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Cottages in Annapolis

Find the cottages that appeal to you the most

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The best cottages in Annapolis

Check out our pick of great cottages 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, cottage 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, cottage 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. The property is non-smoking and is situated 5.9 km from Annapolis Harbor.

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

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9.6
Exceptional
19 reviews
Price from
£107
per night
Check availability
Waterfront Annapolis Home Fire Pit and Fishing Pier, cottage 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. Free WiFi is featured throughout the property and private parking is available on site. The property is non-smoking and is situated 46 km from Carroll Park.

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

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9.1
Superb
7 reviews
Price from
£299
per night
Check availability
USNA Home Downtown Annapolis, cottage in Annapolis

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. The property is around 48 km from Baltimore Convention Center, 49 km from Historic Ships in Baltimore and 49 km from Inner Harbor. The property is non-smoking and is located 48 km from Sports Legends Museum at Camden Yards.

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7.7
Good
4 reviews
Price from
£417
per night
Check availability
Stylish + fresh bungalow 2 blocks from N-MC Stadium, cottage 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 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
£338
per night
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Anchors Away Abode, cottage in Annapolis

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
Superb
3 reviews
Price from
£355
per night
Check availability
Cozy 2br home w/ parking in downtown Annapolis, cottage in Annapolis

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. Among the facilities at this property are a 24-hour front desk and full-day security, along with free WiFi throughout the property. The property is allergy-free and is located 48 km from Sports Legends Museum at Camden Yards.

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5.5
Review score
2 reviews
Price from
£300
per night
Check availability
The Pearl of Oyster Harbor, cottage in Annapolis

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
£429
per night
Check availability
Vintage Charm: Annapolis Retreat, cottage in Annapolis

Boasting air-conditioned accommodation with a patio, Vintage Charm: Annapolis Retreat is situated in Annapolis. This property offers access to a terrace, free private parking and free WiFi. The property is non-smoking and is set 3 km from Annapolis Harbor.

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Price from
£357
per night
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Captain's Quarters - Eastport!, cottage in Annapolis

Set in Annapolis, Captain's Quarters - Eastport! provides accommodation 50 km from Sports Legends Museum at Camden Yards and 50 km from Baltimore Convention Center. The air-conditioned accommodation is 1.5 km from Annapolis Harbor, and guests can benefit from on-site private parking and complimentary WiFi. The property is non-smoking and is located 44 km from Addison Road-Seat Pleasant.

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Price from
£569
per night
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All cottages in Annapolis

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Cottages are perfect for travellers who enjoy feeling cosy and independent in the countryside. Usually small, traditionally built houses, cottages spread across one or two floors, making them great for families, or holidays with a little more privacy.
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Most booked cottages 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

    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

    Boasting air-conditioned accommodation with a patio, Vintage Charm: Annapolis Retreat is situated in Annapolis. This property offers access to a terrace, free private parking and free WiFi.

  • Fisher House - Downtown Annapolis!

    Situated in Annapolis, 48 km from Carroll Park and 48 km from Sports Legends Museum at Camden Yards, 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.

  • 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.

These cottages in Annapolis have options with FREE cancellation

  • Beautiful 6BR home in Annapolis
    Free cancellation options available

    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.

  • 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 air conditioning.

  • Skyline Sanctuary
    Free cancellation options available

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

  • Anchors Away Abode
    Free cancellation 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
    Free cancellation options available

    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
    Free cancellation 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
    Free cancellation 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.

Travelling by car? These cottages in Annapolis offer free parking!

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