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VRBO is part of the HomeAway family, the world leader in vacation rentals with over 1 million listings. We offer the largest selection of properties for any travel occasion and every budget. We’re committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together. Learn More

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This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation

Recent Annapolis property reviews

  • Wonderful retreat

    "Me and my extended family thoroughly enjoyed the comforts of this lovely home. Water play by day and exquisite sunsets at night. As a previous renter mentioned, the home is beautifully decorated and extremely clean and maintained. Transacting with the owner has been an wonderful experience, too. Very organized and responsive. Highly recommend this property for you and your family! Enjoy!!"
    Guest: JmH Date of Stay: June 2014 Review Submitted: June 26, 2014
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  • Weekend Stay

    "The place was very clean and in excellent shape. I would definitely recommend this place to those who love staying on the water. We were able to bring our boats, and the dock is just a few minutes from the bay."
    Guest: Bob Date of Stay: July 2014 Review Submitted: July 22, 2014
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  • Great spot!

    "We had a great time at Chestnut House - it is even prettier than the pictures! We stayed with our 4 children and they enjoyed fishing and watching the deer, birds, sheep, dogs, etc, as well as curling up in the hammock. Our hosts and the farm manager were amazing, and the house had everything we needed in the kitchen, including a washer and dryer. It is so quiet and peaceful at night - hard to believe we were still so close to everything! We look forward to coming back - thank you!!"
    Guest: Deb G Date of Stay: July 2014 Review Submitted: August 27, 2014
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  • Don't Miss Out! on this experience!

    "I had searched and searched for a hotel or B&B close to the water. There were many selections, but rates always seemed to jump to double for the weekend. This is a common practice during the Summer, but I just didn't want to spend that much. Searching through this website I came across this title..."Waterfront Accommodations - ON THE WATER! Got my attention so I read further. Do not pass this up! The staff is amazing and the accommodations were just what they advertised - ON THE WATER! I was at the end of the dock where I photographed Osprey, ducks, sailboats, people, incredible sunsets and had 2 decks to choose from where I enjoyed a glass of wine every evening. I was 5 blocks from The Chart House, where I had dinner and picked up the local water taxi that whisked me away across the Bay to Annapolis! Can't get much better than that!"
    Guest: Diane M. Date of Stay: August 2014 Review Submitted: August 12, 2014
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Annapolis Travel Tips

Adventures Await You in Annapolis Vacation Rentals

Are you up for a pirate adventure? How about a little live, local theater? Maybe your vacation to Annapolis, Maryland includes young children so a visit to one of the best children’s museums in Maryland is on the agenda. No matter what adventures you choose, Annapolis vacation rentals are close to the action.

Treasure Hunting and Pirates Make Annapolis Vacation Rentals Famous

Make staying at Annapolis lodging a whole lot more adventurous with a visit to Pirate Adventures on the Chesapeake. Learn how to read a treasure map and find the treasure. You may even get to meet the smelliest pirate on the seven seas--Pirate Pete! All sorts of adventures await kids of all ages when you book Maryland rentals. You won’t find too many pirate adventures on your vacation so take advantage of this opportunity.

Live Theater close to Annapolis Lodging

The Colonial Players always present a fine production whether they are performing comedies or tragedies. Maryland rentals near East Street in the heart of historic Annapolis are very close to the Colonial Players who always have a new production in the works. Annapolis lodging keeps you in the thick of things so when you book Annapolis vacation rentals, make a note of the addresses so you can find nearby entertainment opportunities.

Guests of Maryland Rentals Enjoy the Children’s Museum

Don’t hang around your Annapolis vacation rentals all day. Entertain the kids with a visit to the Chesapeake Children’s Museum and get their minds and bodies working. Explore the woods surrounding Annapolis lodging, learn about turtles and trucks, and create some fine art to take back to your Maryland rentals to really jazz up your accommodations. You may even be able to sneak into one of the classes the CCM offers; just ask if there’s space for you and your kids.

Other popular and affordable Maryland vacation destinations include Ocean City Maryland rentals, Deep Creek Lake accommodation, or St Michaels MD vacation homes. You will have no problem finding an ideal vacation rental home for your next Maryland family trip.

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