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Holiday Homes in Annapolis

Find the holiday homes that appeal to you the most

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The best holiday homes in Annapolis

Check out our pick of great holiday homes in Annapolis

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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Annapolis Vacation Home 2 Mi to Quiet Waters Park, holiday home in Annapolis

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
£467
per night
Check availability
Gaia House, holiday home in Annapolis

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
£117
per night
Check availability
Waterfront Annapolis Home Fire Pit and Fishing Pier, holiday home in Annapolis

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
Superb
7 reviews
Price from
£296
per night
Check availability
Neptune By The Water, holiday home in Annapolis

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
£442
per night
Check availability
USNA Home Downtown Annapolis, holiday home in Annapolis

The spacious villa features 3 bedrooms, a flat-screen TV, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a bath. Towels and bed linen are featured in the villa. For added privacy, the accommodation features a private entrance.

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7.7
Good
4 reviews
Price from
£314
per night
Check availability
Stylish + fresh bungalow 2 blocks from N-MC Stadium, holiday home in Annapolis

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. Both free WiFi and parking on-site are available at the holiday home free of charge. The property is non-smoking and is situated 45 km from Sports Legends Museum at Camden Yards.

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9.5
Exceptional
2 reviews
Price from
£349
per night
Check availability
Anchors Away Abode, holiday home in Annapolis

The spacious holiday home has 3 bedrooms, a TV, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 3 bathrooms with a bath. Towels and bed linen are offered in the holiday home. The property has an outdoor dining area.

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9.3
Superb
3 reviews
Price from
£274
per night
Check availability
Cozy 2br home w/ parking in downtown Annapolis, holiday home in Annapolis

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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5.5
Review score
2 reviews
Price from
£319
per night
Check availability
The Pearl of Oyster Harbor, holiday home in Annapolis

The air-conditioned holiday home consists of 3 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with an a bath or shower and a hair dryer. Towels and bed linen are featured in the holiday home. The property has an outdoor dining area.

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9.5
Exceptional
2 reviews
Price from
£492
per night
Check availability
Vintage Charm: Annapolis Retreat, holiday home in Annapolis

The spacious holiday home has 3 bedrooms, 2 bathrooms, bed linen, towels, a flat-screen TV with streaming services, a fully equipped kitchen, and a terrace with garden views. Guests can enjoy a meal on an outdoor dining area while overlooking the quiet street views. For added privacy, the accommodation features a private entrance.

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Price from
£357
per night
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.
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  • Annapolis Vacation Home 2 Mi to Quiet Waters Park
    9.9
    Scored 9.9
    Exceptional
    Rated exceptional
     · 8 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
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 19 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.

  • Waterfront Annapolis Home Fire Pit and Fishing Pier
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 7 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.

  • Vintage Charm: Annapolis Retreat

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

  • Captain's Quarters - Eastport!

    Located in Annapolis, 1.5 km from Annapolis Harbor and 44 km from Addison Road-Seat Pleasant, Captain's Quarters - Eastport! offers air conditioning.

  • Fisher House - Downtown Annapolis!

    Situated in Annapolis, 1.7 km from Annapolis Harbor and 48 km from Carroll Park, Fisher House - Downtown Annapolis! offers air conditioning.

  • USNA Home Downtown Annapolis
    7.7
    Scored 7.7
    Good
    Rated good
     · 4 reviews

    Set in Annapolis, 2.7 km from Annapolis Harbor and 47 km from Carroll Park, USNA Home Downtown Annapolis offers air-conditioned accommodation with a balcony and free WiFi.

  • Annapolis Retreat - 7 mins from DTA!

    Complete with a bar, Annapolis Retreat - 7 mins from DTA! is set in Annapolis, 50 km from Sports Legends Museum at Camden Yards and 50 km from Baltimore Convention Center.

Save money on holiday homes in Annapolis – budget options available!

  • Bennett House Entirehaven In Historic Annapolis

    Bennett House Entirehaven In Historic Annapolis is situated in Annapolis, 2.8 km from Annapolis Harbor, 46 km from Carroll Park, and 46 km from Sports Legends Museum at Camden Yards.

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

  • Skyline Sanctuary
    Budget options available

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

  • Anchors Away Abode
    Budget options available
    9.3
    Scored 9.3
    Superb
    Rated 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 Compass Rose by Leavetown Vacations

    Situated in Annapolis, 6.7 km from Annapolis Harbor and 46 km from Addison Road-Seat Pleasant, The Compass Rose by Leavetown Vacations offers a garden and air conditioning.

  • Cozy 2br home w/ parking in downtown Annapolis
    5.5
    Scored 5.5
    Average
    Rated passable
     · 2 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.

  • Downtown Annapolis
    Budget options available

    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.

  • The Pearl of Oyster Harbor
    Budget options available
    9.5
    Scored 9.5
    Exceptional
    Rated 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.

Great access to the city centre! Check these holiday homes in Annapolis

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

    Set in Annapolis in the Maryland region, Neptune By The Water features a balcony.

  • Anchors Aweigh
    Central location
    10.0
    Scored 10.0
    Exceptional
    Rated 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.

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

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

  • Oyster Harbor Vacation Home
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 2 reviews

    Located in Annapolis and only 7.1 km from Annapolis Harbor, Oyster Harbor Vacation Home provides accommodation with sea views, free WiFi and free private parking.

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

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

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

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

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

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

  • * Midcentury Modern Getaway * Prime Location *
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2 reviews

    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.

  • Blue Angel's Nest
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2 reviews

    Located in Annapolis, 1.6 km from Annapolis Harbor and 48 km from Carroll Park, Blue Angel's Nest provides air-conditioned accommodation with a patio and free WiFi.

  • The Ship's Bridge
    9.0
    Scored 9.0
    Superb
    Rated 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.

  • The Salty Crab
    Central location
    9.0
    Scored 9.0
    Superb
    Rated 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!
    9.0
    Scored 9.0
    Superb
    Rated 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.

  • Family-sized Contemporary in Spacious Neighbourhood
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 4 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.

  • Seas The Bay
    Central location
    8.0
    Scored 8.0
    Very good
    Rated 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
    8.0
    Scored 8.0
    Very good
    Rated 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.

  • Pine Whiff Gardens
    8.0
    Scored 8.0
    Very good
    Rated 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.

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

    Situated in Annapolis, 1.9 km from Bay Ridge Beach and 7.4 km from Annapolis Harbor, The Admiral's Retreat features air-conditioned accommodation with a patio and free WiFi.

  • Pine Whiff Beach House
    7.0
    Scored 7.0
    Good
    Rated 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.

  • The Little House
    4.0
    Scored 4.0
    Disappointing
    Rated 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.

  • Beautiful 6BR home in Annapolis

    Beautiful 6BR home in Annapolis is located in Annapolis, 46 km from Carroll Park, 46 km from Sports Legends Museum at Camden Yards, as well as 47 km from Historic Ships in Baltimore.

  • 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!

  • St Johns Adjacent

    Situated in Annapolis, 2.5 km from Annapolis Harbor and 47 km from Carroll Park, St Johns Adjacent features air-conditioned accommodation with a patio 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.

  • The Master Shipwright

    Situated in Annapolis, 1.7 km from Annapolis Harbor and 48 km from Carroll Park, The Master Shipwright features air-conditioned accommodation with a patio and free WiFi.

  • Third Street Retreat

    Situated in Annapolis, 500 metres from Annapolis Harbor and 49 km from Carroll Park, Third Street Retreat features air-conditioned accommodation with a patio and free WiFi.

  • Eastport Haven
    Central location

    Located in Annapolis in the Maryland region, Eastport Haven features a patio.

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