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.

Private room · Annapolis
Chesapeake Mornings
Sun-filled corner room with queen-sized bed, walk-in closet and mini fridge, 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. The guest bath is just down the hall - not en suite - and is for the exclusive use of guests. Perfect location for someone who loves to walk and bike or just relax on the back patio.
Aug 26 – Sep 2
$40 per night
Superhost
Apartment · Annapolis
Private Annapolis Inlaw Apartment
In-law apartment in beautiful Annapolis home. Close to downtown Annapolis but also has easy access to major highways. Quiet neighborhood. Private front entrance to apartment. In addition to king size bed in bedroom there are two queen size blow up beds as well as a large sectional sofa. So it comfortably sleeps 4. Off street parking for 2-3 vehicles.
Dec 12 – 19
$98 per night
Superhost
Guest suite · Annapolis
right downtown garden oasis (dog-friendly)
Right downtown! Yet secluded. Private entrance - easy in and out. Self-check in. Free street parking week nights with car license plate state and number. Historic Annapolis while you sleep - Queen Anne style featured in Baltimore Sun. Go Navy! Views of USNA Chapel. Private garden courtyard featured on Annapolis' Secret Garden Tour - try forest bathing. Additional services with notice: dogs ($25/stay/pet), extended stays, garden BBQ parties ($50), kayak, extra rooms.
Feb 15 – 22
$113 per night
Superhost

Vacation rentals for every style

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Stay near Annapolis's top sights

Photo of United States Naval Academy
United States Naval Academy51 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 Downtown Annapolis Partnership
Downtown Annapolis Partnership10 locals recommend
Photo of Truxtun Park
Truxtun Park11 locals recommend
Photo of Jonas Park
Jonas Park6 locals recommend

Annapolis waterfront vacation rentals

Apartment · Annapolis
Private Apartment - Minutes to USNA
Mar 26 – Apr 2
$124 per night
Superhost
Cottage · Deale
Chesapeake Bay Cottage
Aug 25 – Sep 1
$263 per night
Superhost
Home · Annapolis
Country House on the Bay
Mar 15 – 22
$143 per night
Superhost
Cottage · Annapolis
Waterfront Chesapeake Cottage in Oyster Bay - Dock
Aug 1 – 8
$582 per night
Guest suite · Annapolis
Bayside Beach Getaway
Jun 6 – 13
$129 per night
Home · Annapolis
Charming Annapolis Water View Home
Nov 11 – 18
$444 per night
Superhost
Home · Annapolis
Waterfront Vacation Home with Amazing Views
Feb 3 – 10
$750 per night
Superhost
Cottage · Pasadena
Ft. Smallwood Overlook. It's all about the water!
Feb 28 – Mar 7
$237 per night
Superhost
Place to stay · Shady Side
Round House -- Panoramic Views -- Chesapeake Bay
Jul 15 – 22
$514 per night
Superhost
Home · Annapolis
Waterfront Vacation Home
Mar 6 – 13
$387 per night
Apartment · Deale
Modern Chesapeake Waterfront Studio Apt & Solarium
Aug 6 – 13
$189 per night
Superhost
Home · Annapolis
Annapolis Shore House-Family retreat near the Bay
May 21 – 28
$608 per night

Annapolis fishing vacation rentals

Private room · Annapolis
Private & Spacious - 3 miles to Downtown Annapolis
Dec 20 – 27
$70 per night
Superhost
Home · Annapolis
Luxury Waterfront Home Annapolis with beach & dock
Jan 9 – 16
$1,000 per night
Superhost
Guest suite · La Plata
Beautiful Rural Suite near Washington, D.C.
Jan 9 – 16
$85 per night
Superhost
Apartment · Baltimore
Beautiful Bright Victorian Apartment by the Lake
Sep 15 – 22
$80 per night
Superhost
Home · College Park
Holly House: Peace between a Forest and a Lake
Nov 9 – 16
$106 per night
Home · Berwyn Heights
Cheerful & Newly Renovated spacious 5 BR Home
Aug 28 – Sep 4
$428 per night
Home · College Park
Perfect for family visits to Washington DC or UMD!
Jan 12 – 19
$265 per night
Superhost
Home · Wye Mills
⫷ Massey on the Lake
Jun 2 – 9
$335 per night
Superhost
Home · Wye Mills
⇚Family Getaway⇛| Lakeside + A Nature View |
Sep 16 – 23
$486 per night
Superhost
Apartment · Annapolis
Pet-friendly Coastal Suite with water views
Feb 1 – 8
$261 per night
Apartment · Greenbelt
Spacious, Stylish & 3BR ~ 5★ Location,♛Royal Beds
May 14 – 21
$185 per night

Annapolis house rentals

Private room · Annapolis
Telescope Single Bed Room
May 21 – 28
$94 per night
Superhost
Private room · Annapolis
Cozy private room in Annapolis home
May 2 – 9
$69 per night
Superhost
Home · Annapolis
New Hotel Chic
Sep 24 – Oct 1
$171 per night
Superhost
Home · Annapolis
Cozy home in Historic Annapolis with Parking
Feb 25 – Mar 4
$149 per night
Superhost
Private room · Annapolis
Blue Room - Private Room in Annapolis
Dec 15 – 22
$59 per night
Superhost
Home · Annapolis
Charming Row House in Historic District
Nov 20 – 27
$425 per night
Plus
Home · Annapolis
Blocks to Main St, Walk-up Rowhouse
Jan 17 – 24
$112 per night
Superhost
Private room · Arnold
Academy Room- 3 miles from US Naval Academy Gate 8
Nov 30 – Dec 7
$45 per night
Superhost
Private room · Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
Jan 23 – 30
$68 per night
Superhost
Private room · Annapolis
Beautiful Private Room and Bath - Edge of Eastport
Dec 26 – Jan 2
$72 per night
Private room · Annapolis
Lovely Private Master Bedroom
Mar 12 – 19
$101 per night
Superhost
Home · Shady Side
Luxe Modern Chesapeake Waterfront Oasis
Apr 8 – 15
$495 per night
Superhost

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.