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The best villas in Annapolis

Check out our selection of great villas in Annapolis

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Review Score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest Price First Star rating and price Top reviewed

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The spacious holiday home features 4 bedrooms, a TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. Towels and bed linen are available in the holiday home. The accommodation offers a fireplace.

The house is very tastefully decorated and had all the mentalities one would need. The location - under 15 minutes drive from center of town (Annapolis dock) - was very convenient. The host was very easy to contact and always got back promptly.

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9.9
Exceptional
8 reviews
Price from
$371
per night

The villa features 2 bedrooms, a flat-screen TV with cable channels, a fully equipped kitchen with a microwave and a fridge, a washing machine, and 1 bathroom with a bath. For added privacy, the accommodation features a private entrance.

Clean, welcoming, nice and calm neighbourhood, nice small terrace and garden.

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9.6
Exceptional
19 reviews
Price from
$118.80
per night

The spacious holiday home features 3 bedrooms, a flat-screen TV, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom with a bath. Towels and bed linen are available in the holiday home. For added privacy, the accommodation features a private entrance.

Very quiet and peaceful. Loved the decor and the use of the dock.

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9.1
Wonderful
7 reviews
Price from
$217
per night

The air-conditioned holiday home is composed of 5 separate bedrooms, 3 living rooms, a fully equipped kitchen with a dishwasher and microwave, and 2 bathrooms. Towels and bed linen are provided in the holiday home.

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10
Exceptional
1 reviews
Price from
$256
per night

The spacious holiday home features a patio, 2 bedrooms, a living room and a well-equipped kitchen with a dishwasher and an oven. A TV is provided. For added privacy, the accommodation features a private entrance.

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9.5
Exceptional
2 reviews
Price from
$182
per night

Situated in Annapolis, 4.9 km from Annapolis Harbor and 40 km from Addison Road-Seat Pleasant, Anchors Away Abode features air-conditioned accommodation with a patio and free WiFi. The property is set 45 km from Sports Legends Museum at Camden Yards, 46 km from Historic Ships in Baltimore and 46 km from Inner Harbor. The property is non-smoking and is located 45 km from Carroll Park.

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9.3
Wonderful
3 reviews
Price from
$216.67
per night

This holiday home is fitted with 2 bedrooms, a kitchen with a dishwasher and an oven, a flat-screen TV, a seating area and 1 bathroom fitted with an a bath or shower. Guests can enjoy a meal on an outdoor dining area while overlooking the garden views. The holiday home offers bed linen, towels and laundry service.

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6.7
Review score
3 reviews
Price from
$279.45
per night

Located in Annapolis in the Maryland region, The Pearl of Oyster Harbor features a patio. Set 46 km from Addison Road-Seat Pleasant, the property provides a garden. Free WiFi is available throughout the property and Annapolis Harbor is 7.1 km away.

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9.5
Exceptional
2 reviews
Price from
$408
per night

The air-conditioned holiday home consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 3 bathrooms with an a bath or shower and a hair dryer. Towels and bed linen are featured in the holiday home. For added privacy, the accommodation features a private entrance.

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Price from
$388.50
per night

Baltimore Convention Center is 46 km from the holiday home, while Historic Ships in Baltimore is 47 km from the property. The nearest airport is Baltimore - Washington International Airport, 32 km from Vintage Charm: Annapolis Retreat.

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Price from
$247.50
per night

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Perfect for families, groups, or couples who enjoy luxury and independence while traveling. Enjoy the space and privacy of these fully-furnished, free-standing mansions – travelers can cook, lounge, and explore at their own pace. Note that in Bali, a resort will also be called a villa.
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Most booked villas in Annapolis this month

Enjoy breakfast in Annapolis!

  • Annapolis Vacation Home 2 Mi to Quiet Waters Park
    9.9
    Scored 9.9
    Exceptional
    Rated exceptional
     · 8 reviews

    Annapolis Vacation Home 2 Mi to Quiet Waters Park is located in Annapolis, just 1.8 miles from Carrs Beach and 3.2 miles from Annapolis Harbor.

    Stylish Decor. Clean Comfortable furnishings Deck was great

  • Gaia House
    Breakfast options
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 19 reviews

    Gaia House offers accommodations in Annapolis, 3.7 miles from Annapolis Harbor and 24 miles from Addison Road-Seat Pleasant.

    It was clean and very comfortable. There were also plenty of amenities.

  • Waterfront Annapolis Home Fire Pit and Fishing Pier
    9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 7 reviews

    Waterfront Annapolis Home Fire Pit and Fishing Pier is located in Annapolis, just 8.7 miles from Annapolis Harbor and 26 miles from Inner Harbor.

    Owner was easy to contact for questions. Plenty of towes.

  • Plebe's Paradise
    Breakfast options

    Plebe's Paradise offers accommodations in Annapolis, 30 miles from Carroll Park and 30 miles from Sports Legends Museum at Camden Yards.

  • Fisher House - Downtown Annapolis!

    Fisher House - Downtown Annapolis! offers accommodations in Annapolis, 30 miles from Carroll Park and 30 miles from Sports Legends Museum at Camden Yards.

  • Annapolis Retreat - 7 mins from DTA!

    Annapolis Retreat - 7 mins from DTA! is located in Annapolis, just 31 miles from Sports Legends Museum at Camden Yards and 31 miles from Baltimore Convention Center.

  • Bennett House Entirehaven In Historic Annapolis

    Bennett House Entirehaven In Historic Annapolis enjoys a location in Annapolis, 1.7 miles from Annapolis Harbor and 29 miles from Carroll Park.

  • Stylish + fresh bungalow 2 blocks from N-MC Stadium
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 2 reviews

    Stylish + fresh bungalow 2 blocks from N-MC Stadium offers accommodations in Annapolis, 2.7 miles from Annapolis Harbor and 28 miles from Carroll Park.

Great access to the city center! Check these villas in Annapolis

  • Neptune By The Water
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Neptune By The Water offers accommodations in Annapolis, 10 miles from Annapolis Harbor and 23 miles from Inner Harbor. This vacation home provides accommodations with a balcony.

  • Anchors Aweigh
    Central location
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Anchors Aweigh offers accommodations in Annapolis, 1.2 miles from Annapolis Harbor and 30 miles from Carroll Park. This vacation home offers air-conditioned accommodations with a patio and free Wifi.

  • Harrison Hall
    Central location
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Harrison Hall is located in Annapolis, just 31 miles from Sports Legends Museum at Camden Yards and 31 miles from Baltimore Convention Center.

  • Chase Creek Retreat
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Chase Creek Retreat is located in Annapolis, just 21 miles from Inner Harbor and 23 miles from Carroll Park. With river views, this accommodation features a patio.

  • Annapolis Charm Waterfront Getaway - Near Beach - FISH & CRAB from your PRIVATE PIER!
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 3 reviews

    Annapolis Charm Waterfront Getaway - Near Beach - FISH & CRAB from your PRIVATE PIER! is a recently renovated villa in Annapolis where guests can make the most of the garden and barbecue facilities.

  • Admiral's Glen
    Central location
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 2 reviews

    Admiral's Glen is located in Annapolis, just 25 miles from Addison Road-Seat Pleasant and 28 miles from Carroll Park. This vacation home features accommodations with a patio.

  • The Pearl of Oyster Harbor
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 2 reviews

    The Pearl of Oyster Harbor offers accommodations in Annapolis, 29 miles from Addison Road-Seat Pleasant. Guests staying at this vacation home have access to a patio.

  • Anchors Away Abode
    9.3
    Scored 9.3
    Wonderful
    Rated wonderful
     · 3 reviews

    Anchors Away Abode is located in Annapolis, just 3.1 miles from Annapolis Harbor and 25 miles from Addison Road-Seat Pleasant.

  • Private Single Family Home Close to Both Water and Downtown!
    9.3
    Scored 9.3
    Wonderful
    Rated wonderful
     · 4 reviews

    Private Single Family Home Close to Both Water and Downtown! is located in Annapolis, just 1.2 miles from Carrs Beach and 3.1 miles from Annapolis Harbor.

  • * Midcentury Modern Getaway * Prime Location *
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 2 reviews

    Providing a garden, * Midcentury Modern Getaway * Prime Location * provides accommodations in Annapolis. With inner courtyard views, this accommodation offers a patio.

  • Blue Angel's Nest
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 2 reviews

    Blue Angel's Nest offers accommodations in Annapolis, 30 miles from Carroll Park and 30 miles from Sports Legends Museum at Camden Yards. Guests staying at this vacation home have access to a patio.

  • The Ship's Bridge
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 1 review

    The Ship's Bridge is located in Annapolis, just a few steps from Bay Ridge Beach and 5 miles from Annapolis Harbor. This beachfront property offers access to free Wifi.

  • The Salty Crab
    Central location
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 2 reviews

    The Salty Crab is located in Annapolis, just a 11-minute walk from Bay Ridge Beach and 4.4 miles from Annapolis Harbor. This beachfront property offers access to a patio and free Wifi.

  • Coastal Edgewater Home with Private Hot Tub!
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 1 review

    The air-conditioned accommodation is 22 miles from Addison Road-Seat Pleasant. Free Wifi is available throughout the property and Annapolis Harbor is 13 miles away.

  • Family-sized Contemporary in Spacious Neighbourhood
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 4 reviews

    Family-sized Contemporary in Spacious Neighbourhood is located in Annapolis, just 6.6 miles from Annapolis Harbor and 24 miles from Carroll Park.

  • Seas The Bay
    Central location
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 1 review

    Seas The Bay offers accommodations in Annapolis, 1.7 miles from Annapolis Harbor and 30 miles from Carroll Park. This vacation home features air-conditioned accommodations with a patio and free Wifi.

  • Pine Whiff Gardens
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 1 review

    Pine Whiff Gardens offers accommodations in Annapolis, 30 miles from Carroll Park and 30 miles from Sports Legends Museum at Camden Yards.

  • The Admiral's Retreat
    7.0
    Scored 7.0
    Good
    Rated good
     · 1 review

    The Admiral's Retreat is located in Annapolis, just 4.6 miles from Annapolis Harbor and 29 miles from Addison Road-Seat Pleasant. Guests are welcome to go for a swim in the private pool.

  • Pine Whiff Beach House
    7.0
    Scored 7.0
    Good
    Rated good
     · 1 review

    Pine Whiff Beach House is located in Annapolis, just 8.6 miles from Annapolis Harbor and 20 miles from Addison Road-Seat Pleasant.

  • Cozy 2br home w/ parking in downtown Annapolis
    6.7
    Scored 6.7
    Pleasant
    Rated pleasant
     · 3 reviews

    Cozy 2br home w/ parking in downtown Annapolis offers accommodations in Annapolis, 30 miles from Carroll Park and 30 miles from Sports Legends Museum at Camden Yards.

  • The Little House
    4.0
    Scored 4.0
    Disappointing
    Rated disappointing
     · 1 review

    The Little House offers accommodations in Annapolis, 1.5 miles from Annapolis Harbor and 29 miles from Carroll Park.

  • Vintage Charm: Annapolis Retreat

    Offering a garden, Vintage Charm: Annapolis Retreat offers accommodations in Annapolis. The vacation home, set in a building dating from 1909, features free Wifi and free private parking.

  • Captain's Quarters - Eastport! offers accommodations in Annapolis, a 18-minute walk from Annapolis Harbor and 27 miles from Addison Road-Seat Pleasant.

  • Beautiful 6BR home in Annapolis

    Beautiful 6BR home in Annapolis offers accommodations in Annapolis, 28 miles from Carroll Park and 28 miles from Sports Legends Museum at Camden Yards.

  • Captain’s Retreat! Newly Renovated - Beach House!

    Captain’s Retreat! Newly Renovated - Beach House! is a recently renovated vacation home in Annapolis where guests can make the most of the private beach area and garden.

  • Downtown Annapolis

    Downtown Annapolis is located in Annapolis, just 1.1 miles from Annapolis Harbor and 30 miles from Carroll Park. This vacation home offers air-conditioned accommodations with a patio and free Wifi.

  • Submariners Gate

    Submariners Gate offers accommodations in Annapolis, 30 miles from Carroll Park and 30 miles from Sports Legends Museum at Camden Yards.

  • Skyline Sanctuary

    Skyline Sanctuary is located in Annapolis, just 30 miles from Carroll Park and 30 miles from Sports Legends Museum at Camden Yards. This vacation home provides accommodations with a patio.

FAQ about villas in Annapolis



Villas That Guests Love in Annapolis

  • Avg. price/night: $92.33
    6.7
    Scored 6.7
    Pleasant
    Rated pleasant
     · 147 reviews
    Very kind and welcoming personnel. Rooms large and clearly not luxury but cleaned and in reasonably good conditions for the price
    Enrico
    Solo traveler
  • Avg. price/night: $603.06
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 1,329 reviews
    Beautiful, clean hotel with quite luxurious rooms. Very welcoming staff.
    Caroline
    Young couple
  • 9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 30 reviews
    This is an outstanding hotel / Inn to spend the holidays. We loved it so much. Not only does the house provide beautiful rooms, very clean bathrooms and an outstanding dining room for breakfast, it is also run by such a special family that you feel home there. We enjoyed a luxury breakfast together with all the assistance one can offer. Anytime we come back to Annapolis, we would for sure stay there again.
    Michaela
    Family with young children
  • Avg. price/night: $110.01
    6.1
    Scored 6.1
    Pleasant
    Rated pleasant
     · 180 reviews
    We were 2 miles from Sandy point State Park. The Village Inn is all on one level. I could park right outside the door to our room. The Village Inn offered "smoking" rooms which seemed neglected in comparison with other rooms. It was as though smokers were being treated as second class demographic.
    Kevin
    Young couple

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