter routes and public transportation! -0.5 ...
Click For PricingVRBO
- From $410 per night (USD)
Expedia
Annapolis Downtown Entire Townhome 3 bed 6 guests
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Immerse yourself in the best that the downtown Historic District of Annapolis has to offer while stayin ...
From $410 per night (USD)Expedia
- From $953 per night (USD)
VRBO
Center of Downtown Annapolis with Free Parking at Randall House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
The Randall House is an historic gem in the heart of Downtown Annapolis with PARKING for 3 cars! Built in 1880, The R ...
From $953 per night (USD)VRBO
- From $1539 per night (USD)
Expedia
5 BDRM across from the USNA Stadium
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Across the street from the Naval Academy Stadium. Open floor plan with stainless steel appliances, two islands, 8-10 per ...
From $1539 per night (USD)Expedia
- From $699 per night (USD)
VRBO
The Navy House~ Walk to Downtown! 3 Bed Bungalow across from Navy Stadium
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Our quiet 3 bed 2.5 bath home is the perfect Annapolis getaway! On a dead end road. A quick walk to the best downtown r ...
From $699 per night (USD)VRBO
- From $755 per night (USD)
Expedia
Waterfront dog-friendly Private Pier, Game Room, mins to Annapolis Jolly Roger
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Arrive by car or boat to this waterfront home, located in Crownsville, just outside of Annapolis. The private pier is o ...
From $755 per night (USD)Expedia
- From $409 per night (USD)
VRBO
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Just finished with a few updates to kitchen and bedrooms + all new sheets and towels!new pictures coming soon!! Fantasti ...
From $409 per night (USD)VRBO
- From $621 per night (USD)
Expedia
1 Block to USNA and Boat Shows with Chapel Views big back patio and off-site parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
When the owners decided to find their Annapolis home base, they knew they had to be within walking distance to the one’s ...
From $621 per night (USD)Expedia
- From $718 per night (USD)
VRBO
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
1930's Single family home on adorable cul-de-sac downtown Annapolis with off-street parking! Located off West Street in ...
From $718 per night (USD)VRBO
- From $496 per night (USD)
Expedia
Free Parking with private fenced-in backyard with pool table at Weekender
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This newly-renovated duplex townhome in Annapolis is walkable to Eastport and just 1.5 miles to the Annapolis Waterfront ...
From $496 per night (USD)Expedia
- From $131 per night (USD)
VRBO
Bright and cheery home. Just a short 2 blocks from the beach.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
RENT-001177-2024 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BE ...
From $131 per night (USD)VRBO
- From $940 per night (USD)
VRBO
Brand New Luxury Waterfront Home
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 10
This home boasts breathtaking views from both in and outside the home. Enjoy your morning coffee on the deck or warm up ...
From $940 per night (USD)VRBO
- From $448 per night (USD)
VRBO
Steps to the marinas with Private back deck, yard and Easy parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
This professionally-decorated and furnished 2 bedroom, 1.5 bath is located across the Annapolis Waterfront drawbridge in ...
From $448 per night (USD)VRBO
- Click For Pricing
Expedia
\"Dreams upon Weems\" Waterfront Cottage on Weems Creek in Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Waterfront Home on Weems Creek in Annapolis with private water access for paddleboarding, kayaking, boating. Waterfro ...
Click For PricingExpedia
- From $110 per night (USD)
VRBO
Convenient Eastport condo with beautiful water views and community pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
REN - 144875 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $110 per night (USD)VRBO
- From $151 per night (USD)
VRBO
This Eastport condo has a large deck with amazing views of Spa Creek and downtown Annapolis.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
REN - 144911 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $151 per night (USD)VRBO
- From $370 per night (USD)
VRBO
Renovated historic apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the historic neighborhood of Murray Hill! The Bennett House is a charming, light- filled detached home with a ...
From $370 per night (USD)VRBO
- From $408 per night (USD)
Expedia
Renovated historic apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the historic neighborhood of Murray Hill! The Bennett House is a charming, light- filled detached home with a ...
From $408 per night (USD)Expedia
- From $1051 per night (USD)
VRBO
Deep in the Heart of Annapolis; Parking for days!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this gorgeous Texas-themed downtown Annapolis home. Every inch of this home has custom finishes and has been ...
From $1051 per night (USD)VRBO
- Click For Pricing
Expedia
New Listing! Walk to USNA\/Capitol\/Downtown
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Want to enjoy being in downtown Annapolis, but on one of the quieter streets? If that sounds good, this is the place fo ...
Click For PricingExpedia
- From $242 per night (USD)
VRBO
Downtown Annapolis Condo w\/ Free Parking + Coffee
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This newly constructed property brings chic, low-maintenance living to the heart of the Arts District in Annapolis. No ...
From $242 per night (USD)VRBO
- From $853 per night (USD)
Expedia
WATERFRONT Historic Home on the Chesapeake Bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
WATERFRONT - Beautiful 4 bedroom, 2 1/2 bathrooms newly renovated charming historic home ON the Chesapeake Bay. New mode ...
From $853 per night (USD)Expedia
- Click For Pricing
VRBO
Annapolis House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Traditional 4 bedroom house in neighborhood with loft. Lots of room to move around in with gated back yard. Only 3 mi ...
Click For PricingVRBO
- From $428 per night (USD)
Expedia
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Custom home with inlaid floor, wood counters, hand made cabinets, and artistic touches. Beautifully landscaped large pri ...
From $428 per night (USD)Expedia
- From $426 per night (USD)
VRBO
Charming 4BR 2BA w\/ outdoor patio & fire pit! 5 min walk to Navy Stadium and DT
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Come stay at this fully updated cozy 4-bedroom 2-bathroom home. Conveniently located with a .6 mile walk to the Naval Ac ...
From $426 per night (USD)VRBO
- From $515 per night (USD)
Expedia
One-level living and 1 mile to Navy Stadium with Backyard with 4 King Beds
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to this completely renovated midcentury ranch Annapolis home, jut a mile from the Naval Academy Football Stadium ...
From $515 per night (USD)Expedia
- From $417 per night (USD)
VRBO
Spectacular Location: State Circle Apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Stay in this iconic building at the intersection of State Circle and Maryland Avenue in the Historic District of Annapol ...
From $417 per night (USD)VRBO
- From $572 per night (USD)
Expedia
Easy walk to DTA from Historic multi-level Firehouse with parking, dog-friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This is a unique home like none other in downtown Annapolis. Originally the Eastport Volunteer Fire Company, founded in ...
From $572 per night (USD)Expedia
- From $495 per night (USD)
VRBO
Multiple family spaces both inside and out 13 mins to USNA
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
From the moment you walk into this lovely home, you will feel the presence of the long serving navy family, ship captain ...
From $495 per night (USD)VRBO
- From $341 per night (USD)
Expedia
Annapolis Condominium in the heart of the historic center
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Don’t miss our unique two floor condominium in Historic Annapolis downtown with 3 bedrooms (one queen, two rooms with tw ...
From $341 per night (USD)Expedia
- From $415 per night (USD)
VRBO
Chic Condo w\/ Balcony in the Heart of 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 $415 per night (USD)VRBO
- From $228 per night (USD)
Expedia
Cozy 1st Floor King George one bedroom apartment right across from USNA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy this one bedroom first floor apartment that's right across from Gate 2 of the U.S. Naval Academy. It's a short 1 ...
From $228 per night (USD)Expedia
- From $308 per night (USD)
VRBO
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This 2nd floor unit has all new furniture, bedding and housewares. This is directly across from Gate 2 at the Naval Acad ...
From $308 per night (USD)VRBO
- From $195 per night (USD)
Expedia
Charming Downtown 3rd Floor 1 Bedroom Apt
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perfect location for all that downtown Annapolis offers, right across from USNA gate 2. Super convenient, park your car ...
From $195 per night (USD)Expedia
- From $1278 per night (USD)
VRBO
Stay at Lux Red Door Gem with 3 Parking Spots
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The gorgeous Downtown Annapolis home was meticulously remodeled from top-to-bottom in a luxurious fashion. This fully-r ...
From $1278 per night (USD)VRBO
- From $628 per night (USD)
Expedia
Steps to Main Street and City Dock w View of the Capital free off-site parking and patio
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This 4-bedroom home in the heart of Historic Annapolis is located directly behind Main Street. The stunning view in th ...
From $628 per night (USD)Expedia
- From $623 per night (USD)
VRBO
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Hello and Welcome to Annapolis! You are going to love this home. IMPORTANT: if you are inquiring about USNA Commission ...
From $623 per night (USD)VRBO
- From $570 per night (USD)
Expedia
Walkable to Main Street at Seashell in the City with 2 parking spots
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this gorgeous fully-renovated home, restored to a new modern grandeur, which includes coveted parking for 2 c ...
From $570 per night (USD)Expedia
- From $425 per night (USD)
VRBO
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This home is spacious and clean and will make your vacation plans a breeze from this central location. Many families, g ...
From $425 per night (USD)VRBO
- From $648 per night (USD)
VRBO
Downtown Annapolis Townhome ! Beautiful!!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful Remodeled Townhome ! We have thought of everything you will need for an amazing stay. Fully loaded kitchen , ...
From $648 per night (USD)VRBO
- From $419 per night (USD)
VRBO
Eastport Cottage .5 mi from Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Charming Eastport Cottage just 3 blocks from restaurants and bars (Ruth's Chris, Boatyard, O'leary's, Carol's Creek, to ...
From $419 per night (USD)VRBO
- From $560 per night (USD)
Expedia
Walk to waterfront & USNA with Parking at Historic Wisteria
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
How many homes in Downtown Annapolis have 4 Bedrooms with 4 Baths (3 of which are en-suite)?! Just 1-2 blocks from the ...
From $560 per night (USD)Expedia
- From $633 per night (USD)
VRBO
Bennett House (entire):Haven in Historic Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to the historic neighborhood of Murray Hill! The Bennett House is a charming, light- filled detached home with 3 ...
From $633 per night (USD)VRBO
- From $139 per night (USD)
Expedia
Cozy place close to the city dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Annapolis; where history and nature coincide! You will feel right at home in this confortable 1 bedroom 1 bat ...
From $139 per night (USD)Expedia
- From $584 per night (USD)
VRBO
\"Around the corner\" from everything with private fenced-in yard and parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
*Flexible Commissioning Week Cancellation Policy* Welcome to this charming remodeled Eastport Victorian home "Around th ...
From $584 per night (USD)VRBO
- Click For Pricing
Expedia
A Delight on Dean
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sitting on a quiet, tree lined street, this home enjoys being located in the sought after neighborhood of Murray Hill. ...
Click For PricingExpedia
- From $307 per night (USD)
VRBO
Cozy 2br home w\/ parking in downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A's by the Cove is ideally located in the heart of downtown Annapolis's Historic and Art Districts. It is a fully update ...
From $307 per night (USD)VRBO
- From $261 per night (USD)
Expedia
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Quaint 2 BR 1 BA Guest House nestled in the trees by USNA stadium. Enjoy Annapolis historic charm in this rare 2 BR 1 BA ...
From $261 per night (USD)Expedia
- From $469 per night (USD)
VRBO
Close to USNA Stadium with screened-in porch and parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to this charming Cape Cod on half an acre right outside downtown Annapolis. Just 4 minutes to the Stadium and a ...
From $469 per night (USD)VRBO
- From $181 per night (USD)
Expedia
Calico Cottage Guest House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cute-as-a-bugs ear West Annapolis guest cottage. In settled neighborhood just 1.5 miles from the Navy Stadium and less t ...
From $181 per night (USD)Expedia
- From $485 per night (USD)
VRBO
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Charming house - a 10-15 min walk to Navy Marine Corps Stadium (<.75mile), a 5 min drive from the US Naval Academy (<1mi ...
From $485 per night (USD)VRBO
- From $235 per night (USD)
Expedia
Jode's Retreat \"Your home away from home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Clear the calendar for an easy-going getaway at "Jode's Retreat"; ideal for USNA events (a 2-minute drive to the stadium ...
From $235 per night (USD)Expedia
- From $954 per night (USD)
VRBO
Perfect historic home + Peloton, walk to downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lovely historic home within walking distance from downtown (1 mile from Church Circle) & Navy stadium (5 blocks), hardwo ...
From $954 per night (USD)VRBO
- From $307 per night (USD)
Expedia
Charming garden row home, easy 4 block walk to the heart of Annapolis.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Incredible location in the Historic District of Annapolis. Walking distance to the Naval Academy, St. Johns College, an ...
From $307 per night (USD)Expedia
- From $360 per night (USD)
VRBO
Charming Charles Retreat- The perfect space for fun and relaxation!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history and vibr ...
From $360 per night (USD)VRBO
- From $482 per night (USD)
Expedia
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Your family will be close to everything when you stay at this centrally-located place. Two blocks to Main Street, the Na ...
From $482 per night (USD)Expedia
- From $966 per night (USD)
VRBO
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Located on one of the most coveted streets in downtown Annapolis, walk to Main St. and City Dock. The Thomas Hyde House ...
From $966 per night (USD)VRBO
- From $587 per night (USD)
Expedia
WALK TO DOWNTOWN ANNAPOLIS, EGO ALLEY, NAVAL STADIUM & ACADEMY
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This home was newly renovated in 2021 and is located in the highly desirable Murray Hill Neighborhood. Conveniently loc ...
From $587 per night (USD)Expedia
- From $421 per night (USD)
VRBO
Gorgeous & bright retreat with patio, firepit, W\/D, & stunning rooftop views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Skyline Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $421 per night (USD)VRBO
- From $2622 per night (USD)
VRBO
Premium Home in West Annapolis: Perfect for Navy Events, Boat Shows, Walkable!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
You will be close to everything when you stay at this well appointed, centrally-located home. This elegant, stylish, a ...
From $2622 per night (USD)VRBO
- From $2230 per night (USD)
VRBO
Elegant Eastport Entertaining Dream House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
NBS23-145363 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $2230 per night (USD)VRBO
- From $1518 per night (USD)
Expedia
Stately Brick Ranch On Corner Lot with Private Backyard for Entertaining
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
STR00803 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $1518 per night (USD)Expedia
- From $1549 per night (USD)
VRBO
Marvelous Home with Backyard Living Room in Murray Hill
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
NBS23-145336 Welcome to our charming vacation rental house nestled in the picturesque Murray Hill neighborhood of Annapo ...
From $1549 per night (USD)VRBO
- From $603 per night (USD)
Expedia
Eastport Oasis 4 BR 2 BA fully renovated home on quiet street with parking
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $603 per night (USD)Expedia
- From $516 per night (USD)
VRBO
Cute bungalow blocks to Stadium
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This stylish two bedroom home is conveniently located in Annapolis' Germantown neighborhood off West Street, ne ...
From $516 per night (USD)VRBO
- From $555 per night (USD)
Expedia
WATERFRONT 2-Bdrm Townhome, SPA Bthrm, Private Patio, WiFi-Eastport, Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Nestled in a waterfront tranquil setting on Spa Creek, guests can unwind in this superb accommodation. Enjoy the luxury ...
From $555 per night (USD)Expedia
- From $745 per night (USD)
VRBO
Experience Annapolis like a local - 4 BR Apartment overlooking Main Street in Annapolis -
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Above it All - Downtown Historic Annapolis Vacation Rental on Main Street - PLEASE NOTE: THIS PROPERTY IS MANAGED BY AN ...
From $745 per night (USD)VRBO
- From $539 per night (USD)
Expedia
City Gate: Townhome in Downtown Annapolis with private backyard patio and parking
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to City Gate, conveniently located in downtown Annapolis, just steps from all the shops and restaurants in the H ...
From $539 per night (USD)Expedia
- From $554 per night (USD)
VRBO
Beat Army Bungalow: Steps to Stadium & mins to DTA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your home away from home! Nestled in a prime location, this charming 3-bedroom, 2-bathroom house is the perfe ...
From $554 per night (USD)VRBO
- From $491 per night (USD)
Expedia
Eastport Third Time's the Charm – Steps from Marinas, Dining, and Historic Annapolis
- Bedrooms:
- 2
- 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 $491 per night (USD)Expedia
- From $418 per night (USD)
VRBO
Charming 3-bedroom house in Annapolis ⚓️🛥️⛵️ on the Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make yourself at home in this delightful 3-bedroom Annapolis retreat. With a king bed, queen bed, and full bed, this hou ...
From $418 per night (USD)VRBO
- From $627 per night (USD)
Expedia
Charming 3-bedroom house in Annapolis two blocks from the Navy Stadium
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Peaceful house on a quiet street two blocks from the Navy Stadium with easy access to downtown Annapolis via the stadium ...
From $627 per night (USD)Expedia
- From $1049 per night (USD)
VRBO
Waterviews, steps to the water, restaurants and downtown from custom-built First Mate
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Stunning 4 Bedroom / 3.5 Bath Home in Eastport with Water Views and Expansive Yard Experience the best of Eastport in t ...
From $1049 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:
- 2
- 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
- Click For Pricing
VRBO
Gorgeous House in the Heart of Annapolis, Walk to Everything!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located within walking distance of everything Annapolis has to offer, this 3BR/2.5 Bath historic Craftsman home is beaut ...
Click For PricingVRBO
- From $966 per night (USD)
Expedia
Luxury Home with Pool for 20
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 20
Vacation in luxury with 20 of your closest friends and family. This 5000+ square foot home with a pool sits at the end o ...
From $966 per night (USD)Expedia