
Severn River Rentals

- From $875 per night (USD)
VRBO
Custom New Home in Eastport. Less than one mile to Naval Academy and City Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by the host ...
From $875 per night (USD)VRBO
- From $644 per night (USD)
VRBO
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This new 4 bed / 3 bath modern luxury home sleeps 10 and is located in a quiet neighborhood near the Westin Hotel. Once ...
From $644 per night (USD)VRBO
- From $329 per night (USD)
VRBO
Charming Annapolis Guest House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This charming guest house with private access is in a great location! Just 2 miles from the Naval Academy, Downtown Anna ...
From $329 per night (USD)VRBO
- From $762 per night (USD)
VRBO
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Absolutely gorgeous downtown waterfront home. Loaded with historical significance and character, all while minutes walki ...
From $762 per night (USD)VRBO
- From $232 per night (USD)
VRBO
Brand New Reno in Historic Dist w 2 Parking spots
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Spotless / sanitized !! Renovated upstairs unit two bedroom with TWO parking spots in the Historic District . Everythi ...
From $232 per night (USD)VRBO
- From $684 per night (USD)
VRBO
Quiet Relaxing Waterfront Suisse Chalet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This spacious, airy and relaxing 3 bedroom house, comes with a beautiful loft and an additional queen pull out sofa be ...
From $684 per night (USD)VRBO
- From $561 per night (USD)
VRBO
★ Midcentury Modern Getaway ★ Prime Location ★
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Immerse yourself in the best that the downtown Historic District of Annapolis has to offer while staying in this complet ...
From $561 per night (USD)VRBO
- From $591 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 $591 per night (USD)VRBO
- From $673 per night (USD)
VRBO
Private Waterfront Woods | Dock, Kayaks, Views
- Bedrooms:
- 3
- 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 $673 per night (USD)VRBO
- From $673 per night (USD)
VRBO
Restriction Retreat - Relax & walk to Main St
- Bedrooms:
- 2
- 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 $673 per night (USD)VRBO
- From $990 per night (USD)
VRBO
USNA Stay w/ Private Pool, King Beds, Furbabies & CHILD FRIENDLY GEAR
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
USNA Family Stay w/Pool - Infant/Toddler Friendly! Enjoy the newest addition to my “Family Friendly Staycation” home ho ...
From $990 per night (USD)VRBO
- From $360 per night (USD)
VRBO
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
- Bedrooms:
- 1
- 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 $360 per night (USD)VRBO
- From $449 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 $449 per night (USD)VRBO
- From $518 per night (USD)
VRBO
Large Luxury Apartment In Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bed/2 Bath Apartment with additional family room with brand new queen sleeper sofa in Historic Downtown Annapolis step ...
From $518 per night (USD)VRBO
- From $753 per night (USD)
VRBO
Waterfront Oasis in Eastport-Easy Walk to Downtown
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our Waterfront Oasis in the desirable Eastport section of Annapolis. With 4 bedrooms and an open studio spac ...
From $753 per night (USD)VRBO
- From $449 per night (USD)
Expedia
PERFECT LOCATION in the heart of history
- Bedrooms:
- 2
- 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 $449 per night (USD)Expedia
- From $378 per night (USD)
VRBO
Walk everywhere . . .just minutes to historic Annapolis, Updated.
- Bedrooms:
- 1
- 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 $378 per night (USD)VRBO
- From $513 per night (USD)
VRBO
Heart of Historic District!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This three story 1875 home is located in the Heart of Historic Annapolis. Shops, restaurants, historic sites and the Cit ...
From $513 per night (USD)VRBO
- From $948 per night (USD)
VRBO
Beautiful Blend of Restoration and Renovation in this Downtown Home
- Bedrooms:
- 3
- 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 $948 per night (USD)VRBO
- From $595 per night (USD)
Expedia
Waterfront home with private pier mins to Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the magnificent waterfront views from this custom-built home with a private pier! Nestled in the quiet Arden on th ...
From $595 per night (USD)Expedia
- From $1039 per night (USD)
VRBO
Unique Listing! Entire Downtown Triplex w/Private Parking. Sleeps 12-18. Pets ok
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 18
*** Commissioning Wk 2024 AVAILABLE*** Unique opportunity to rent an entire triplex Downtown Annapolis! One property wi ...
From $1039 per night (USD)VRBO
- Click For Pricing
Expedia
USNA Commissioning Week - 2 Blocks Away
- Bedrooms:
- 2
- 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 $1744 per night (USD)
VRBO
3-story home near river with patio, firepit, Ping-Pong, grill and wood fireplace
- Bedrooms:
- 6
- 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 $1744 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $394 per night (USD)
VRBO
Charming 1926 Four Bedroom Home w Ample Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A centrally located home that exceeds all needs and comfort or your family. Both cozy and spacious from well thought ou ...
From $394 per night (USD)VRBO
- From $657 per night (USD)
Expedia
Freshly renovated 3-story home 1 block from USNA!
- Bedrooms:
- 2
- 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 $657 per night (USD)Expedia
- Click For Pricing
VRBO
Stunning Waterfront Home with Incredible Views
- Bedrooms:
- 5
- 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 ...
Click For PricingVRBO
- From $597 per night (USD)
Expedia
Steps to USNA with Large Private Patio & Free Off-Site Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in this restored historic Annapolis home, located just steps from both USNA Gates 1 and 3. The proud Navy graduate ...
From $597 per night (USD)Expedia
- From $604 per night (USD)
VRBO
Historic downtown townhome with brick courtyard, sunroom & parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Corner Courtyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $604 per night (USD)VRBO
- From $444 per night (USD)
Expedia
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
- 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 $444 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 $674 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 $674 per night (USD)VRBO
- From $533 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 $533 per night (USD)VRBO
- From $547 per night (USD)
Expedia
Waterfront Condo with Rooftop Pool, Spa Creek Views & Prime Eastport Location with Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Waterfront Condo with Spa Creek Views, Rooftop Pool & Prime Eastport Location Experience Annapolis from this beautifull ...
From $547 per night (USD)Expedia
- From $659 per night (USD)
VRBO
History & Charm Are Only Steps from Main Street and City Dock at Catch 22
- Bedrooms:
- 2
- 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 $659 per night (USD)VRBO
- From $967 per night (USD)
VRBO
Hidden Treasure on Weems Creek
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
STR00704 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $967 per night (USD)VRBO
- From $1462 per night (USD)
VRBO
Bay Ridge Beauty with Wooded Serenity and Community Water Views
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
STR00711 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $1462 per night (USD)VRBO
- From $987 per night (USD)
Expedia
USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Summary: This is a gorgeous 4 story home with in ground salt water pool & hot tub! **Please note that we can heat either ...
From $987 per night (USD)Expedia
- From $865 per night (USD)
VRBO
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 $865 per night (USD)VRBO
- From $1059 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 $1059 per night (USD)Expedia
- From $598 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 $598 per night (USD)VRBO
- From $836 per night (USD)
Expedia
The General's House S
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: Look no further for your next vacation home in Annapolis! Relax, unwind or entertain friends and family in this ...
From $836 per night (USD)Expedia
- From $324 per night (USD)
VRBO
Naval Academy Gate 1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This 2-bed, 1.5-bath townhome mixes modern renovations with 1900 classic charm. It's been lovingly decorated to accommod ...
From $324 per night (USD)VRBO
- From $536 per night (USD)
VRBO
Charming on Charles
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our elegant stand alone charming home on Charles Street in Historic Annapolis . This 3 bedroom 2.5 bath is ju ...
From $536 per night (USD)VRBO
- From $513 per night (USD)
VRBO
Five Star Charmer! Great Location Downtown & Stadium! 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 $513 per night (USD)VRBO
- From $153 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 $153 per night (USD)VRBO
- From $486 per night (USD)
VRBO
Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This beautifully-restored 1 bedroom apartment is on the lower level of a 2-unit building in the charming Eastport neighb ...
From $486 per night (USD)VRBO
- From $728 per night (USD)
Expedia
Stay at Waterfront Home with Pier & Community Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the perfect waterfront escape near Annapolis! This charming 3-bedroom, 2-bathroom home offers stunning waterfro ...
From $728 per night (USD)Expedia
- From $1378 per night (USD)
VRBO
Eastport Classic Charm
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to our Eastport home where hardwood floors, large windows that allow ample natural light, and a cozy fi ...
From $1378 per night (USD)VRBO
- From $717 per night (USD)
Expedia
Charming 3-bedroom house with AC and WiFi in enchanting Annapolis/Eastport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay comfortably in Annapolis at this 3-bedroom house. With 1 king bed, 1 queen bed, and 1 full bed, this tremendous pro ...
From $717 per night (USD)Expedia
- From $554 per night (USD)
VRBO
Ahoy! Game Room, Screened Porch, Yard Mins to DTA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to The Buccaneer, a family-friendly home located just 3 miles from Historic Downtown Annapolis and Eastport. Thi ...
From $554 per night (USD)VRBO
- From $3136 per night (USD)
VRBO
Stunning remodel in Murray Hill
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to 9th wing (USNA reference for the boat schoolers out there!) We just completed renovations on this spacious h ...
From $3136 per night (USD)VRBO
- From $278 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 $278 per night (USD)VRBO
- From $443 per night (USD)
Expedia
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this delightful three-bedroom getaway nestled within the ancient Annapolis historical area! Nestled just a 17-m ...
From $443 per night (USD)Expedia
- Click For Pricing
VRBO
Large House Downtown Annapolis with 2 Hot Tubs and 4 parking places
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
This Navy Themed house is located jn downtown annapolis, walking distance to all the shops and restaurants in annapolis ...
Click For PricingVRBO
- From $1338 per night (USD)
VRBO
Fabulous Waterfront Contemporary with Rooftop Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
RENT-000856-2025 THIS PROPERTY IS MANAGED BY ANNAPOLIS ACOCMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL A TEAM M ...
From $1338 per night (USD)VRBO
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $436 per night (USD)
Expedia
Annapolis Blue and Gold Haven
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Nestled in the heart of Annapolis, this charming 2-bedroom townhome offers the perfect blend of comfort and con ...
From $436 per night (USD)Expedia
- From $316 per night (USD)
VRBO
Cozy 2-bedroom home with WiFi and huge backyard minutes from downtown Annapolis.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Annapolis, this delightful house is a dream. With 2 cozy bedrooms, heating, AC, WiFi, and a washing machine, ...
From $316 per night (USD)VRBO
- From $1112 per night (USD)
Expedia
Available for Commissioning Week and Boat shows. Heated Pool and great backyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stay comfortably in my home in Annapolis at this 3-bedroom house. With a king bed, queen bed, and two cozy sofa beds, t ...
From $1112 per night (USD)Expedia
- From $743 per night (USD)
VRBO
Quiet House on Saltworks Creek in Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This is a unique, water view, post-and-beam constructed house located at the end of a private road and just minutes from ...
From $743 per night (USD)VRBO
- From $691 per night (USD)
Expedia
Charming Annapolis Townhome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Historic Annapolis Living! Welcome to your captivating 2-bedroom, 1.5-bath home. This stunning retreat offers a ...
From $691 per night (USD)Expedia
- From $717 per night (USD)
VRBO
Historic Row Home 1 Block from Gate 1 at USNA!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Summary: Steps away from the Naval Academy, St. John's College, State House, City Dock, Yacht Club, St. Mary's Church an ...
From $717 per night (USD)VRBO
- From $447 per night (USD)
Expedia
Dean Street's Lower Deck House!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: Welcome to our charming 1-bedroom retreat in the heart of Annapolis’ Historic District! Just steps from shops, ...
From $447 per night (USD)Expedia
- From $475 per night (USD)
VRBO
Annapolis Gem: Stylish and Cozy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Summary: Gather your loved ones and experience the charm of this comfortable, stylish apartment, designed for pleasure a ...
From $475 per night (USD)VRBO
- From $794 per night (USD)
VRBO
Modern condo in the heart of DTA with garage parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in the heart of downtown Annapolis in this bright, modern 2 bed, 2 bath condo with your own private balcony—just st ...
From $794 per night (USD)VRBO
- From $662 per night (USD)
VRBO
New! All Star Annapolis Retreat - Walk to Stadium
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Welcome to our Town- House in Annapolis Maryland. This charming 1.5-story retreat offers 2,400 square feet of ...
From $662 per night (USD)VRBO
- From $502 per night (USD)
Expedia
Newly renovated in DTA w parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom, 2.5-bath single-family home mixes modern renovations with 1896 classic charm. It's been decorated with u ...
From $502 per night (USD)Expedia
- From $483 per night (USD)
VRBO
Walking distance to Navy Stadium! No cleaning fees!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This centrally located 3-story rental is steps away from everything Annapolis offers! Whether you're in town to explore ...
From $483 per night (USD)VRBO
- From $494 per night (USD)
Expedia
Marymont Cottage in awesome Annapolis walking distance to local pub!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Discover this adorable 3-bedroom gem in Annapolis, just across the creek from sought after West Annapolis. This charming ...
From $494 per night (USD)Expedia
- From $294 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 $294 per night (USD)VRBO
- From $376 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 $376 per night (USD)Expedia
- From $353 per night (USD)
VRBO
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom bungalow in Annapolis is perfect for your escape. With 2 full beds and 1 full sofa bed in the 3rd room. I ...
From $353 per night (USD)VRBO
- From $695 per night (USD)
Expedia
Admiral's Abode - Charming Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Charming 4-bedroom, 3-bath home in the heart of downtown Annapolis! This beautifully updated property is steps from the ...
From $695 per night (USD)Expedia
- From $612 per night (USD)
VRBO
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 15
Summary: This charming 5 BR (3x true bedrooms and 2x basement rooms with bunk beds) home is conveniently located in Anna ...
From $612 per night (USD)VRBO
- From $518 per night (USD)
Expedia
Charming Historic Row House in The Heart of Eastport's Horn Point
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this stunning historic rowhouse located in the charming and highly sought-after neighborhood of Horn Point Ea ...
From $518 per night (USD)Expedia
- From $375 per night (USD)
VRBO
Charming apt in the heart of Eastport & Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Start your Annapolis adventure in this charming 1-bedroom apartment, comfortably accommodating up to 7 guests. Located i ...
From $375 per night (USD)VRBO
- From $211 per night (USD)
VRBO
Robert Johnson Queen at Historic Inns of Annapolis
- 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 $211 per night (USD)VRBO
- From $211 per night (USD)
VRBO
Explore Local Attractions, Just Across Maryland 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 $211 per night (USD)VRBO
- From $394 per night (USD)
VRBO
Robert Johnson Suite at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $394 per night (USD)VRBO
- From $394 per night (USD)
VRBO
Experience History in Annapolis, Near Chesapeake Bay & Beaches!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $394 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Worry-free Stay, Allergy-friendly Room, Exceeds HEPA Standards
- 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 $200 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Robert Johnson 2 Double Beds Pure Wellness Room at Historic Inns of Annapolis
- 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 $200 per night (USD)VRBO
- From $205 per night (USD)
VRBO
Robert Johnson 1 King Bed Pure Wellness Room at Historic Inns of Annapolis
- 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 $205 per night (USD)VRBO
- From $209 per night (USD)
VRBO
Robert Johnson 1 Queen Bed Pure Wellness Room at Historic Inns of Annapolis
- 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 $209 per night (USD)VRBO
- From $205 per night (USD)
VRBO
Prime Location! Close to Chesapeake Bay & Beaches
- 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 $205 per night (USD)VRBO
- From $209 per night (USD)
VRBO
Allergy-friendly Unit, Short Drive to Annapolis Westfield Mall
- 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 $209 per night (USD)VRBO
- From $201 per night (USD)
VRBO
Surrounded with History! Pet-friendly Accommodation
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $201 per night (USD)VRBO
- From $409 per night (USD)
VRBO
Pet-friendly Accommodation at Historic Inns of Annapolis! Enjoy Historic Views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $409 per night (USD)VRBO
- From $201 per night (USD)
VRBO
Maryland Inn Queen at Historic Inns of Annapolis, Pets Allowed
- 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 $201 per night (USD)VRBO
- From $409 per night (USD)
VRBO
Maryland Inn Suite at Historic Inns of Annapolis, Pet-friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $409 per night (USD)VRBO
- From $240 per night (USD)
VRBO
Top Location! Accommodation Close to Annapolis Historic Sites!
- 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 $282 per night (USD)
VRBO
Governor Calvert King Balcony at Historic Inns of Annapolis
- 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 $282 per night (USD)VRBO
- From $381 per night (USD)
VRBO
Governor Calvert Suite at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $381 per night (USD)VRBO
- From $282 per night (USD)
VRBO
Right Where History Is! Just Across Maryland 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 $282 per night (USD)VRBO
- From $240 per night (USD)
VRBO
Governor Calvert Historic King at Historic Inns of Annapolis
- 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 $381 per night (USD)
VRBO
Historic Architecture In and Out, Memorable Stay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $381 per night (USD)VRBO
- From $1100 per night (USD)
Expedia
Oasis by the Bay - Waterfront Heated Pool Hot Tub!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 18
Summary: Located only 5 miles from Annapolis, this newly updated, 3-story home with great views of the Chesapeake Bay is ...
From $1100 per night (USD)Expedia
- From $691 per night (USD)
VRBO
New Eastport home with parking, dog-friendly & steps to shops with backyard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
New listing available for Commissioning Week 2025! Charming 1905 Eastport Duplex: Historic Character Meets Modern Comfo ...
From $691 per night (USD)VRBO
- From $401 per night (USD)
Expedia
Timeless Charm Meets Modern Comfort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This charming 3-bedroom, 2.5 bath historic duplex in downtown Annapolis offers a perfect blend of timeless character and ...
From $401 per night (USD)Expedia