Vacation rentals in Annapolis
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Top-rated vacation rentals in Annapolis
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Relaxing Water Views - Mill Creek Cottage
Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.
Elegant & Authentic Annapolis
Enjoy comfortable elegance in this historic beauty on one of the prettiest streets in Downtown Annapolis--Main Street and the Water only 2 blocks away. This private unit is the full main level with its own eat-in kitchen, living room, front porch and back patio. Bedroom features queen size bed, dresser and walk-in closet. Bathroom has shower/tub and counterspace for your comfort. Street parking is available or public garage parking is a short stroll away. Relish this quiet & convenient location.
Cheerful & Spacious Shore Life Beauty!
Welcome to our charming yet peaceful abode & island oasis where sailing, marine life, & bay exploration exceed the standard! This exceptional home is conveniently located to a variety of high quality restaurants, parks, outdoor activities, spas, beaches, wedding venues, & other entertainment including live music, hunting, & antiquing while also being 20-minutes from Annapolis & 1-hour from Baltimore City & DC. Let this be your definitive choice for a magical destination you'll forever remember.
Cozy 2br home w/ parking in downtown Annapolis
Ideally located in the heart of downtown Annapolis's Historic & Art Districts. Detached home with historic charm & an inviting front porch, 1 car parking included. Open floor plan to include a living room (with queen sleeper sofa), workspace, 1/2 bath & eat in kitchen on the 1st floor. 2 bedrooms and a full bath upstairs. Enclosed rear yard provides an opportunity to create a lovely quiet space out our back door. A perfect location for C-Week, Boat Shows & other festivals in Historic Annapolis.
Quaint in the Heart of Annapolis
Quaint 2 bedroom, 1 bath home located in the heart of historic Annapolis. Completely remodeled with free off-street parking. Located towards the end of a safe, quiet, dead end road, less than 3 miles from downtown Annapolis, the Naval Academy, the Annapolis Mall, St. John’s College, and the Navy-Marine Corps Memorial Stadium. Walk downtown or to the Annapolis Town Center, restaurants, shops, and so much more! -Wi-Fi -2 free parking spaces -Keurig Coffee -TV -Toothbrushes/Paste -Shampoo/Soaps
Calico Cottage Guest House, king bed, free parking
Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.
Stay aboard the S/V MY STUDIO on Annapolis Harbor
Discover life aboard a comfortably equipped sailing yacht. Great for couples on a weekend getaway, and child friendly for families looking to include their little pirates. Hands down this is a wonderful way to visit Historic Annapolis and Naval Academy. We love the opportunity to share our boat, and help create a memorable vacation. Weather permitting, Private Sailing Cruises can be arranged during your stay for an additional charge. Cheers, and I look forward to welcoming you aboard.
Charming Downtwn Home- Private Parking Patio&Yard!
Welcome home to this Annapolis gem. An adorable 1930 American foursquare with private driveway, located on a quiet cul-de-sac off in downtowns Art's District. This cozy, three bedroom home can hold you and nine guests with plenty of sleeping arrangements for everyone. Enjoy a spacious backyard patio with string lights and deck chairs giving you and your guests plenty outdoor entertaining options. This house is fully furnished. Short walk to everything downtown offers, it just needs you!
Annapolis Waterfront Condo - Unit #: A-203
Cozy, comfortable condo. Great views - 2nd flr. Fireplace 1 bed/bath condo, sleeps 4 max, covered, water front deck, reserved parking! .5 mile walk to dwnt Annapolis and the Naval Academy, 1.9mi to the Navy stadium. Book NOW for the Summer! Easy access to Spring/Fall boatshows. 12 stairs, no elevator. Pool Memorial to Labor Day: MWTh 4pm-8 Tues: Closed FSS and Holidays: 12pm-8 The pool is one of the best places to be on a hot summer day. If hours are unacceptable, pls select another
Historic Annapolis Rental Minutes from Downtown
Immerse yourself in all Annapolis has to offer in this newly restored historic home. This charming rental neighbors the Naval Academy and is just a 5 minute walk to the heart of downtown Annapolis. This home has 2 bedroom and 1 full bath. This is the perfect place to stay whether you're looking to explore historic Annapolis, the Naval Academy grounds, or even taking a day trip to Washington D.C. Inside the home you'll find cozy furniture, new finishing's, and wifi throughout the house.
Cape St Claire waterfront getaway "The Apartment"
This is a private over the garage apartment located in Cape St Claire, about 5 miles from downtown Annapolis, 2 miles to the Bay Bridge. Private entrance, on site parking, 1- 2 guests. We encourage our guests to enjoy the large back yard patio with magnificent views of the Magothy River and Chesapeake Bay ! Approximately 30 miles to Washington, and Baltimore. 30 minutes to BWI airport. TV and internet. A community beaches just a short walk away. ADULTS ONLY, NO SMOKING, NO PETS.
Welcome Aboard!
Unique accommodations on a comfortably equipped 43 foot Hatteras yacht, just a 5 minute drive to historic downtown Annapolis and the Naval Academy. 15 minute drive to the Navy Stadium, 15 minutes drive to Rt 50. THIS LISTING IS FOR ACCOMODATIONS ONLY; BOAT MAY NOT BE DRIVEN! Forward cabin has bunk beds. Aft cabin has a queen bed. Fully equipped galley (kitchen) with 2-burner cook top, microwave/oven, fridge, toaster oven and Keurig. Boat has WIFI, heat, AC and hot water!
Popular amenities for Annapolis vacation rentals
Annapolis home rentals
Charming house; walk to everywhere in Annapolis
Marymont Cottage
Beautiful Baycation Stay
Crab Cakes and Football Historic District
Waterfront Oasis in Eastport-Easy Walk to Downtown
Kent Island Waterfront Home with Amazing Sunsets
Enchanting West River Retreat
Cozy Stay in Downtown Naptown
Other great vacation rentals in Annapolis
Naptown's Nauti Apartment
King George Hideaway 1st floor
Private | Near BayBridge | Wedding Venue Proximity
Charming, Chic Downtown Annapolis Apartment
Eastport Historic Firehouse with Parking, Dogs OK
Wonderful Cottage Nestled On Chesapeake Bay
The Little House of Rockaway Beach, Maryland
Uptown Condo w 2 Parking Spots
When is the best time to visit Annapolis?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$50,183 GYD | G$48,719 GYD | G$50,601 GYD | G$56,874 GYD | G$67,538 GYD | G$61,474 GYD | G$58,547 GYD | G$61,265 GYD | G$61,683 GYD | G$69,420 GYD | G$58,129 GYD | G$60,220 GYD |
| Avg. temp | 1°C | 3°C | 7°C | 13°C | 18°C | 23°C | 26°C | 25°C | 21°C | 14°C | 8°C | 4°C |
Frequently Asked Questions
What are the best places to stay in Annapolis?
Many guests choose accommodations in the Historic District for walkable access to waterfront sights, local shops, and dining. Eastport, just across the harbor, has a laid-back vibe and maritime charm that is often recommended.
What are the best things to do in Annapolis with kids?
Families frequently explore the U.S. Naval Academy, visit local museums, or enjoy sailing lessons around the harbor. Parks and waterfront trails also provide space for outdoor play and discovery.
What are some of the best things to do in Annapolis?
Explore historic sites like the Maryland State House, wander local marina areas, and discover galleries and cafes in the Historic District. Sailing or taking guided boat tours is often suggested for experiencing the city’s maritime culture.
How is the weather in Annapolis?
Annapolis has crisp winters around 25–43°F (-4–6°C) and warm, humid summers between 68–89°F (20–32°C). Rain is fairly consistent year-round, so packing layers and a rain jacket is helpful.
What are the best places to visit in Annapolis?
Explore the U.S. Naval Academy’s historic grounds, the Maryland State House, and quiet corners of the Historic District. City Dock is frequently suggested for people-watching, local snacks, and harbor views.
What are some hiking trails in Annapolis?
Quiet Waters Park has wooded trails, art installations, and water views, making it a favorite for walkers and nature lovers. Greenbury Point is another area with paths winding through natural habitats near the water.
What are some family activities we can do in Annapolis?
Families often enjoy exploring interactive exhibits at local museums, sailing or kayaking together, and strolling city parks for outdoor fun. Many neighborhoods have playgrounds and green spaces for all ages.
What are some of the best day trip ideas from Annapolis?
Explore vibrant waterfront towns on the Chesapeake Bay, discover local wineries and farms around the region, or visit natural preserves just outside the city. State parks and small historic communities are also frequently suggested.
Are there any pet friendly accommodations available in Annapolis?
Many rentals in the Historic District and Eastport area welcome pets, making it easy to explore the city’s parks and waterfront trails together. Some hosts provide amenities for pets, such as bowls and outdoor spaces.
What are some local tips for visiting Annapolis?
Walking is a great way to explore narrow historic streets and see waterfront sights. Trying a sailing experience, sampling local crab dishes, and checking out neighborhood art galleries help connect with Annapolis’s distinct maritime culture.
What is Annapolis known for?
Annapolis is known for its maritime heritage, historic architecture, and the presence of the U.S. Naval Academy. The city has a vibrant sailing culture, colonial-era sites, and crab-focused cuisine.
What are the best hidden gems to explore in Annapolis?
Artists’ studios in West Annapolis, cozy bookshops in the historic area, and small galleries along quaint side streets allow visitors to connect with the local creative community. The Kunta Kinte-Alex Haley Memorial offers space for reflection near the water.
What are the best foods to try in Annapolis?
Annapolis has Maryland blue crab specialties such as crab cakes and creamy crab soup, along with fresh oysters and locally made ice cream. You’ll also find regional dishes rooted in Chesapeake Bay traditions.
What should I bring for a trip to Annapolis?
Pack comfortable walking shoes, layered clothing, and a rain jacket for changing weather. A wide-brim hat and sunscreen are useful for sunny days spent exploring the waterfront or hopping on boat tours.
What is the nightlife in Annapolis like?
Annapolis has lively bars, local breweries, and music venues clustered around the Historic District and Eastport. Jazz nights, open mics, and waterfront pubs create a relaxed evening atmosphere.
What are the most popular events or festivals in Annapolis?
The city hosts boat shows in spring and fall, and the Maryland Renaissance Festival takes place nearby in late summer and early fall. Local parades and seafood celebrations add to the festive calendar.
Are there family friendly vacation rentals in Annapolis?
Vacation rentals in neighborhoods like the Historic District and Eastport often have kid-friendly sleeping arrangements and amenities such as kitchens and outdoor spaces. Many hosts are welcoming to families and provide helpful local tips.
When is the best time to visit Annapolis?
Late spring through early fall is often recommended for milder temperatures and frequent waterfront events. The changing leaves in autumn create pleasant scenery for city walks and harbor outings.
All about Annapolis
The capital of Maryland, Annapolis sits on the banks of Chesapeake Bay and is known for its historic neighborhoods and 18th-century Colonial, Georgian, and Victorian homes. With its reputation as the sailing capital of the United States, and home to the U.S. Naval Academy, Annapolis holds several significant historical credentials, including a founding that dates back to 1649. St. John's College, one of the oldest universities in the country, still stands proud on Annapolis soil.
Today, this prosperous East Coast city is known more for its thriving downtown Historic District with boutique shops, galleries, and architectural sites that provide a day of exploration before heading to the Eastport District, where the Annapolis culinary scene emphasizes locally sourced oysters, crabs, and scallops. For nightlife, West Street is where you will find several bars, clubs, and restaurants, many of which regularly host live music on the weekends.
What are the top things to do in Annapolis?
Annapolis Maritime Museum
This waterfront museum houses several exhibitions and displays that detail the area's maritime history and the ocean's significance in its economic, social, and cultural developments. Exhibits explain Chesapeake Bay’s unique ecological makeup and how it has impacted the fishing industry over the years. In addition, several art and photography displays highlight the region's social makeup through contributions by local and internationally renowned artists.
Historic London Town
Located just outside of Annapolis in the town of Edgewater, this 23-acre park is a recreation of a lost 18th-century colonial village that would have been common in the area at the time. A carpenter's shop, mayor's tenement, picnic areas, and ten acres of woodland and ornamental gardens are all waiting to be explored in the area. Recreated through a series of archeological discoveries, most of the buildings are full of everyday objects that would have been found and used at the time.
Lake Waterford Park
This 108-acre park is where the locals come to stretch out when the weather is nice. It includes a full lineup of recreational activities, from tennis courts to football fields. Walking trails and hiking paths meander through much of the wooded park, and there’s a 12-acre lake for spotting waterfowl and fishing from the shores.
Quick stats about vacation rentals in Annapolis
Total vacation rentals
Explore 660 vacation rentals in Annapolis
Nightly prices starting at
Annapolis vacation rentals start at G$2,091 GYD per night before taxes and fees
Verified guest reviews
Over 34,100 verified reviews to help you choose
Family-friendly vacation rentals
450 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 190 rentals that welcome pets
Vacation rentals with a pool
30 properties feature pools
Rentals with dedicated workspaces
360 properties have a dedicated workspace
Wi-Fi availability
650 of Annapolis vacation rentals include wi-fi access
Popular amenities for guests
Guests love Monthly stays, Self check-in, and Gym across Annapolis rentals
4.9 Average rating
Annapolis stays are highly rated by guests—averaging 4.9 out of 5!
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- Georgetown University
- Walter E Washington Convention Center
- National Mall
- M&T Bank Stadium
- Nationals Park
- The White House
- District Wharf
- National Museum of Natural History
- Capital One Arena
- Baltimore Convention Center
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Arlington National Cemetery
- Howard University
- Betterton Beach
- Sandy Point State Park
- Georgetown Waterfront Park
- Washington Monument
- Patterson Park
- National Harbor
- Smithsonian American Art Museum
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- Six Flags America
- The Pentagon