The 10 best holiday homes in Annapolis, USA | Booking.com
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Holiday Homes in Annapolis

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The best holiday homes in Annapolis

Check out our pick of great holiday homes in Annapolis

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Vintage Charm: Annapolis Retreat

Annapolis

Situated in Annapolis, 3 km from Annapolis Harbor and 46 km from Sports Legends Museum At Camden Yards, Vintage Charm: Annapolis Retreat offers a garden and air conditioning.

Scored out of 10, guest rating 10.0
Exceptional - What previous guests thought, 7 reviews
Price from
US$315
1 night, 2 adults
Check availability

Neptune By The Water

Annapolis

Located in Annapolis, 15 km from Annapolis Harbor and 42 km from Sports Legends Museum At Camden Yards, Neptune By The Water provides spacious air-conditioned accommodation with a patio and free WiFi....

Scored out of 10, guest rating 10.0
Exceptional - What previous guests thought, 6 reviews
Price from
US$213
1 night, 2 adults
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Fisher House - Downtown Annapolis!

Annapolis

Situated in Annapolis, 1.7 km from Annapolis Harbor and 48 km from Sports Legends Museum At Camden Yards, Fisher House - Downtown Annapolis!

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 6 reviews
Price from
US$387
1 night, 2 adults
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Edgewatermayo Getaway!

Edgewater (Near Annapolis)

Featuring a spa bath, Edgewatermayo Getaway! is set in Edgewater. The air-conditioned accommodation is 19 km from Annapolis Harbor, and guests can benefit from on-site private parking and...

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 5 reviews
Price from
US$261
1 night, 2 adults
Check availability

Weems Creek Cottage, Annapolis Waterfront

Annapolis

Set in Annapolis and only 4.3 km from Annapolis Harbor, Weems Creek Cottage, Annapolis Waterfront offers accommodation with sea views, free WiFi and free private parking.

Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 8 reviews
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Walk to Everything Historic Arts District

Annapolis

Situated in Annapolis, 3 km from Annapolis Harbor and 46 km from Sports Legends Museum At Camden Yards, Walk to Everything Historic Arts District offers air conditioning.

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 8 reviews
Check availability

Anchors Away Abode

Annapolis

Boasting air-conditioned accommodation with a patio, Anchors Away Abode is situated in Annapolis.

Scored out of 10, guest rating 10.0
Exceptional - What previous guests thought, 6 reviews
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Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!

Annapolis

Boasting lake views, Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER! features accommodation with a garden and a patio, around 14 km from Annapolis Harbor.

T
Timothy
From
United States
Very nice and clean. Quiet and well maintained.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 9 reviews
Check availability

Private Single Family Home Close to Both Water and Downtown!

Annapolis

Featuring air-conditioned accommodation with a patio, Private Single Family Home Close to Both Water and Downtown! is located in Annapolis.

F
Francois
From
Canada
The RBNB is well equip and everything was easy to found and identify Thank you
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 7 reviews
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Waterfront Annapolis Home Fire Pit and Fishing Pier

Annapolis

Located in Annapolis, 14 km from Annapolis Harbor and 46 km from Sports Legends Museum At Camden Yards, Waterfront Annapolis Home Fire Pit and Fishing Pier offers air conditioning.

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 7 reviews
Check availability
All holiday homes in Annapolis

Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.

Most booked holiday homes in Annapolis and surroundings in the past month

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Holiday Homes with swimming pools in Annapolis and nearby

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    Boasting air-conditioned accommodation with a private pool, Oasis by the Bay - Waterfront Heated Pool Hot Tub is set in Annapolis.

  • Boasting air-conditioned accommodation with a private pool, Thomas Point Tranquility is set in Annapolis. This holiday home offers accommodation with a patio.

  • Boasting air-conditioned accommodation with a balcony, Porter Point is set in Annapolis. Guests can benefit from a patio and an outdoor fireplace.

Enjoy breakfast in Annapolis and nearby

  • Westside Storied

    Annapolis
    Breakfast options

    Set 2.3 km from Annapolis Harbor, 47 km from Sports Legends Museum At Camden Yards and 48 km from Baltimore Convention Center, Westside Storied offers accommodation situated in Annapolis.

  • Boasting air-conditioned accommodation with a patio, Downtown Annapolis is set in Annapolis.

  • Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 4 reviews

    Set in Annapolis, 2.2 km from Annapolis Harbor and 48 km from Sports Legends Museum At Camden Yards, Cozy 2br home w/ parking in downtown Annapolis offers a garden and air conditioning.

    From US$344.72 per night

  • The Little House

    Annapolis
    Breakfast options
    Scored out of 10, guest rating 4.0
    Disappointing - What previous guests thought, 1 review

    Boasting air-conditioned accommodation with a patio, The Little House is set in Annapolis.

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 4 reviews

    Set in Annapolis, 2 km from Annapolis Harbor and 48 km from Sports Legends Museum At Camden Yards, * Midcentury Modern Getaway * Prime Location * offers air-conditioned accommodation with a balcony...

    From US$540.44 per night

  • Boasting air-conditioned accommodation with a patio, St Johns Adjacent is situated in Annapolis.

  • Offering barbecue facilities and garden view, 1879 Downtown Annapolis Home with Koi Ponds and Gardens is set in Annapolis, 48 km from Sports Legends Museum At Camden Yards and 48 km from Baltimore...

  • Situated in Annapolis, 2.5 km from Annapolis Harbor and 48 km from Sports Legends Museum At Camden Yards, Timeless Charm, Modern Comfort features spacious air-conditioned accommodation with a patio...

Save money on holiday homes in Annapolis and nearby – budget options available

  • Naval Academy Gate 1

    Annapolis
    Budget options available

    Located in Annapolis, 1.8 km from Annapolis Harbor and 41 km from Inner Harbor, Naval Academy Gate 1 provides air-conditioned accommodation with a patio and free WiFi.

  • Located in Annapolis, 1.8 km from Annapolis Harbor and 48 km from Sports Legends Museum At Camden Yards, Historic Row Home in Downtown Annapolis provides air-conditioned accommodation with a patio and...

  • Skyline Sanctuary

    Annapolis
    Budget options available
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    Featuring air-conditioned accommodation with a patio, Skyline Sanctuary is located in Annapolis.

  • Anchors Aweigh

    Annapolis
    Budget options available
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Featuring air-conditioned accommodation with a patio, Anchors Aweigh is set in Annapolis.

  • Seas The Bay

    Annapolis
    Budget options available
    Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 1 review

    Boasting air-conditioned accommodation with a patio, Seas The Bay is situated in Annapolis.

  • Located in Annapolis, 2.6 km from Annapolis Harbor and 41 km from Inner Harbor, Newly Renovated In Dta W Parking provides spacious air-conditioned accommodation with a patio and free WiFi.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    Situated in Annapolis, 1.8 km from Annapolis Harbor and 48 km from Sports Legends Museum At Camden Yards, Historic Row Home 1 Block from Gate 1 at USNA features air-conditioned accommodation with a...

  • Crew's Quarters

    Annapolis
    Budget options available

    Situated in Annapolis, 2.6 km from Annapolis Harbor and 48 km from Sports Legends Museum At Camden Yards, Crew's Quarters offers air conditioning.

Great access to the city centre. Check these holiday homes in Annapolis and nearby

  • Boasting air-conditioned accommodation with a balcony, The Master Shipwright is situated in Annapolis. Guests staying at this holiday home have access to a patio.

  • Situated in Annapolis in the Maryland region, Unique And Central In Eastport has a patio.

  • Boasting air-conditioned accommodation with a patio, Walk to the stadium, downtown, West St - close to everything is situated in Annapolis.

    From US$286.25 per night

  • Eden on Adams

    Annapolis
    Central location

    Eden on Adams is situated in Annapolis, 1.4 km from Annapolis Harbor, 43 km from Addison Road-Seat Pleasant, and 49 km from Sports Legends Museum At Camden Yards.

  • Harrison Hall

    Annapolis
    Central location
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Boasting air-conditioned accommodation with a patio, Harrison Hall is set in Annapolis.

  • Set in Annapolis, 3.5 km from Annapolis Harbor and 40 km from Addison Road-Seat Pleasant, Historic 3 BR Home - 15 Min Walk to N-MC Stadium offers air-conditioned accommodation with a patio and free...

  • Boasting air-conditioned accommodation with a patio, Beautiful 4BR - Walking Distance to Stadium is situated in Annapolis.

  • Lighthouse Inn

    Annapolis
    Central location

    Lighthouse Inn is set in Annapolis, less than 1 km from Annapolis Harbor, 49 km from Sports Legends Museum At Camden Yards, and 50 km from Baltimore Convention Center.

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