Maryland’s slogan, “Land of Pleasant Living,” is right on the mark here in Annapolis. This is upscale waterfront living at its best, and if you are at all connected to the U.S. Navy and its Naval Academy here in town, you know that Annapolis is the heart of everything! Below you will find some of the best places to stay in Annapolis and why you should book!
This historic city has a variety of communities to choose from, each with its own unique features, character and amenities. From the hustle and bustle of historic downtown Annapolis to quiet suburbs surrounding the city. Selecting a vacation rental from all these lovely choices may be the hardest part of your trip. So, in no particular order, here is a little bit about the best places to stay while you’re vacationing here in lovely, historic Annapolis.
Downtown Annapolis truly is the heart of things. Overflowing with historic charm at every step, with buildings whose architecture spans centuries jammed together along brick-paved sidewalks and cobblestone streets, there’s over 400 years of history here and you can see every bit of it when you walk through the city. At Home Annapolis offers a variety of vacation homes right in the middle of the historic district, so you can immerse yourself in its rich history every minute of your stay. Choose from cozy, narrow townhomes to spacious, detached homes, all with the amenities you want. And most of our vacation homes here in downtown are on the National Historic District Site & Building Registry. We also offer a few vacation homes located on quiet streets with amazing water views that are still just a quick walk to the heart of historic downtown.
Annapolis is a perfectly pedestrian, walking city where you’ll be steps away from the rough, bustling charm of the picturesque downtown streets lined with flowering trees, quaint shopfronts, bars and restaurants, museums and so much more. Bring your comfy walking shoes and get ready to enjoy yourself.
All of our Edgewater homes have been recently renovated, with new stainless steel appliances, bright interiors and comfy furnishings. Many of our vacation homes in the Edgewater Area sit right on the shore of the South River, and come complete with large outdoor living spaces where you can dine al fresco or just sit and watch all the action on the river. Many have private piers, outdoor showers and gas grilles. Plus, there are lots of windows to enjoy the view and the balmy breeze when the weather’s nice.
Located just across the South River from Annapolis, and less than 10 miles from downtown, Edgewater offers its residents several parks like the popular South River Park and the Mayo Beach Park on the waterfront, and The Historic London Town and Gardens, a “lost colonial town and garden sanctuary” on the water with the historic William Brown House and its lovely gardens including the Sound and Sensory Garden and the beautiful Ornamental Gardens.
While the Arnold Area is considered a suburb of Annapolis, you’ll feel like you’re out in the country, and certainly not less than 10 minutes from the busy hub of Annapolis. A drive down country roads lined with grassy, green meadows and fields with the occasional horse or two, Arnold is just north of the city, across the Severn River.
Most of our Arnold homes have private access to the water, with docks and the all essential crabbing equipment you’ll need. If you can remember to throw the crab pot into the water each morning, you’ll be rewarded with fresh, delicious crabs in the afternoon. Nothing could be easier. And the gourmet kitchens in our Arnold homes make it even easier to fix those crab legs, crab cakes or Low Country Boil for your hungry guests.
Our Arnold vacation homes have three to six bedrooms, perfect for families or a few of your best buddies from the academy. Many have in-ground pools too, where you can splash about or just enjoy the sun and the Severn River views. These lovely vacation homes are in the perfect spot for watching the Blue Angels practice their flying routines too.
A few miles from downtown, you’ll find great shopping and dining along the Chesapeake Bay. Eastport is across the Annapolis Harbor from the Naval Academy, and just a few blocks from the City Dock and the Eastport Bridge. You’ll be able to walk everywhere from your Eastport vacation home or take the water taxi across Spa Creek to Downtown and the Yard.
All of our Eastport homes are newly renovated too, with fully equipped kitchens, bright open interiors, free Wi-Fi, lovely landscaped yards and gardens, gas grills out on the deck and plenty of outdoor living areas. Many offer screened porches, fire pits and off street parking.
Bay Ridge Area
Every one of our lovely, spacious Bay Ridge homes and condo feature amazing waterfront views, and many offer private access to the water with docks. Bay Ridge is less than a 5-mile drive from downtown Annapolis, but you’ll feel like a world away with the stunning panoramic views of Lake Ogleton, the Severn River and the Chesapeake Bay that our Bay Ridge vacation homes offer.
This area is known for its exceptional crabbing, and you can enjoy catching and cooking your own crabs right off your private dock. Many of our waterfront homes will feature all the equipment and gear you need to catch fresh crabs for lunch and dinner, and these homes also have large outdoor living areas perfect for enjoying your fresh catch. The ease of enjoying fresh, caught crab is just one more thing about Annapolis to love.
Stadium Vacation Rentals
Football! If you’ve come to town for a Navy football game, this is where you want to be. Leave the hassles of driving and parking behind, because these lovely vacation homes are within walking distance to the stadium and all the excitement. And there are large flat screens and free Wi-Fi throughout each of these homes, so after the Navy game, everyone can watch the game or movie of their choice.
These lovely vacation homes are within walking distance of the stadium, in fact, you can see the stadium from a few of these homes. Enjoy all the Navy football you want, as well as college and professional lacrosse games, and of course, the U.S. Naval Academy graduation ceremony is held here too. You’ll be within walking distance to not only to the stadium, but to the Academy, and Historic Downtown.
Big backyards and lush gardens, patios and screened in porches, outdoor fireplace, gas grill are pretty standard for these vacation homes. Many of our stadium area homes are constructed from unique stone, feature plenty of interior wood detailing, vaulted or coffered ceilings, and offer a choice of traditional or modern interiors. And, there’s private, driveway parking too!
West Annapolis Area Vacation Rentals
Our West Annapolis vacation homes are spacious homes in quiet neighborhoods near the Chesapeake Bay or the Severn River. You can choose from historic homes with charm and style, expansive brick estates with a private heated pool and acres of manicured lawns. Many are newly renovated with lots of extras like putting greens, outdoor ping pong table, Rec/Game Rooms, vaulted ceilings, bright modern interiors, screened in porches, gourmet kitchens and stone fireplaces.
Many have private water access, sprawling lawns and lush gardens, fire pits, heated pools and spas, several are located in waterfront communities, and are just a short walk from the Stadium’s downtown trolley, the Academy and downtown West Annapolis.
A Few Area Attractions to Visit
Of course, the main attraction in Annapolis (besides the historic city itself) is the U.S. Naval Academy. You can tour the museum, watch the midshipmen march in formation at noon and take the guided walking tour of the campus to learn the academy’s naval history, and about the academy’s interesting beaux-arts architecture and landscaping.
If you love history and museums, you’ll never want to leave Annapolis. A few of our favorites are the Annapolis Maritime Museum and Park (learn about the area’s maritime heritage as well as the Chesapeake Bay’s ecology), the U.S. Naval Academy Museum, Hogshead (a lovingly restored gambrel-roofed home showing what life was like for the city’s lower and “middling” 18th century inhabitants), the Banneker-Douglas Museum (housed in the Victorian-Gothic former Mount Moriah African Methodist Episcopal Church and named for the black scientist Benjamin Banneker and black social crusader Frederick Douglass), the Hammond-Harwood House (the “jewel of Annapolis”) and the William Paca House and Garden (the restored 18th century home of William Paca, one of the signers of the Declaration of Independence). And a visit to the Museum of Historic Annapolis offers exhibits of the stories of the people of this historic town throughout 400 years of history.
The Maryland WWII Memorial, right on the Severn River across from downtown Annapolis, is an amphitheater surrounded by columns and granite slabs etched with the names of the 6,454 Marylanders who died in the war, as well as plaques explaining the state’s role in the war. The impressive memorial on its overlook faces the river and the Naval Academy.
Don’t Miss These Area Activities
Commissioning Week in May is the big event here. A time of celebration for midshipmen, their friends and family and really all of Annapolis, including the graduation and commissioning ceremony at the Navy-Marine Corps Memorial Stadium. Oh, and you can watch the Blue Angels show off too.
Since 1970, the Annapolis Sailboat Show in the spring shows off the latest and greatest in new boats and all the gear that goes with sailing. Displays include catamarans, mono hulls, racing boats and inflatables.
It’s time for crabs! It’s the world’s largest crab feast and all-you-can-eat-and-drink extravaganza focusing on Maryland’s famous blue crabs. This feast is organized by the Rotary Club of Annapolis to raise money for local charities.
If you’re visiting Annapolis in March, you’ll be able to enjoy the St. Patrick’s Day Celebrations, Maryland Day Celebrations and Restaurant Week where over 40 area restaurants participate in fixed-price tasting menus.
The Maryland Renaissance Festival, set in 16th century Revel Grove, (a 27-acre village overseen by King Henry VIII), is overflowing with performance stages, street vendors and craft booths, wenches, jesters and valiant knights, rakes and rouges, magicians and minstrels, sportsmanship events, plenty of food, drink, musicians and more.
Our Best Rentals
All of our vacation homes feature expansive decks, patios and porches so you can enjoy their spacious backyards and gardens and/or your river view and all the action on it. These vacation homes have plenty of outdoor living space where you can sit quietly sipping a nice adult beverage, dine al fresco under the stars, or party (quietly) with your friends and family.
Our vacation homes have comfortable, cozy seating, gourmet kitchens with high-end stainless steel appliances, free Wi-Fi, large flat screens throughout the home, and plenty of gathering areas for your group. Choose from open floor plans or traditional layouts, and modern or traditional interior styling. Many of our vacation homes feature extra amenities like private waterfront access, fire pits, coffee bars, porch swings, pizza ovens, Game Rooms, outdoor kitchens and fireplaces. And many have private, heated pools and hot tubs for your enjoyment.
Our Annapolis vacation rentals are located throughout the city and the surrounding neighborhoods, with a variety of styles, locations and amenities for your selection. Whether you want a private dock so you can arrive and move around by boat, or want to be right in the heart of things in downtown historic Annapolis, or want more privacy out in the suburbs with acres of groomed lawns and lush gardens around, we’ll have several vacation rentals that fit the bill. If you need help selecting a vacation rental close to one particular attraction, like the stadium or the William Paca House and Garden, or want the best vacation rental location for Restaurant Week or the Annapolis Film Festival, just give our friendly, knowledgeable staff a call. We’d love to help. Get started planning your Annapolis vacation today!