Holiday Rentals in Bishops Head

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Holiday Rentals in Bishops Head

Deal Island Bay Cottage

9.6 out of 10, Exceptional, (55)
"We got every year and stay here, it’s great! "
The price is €213
includes taxes & fees
2 Dec - 3 Dec
Deal Island Bay Cottage

Waterfront Scotland Beach Retreat w/ Private Beach

10.0 out of 10, Exceptional, (41)
"The house is lovely and very comfortable for our group of 8 friends. We would highly recommend!"
Waterfront Scotland Beach Retreat w/ Private Beach

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

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. 🏝️🦀🎣

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 €274
includes taxes & fees
15 Dec - 16 Dec
Waterfront Getaway with Dock

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

18-Acre Waterfront Sanctuary: Peace & Privacy

9.6 out of 10, Exceptional, (5)
"Lots to do and very quiet."
18-Acre Waterfront Sanctuary: Peace & Privacy

The Blackwater refuge country house on a quiet 12 acres

9.8 out of 10, Exceptional, (8)
"Listing and photos accurately describe accommodations. We were comfortable and satisfied. A nice rural location for perusing outdoor activities - fishing, hunting, boating, paddling, birdwatching. Good parking for a boat trailer. "
The Blackwater refuge country house on a quiet 12 acres

Bay Estate by AvantStay | Waterfront, Private Pond

10.0 out of 10, Exceptional, (1)
"Such a beautiful house, very nice for family or friends get together."
Bay Estate by AvantStay | Waterfront, Private Pond

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!

Cottage on the Bay

9.8 out of 10, Exceptional, (6)
"Clean and accommodating host. Has many of the necessities for the home, including washer/dryer , soaps , trash bags , cleaning essentials , plates/bowls/cups, kitchen gadgets , and more. Home feels safe away from predator animals . Couple deers around. Bring insect repellent."
Cottage on the Bay

Riverfront Cabin Getaway at The Brackish - Pet Friendly!

2.0 star property
8.0 out of 10, Very good, (11)
"If you want peace and serenity, this is your place! I adore a cottage that has personality and this one delivers. The owner was communicative and helpful"
Riverfront Cabin Getaway at The Brackish - Pet Friendly!

Quaint Island Getaway

10.0 out of 10, Exceptional, (13)
"Staying at the Quaint Island Getaway is always a pleasure! Sarah is an accessible host, the property is cozy and clean. My party loved the new firepit."
Quaint Island Getaway

The Sportman's Cottage House- Perfect for relation, fun and enjoying beautiful views

9.8 out of 10, Exceptional, (6)
"We spent one evening at this quaint cottage. The setting is rustic; yet calm and quiet. The house has been completely updated, and many thoughtful extra items were included. The beds were comfortable. The listing said that there were two bathrooms. There was only one. Of special interest was a garage with several nice kayaks for our use."
The Sportman's Cottage House- Perfect for relation, fun and enjoying beautiful views

Sunset Retreat on the Nanticoke

10.0 out of 10, Exceptional, (11)
"This property was exactly what we were looking for our family vacation. Location on the water, the amenities were above and beyond, comfortable beds, and land as far as you could see. The fishing and crabbing was exceptional for all ages. The kids loved crabbing, new to us, caught some turtles as well, all released back. Paddle boarding and kayaking on morning water (like glass), was on the daily. There is a perfect fire pit area to enjoy. The large open concept home is perfect for the...
Sunset Retreat on the Nanticoke

New Island Home on the Chesapeake Bay Sunsets

10.0 out of 10, Exceptional, (5)
"A well stocked and well kept house on the water with fantastic sunset views, a big yard for games, and a game room and fire pit for the night. "
New Island Home on the Chesapeake Bay Sunsets

Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths

9.0 out of 10, Wonderful, (13)
"The place was perfect for our group of friends (4 couples) Everyone had a King Bed, and their own bathroom, We rent our home in NJ so really appreciate how well the house was appointed. It had everything we needed. My only suggestion is a repeater so the internet connectivity is less spotty than we experienced. The TV's kept buffering in the bedrooms. "
Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths

BEAUTIFUL PEACEFUL, SCENIC, ENJOY CRABS N FISH MEMORABLE, FREE TOUR OF AREA!

10.0 out of 10, Exceptional, (62)
"A wonderful long weekend getaway on Hoopers Island--close to the bay and to the attractions of the island. Laura is a great host who ensured we had everything we needed for our stay--a roomy house with a great screened in gazebo and plenty of activities for our elementary school aged kids. Highly recommend it!"
BEAUTIFUL PEACEFUL, SCENIC, ENJOY CRABS N FISH MEMORABLE, FREE TOUR OF AREA!
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 Bishops Head you may be interested in

Swanendele Inn at St. Mary's Maryland

5.0 star property
10.0 out of 10, Exceptional, (20)
"Beautiful inn with attentive and welcoming staff."
The price is €323
includes taxes & fees
30 Nov - 1 Dec
Swanendele Inn at St. Mary's Maryland

Deal Island Bay Cottage

9.6 out of 10, Exceptional, (55)
"We got every year and stay here, it’s great! "
The price is €213
includes taxes & fees
2 Dec - 3 Dec
Deal Island Bay Cottage

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
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.

Frequently asked questions

Can I find a holiday rental in Bishops Head?

Yes, there are holiday rentals close to the most popular sights in Bishops Head, 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 Bishops Head has to offer?

Waterfront Scotland Beach Retreat w/ Private Beach: This holiday home rental outside of Bishops Head is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a microwave, kitchenware and a coffee maker, so that you can cook with friends or family. You can relax into your holiday with a private garden and a selection of games.

What can I see and do in Bishops Head?

While you're exploring the area, Blackwater National Wildlife Refuge and Harriet Tubman Underground Railroad National Historical Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Lower Hooper Island and Harriet Tubman Birthplace Marker.

What are holiday rentals like in Bishops Head?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Bishops Head. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family trip.