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The best villas in Annapolis

Check out our pick of great villas in Annapolis

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Waterfront Annapolis Home Fire Pit and Fishing Pier, hotel in Annapolis

Located in Annapolis, 14 km from Annapolis Harbor and 42 km from Inner Harbor, Waterfront Annapolis Home Fire Pit and Fishing Pier offers air conditioning.

Scored 9.3
9.3
Rated superb
Superb
8 reviews
Family-sized Contemporary in Spacious Neighbourhood, hotel in Annapolis

Located in Annapolis and only 11 km from Annapolis Harbor, Family-sized Contemporary in Spacious Neighbourhood provides accommodation with garden views, free WiFi and free private parking.

The house was extremely clean and spacious , the beds were comfortable, some board games were available; there were several bathrooms, the garden was big, our pup Teddy was allowed in the property, the owners were easy to communicate with and were very nice!
Scored 9.0
9.0
Rated superb
Superb
5 reviews
Annapolis Vacation Home 2 Mi to Quiet Waters Park, hotel in Annapolis

Situated in Annapolis, 2.9 km from Carrs Beach and 5.2 km from Annapolis Harbor, Annapolis Vacation Home 2 Mi to Quiet Waters Park offers air conditioning.

This was one of the loveliest homes we've ever stayed in. It was super comfortable. There was plenty of room for everyone. Everything worked. We even loved the way it was decorated. Asem, our host was great at communicating and super responsive. We also like that all the house information was provided way ahead of time so that we could all arrive on our own schedules. It was great! Thank you!
Scored 9.5
9.5
Rated exceptional
Exceptional
11 reviews
Gaia House, hotel in Annapolis

Featuring air-conditioned accommodation with a patio, Gaia House is located in Annapolis. This property offers access to a balcony, free private parking and free WiFi.

Great property. Stayed here as a family. Great base for us. Local supermarket (across the road) was brilliant and had everything we needed. There was a small problem with the Air conditioning and the owner went over and above to sort this out for us. Owners were so friendly and kind - cannot fault Gaia House - great value for money.
Scored 9.6
9.6
Rated exceptional
Exceptional
26 reviews
Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!, hotel in 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.

Very nice and clean. Quiet and well maintained.
Scored 9.7
9.7
Rated exceptional
Exceptional
6 reviews
Searenity Stays, hotel in Annapolis

Set in Edgewater and only 700 metres from Triton Beach, Searenity Stays offers accommodation with sea views, free WiFi and free private parking.

Everything is spotlessly clean and it is a very very comfortable house. The location is lovely, in a very quiet residential neighbourhood. It is the nicest holiday rental we have ever stayed in.
Scored 9.8
9.8
Rated exceptional
Exceptional
8 reviews
Luxe Chesapeake Bay Getaway Less Than 20 Mi to Annapolis!, hotel in Annapolis

Featuring sea views, Luxe Chesapeake Bay Getaway Less Than 20 Mi to Annapolis! is located in Shady Side, 46 km from Addison Road-Seat Pleasant.

Scored 9.6
9.6
Rated exceptional
Exceptional
11 reviews
Calloway Drive Retreat, hotel in Annapolis

Set in Deale, 35 km from Annapolis Harbor and 46 km from Addison Road-Seat Pleasant, Calloway Drive Retreat offers air-conditioned accommodation with a patio and free WiFi.

Scored 9.5
9.5
Rated exceptional
Exceptional
6 reviews
Idyllic Pasadena Retreat with Garden and Hot Tub!, hotel in Annapolis

Located in Glen Burnie, 24 km from Inner Harbor and 25 km from Annapolis Harbor, Idyllic Pasadena Retreat with Garden and Hot Tub! offers air conditioning.

Scored 9.0
9.0
Rated superb
Superb
5 reviews
Lrge Home Near Wash DC-Pool, Hot Tub, Gym, Game Rm, hotel in Annapolis

Boasting air-conditioned accommodation with a private pool, Lrge Home Near Wash DC-Pool, Hot Tub, Gym, Game Rm is located in Bowie.

Scored 9.8
9.8
Rated exceptional
Exceptional
5 reviews
All villas in Annapolis
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Enjoy breakfast in Annapolis!

  • Family-sized Contemporary in Spacious Neighbourhood
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 5 reviews

    Located in Annapolis and only 11 km from Annapolis Harbor, Family-sized Contemporary in Spacious Neighbourhood provides accommodation with garden views, free WiFi and free private parking.

  • Annapolis Vacation Home 2 Mi to Quiet Waters Park
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 11 reviews

    Situated in Annapolis, 2.9 km from Carrs Beach and 5.2 km from Annapolis Harbor, Annapolis Vacation Home 2 Mi to Quiet Waters Park offers air conditioning.

    Stylish Decor. Clean Comfortable furnishings Deck was great

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

    Featuring air-conditioned accommodation with a patio, Gaia House is located in Annapolis. This property offers access to a balcony, free private parking and free WiFi.

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

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

    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.

    Just beautiful! Heather and family very responsive and communicative.

  • Waterfront Annapolis Home Fire Pit and Fishing Pier
    Scored 9.3
    9.3
    Rated superb
    Superb
     · 8 reviews

    Located in Annapolis, 14 km from Annapolis Harbor and 42 km from Inner Harbor, Waterfront Annapolis Home Fire Pit and Fishing Pier offers air conditioning.

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

  • Pet-Friendly Annapolis Home Walk to Beach!

    Boasting air-conditioned accommodation with a patio, Pet-Friendly Annapolis Home Walk to Beach! is situated in Annapolis.

  • Weems Creek Cottage, Annapolis Waterfront

    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.

  • Adventure Annapolis

    Set in Annapolis, 33 km from Addison Road-Seat Pleasant and 49 km from Carroll Park, Adventure Annapolis offers a garden and air conditioning.

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

  • Fisher House - Downtown Annapolis!
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Situated in Annapolis, 1.7 km from Annapolis Harbor and 48 km from Carroll Park, Fisher House - Downtown Annapolis! features air-conditioned accommodation with a patio and free WiFi.

  • Neptune By The Water
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 2 reviews

    Located in Annapolis, 15 km from Annapolis Harbor and 38 km from Inner Harbor, Neptune By The Water provides spacious air-conditioned accommodation with a patio and free WiFi.

  • Skyline Sanctuary
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Located in Annapolis in the Maryland region, Skyline Sanctuary features a patio.

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

    Set in Annapolis, 1.9 km from Annapolis Harbor and 48 km from Carroll Park, Anchors Aweigh offers air-conditioned accommodation with a patio and free WiFi.

  • Vintage Charm: Annapolis Retreat
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Situated in Annapolis, 3 km from Annapolis Harbor and 46 km from Carroll Park, Vintage Charm: Annapolis Retreat offers a garden and air conditioning.

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

    Set in Annapolis, less than 1 km from Annapolis Harbor and 49 km from Carroll Park, Harrison Hall offers air-conditioned accommodation with a patio and free WiFi.

  • Chase Creek Retreat
    Scored 7.7
    7.7
    Rated good
    Good
     · 3 reviews

    Situated in Annapolis, 34 km from Inner Harbor and 38 km from Carroll Park, Chase Creek Retreat offers air conditioning.

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

    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.

  • Walk to Everything Historic Arts District
    Scored 9.3
    9.3
    Rated superb
    Superb
     · 3 reviews

    Situated in Annapolis, 3 km from Annapolis Harbor and 46 km from Carroll Park, Walk to Everything Historic Arts District offers air conditioning.

  • Stylish + fresh bungalow 2 blocks from N-MC Stadium
    Scored 9.3
    9.3
    Rated superb
    Superb
     · 3 reviews

    Located in Annapolis, 4.4 km from Annapolis Harbor and 45 km from Carroll Park, Stylish + fresh bungalow 2 blocks from N-MC Stadium offers a garden and air conditioning.

  • Anchors Away Abode
    Scored 9.3
    9.3
    Rated superb
    Superb
     · 3 reviews

    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 Ship's Bridge
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 1 review

    Boasting air-conditioned accommodation with a patio, The Ship's Bridge is situated in Annapolis. This beachfront property offers access to a balcony and free WiFi.

  • Bella Chateau
    Central location
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 1 review

    Situated in Annapolis, less than 1 km from Bay Ridge Beach and 7.2 km from Annapolis Harbor, Bella Chateau features air-conditioned accommodation with a patio and free WiFi.

  • The Salty Crab
    Central location
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 2 reviews

    Situated in Annapolis, less than 1 km from Bay Ridge Beach and 7.1 km from Annapolis Harbor, The Salty Crab offers air conditioning. This beachfront property offers access to a patio and free WiFi.

  • Coastal Edgewater Home with Private Hot Tub!
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 1 review

    Located in Annapolis, within 36 km of Addison Road-Seat Pleasant, Coastal Edgewater Home with Private Hot Tub! offers accommodation with air conditioning.

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

    Situated in Annapolis, 2.8 km from Annapolis Harbor and 48 km from Carroll Park, Seas The Bay features air-conditioned accommodation with a patio and free WiFi.

  • Cozy Maryland Retreat Near Sandy Pointe State Park
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 1 review

    Located in Annapolis, 47 km from Carroll Park and 48 km from Sports Legends Museum at Camden Yards, Cozy Maryland Retreat Near Sandy Pointe State Park offers air conditioning.

  • Admiral's Glen
    Central location
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 3 reviews

    Situated in Annapolis in the Maryland region, Admiral's Glen has a patio.

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

    Located in Annapolis, 33 km from Addison Road-Seat Pleasant and 48 km from Carroll Park, Pine Whiff Gardens offers a garden and air conditioning.

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

    Located in Annapolis, 33 km from Addison Road-Seat Pleasant and 48 km from Carroll Park, Pine Whiff Beach House offers air conditioning.

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

    Set in Annapolis, 2.2 km from Annapolis Harbor and 48 km from Carroll Park, Cozy 2br home w/ parking in downtown Annapolis offers a garden and air conditioning.

  • Captain's Quarters - Eastport!
    Scored 5.0
    5.0
    Rated passable
    Average
     · 1 review

    Featuring a spa bath, Captain's Quarters - Eastport! is located in Annapolis. This property offers access to a patio, free private parking and free WiFi.

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

    Set in Annapolis, 2.5 km from Annapolis Harbor and 47 km from Carroll Park, The Little House offers air-conditioned accommodation with a patio and free WiFi.

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

    Set in Annapolis in the Maryland region and Annapolis Harbor reachable within 8.4 km, Captain’s Retreat! Newly Renovated - Beach House!

  • Downtown Annapolis

    Set in Annapolis, 1.8 km from Annapolis Harbor and 48 km from Carroll Park, Downtown Annapolis offers air-conditioned accommodation with a patio and free WiFi.

  • * Midcentury Modern Getaway * Prime Location *

    Set in Annapolis, 2 km from Annapolis Harbor and 48 km from Carroll Park, * Midcentury Modern Getaway * Prime Location * offers air-conditioned accommodation with a balcony and free WiFi.

  • Submariners Gate

    Situated in Annapolis, 2.5 km from Annapolis Harbor and 48 km from Carroll Park, Submariners Gate features air-conditioned accommodation with a balcony and free WiFi.

  • The Robins Nest
    Central location

    Set in Annapolis, 48 km from Carroll Park and 48 km from Sports Legends Museum at Camden Yards, The Robins Nest offers air conditioning.

FAQ about villas in Annapolis

Villas that guests love in Annapolis

  • Avg. price/night: £84.13
    Scored 6.6
    6.6
    Rated pleasant
    Pleasant
     · 168 reviews
    Very kind and welcoming personnel. Rooms large and clearly not luxury but cleaned and in reasonably good conditions for the price
    Enrico
    Solo traveller
  • Avg. price/night: £313.52
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 1,193 reviews
    Beautiful, clean hotel with quite luxurious rooms. Very welcoming staff.
    Caroline
    Young couple
  • Avg. price/night: £304.94
    Scored 8.9
    8.9
    Rated fabulous
    Fabulous
     · 29 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: £70.54
    Scored 6.1
    6.1
    Rated pleasant
    Pleasant
     · 162 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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