Church Creek Holiday Rentals

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Holiday Rentals in Church Creek

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (17)
"Beautiful and quiet in the fall. A great place for relaxing. Clean, great communication. End of the street with views of the bay. "
The price is AU$488
includes taxes & fees
24 Nov - 25 Nov
Soul Oasis - home on the Chesapeake Bay

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

10.0 out of 10, Exceptional, (4)
"We had the most wonderful time at this charming house on Tillman Island! While the pics are great, it is even better in person. The house is perfectly nestled on the waterway, offering stunning views. The backyard pool was a true highlight, and we spent countless hours splashing around, the pool in the sun."
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (17)
" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Belle of the Chesapeake Bay

9.6 out of 10, Exceptional, (9)
"We initially booked due to location (we have family in the neighborhood). We are so glad we did! The property had plenty of space for 6 and offered rest and relaxation after a busy wedding weekend. The only con I can think of with the property is that all bathrooms are on the smaller side. The comfort, convenience, and amenities offered far outweighs this. This property is sure to become our go to when visiting the area. "
Belle of the Chesapeake Bay

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Had a great visit. House was perfect and the area is absolutely gorgeous"
Eastern Shore Waterside Cottage Near St. Michaels

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (63)
"My boyfriend and I needed to get away. This house and location was just what we needed. Beautiful scenery, cozy home. We started a full week and I was sad to go at the end of our trip. We look forward to visiting again in the future! "
Waterfront Cottage in Beautiful Hoopers Island

The Schultz Estate

8.8 out of 10, Excellent, (14)
"What a wonderful stay we had! The house was so comfortable with plenty of space for everyone to relax and enjoy each other's company. We enjoyed the brisk mornings on the porch and the gorgeous sunsets in the evenings. Very comfortable beds and linens. The scenery and landscape in the area are breathtaking. Every turn provided another incredible view of the water. Fishing Creek is close to so many beautiful, quaint towns along the Chesapeake Bay. Highly recommend!"
The Schultz Estate

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

10.0 out of 10, Exceptional, (7)
"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (37)
"Every morning I made coffee, lit the fire pit on the dock and spent at least from 30 minutes before sunrise to 30 after. Used Merlin to identify bird calls. Heard and saw bald eagles, a belted kingfisher and an eastern bluebird. Watched a great blue heron fishing. Heard many many different birds. Truly an awesome location to slow down and enjoy the moment "
The price is AU$432
includes taxes & fees
24 Dec - 25 Dec
Waterfront Getaway with Dock

Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣

10.0 out of 10, Exceptional, (46)
"Great experience, wonderful cozy cottage with thoughtful touches throughout. Remote, peaceful location with excellent fishing and crabbing all around you. Fantastic eating at Old Salty's less than a couple of miles away. Very dog friendly cottage and lovely screened in porch area to sit and watch the sunsets. We will be booking again next year."
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣

Stunning secluded Luxury waterfront cottage with private deep water pier!

10.0 out of 10, Exceptional, (72)
"Great location. Spacious and clean. Easy checking in and communicate with owner."
Stunning secluded Luxury waterfront cottage with private deep water pier!

Cottage on Cabin Creek

10.0 out of 10, Exceptional, (100)
"I highly recommend staying here for a cozy couples weekend. It was absolutely beautiful and quiet. The host was so nice and made us feel welcome. I can’t wait to stay here again."
The price is AU$565
includes taxes & fees
1 Dec - 2 Dec
Cottage on Cabin Creek

Bay Views & Fire Pit: Taylor’s Island Retreat

9.8 out of 10, Exceptional, (10)
"This is a hidden jewel. We had so much fun fishing and crabbing. The home was everything you could ever ask for. We will definitely be back next year for a longer stay. If you are looking for some peace and quiet, this is the place to be. Thank you to the owners for making this a great place. "
Bay Views & Fire Pit: Taylor’s Island Retreat

Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

9.8 out of 10, Exceptional, (18)
"The property is perfect for family gatherings "
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks

9.8 out of 10, Exceptional, (6)
"We enjoyed our time at the house very much. We went out to dinner only once and the rest of the time we ate in. We grilled two nights and made a roast one night. The views and the pool were more than you could imagine."
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks

Autumn Charm Beautiful Waterfront Retreat Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (37)
"Great rental experience. Barb was fantastic at communicating. The house was perfect for our group, including some adults and some young children. Yard and dock were a blast for playing and fishing. "
Autumn Charm Beautiful Waterfront Retreat Near Historic St. Michaels & Royal Oak

Maryland Vacation Rental w/ Private Pool & Dock

10.0 out of 10, Exceptional, (6)
"We needed a house for a quick stay in Lusby. The hosts have thought of everything to make the stay easy. They communicated ahead of our trip and were easy to work with. "
Maryland Vacation Rental w/ Private Pool & Dock

Cozy Cottage with access to and partially obstructed views of the bay.

9.4 out of 10, Exceptional, (13)
"Away from the hustle and bustle of any city but close enough to get anything you need. Our stay was very relaxing and Hyrum and Lisa were the best hosts we have had so far... Will definitely look for them again if we are in the area again..."
Cozy Cottage with access to and partially obstructed views of the bay.

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (39)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Historic Hoopersville Getaway on Chesapeake Bay!

9.6 out of 10, Exceptional, (10)
"Our vacation on Chesapeake Bay was wonderful. The house was clean and comfortable. It is an older home, but we loved the character and charm. There is a very large yard for playing, bikes and some board games/puzzles that we enjoyed. The island was very quiet so made for a relaxing vacation. The home came with kayaks, and we had a blast kayaking with our 2 and 4 year old on the ocean. I would highly recommend this home for a big gathering or small family like our trip. We felt so rested after...
Historic Hoopersville Getaway on Chesapeake Bay!
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.
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Other types of properties in Church Creek you may be interested in

Hyatt Regency Chesapeake Bay

4.0 star property
8.8 out of 10, Excellent, (1005)
"Best vacation ever!"
The price is AU$369
includes taxes & fees
4 Dec - 5 Dec
Hyatt Regency Chesapeake Bay

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1007)
"The staff and hosts were incredibly cheerful,, and helpful. Maintenance was a bit of a problem with towel bars falling off walls and broken up bathroom door. There was heavy stomping across the ceiling that went on for a long time early in the morning that kept me awake. May have been a guest or maybe the exercise studio was lined up above my room. All and all, the staff were wonderful and appeasing and the bed was comfortable. This Inn is a "bang for your buck" for being very close to downtown...
The price is AU$145
includes taxes & fees
8 Dec - 9 Dec
St Michaels Inn

Days Inn & Suites by Wyndham Cambridge

2.5 star property
6.6 out of 10, (1009)
"easy location"
The price is AU$102
includes taxes & fees
1 Dec - 2 Dec
Days Inn & Suites by Wyndham Cambridge
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find holiday rentals in Church Creek?

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

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

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!: This holiday home rental outside of Church Creek is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

What’s there to see and do in Church Creek?

While exploring the area, visit family-friendly sights like Richardson Maritime Museum, or get outside and enjoy nature at Harriet Tubman Underground Railroad National Historical Park. In the wider area, you’ll find Blackwater National Wildlife Refuge and Harriet Tubman Museum and Educational Center.

What are holiday rentals like in Church Creek?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Church Creek. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for families.