Romancoke Holiday Rentals

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Holiday Rentals in Romancoke

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, 4 reviews
"Incredibly beautiful home! The house is a perfect place to host your family for commissioning week or for any stay. The pool and river offer a great places to relax. The views are gorgeous and the property is located in a very peaceful neighborhood. The property has amazing amount space to accommodate our large family. We enjoyed eating on the patio, swimming in the pool, kayaking and playing pickle ball. We hope to come back just to vacation here!"
The price is NZ$2,351
includes taxes & fees
4 Jun - 5 Jun
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, 180 reviews
"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."
Directly Across from Gate One & Steps from the Waterfront
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, 186 reviews
"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, 26 reviews
"The stay was a perfect location for doing things in downtown St. Michael's, everything is within walking distance. The property managers were prompt with all communications and pleasant to work with on a few questions I had."
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
10.0 out of 10, Exceptional, 61 reviews
"We had a great time at this very cute cottage and really appreciated the extra touches of the hosts, who were very helpful. The yard is truly a great place to hangout but there were also lots of places to enjoy close by."
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, 44 reviews
"This house was perfect for a group of friends celebrating a 50th birthday! The house was so clean and well cared for! The front porch and outdoor backyard space provided even more room for us to gather together. We will be back!"
Recently Renovated Annapolis Home - Conveniently Located
Cozy place close to the city dock
10.0 out of 10, Exceptional, 54 reviews
"It is a very nice home for our short stay. We came for a graduation ceremony and the convenience and location were perfect. We will stay here in the future."
Cozy place close to the city dock
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, 14 reviews
"We really enjoyed our (much too short) stay at this waterfront gem!! The property was very clean, had all the amenities that we needed for our time away.... the only complaint is that we didn't have enough time to enjoy it all!! : ) thank you so much, we will be back!"
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, 21 reviews
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 105 reviews
"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, 81 reviews
"421Irie is a great property, well managed and maintained by Liz. It was perfect for a weekend of sailing, golf, family and friends. We hosted a small cookout for eight one night, and the cottage was just right for the group. The kitchen is well stocked, the big grill outside was just fine, and the multiple seating locations were ideal for the various attendees. We would love to stay at the cottage again next time we are in Annapolis"
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, 25 reviews
"A few of us girls got together-sisters, cousins, and a few friends to celebrate a wedding coming up. We spent time in the different lovely areas of the house and outdoors. It was the most spacious and gorgeous lay out. A weekend of rain didn’t matter becusee we had to much to do with the indoor games provider, the hot tub, the beautiful kitchen area. We loved our stay!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, 108 reviews
"VRBO link hasn’t enabled me to communicate with property manger/owner as I’m unable to access account via the VRBO link. I’ve re-registered multiple times now."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, 43 reviews
"Beautiful house and views. Amenities and grounds were great. Loved the playground and beach. Peace and quiet at its finest in nature."
The price is NZ$1,253
includes taxes & fees
6 Jun - 7 Jun
Charming Annapolis WaterVIEW Home
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, 39 reviews
"It was clean and had everything we needed. We had a very comfortable stay. There are one or two steps between many of the rooms so keep that in mind."
The Blue Crab Beach House - Free beach passes
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
9.4 out of 10, Exceptional, 8 reviews
"The home was lovely. We very much enjoyed our stay. The one thing that I would recommend is direction on the heat and air. We were unable to figure out what to do The downstairs was cold and when we tried to raise the temp the upstairs was unbearably hot. I also wanted to let you know there was a leak from the ceiling in the master bedroom. Lastly, My daughter lost a small hoop earring. If you find it could you please contact me to have it returned. Thank you,"
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
10.0 out of 10, Exceptional, 73 reviews
"The cottage provides a wonderful way to experience Deale and the surrounding area. Well equipped and clean, I had everything I needed and didn't want to leave,"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Waterfront Cottage on the Eastern Shore
8.0 out of 10, Very good, 1 review
"Check-in was seamless, my family enjoyed the accommodations even though the weather outside was dismal. Parked by at times was challenging but we dealt with it. I must admit NO dishwasher at a vacation rental came as a surprise. None of us cared to deal with that chore. Septic issues cut bathroom access and shower access down significantly. But the biggest concern to me as the Mimi(Grandmother) was that someone had downstairs access while my two granddaughters were sleeping. They saw lights,...
The price is NZ$1,846
includes taxes & fees
26 Jun - 27 Jun
Waterfront Cottage on the Eastern Shore
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, 65 reviews
"Extremely responsive host and beautiful cottage. Incredible location with tranquil views of the water. 5 minute walk to ice cream and nice restaurants. Easy walk (20-25 mins) otherwise into more bustling downtown Annapolis."
Amazing views, short walks to great dining!
Chesapeake Houseboat Getaway on Kent Island, Maryland
10.0 out of 10, Exceptional, 7 reviews
"My husband and I and our dog had a lovely getaway on "Julia's Arc". This was our first time on a Houseboat and it was a wonderful experience. So much light! And the movement of the boat was just enough to be comforting. The home was very clean and beautifully adorned with great attention to detail. Julia, the host, was very responsive and very generous in doing all she could to make our trip as comfortable and pleasurable as possible. The views over the water were gorgeous and we really...
Chesapeake Houseboat Getaway on Kent Island, Maryland
Don't see what you're looking for?
See all available properties in Romancoke
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Romancoke you may be interested in

Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, 1,616 reviews
"Absolutely love these properties and the so-rounding area! Great places to eat and shop all within walking distance. "
The price is NZ$321
includes taxes & fees
16 Jun - 17 Jun
Historic Inns of Annapolis
Crowne Plaza Annapolis, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, 1,004 reviews
"Property was great. But for the price a complementry breakfast would have been nice."
The price is NZ$251
includes taxes & fees
6 Jun - 7 Jun
Crowne Plaza Annapolis, an IHG Hotel
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, 1,036 reviews
"Spacious rooms"
The price is NZ$395
includes taxes & fees
16 Jun - 17 Jun
Graduate Annapolis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Romancoke holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Romancoke. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Romancoke. Seeing all the best attractions is bound to make you fall in love with Romancoke. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Romancoke short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Romancoke?

Yes, there are holiday rentals close to the most popular sights in Romancoke, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Romancoke has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Romancoke offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

What can I see and do in Romancoke?

Explore the area and family-friendly sights such as Chesapeake Bay Maritime Museum, or get out into nature at a spot like Chesapeake Bay Environmental Center. In the wider area, you’ll find St. Michaels Winery and Annapolis Landing Marina.

What are holiday rentals like in Romancoke?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Romancoke. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a family getaway.

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