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Annapolis vacation rentals

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Top-rated vacation rentals in Annapolis

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Private room · Annapolis
Jorge's Pousada
Enjoy this quiet place and close to downtown Annapolis , safe area and free park
$55 per night
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Private room · Annapolis
Blue Room - Private Room in Annapolis
Keep it simple at this peaceful and centrally located home in a charming eclectic neighborhood close to the Historic Downtown and major shopping districts. You will feel at home as soon as you walk in the door. The house has that old charm with modern touches and a spacious yard with colorful gardens.
$51 per night
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Private room · Annapolis
Chesapeake Mornings
Sun-filled corner room with queen-sized bed, walk-in closet, lovely window shades with pretty views of the front yard. The room is located in a colonial home where people from all backgrounds are very welcome! Perfect location for someone who loves to walk and bike or just relax on the back patio.
$67 per night

Vacation rentals for every style

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Stay near Annapolis's top sights

Photo of United States Naval Academy
United States Naval Academy49 locals recommend
Photo of St. Anne's Parish
St. Anne's Parish4 locals recommend
Photo of US Naval Academy Museum
US Naval Academy Museum15 locals recommend
Photo of Truxtun Park
Truxtun Park10 locals recommend
Photo of Downtown Annapolis Partnership
Downtown Annapolis Partnership10 locals recommend
Photo of Jonas Park
Jonas Park5 locals recommend

Annapolis waterfront vacation rentals

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Entire cottage · Deale
Chesapeake Bay Cottage
$290 per night
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Entire guesthouse · Annapolis
Cape St Claire waterfront getaway
$125 per night
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Entire rental unit · Annapolis
Private Apartment - Minutes to USNA
$103 per night
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Entire cottage · Annapolis
Waterfront Chesapeake Cottage in Oyster Bay - Dock
$225 per night
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Entire home · Annapolis
Country House on the Bay
$181 per night
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Entire guest suite · Stevensville
Kent Island Haven - A Waterfront Getaway
$160 per night
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Entire home · Shady Side
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
$194 per night
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Entire home · Edgewater
Waterfront house near Annapolis
$175 per night
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Entire rental unit · Deale
Modern Chesapeake Waterfront Studio Apt & Solarium
$199 per night
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Entire home · Annapolis
Charming Annapolis Water View Home
$508 per night
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Entire cottage · Pasadena
Ft. Smallwood Overlook. It's all about the water!
$320 per night
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Entire home · Annapolis
Getaway On The Bay
$450 per night

Annapolis fishing vacation rentals

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Private room · Annapolis
Private & Spacious - 3 miles to Downtown Annapolis
$72 per night
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Entire home · Arnold
Bring A Boat! Waterfront home-w/basement apt+dock!
$179 per night
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Entire guest suite · Severn
Retreat on Sage Brush Court
$79 per night
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Private room · Severn
Welcoming Room in a Townhouse
$47 per night
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Entire home · Annapolis
The Cape Nest - Private 2bd 1bth basement
$158 per night
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Private room · Severn
Severn Ivy Tree Estates
$47 per night
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Entire guest suite · Severn
Fun and Cozy
$59 per night
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Entire home · Annapolis
Spacious 3 bedroom house, perfect for entertaining
$236 per night
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Entire rental unit · Arnold
Private Annapolis Area Waterfront
$364 per night
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Entire cottage · Arnold
Sail, Power Boat into Deep Creek Arnold Getaway
$216 per night
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Entire home · Annapolis
Lovely family home just minutes from Annapolis
$275 per night
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Entire rental unit · Hanover
Private and remodeled one-bedroom apartment.
$80 per night

Annapolis house rentals

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Private room · Annapolis
Single room
$43 per night
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Entire home · Annapolis
New Hotel Chic
$248 per night
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Private room · Annapolis
A Cottage Room in Presidents Hill
$92 per night
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Entire home · Annapolis
Cozy home in Historic Annapolis with Parking
$253 per night
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Entire home · Annapolis
Spacious House + Patio Steps to Downtown / Main St
$216 per night
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Private room · Annapolis
Telescope Single Bed Room
$110 per night
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Private room · Annapolis
Cozy private room in Annapolis home
$69 per night
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Entire home · Annapolis
As mentioned in the Washington Post
$243 per night
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Entire home · Annapolis
Charming Renovated Historic Home Downtown wparking
$309 per night
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Entire home · Annapolis
Historic Downtown House with Off Street Parking
$338 per night
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Entire home · Annapolis
Naptown Suite
$101 per night
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Private room · Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
$75 per night

Your guide to Annapolis

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.


When is the best time to stay in a vacation rental in Annapolis?

Annapolis experiences drastic weather changes from season to season. The summer months tend to be hot and humid, with moderate precipitation and long pleasant nights. Several festivals occur during the summer days, like a Renaissance fair in a fictional 16th-century village with costumed events, vendors, and medieval-era arts and crafts. Or the weekly Wednesday Night Sailboat Races that take place from May through September.

The winter sees temperatures drop to below freezing with an occasional dusting of snow. However, Annapolis’ warm cafes and cozy street-side restaurants can make brisk days feel quite pleasant. The shoulder seasons are an excellent time to look for vacation rentals in Annapolis, as the spring weather conditions that are temperate also mark the beginning of the sailing season. The fall hosts a brilliant display of autumn hues in the treetops throughout the city with similar weather patterns to that of spring.


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.