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The best cottages in Saint Michaels

Check out our selection of great cottages in Saint Michaels

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Luxe Chesapeake Bay Getaway Less Than 20 Mi to Annapolis!, hotel in Shady Side

Luxe Chesapeake Bay Getaway Less Than 20 Mi to Annapolis! offers accommodations in Shady Side, 29 miles from Addison Road-Seat Pleasant.

The home was charming. Backyard is Chesapeake Bay! Owners extremely nice and accommodating. Would definitely recommend to anyone. Will stay here again.
Scored 9.6
9.6
Rated exceptional
Exceptional
10 reviews
Calloway Drive Retreat, hotel in Deale

Calloway Drive Retreat offers accommodations in Deale, 21 miles from Annapolis Harbor and 29 miles from Addison Road-Seat Pleasant.

Absolutely a great place to stay. We received the door code via email the day prior to check-in. The house is fully equipped to include a fully equipped kitchen. The grocery is about a 7-minute drive from the house. There is an isolated beach about a 10-minute walk away from the house. Washer and dryer worked well. Check-out was easy.
Scored 9.5
9.5
Rated exceptional
Exceptional
7 reviews
Grasonville Home with Private Pool on the Water, hotel in Grasonville

Grasonville Home with Private Pool on the Water is located in Grasonville, just 22 miles from Annapolis Harbor and 13 miles from Sandy Point State Park.

Excellent communication, Scott was wonderful and very informative and location was fabulous. Great place for us for wedding attending nearby . This home was unique , eceletic, clean as a whistle and wonderful.
Scored 9.4
9.4
Rated wonderful
Wonderful
5 reviews
All cottages in Saint Michaels
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Cottages are perfect for travelers who enjoy feeling cozy and independent in the countryside. Usually small, traditionally built houses, cottages are spread across one or two floors – making them great for families or vacations with a little more privacy.

Cottages That Guests Love in Saint Michaels

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  • Avg. price/night: $190.30
    Scored 8.0
    8.0
    Rated very good
    Very Good
     · 69 reviews
    Fantastic view, peaceful, offers water boats, sauna, clean room, balcony with sitting area by bungalows, staff and people in community are very nice, has a pool, has an outdoor crab shack, has open firepits and outdoor heaters
    Erin
    Family with young children
  • Avg. price/night: $471.90
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 56 reviews
    The breakfast was delicious and the wait staff was attentive. We stayed for several days, so we would've enjoyed more variety in the breakfast menu. The room was cozy and beautifully decorated. The bedding was luxurious and we thoroughly enjoyed relaxing on the dock. The staff, especially Lamond, is polite, professional, and dedicated to providing an exemplary experience.
    T
    Young couple
  • Avg. price/night: $519.09
    Scored 9.1
    9.1
    Rated wonderful
    Wonderful
     · 47 reviews
    We have stayed at the Inn at Perry Cabin so many times. It is just a lovely property in a beautiful location. I cannot wait to go back again.
    Vito-Luigi
    Young couple
  • Avg. price/night: $471.90
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 56 reviews
    Beautiful interior design and spacious cottage. Fantastic breakfast! and wonderfully kind and helpful staff. We will return soon. Highly recommend booking the cottage.
    susan
    Group