Anne Arundel Area Rentals
- From $400 per night (USD)
VRBO
Great Entertaining Spot for any Occassion!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
This newly built 2012 Carriage House has all the bells and whistles for a relaxed fiiends and family stay. Enjoy this u ...
From $400 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Lovely Family Home Just Minutes From Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Cape! We offer our recently upgraded home in the Cape St Claire neighborhood of Annapolis. Just minutes f ...
From $275 per night (USD)VRBO
- From $189 per night (USD)
VRBO
New Bungalow with view of South River!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the quiet Sylvan Shores neighborhood and a view of the South River and bridges in this new modern bungalow that ha ...
From $189 per night (USD)VRBO
- From $871 per night (USD)
VRBO
Spacious Luxury 6 BR Home, Sleeps 15, Private Pool, In Nature, Convenient to DC
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 15
Stunning 6 bedroom, 5½ bath home on 34 acres with panoramic woodland views, and private salt-water pool, perfect for tha ...
From $871 per night (USD)VRBO
- From $444 per night (USD)
VRBO
Tastefully decorated fully-equipped 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 $444 per night (USD)VRBO
- From $454 per night (USD)
Expedia
Private Waterfront Home w\/ Pier and 2+ Acres!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
For endless water views and enviable privacy - look no further! Situated on two acres of lush green grass, this true pen ...
From $454 per night (USD)Expedia
- From $147 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 $147 per night (USD)VRBO
- From $207 per night (USD)
Expedia
Nice retreat apartment\/private patio, min. away from USNA & Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nice 2 bedrooms / 1 bathroom appartment in the lower level of a single home, private entrance and patio in the back of t ...
From $207 per night (USD)Expedia
- From $232 per night (USD)
VRBO
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Welcome to Firefly Cottage in beautiful Cape St. Claire! Our cozy cottage sits on a ¼ acre of land for your exclusive u ...
From $232 per night (USD)VRBO
- From $269 per night (USD)
VRBO
Waterfront With Relaxing Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The house has 2 master bedrooms on upper level. One of them has private deck and panoramic views. There is one bedroom ...
From $269 per night (USD)VRBO
- From $182 per night (USD)
VRBO
Sweet Bamboo Beach Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
If you are looking for a sweet, comfortable and clean home for your stay while visiting our beaches or other Calvert Cou ...
From $182 per night (USD)VRBO
- From $275 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 $275 per night (USD)VRBO
- From $1075 per night (USD)
VRBO
Prestigious Historic Annapolis home, parking for 5 cars, walk to everything!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Spacious historic Annapolis home, located mere steps to the Naval Academy and St. John's College. Two blocks from the St ...
From $1075 per night (USD)VRBO
- From $160 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 $160 per night (USD)Expedia
- From $513 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 $513 per night (USD)VRBO
- From $700 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 $700 per night (USD)VRBO
- From $808 per night (USD)
VRBO
Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Lovely 3 bedroom house, beautifully furnished, 2 gourmet kitchens, outdoor oasis with pool, jacuzzi, sauna, steam room ...
From $808 per night (USD)VRBO
- From $455 per night (USD)
VRBO
Huge Beach Bungalow w\/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This huge, newly designed home has 4 bedrooms (2 king beds + 2 queen beds). It is a few minutes to the beach, restaurant ...
From $455 per night (USD)VRBO
- From $600 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 $600 per night (USD)VRBO
- From $488 per night (USD)
VRBO
Our Home on the Cove: waterfront, peaceful, wooded, comfy, family friendly
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 15
Sitting on 8 acres of water front property, Our Home on the Cove is a cottage with 5 bedrooms and room for a family of 4 ...
From $488 per night (USD)VRBO
- From $1375 per night (USD)
VRBO
WATERFRONT DRIFTWOOD LODGE
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Panoramic waterfront views of the Chesapeake Bay, an awe inspiring moment with nature. In a spacious and cozy family own ...
From $1375 per night (USD)VRBO
- Click For Pricing
Expedia
Cozy 1-bed with pool access, just steps from mall.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Studio basement apartment just steps from Waugh Chapel Outdoor Mall & IMAX Theater, Gambrills. Hot Plate/Air Fryer/Micro ...
Click For PricingExpedia
- From $399 per night (USD)
VRBO
Waterfront, Private Beach, Peaceful Family Getaway
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the Chesapeake from your very own front row seat at Murphy Point on the Chesapeake! Watch dolphins, turtles, ...
From $399 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $400 per night (USD)
VRBO
Adorable waterside cottage with pool Beach community
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
1920's two level cottage with multiple decks and a private inground swimming pool. This home boasts water views from eve ...
From $400 per night (USD)VRBO
- Click For Pricing
VRBO
Minutes to BWI airport, major highways, & Baltimore Washington Medical Center.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Cozy modern 2bed/1bath basement apartment with private entrance. Bedroom 1 has a queen size bed while the second bedroom ...
Click For PricingVRBO
- From $149 per night (USD)
VRBO
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)VRBO
- From $285 per night (USD)
Expedia
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 $285 per night (USD)Expedia
- Click For Pricing
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 ...
Click For PricingExpedia
- Click For Pricing
VRBO
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 $75 per night (USD)
VRBO
Central location, Spacious, Private, More for less
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Private basement unit, spacious, tastefully furnished with pvt entrance, on golf course. Lush green backyard, grilling. ...
From $75 per night (USD)VRBO
- 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
- Click For Pricing
Expedia
Beautiful 3-bedroom house with garage 20min from DC and 6 FLags
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Beautiful 3-bedroom house with garage 20min from DC and 6 FLags in a quiet and peaceful neighborhood. Lots a of restaura ...
Click For PricingExpedia
- From $846 per night (USD)
Expedia
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)Expedia
- From $36 per night (USD)
VRBO
Private Room - Creek Side
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Nice and warm cozy room with a queen size bed with a full bathroom, towels and toiletries. Cozy elegant living room to r ...
From $36 per night (USD)VRBO
- From $425 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 $425 per night (USD)VRBO
- Click For Pricing
Expedia
Beautiful & Close to Everything: Private Community Beach, pier, 8mi to Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Unwind Relax. Enjoy yourself at this peaceful, renovated open floor plan home. Walking distance to the community pier an ...
Click For PricingExpedia
- From $292 per night (USD)
Expedia
Escape to this Cape Cod home close to everything!
- 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 $292 per night (USD)Expedia
- From $175 per night (USD)
VRBO
Carriage House on 49 Acres in West River. Just 17 Miles from Annapolis.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Our charming carriage house, nestled in privacy on 42 acres, offers a relaxing Adirondack-type getaway for up to 5 gues ...
From $175 per night (USD)VRBO
- Click For Pricing
Expedia
Waterfront
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 10
Waterfront house on a point where the South River meets Boyd’s Point. House was built in 2021 with huge gourmet kitchen ...
Click For PricingExpedia
- Click For Pricing
Expedia
Brazilian Artsy Townhome with great location and outdoor amenities!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Relax with the whole family in this peaceful townhome. Embed yourself in the quietness of the woods and hear the birds ...
Click For PricingExpedia
- From $700 per night (USD)
VRBO
Wooded retreat minutes from Downtown Annapolis!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $700 per night (USD)VRBO
- From $691 per night (USD)
VRBO
79 Five Star Reviews located in the city of Annapolis
- 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 $691 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Waterfront Apartment with Fantastic Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
We call this recently renovated luxury apartment Hale Kai, which is Hawaiian for 'Sea House.' It is fully furnished and ...
From $200 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 $325 per night (USD)
Expedia
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
The Beachwood Cottage is located near Mayo, Maryland, on the western shore of the Chesapeake Bay. The property sits on R ...
From $325 per night (USD)Expedia
- From $189 per night (USD)
VRBO
Entire House Near BWI Airport Glen Burnie MD
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This is a brand-new house and is fresh and crisp. This house is located in the Ferndale area of Glen Burnie MD. The Fern ...
From $189 per night (USD)VRBO
- From $533 per night (USD)
VRBO
Ultraclean Family Waterfront Home Annapolis Area -185+ Top Reviews!!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Breathtaking views from our waterfront property ... 10 minutes outside Annapolis, Maryland. Light-filled and open floor ...
From $533 per night (USD)VRBO
- From $252 per night (USD)
VRBO
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This upscale 2 bedroom, 1 bathroom water view cottage is located in a private beach community off of the Chesapeake Bay ...
From $252 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 $162 per night (USD)
VRBO
Quaint cottage with serene water view!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still only a 30 minute drive to Annap ...
From $162 per night (USD)VRBO
- From $775 per night (USD)
Expedia
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 16
Spacious 5-bedroom (4 full- and 2 half-baths) waterfront getaway built along the natural topography of Fairhaven Cliffs. ...
From $775 per night (USD)Expedia
- From $486 per night (USD)
VRBO
Waterfront home in Annapolis MD with private pier
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Waterfront home, 2000 sq feet, in Annapolis, MD on Magothy River, overlooking Chesapeake Bay, Gibson Island with private ...
From $486 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 $99 per night (USD)
VRBO
Relax in this 7-mins-Away E’thing Cozy Modern Studio-Near BWI,Arundel Mills etc
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Charming, modern studio/guest room in a house in the heart of Glen Burnie. Just couple blocks away from BWI airport, ama ...
From $99 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 $266 per night (USD)
VRBO
Pasadena, MD close to Annapolis\/WDC\/Baltimore
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Rest, relax in the color and light of the house, breathe and welcome the calm. 20 minutes to Annapolis and Baltimore, 15 ...
From $266 per night (USD)VRBO
- From $395 per night (USD)
Expedia
Relax in our cottage within walking distance of Herrington on the Bay events.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The owner has created your own slice of paradise in the Rose Haven community of North Beach. Walk to Herrington Harbour ...
From $395 per night (USD)Expedia
- From $613 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 $613 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $971 per night (USD)
VRBO
Murray Hill Gem - Your Commissioning Week Home Away from Home
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
NBS22-145072 - PLEASE NOTE: IF YOU BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS TO FINALIZE AN ...
From $971 per night (USD)VRBO
- From $200 per night (USD)
Expedia
Private Cottage on gated estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Completely remodeled guest cottage on gated, private estate. Home is located just minutes from Eastport, Downtown Annapo ...
From $200 per night (USD)Expedia
- From $440 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 or Commissioning Week. They will be given on request. Rates a ...
From $440 per night (USD)VRBO
- From $146 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 $146 per night (USD)VRBO
- From $125 per night (USD)
VRBO
Private Apartment - Minutes to USNA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Entire home You’ll have the apartment to yourself. Great location 100% of recent guests gave the location a 5-star ratin ...
From $125 per night (USD)VRBO
- From $453 per night (USD)
Expedia
Amazing views, short walks to great dining!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Spring: 2024: Welcome El Oso: Naval Bagels by day, transformed into great Mexican takeout in the evenings! 5 min walk! ...
From $453 per night (USD)Expedia
- Click For Pricing
Expedia
Truly Unique! Private Beach ~ Private Pool ~ 100' Dock ~ Outdoor Grill & Gazebo
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Paradise found on the Chesapeake! Only rented for 2 weeks out a year, book now before it’s gone. This truly unique prope ...
Click For PricingExpedia
- 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 $329 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 $329 per night (USD)VRBO
- Click For Pricing
VRBO
Simply Severn - Bright, open, comfortable in Baltimore & DC Area.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Simply Severn is the perfect location to work, explore or play in Baltimore, Annapolis and all of the Washington DC area ...
Click For PricingVRBO
- From $603 per night (USD)
VRBO
Waterfront home on the Magothy River. Perfect for family vacation.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
Waterfront home in Severna Park on the Magothy River. Twenty minutes to the Chesapeake Bay by boat. Three bedrooms and f ...
From $603 per night (USD)VRBO
- Click For Pricing
Expedia
Family Tribute Marine's Gate across from Gate 1
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
*Still available for Commissioning Week - 5-night minimum! This Annapolis home, located directly across the street fro ...
Click For PricingExpedia
- From $490 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 $490 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 $351 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 $351 per night (USD)VRBO
- From $199 per night (USD)
Expedia
Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Your party will have two lovely private spaces, connected by a door, on the second floor of the Chesapeake Paradise Hou ...
From $199 per night (USD)Expedia
- From $408 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 $408 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Gorgeous Annapolis Area Waterfront Home!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Beautiful views of the river as you enter this 5 bedroom waterfront home. Imagine watching boats from the screened-in po ...
From $500 per night (USD)VRBO
- From $700 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 $700 per night (USD)VRBO
- From $2845 per night (USD)
VRBO
Waterfront estate with gorgeous pool, pier, 3 acres of entertainment!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 16
**Note: Pool is open and heated from May 15 through Labor day. Upon request, the pool may be open/heated during other ...
From $2845 per night (USD)VRBO
- From $250 per night (USD)
VRBO
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
It was “MAGIC” when I discovered this town years ago. Beautiful sunrises right here on the Chesapeake Bay & glorious “mo ...
From $250 per night (USD)VRBO
- From $295 per night (USD)
Expedia
Cute Bay Home\/Fantastic View and Sandy Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Cozy three bedroom home with two large decks overlooking the Chesapeake Bay -- and a beautiful sandy beach. The view is ...
From $295 per night (USD)Expedia
- From $184 per night (USD)
VRBO
Bell Estates-Brand New Bay View, Beautiful Cottage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bell Estates is a newly built corner lot across the street from the bay with stunning views of the water from the Master ...
From $184 per night (USD)VRBO
- From $245 per night (USD)
Expedia
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 $245 per night (USD)Expedia
- From $179 per night (USD)
VRBO
National Historic home w\/ Serene & Quiet Setting
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Originally founded in the 1600's, Abington Farm, a.k.a Abbington Manor & Stables, is a historic home and stables in Crow ...
From $179 per night (USD)VRBO
- From $500 per night (USD)
Expedia
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 $500 per night (USD)Expedia
- From $292 per night (USD)
VRBO
Chesapeake Bay & Beach Bungalow Location Trendy for USNA Families & Boat Show
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Charming Bay Cottage just steps from a beautiful beach and the Chesapeake Bay, a short drive or walk to the crabbing an ...
From $292 per night (USD)VRBO
- From $722 per night (USD)
Expedia
River Breezes with a private pier, parking and billiards room
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
*Ask us about renting the 1Bedroom/1Bath River Cottage on the same property. This stunning historic home, located on 3 ...
From $722 per night (USD)Expedia
- From $330 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 $330 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $492 per night (USD)
VRBO
Steps to Main Street w View of the Capital private back patio & free 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 $492 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 $495 per night (USD)
VRBO
Cozy 2 BR home with parking and views of the Annapolis Harbor - Walk to everything!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
STR23-145349 - PLEASE NOTE: IF YOU BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS TO FINALIZE AN ...
From $495 per night (USD)VRBO
- Click For Pricing
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, ...
Click For PricingExpedia
- From $245 per night (USD)
VRBO
Lansdowne, 6BR, 2 BA, totally renovated SFH
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to a beautiful, totally renovated single family home in a quiet private neighborhood. Close to everything, about ...
From $245 per night (USD)VRBO
- From $738 per night (USD)
VRBO
Water Views, Large Rooms, In-ground Pool, Fenced Yard, Near Beach & Fishing Pier
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
5 bedrooms, 3.5 bathrooms, in ground pool, yard with grass, upper and lower decks, BBQ grill, screened-in porch, plenty ...
From $738 per night (USD)VRBO
- From $1267 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 $1267 per night (USD)VRBO
- Click For Pricing
Expedia
Retreat on Sage Brush Court (Basement Suite w\/private entrance)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
- This Home away from Home 1 bedroom (queen bed) - kitchenette (no stove) - electric 2 burner hot plate - the couch c ...
Click For PricingExpedia
- From $100 per night (USD)
VRBO
Whiskey Bottom Saloon by LLOYD SUITES
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
SPACE You will have our entire Saloon for your enjoyment during your stay. The Saloon is located on the first level of t ...
From $100 per night (USD)VRBO
- From $903 per night (USD)
VRBO
A luxurious spa-like retreat near the Chesapeake Bay
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Treat yourself to luxury around every corner in this stunning home appointed with two spacious Primary Bedroom ensuites ...
From $903 per night (USD)VRBO