Vacation rentals in Annapolis
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Top-rated vacation rentals in Annapolis
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Historic 3 Bedroom Downtown Annapolis Townhome
Be close to everything when you stay at this centrally-located, historic townhome! Located steps from the Naval Academy, Downtown Restaurants, Bars, Shopping, and Festivals. Enjoy and relax on your large private, fenced-in patio or in your modern living room. While the restaurant scene is mouth-watering in Annapolis, you can also stay "home" and cook in your gourmet kitchen. Explore all that Annapolis has to offer from the comfort of your home away from home! No on-site parking but lots of off.
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
4 bedrooms, 7 beds, 3 bath completely updated
Not your typical Airbnb. This is our vacation house too and we have it stocked so you can enjoy all of the amenities of home, without having to bring them yourself. Full kitchen with fresh coffee beans, K cups, and tea provided for starters. Breakfast starters provided too. Everything you need if you want to cook. Games for inside (including PS5), and backyard games too. 3 bedrooms on ground floor so no constantly having to go up and down steps. We love our place and know you will too.
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.
Lil’ House - A Serene Tiny Home Experience
Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.
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
Annapolis @Gate 1 steps to the Harbor Free parking
Parking included. The heart of Annapolis 1 street from the harbor, fun restaurants & backs to the Naval Academy. This 1st floor 2 bed / 1 ba condo has been fully renovated with new paint, floors, bath & kitchen. 1 Parking space included & additional paid parking on street. Queen Bed & sleeper couch is a full size. Linens included. Kitchen includes refrigerator, stove/oven, microwave, keurig, dishes silverware, pots and pans. High speed internet included & separate work area.
King George Hideaway
Perfect location for all that downtown Annapolis offers, right across from USNA gate 2. Super convenient, park your car and walk everywhere! Lots of shopping, restaurants, tours, cruises & nightlife. The unit is located on the 3rd floor. My place is perfect for couples, solo and business travelers. There is a large living room space with a full pull out couch, tv and dining table. The bedroom has a queen bed with a tv. There is a small full kitchen and updated bathroom.
1st Floor Condo in Annapolis
This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in Eastport. Within easy walking distance of restaurants (3 min), Main Street/City Dock (10 min) & USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high-speed wifi, free onsite parking lot, a secure building entrance, dock and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.
Sophisticated & Spacious Historic Home w/ Parking!
Located in the Historic District, our home is a unique blend of vintage charm and modern comforts. Off-street parking in a driveway is a rare find, & additional parking spaces in the rear are available with permission. We are 2 blocks to USNA Gate 1, and 1 mile to the Navy Stadium. A shady and quiet backyard is a peaceful respite, with retail shops, restaurants and coffee houses just steps away. STR# RENT-002617-2025
12 M to Naval Academy | Waterfront Paradise
Discover the perfect blend of tranquility and convenience at our charming waterfront property. Nestled away in a serene setting yet close to all the action, this home offers an ideal escape. Imagine unwinding on the expansive screened-in porch, taking in the peaceful views of calm waters, or dropping a crab pot to catch some of Maryland's renowned Blue Crabs.
Popular amenities for Annapolis vacation rentals
Annapolis home rentals
Cheerful & Spacious Shore Life Beauty!
Eastport Haven House
Rachel's BnB
Historic & sunny home steps from USNA/downtown
Charming Annapolis Water View Home
Charming West Annapolis Cottage home
Annapolis Cottage at Bay Ridge, Renovated
Across from stadium - walk to downtown Annapolis!
Other great vacation rentals in Annapolis
Peaceful Waterfront Home in Annapolis 3BR 2BA.
Renovated Apt In Historic Dist w/2 Parking Spots
Cute bungalow blocks to Stadium
Eastport Apartment
Chic Renovation On Fleet Street
Anchors Away
Updated Eastport Gem with Outdoor Fireplace!!
Annapolis Main Street Modern Apartment
When is the best time to visit Annapolis?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$50,141 GYD | G$48,678 GYD | G$50,558 GYD | G$56,826 GYD | G$67,481 GYD | G$61,422 GYD | G$58,497 GYD | G$61,213 GYD | G$61,631 GYD | G$69,361 GYD | G$58,080 GYD | G$60,169 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$2,089 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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