Severn River Rentals
From $421 per night (USD)VRBO
Tastefully decorated Eastport Annapolis house with water views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our renovated 3 story house is located on the peninsula of Eastport, Annapolis. We are across the street from a small m ...
From $421 per night (USD)VRBO
From $201 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 $201 per night (USD)VRBO
From $250 per night (USD)VRBO
Annapolis steps to Harbor and Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Parking included. The heart of Annapolis 1 street from the harbor, fun restaurants & backs to the Naval Academy. This 1s ...
From $250 per night (USD)VRBO
From $1125 per night (USD)VRBO
Prestigious 5-Star rated Annapolis home with ideal historic district locale!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Spacious historic 5-star rated Annapolis home, located on a prominent corner, mere steps to the Naval Academy and St. Jo ...
From $1125 per night (USD)VRBO
From $249 per night (USD)VRBO
West Annapolis Hidden Gem
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Quaint 2 bedroom apartment nestled in the trees. Enjoy the old charm of Annapolis in this apartment with second story ba ...
From $249 per night (USD)VRBO
From $450 per night (USD)VRBO
Beautifully Renovated Historic District Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this meticulously renovated home where no detail has been overlooked. Step into the kitchen and be captivated ...
From $450 per night (USD)VRBO
From $633 per night (USD)VRBO
Charming Historic Annapolis Home With Two Off-street Parking Places!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Charming cedar shake duplex home in Historic Annapolis adjacent to the Paca Gardens and the Naval Academy. Custom kitche ...
From $633 per night (USD)VRBO
From $625 per night (USD)VRBO
Eastport Peninsula Charm
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious historic home in the center of Eastport peninsula. Plenty of space for gathering with two living rooms, dining ...
From $625 per night (USD)VRBO
From $350 per night (USD)VRBO
Lovely Waterfront Retreat in Eastport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perfectly located at Butler's Marina in Eastport. Beautiful views of Back Creek and the Bay. Within walking distance t ...
From $350 per night (USD)VRBO
From $571 per night (USD)VRBO
WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
CHARMING FOUR BEDROOM WATERFRONT COTTAGE ON SCENIC SEVERN RIVER WITH STUNNING VIEWS -- RARE CLOSE-IN LOCATION - JUST MI ...
From $571 per night (USD)VRBO
Click For PricingVRBO
Downtown Annapolis Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Two bedroom and two bathroom in Historic Annapolis, only 1 mile from arts district (west street), 2 miles from downtown ...
Click For PricingVRBO
From $149 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 $149 per night (USD)Expedia
From $964 per night (USD)VRBO
Carriage House in West Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Charming carriage house just a short 5 minute drive from the Naval Academy and walking distance to Navy Marine Corps Mem ...
From $964 per night (USD)VRBO
From $297 per night (USD)Expedia
Pet-friendly Loft in popular Eastport on 2nd Floor
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
**Flexible Commissioning Week Cancellation Policy** The Port is situated in the heart of Eastport’s charm, mere steps f ...
From $297 per night (USD)Expedia
Click For PricingVRBO
1010 VB Eastport, Annapolis MD!!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to historic Eastport! Located in the City of Annapolis, 1.6 miles to the United States Navel Academy. My home is ...
Click For PricingVRBO
From $185 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 $185 per night (USD)Expedia
From $846 per night (USD)VRBO
Duke's Den Downtown home with 2 PARKING spots!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
*Flexible Commissioning Week Cancellation Policy* Large Historic Downtown Annapolis gorgeous home with 2 parking spaces ...
From $846 per night (USD)VRBO
From $385 per night (USD)VRBO
Nautical Feel to This Beautiful Eastport Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
From the minute you walk in the door, you will feel the warmth and charm this home offers. Located on the Eastport si ...
From $385 per night (USD)VRBO
From $362 per night (USD)VRBO
Escape to this Cape Cod home close to everything!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
*Flexible Commissioning Week Cancellation Policy* Welcome to this charming Cape Cod on half an acre right outside downt ...
From $362 per night (USD)VRBO
From $650 per night (USD)VRBO
Wooded retreat minutes from Downtown Annapolis!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by Annapol ...
From $650 per night (USD)VRBO
From $675 per night (USD)VRBO
We Get Repeat Renters!!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This beautifully updated 4 bedroom 3.5 bath home was renovated in 2016 and sleeps 8 comfortably. It is set up 100% for g ...
From $675 per night (USD)VRBO
From $995 per night (USD)VRBO
Relaxing Bay Ridge Lagoon
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Brand new to VRBO! We have been renting out for the Naval Academy Commissioning (Graduation) Week and now the house will ...
From $995 per night (USD)VRBO
From $550 per night (USD)VRBO
Lots free parking, hot tub, tree house, outdoor oasis - NOT party house
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Walk downtown or to grocery, restaurants, etc. We live in a nice modernly decorated duplex adjacent to Navy Stadium. I ...
From $550 per night (USD)VRBO
From $497 per night (USD)VRBO
Family & Pet-Friendly Annapolis Home!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A beautiful family home located in the heart of Annapolis. Large yard and family areas to accommodate any amount of gues ...
From $497 per night (USD)VRBO
From $560 per night (USD)VRBO
Beautiful Waterfront Townhome In Historic Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful waterfront townhome with three bedrooms 3 1/2 baths, recently renovated and beautifully decorated. 5-minu ...
From $560 per night (USD)VRBO
From $399 per night (USD)VRBO
Historic District"Crab Cakes and Football"
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Crab Cakes and Football. Enjoy Historic Downtown Annapolis with convenient walking distance to both City Dock ...
From $399 per night (USD)VRBO
From $1600 per night (USD)VRBO
Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Built in 1875, this delightful house offers total privacy in the heart of downtown Annapolis. Steps from Main St, and t ...
From $1600 per night (USD)VRBO
From $566 per night (USD)VRBO
CHASE CREEK Gem: Charming, Bright, Peaceful, Private **Family Friendly**
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Open spaces and private retreats. Fully renovated with contemporary colors and finishes, this home has all of the making ...
From $566 per night (USD)VRBO
Click For PricingVRBO
Take your Leave of Absence around gardens with driveway parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
**Flexible Commissioning Week Cancellation Policy** Welcome to this gorgeous luxury home tucked into a quiet cul de sac ...
Click For PricingVRBO
From $1177 per night (USD)VRBO
Murray Hill Gem - Your Commissioning Week Home Away from Home
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
NBS22-145072 - Welcome to 110 Monticello Avenue, a true gem in the highly sought after neighborhood of Murray Hill in An ...
From $1177 per night (USD)VRBO
From $417 per night (USD)VRBO
Upscale home with parking for 4 cars in driveway. Walk to downtown.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
NOTE: Posted rates do not apply to Holidays, Boat Shows and Commissioning Week but will be given on reques ...
From $417 per night (USD)VRBO
From $132 per night (USD)VRBO
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This 1920's Craftsman style bungalow is 1/2 block from the Naval Academy Stadium and within walking distance of the Hist ...
From $132 per night (USD)VRBO
From $471 per night (USD)VRBO
West Annapolis Waterfront Stay with Views, Dock & Boat
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
"Having my coffee on the screened in porch overlooking the water was alone worth the price of the stay!” - Eric Welcome ...
From $471 per night (USD)VRBO
From $150 per night (USD)VRBO
Annapolis waterfront "tiny house" in garden setting
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This " Carriage House" is a tiny jewel box, space efficient as a boat and comfortable as a modern home. Located in t ...
From $150 per night (USD)VRBO
From $331 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 $331 per night (USD)VRBO
From $480 per night (USD)Expedia
Family Tribute Marine's Gate across from Gate 1
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
*Flexible Commissioning Week Cancellation Policy* This Annapolis home, located directly across the street from Naval Ac ...
From $480 per night (USD)Expedia
From $575 per night (USD)VRBO
Boutique Historic Home just Steps from the State House!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to the George Taylor House! This lovely historic home dates back to 1810 and has been recently renovated to pro ...
From $575 per night (USD)VRBO
From $185 per night (USD)VRBO
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Known as the “Athens of America,” Annapolis is a city abundant with history and culture. This former capital of the Unit ...
From $185 per night (USD)VRBO
From $368 per night (USD)VRBO
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 $368 per night (USD)VRBO
From $486 per night (USD)VRBO
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to our newest property in The Exclusive Maritime Eastport section of Annapolis . Just a short stroll ( half mile ...
From $486 per night (USD)VRBO
From $750 per night (USD)VRBO
Charming Annapolis Victorian
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. W ...
From $750 per night (USD)VRBO
From $550 per night (USD)Expedia
Gorgeous Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Absolutely Charming! Guests will feel right at home in this beautifully renovated 3+ bedroom/2 bath bungalow. Coastal co ...
From $550 per night (USD)Expedia
From $1262 per night (USD)VRBO
Waterfront estate with gorgeous pool, pier, 3 acres of entertainment!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 18
*Home is available for Commissioning Week 2025. Please send an inquiry to owner for rates.* **Note: Pool is open and ...
From $1262 per night (USD)VRBO
From $322 per night (USD)VRBO
Directly Across from Gate One & Steps from the Waterfront
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Vacations are meant to be carefree! Let the chimes from the Naval Academy chapel start your day. Stroll along our famed ...
From $322 per night (USD)VRBO
From $498 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 $498 per night (USD)VRBO
From $249 per night (USD)Expedia
Welcome Aboard the Back of the Moon
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy the sunrise waking up on the water. The sunsets aren't bad either. This 42' Catamaran Cruiser is comfortable for 4 ...
From $249 per night (USD)Expedia
From $308 per night (USD)VRBO
Historic Downtown Charmer, Water Views and Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Life is beautiful in historic downtown Annapolis, with great restaurants, shops and romantic waterfront at your doorstep ...
From $308 per night (USD)VRBO
From $1277 per night (USD)Expedia
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 $1277 per night (USD)Expedia
From $450 per night (USD)VRBO
Steps to Main Street w View of the Capital private back patio & off-site parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beautifully-decorated 4-bedroom home in the heart of Historic Annapolis is located directly behind Main Street. Th ...
From $450 per night (USD)VRBO
From $750 per night (USD)VRBO
Annapolis -Eastport - -3 Bedroom- 3 bath with parking
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Delightful Arts and Crafts/ Coastal style home. Main Level is open space concept with 9 ft ceilings and plenty of nat ...
From $750 per night (USD)VRBO
From $400 per night (USD)VRBO
Harborview with Stunning Views of the Annapolis Harbor and Ego Alley
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
STR22-145089 The property is in the heart of Annapolis overlooking the Annapolis Harbor with stunning views between the ...
From $400 per night (USD)VRBO
From $355 per night (USD)Expedia
Historic Fisher House steps to Main St with parking and private back patio!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Named after the owner’s great-grandfather, who was instrumental in building both Annapolis and Academy fire departments, ...
From $355 per night (USD)Expedia
From $1200 per night (USD)VRBO
Beautiful Eastport Home walking distance to downtown and USNA. Includes parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy the best of Eastport and downtown Annapolis in this cute historic home. Home has three levels with space for 10-1 ...
From $1200 per night (USD)VRBO
From $915 per night (USD)VRBO
Perfect for Weddings, Crafters, & Commissioning Week- Sleeps 10! Great Reviews.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Naval Academy enough & Wedding Receptions Year after Year! This individual home is ideally located close to bike to down ...
From $915 per night (USD)VRBO
From $693 per night (USD)VRBO
Steps away from the Chesapeake Bay in the unique Bay Ridge community!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Chesapeake living with a view of the Bay from the lovely outdoor dining area and screened in balcony off of the huge mas ...
From $693 per night (USD)VRBO
From $519 per night (USD)Expedia
New rates! 2 parking spots and Walkable to Main Street at Seashell in the City
- 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 $519 per night (USD)Expedia
From $475 per night (USD)VRBO
Annapolis Historic District rowhome w/ parking and rooftop deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by Annapol ...
From $475 per night (USD)VRBO
From $175 per night (USD)Expedia
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 $175 per night (USD)Expedia
From $185 per night (USD)VRBO
“Athens of America,” Annapolis Apartment One B
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Annapolis is a city abundant with history and culture. This former capital of the United States has a little something f ...
From $185 per night (USD)VRBO
From $198 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 $198 per night (USD)Expedia
From $1040 per night (USD)VRBO
Stunning colonial p on a private 1.6 acre lot situated on Broadneck Peninsula.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 9
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by Annapol ...
From $1040 per night (USD)VRBO
From $1040 per night (USD)VRBO
Luxurious home in historic downtown Annapolis!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
NBS22-145083 - Please note: If you request to book this property, your reservation is not confirmed until you are cont ...
From $1040 per night (USD)VRBO
From $288 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 $288 per night (USD)VRBO
From $175 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 $175 per night (USD)Expedia
From $1153 per night (USD)VRBO
Indoor/Outdoor waterfront oasis with indoor heated pool awaits you in Eastport!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Your indoor and outdoor waterfront oasis awaits you in Eastport! Enjoy year-round swimming and lounging at the indoor he ...
From $1153 per night (USD)VRBO
From $360 per night (USD)VRBO
Perfect spot for a Weekend Getaway!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This luxiourious apartment sits right off Main Street and is so centrally located...you can park your car in the city ga ...
From $360 per night (USD)VRBO
From $745 per night (USD)VRBO
Historic Luxury Steps to USNA + Vibrant Waterfront
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Quarterdeck 1880, a beautiful, spacious and sunlit historic home on gorgeous Prince George Street in the hear ...
From $745 per night (USD)VRBO
From $1071 per night (USD)VRBO
Waterfront Gem! Resort-like home with big windows and truly breathtaking water views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by Annapol ...
From $1071 per night (USD)VRBO
From $358 per night (USD)VRBO
Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 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 $358 per night (USD)VRBO
From $178 per night (USD)Expedia
Private Pet-friendly Coastal Suite with water views just minutes to Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
**Be sure to ask about renting the entire home for Commissioning Week and special Annapolis events. Enjoy the serene wa ...
From $178 per night (USD)Expedia
From $500 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 $500 per night (USD)VRBO
Click For PricingExpedia
Historic Downtown House with Off Street Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious living with all the modern amenities. Prime location - 1 block from the water, restaurants, and shops. Park you ...
Click For PricingExpedia
From $458 per night (USD)VRBO
Beautiful Historic Home With Great Location!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The "Philip Clayton House" (Annapolis license STR21-144988) is a fully up-dated, historic home in the Federal style dat ...
From $458 per night (USD)VRBO
From $594 per night (USD)VRBO
Pet-friendly Waterfront Coastal home just minutes to Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
**Flexible Commissioning Week Cancellation Policy** Enjoy the serene water views at this water-privileged home on a qui ...
From $594 per night (USD)VRBO
From $706 per night (USD)VRBO
Luxury home! 1 mi from USNA! 3 Bd/3.5 Ba with Private Heated & Salted Pool!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful newly renovated home located in the quiet Annapolis neighborhood of Eastport. We are a perfect venue for geta ...
From $706 per night (USD)VRBO
Click For PricingVRBO
Spacious, contemporary, wooded home in Epping Forest on the Severn River
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Beautiful home in Epping Forest with large granite counters and stainless kitchen with open floor plan for family gather ...
Click For PricingVRBO
From $210 per night (USD)VRBO
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Completely renovated street level 1 bedroom apartment with all the amenities of home. Perfect for a single traveler or ...
From $210 per night (USD)VRBO
From $350 per night (USD)Expedia
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 $350 per night (USD)Expedia
From $500 per night (USD)VRBO
Waterfront, family-friendly property in quite private setting
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
Spacious, comfortable, family friendly home on a private waterfront lot with great outdoor living that is close to town, ...
From $500 per night (USD)VRBO
From $405 per night (USD)Expedia
New Rates! Dogs Welcome! Walkable to waterfront & USNA with Parking at Historic Wisteria
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
*Flexible Commissioning Week Policy* **Parking is not on premises!! A dedicated parking spot at nearby garage (10/15-wa ...
From $405 per night (USD)Expedia
From $1528 per night (USD)VRBO
Cool 1870's Historic District Home with modern amenities
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
150 year old, five bed and three bath home with 3,000 square feet is centrally situated in the heart of the Historic Di ...
From $1528 per night (USD)VRBO
From $295 per night (USD)VRBO
Available for Maryland Legislative Session 2017! Perfect location!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the essence of Historic Annapolis with this recently renovated Maryland Avenue apartment. Located in the 'Johnson ...
From $295 per night (USD)VRBO
From $425 per night (USD)VRBO
Now Pet Friendly! Hang just 2 blocks from Navy Stadium all on 1 floor
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
**Flexible Commissioning Week Cancellation Policy** Pet-friendly dream location in Annapolis, just 2 blocks from Navy S ...
From $425 per night (USD)VRBO
From $500 per night (USD)Expedia
Quaint, light-filled haven in heart of downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
Welcome to the historic neighborhood of Murray Hill! The Bennett House is a charming, light-filled, detached home with o ...
From $500 per night (USD)Expedia
From $116 per night (USD)VRBO
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 $116 per night (USD)VRBO
From $335 per night (USD)Expedia
"Around the corner" from everything, private backyard and parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
*Flexible Commissioning Week Cancellation Policy* Welcome to this charming remodeled Eastport Victorian home "Around th ...
From $335 per night (USD)Expedia
From $165 per night (USD)VRBO
Brand new Renovation in Historic District with 2 parking spots -walk everywhere
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
***Covid 19 updates. In addition to blocking time between guests per CDC guidelines our professional cleaning staff is p ...
From $165 per night (USD)VRBO
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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. ...
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From $532 per night (USD)VRBO
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Absolutely gorgeous downtown waterfront home. Loaded with historical significance and character, all while minutes walki ...
From $532 per night (USD)VRBO
From $980 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 $980 per night (USD)VRBO
From $355 per night (USD)VRBO
New Rates! Steps from the water, Easy parking private backyard and pet-friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
**Flexible Commissioning Week Cancellation Policy** This newly-decorated and furnished 2 bedroom, 1.5 bath is located a ...
From $355 per night (USD)VRBO
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"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 ...
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From $368 per night (USD)VRBO
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Very cozy bedrooms with two incredible family rooms to enjoy internet tv, game room, built in bar, beautiful screened in ...
From $368 per night (USD)VRBO
From $900 per night (USD)VRBO
Annapolis Family Vacation Rental: Close to downtown and the Naval Academy
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Located: 4.1mi (10 min) from Naval Academy: Annapolis Cove Neighborhood Open floor plan: Kitchen open to living room/sc ...
From $900 per night (USD)VRBO
From $352 per night (USD)VRBO
Historic Carriage House in the Heart of Downtown Annapolis with Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Flexible Commissioning Week Cancellation Policy* Originally built in 1857, this fully-restored home has a rich history ...
From $352 per night (USD)VRBO
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Eastport condo is located in a waterfront community with a community pool & picnic/grilling area
- 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 ...
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From $750 per night (USD)VRBO
This Eastport house is very spacious and close walking distance to everything, just 4 blocks to Annapolis City Dock. Perfect for someone on assignment that wants to live close to town and all the activities Annapolis has to offer.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by Annapol ...
From $750 per night (USD)VRBO
From $1100 per night (USD)VRBO
Beautiful home w/elevator going to every floor. This house is accessible to all.
- 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 Annapol ...
From $1100 per night (USD)VRBO
From $376 per night (USD)VRBO
Delightful little Historic District gem is furnished primarily with antiques that have been in the owner's family for generations. If you book this property you'll be contacted by Annapolis Accommodations to finalize your reservation.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by Annapol ...
From $376 per night (USD)VRBO
From $750 per night (USD)VRBO
This Eastport home is very spacious and close walking distance to everything, only 4 blocks from Annapolis City Dock. Perfect to live close to town and all the activities Annapolis has to offer.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by Annapol ...
From $750 per night (USD)VRBO