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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

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 reviews

  • Amazing stay in Eastport!

    "This gorgeous townhome was the perfect resting spot for my friends and I after our half marathon. This home is lovely and very clean. We hope to rent it again! walking distance to SO many fun places and way more quiet than busy downtown Annapolis. A truly, relaxing experience. The owner was a pleasure to work with, as well."
    Guest: Running group Date of Stay: May 2014 Review Submitted: June 12, 2014
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  • Exceeded all expectations

    "The accommodation was squeaky clean and fresh, a critical consideration in getting comfortable in temporary lodgings. All necessities were in place (nice linens/towels, toiletries, etc) and quite a number of very nice to have items were also available (WIFI, ceiling fans, pots, pans, plates, glasses, condiments, coffee etc.). The condo is spacious with separate spaces for a number of groups and activities. Great floor plan. Very nice to have a coffee shop downstairs and a few good restaurants/grocery store in easy walking distance. It's a longer stroll down to the waterfront (about 20 minutes) but the route using Gate 8 and crossing the Academy grounds makes it an enjoyable journey. I have used VRBO/Homeaway a half dozen times and this Annapolis property is the best, exceptional. Thanks John."
    Guest: 1977 Date of Stay: May 2014 Review Submitted: August 23, 2014
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  • Great family vacation in Annapolis

    "We had the most amazing week in this house on River Rd. It was a family reunion, consisting of five families, two from Raleigh, NC, two from upstate, NY, one from Boston, Mass. In all eight adults, eight children, and we did take the guest house as well. Both Liz. and Kris, the rental agent helped us with all our needs. They were awesome to work with. The house was perfect, the grounds with pool and hot tub perfect, the location perfect, and the visit turned out to be perfect as well. It is everything that is discribed in the add, only problem we had was getting the TV'S in upstairs bedroom's to work. No big deal, we didn't need them anyway. I reccomend this property to most everybody, it was so beautiful."
    Guest: Fran Date of Stay: August 2014 Review Submitted: August 22, 2014
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  • The BEST

    "This is the second time we have stayed in The Chestnut House. It couldn't be more perfect. The serenity there is incredible, being able to sit and watch the water, deer and now the sheep. Our collie loved it too, being able to be outside with all the new smells. The owners are a delight. We hope to be able to stay again the next time we are in the Annapolis region."
    Guest: Deborah W. Date of Stay: September 2014 Review Submitted: September 17, 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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