We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals near Segs in the City

232 West St, Annapolis, Maryland 21401-3424
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $459 Average
    |||
    |||
    $0$1,000+
    Suitability
    Suitability
    More filters
    Travelers to Annapolis are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    All 16 Rentals in Annapolis
    *BOOK NOW* Beautiful Cottage in historic Annapolis1 / 25
    (19)Excellent
    0.5 miles from Segs in the City
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Charming and Spacious Annapolis Victorian1 / 19
    (6)Excellent
    0.3 miles from Segs in the City
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Beautiful Murray Hill Home (Annapolis)1 / 30
    (3)Very good
    0.3 miles from Segs in the City
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    0.4 miles from Segs in the City
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • DVD Player
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We bought and renovated this rowhouse in 2007 for a second home for friends and family to stay when they visited and it eventually evolved into one of the most popular rental properties in all of Historic Annapolis. A former ' Home of the Week' in the Capital Gazette it is also one of the most...
    View all property information
    Location Information
    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Inquiry
    4.5 miles from Segs in the City
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Balcony
    • Terrace
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming Annapolis home, just 150 feet from the water, with floor to ceiling windows overlooking the expansive waters of the Chesapeake Bay. Water views from almost every room. Features 4 bedrooms and 4 bathrooms with luxury upgrades, viking kitchen appliances, comfortable couches for sleeping...
    View all property information
    Location Information
    Annapolis, Maryland
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 11
    Make Inquiry
    4.7 miles from Segs in the City
    5 Bedrooms, 3 Bathrooms, Sleeps 20 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Ocean Views
    • Hot Tub
    • Internet Access
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfort & Style: Enjoy stunning Chesapeake Bay Views, Beach, Pier, Boat Slips, Park, Water Access, Fire Pit, Patio Heater and more! Charming cottage & detached studio/game room (both upgraded in 2013) offer gourmet kitchen with new stainless steel appliances, a second full kitchen in garden...
    View all property information
    Location Information
    Annapolis, Maryland
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 20
    Make Inquiry
    Charming Townhouse - Steps to City Dock and USNA1 / 7
    (1)Terrible
    0.7 miles from Segs in the City
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • DVD Player
    • Central Heating
    • Internet Access
    • Grill
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shellback house is a three bedroom, one and 1/2 bath historic townhouse in the heart of Downtown Annapolis with a private garden. The house has views of Ego Alley (Annapolis Waterfront) from the front stoop and the master bedroom. BOOK NOW FOR 2015 LEGISLATIVE SESSION AT STIPEND RATES! Please...
    View all property information
    Location Information
    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Walk to Shops/Eateries Charming Cottage. Dogs Wel.1 / 51
    (2)Excellent
    0.8 miles from Segs in the City
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Housekeeping Included
    • Patio
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    We stayed at the cottage for an extended period of time and it was very enjoyable. The house itself was well put together and had everything that we could have needed. The...
    See all reviews
    About this property
    This City-inspected vintage cottage in Upper Eastport, located on a cul de sac, is a short walk to the Historic Harbor & just blocks from Spa Creek. History, waterfront, rooftop restaurants, wine bars, sailing, kayaking and more. We have everything here in Annapolis - USNA, sailing, culture,...
    View all property information
    Location Information
    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    3.4 miles from Segs in the City
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Yellow House is a magnificent Waterfront Property, with interior and exterior appointments, that are truly outstanding-76 five Star reviews can be viewed on our sister site-vacation rentals by owner dot com. 230476 With its magazine worthy gardens, and spacious 6 bedrooms, designed and...
    View all property information
    Location Information
    Annapolis, Maryland
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
    Make Inquiry
    1.0 miles from Segs in the City
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Best location in Eastport ,We restored this lovely victorian house over the past sixteen years. The upstairs is modern and has all the great amenities that a renovated building provides. anderson windows to keep the place warm and toasty. Seperate heating/air conditioning controls.Wooden floors,...
    View all property information
    Location Information
    Annapolis, Maryland
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Inquiry
    Save time - get the best Annapolis rentals sent straight to your email!
    Get the List
    0.8 miles from Segs in the City
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Private Yard
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk to historic City Dock, waterfront restaurants, U.S. Naval Academy. Open, sunny floor plan ideal for entertaining. Craftsman style 3 BRM + den + office + front porch swing + screened back porch + game room + ample parking. Well-furnished. Sleeps 6-8 comfortably or up to 10 with available...
    View all property information
    Location Information
    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Inquiry
    Charming Home close to historic district1 / 31
    (4)Excellent
    0.1 miles from Segs in the City
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Wi-Fi
    • Grill
    • Porch
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 19, 2017
    This is a great house to rent with another couple or with a family. The house is Within easy walking distance to all the fun in downtown And the waterfront. It has all the...
    Reviewed August 20, 2017
    We had a lovely stay in this spacious and tastefully furnished house. It was perfect for my husband and I and our three boys (8, 14 and 16). The rooms were larger than I...
    See all reviews
    About this property
    A Charming detached one-family home located in one of the most vibrant neighborhoods of Annapolis. Perfectly located in a quiet residential street, only 0.8 miles from the United States Naval Academy and a short walk from Main street. The home is situated only a few steps away from West street and...
    View all property information
    Location Information
    Annapolis, Maryland
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    0.4 miles from Segs in the City
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Terrace
    • DVD Player
    • Central Heating
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is in a very nice, safe neighborhood (two blocks to firehouse and 2 blocks to police station) within walking distance to historic downtown Annapolis. It is also less than a block to the Navy football stadium and easily walkable to grocery store, pharmacy, liquor store and...
    View all property information
    Location Information
    Annapolis, Maryland
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    4.1 miles from Segs in the City
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the newly renovated 780 sf studio unit that is on the ground floor of a main house that is similarly titled and on the same property. Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation of the main house with exposed structure and mechanical systems that serves as...
    View all property information
    Location Information
    Annapolis, Maryland
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    1.2 miles from Segs in the City
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Outdoor Dining Area
    • DVD Player
    • Balcony
    • Washer
    • Parking
    • Porch
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    HOUSE This fully renovated, circa 1890 ,Victorian house is located in the middle of the Eastport peninsula . The house is within walking distance, or a three minute taxi ride, to downtown historic Annapolis and the US Naval Academy, as well as shopping, several marinas, theater, numerous...
    View all property information
    Location Information
    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Make Inquiry
    Luxury Boat & Bed 78' Motor Yacht 'Laid Off'1 / 4
    (1)Excellent
    3.1 miles from Segs in the City
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Patio
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    We stayed aboard the Laid Off for a friends 40th birthday celebration and had a wonderful evening watching the sunset surrounded by friends and family! It was a relaxing evening...
    See all reviews
    About this property
    Our luxury 78' Hatteras Motor Yacht, 'Laid Off' is an exciting experience to stay on for the day, overnight, weekend or a week. The Yacht offers 4 luxury staterooms each with its own bathroom. The large living room has a piano, lounge seating, flat screen TV/entertainment center with karaoke....
    View all property information
    Location Information
    Edgewater, Maryland
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Inquiry
    List your property
    Owner log in