Holiday Homes in Hoopers Island

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Featured Holiday Homes in Hoopers Island

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

9.6 out of 10, Exceptional, (29)
"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

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

Beautiful Peaceful Home

10.0 out of 10, Exceptional, (2)
"I was deciding between booking a hotel or a home and thankful that we decided on this home for our weekend getaway. After visiting the museums in Cambridge, we were welcomed to our home away from home. Very relaxing, comfortable and spacious for our family. Conveniently located to downtown and nice neighborhood. If looking for a home to stay when in the Cambridge area, this is an excellent choice."
Beautiful Peaceful Home

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

9.6 out of 10, Exceptional, (19)
" 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!

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

9.8 out of 10, Exceptional, (110)
"Very nice place we found, great views, very clean, quiet, great place to relax for the weekend. everything went well and we would highly recommend anyone for a stay here. we will be back next year"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

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

9.8 out of 10, Exceptional, (19)
"The house was very comfortable and well stocked! It has everything you need for a relaxing time. "
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

10.0 out of 10, Exceptional, (10)
"Great place to stay while in the area. Thank you!"
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

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

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

Waterfront Maryland Vacation Home: Private Beach!

10.0 out of 10, Exceptional, (8)
"We had such a peaceful stay! We felt the love you put into your family’s farmhouse! It was perfect! You didn’t miss a detail! The view was beautiful and we enjoyed the beach as well! Thank you for providing the kayaks and bikes! Our experience truly was heaven on earth! We look forward to coming back!"
Waterfront Maryland Vacation Home: Private Beach!

Secluded River Front Cottage

9.4 out of 10, Exceptional, (3)
"The home and property are exactly as advertised. I loved being five minutes away from Point Lookout, the sunset views, and the waterfront. "
Secluded River Front Cottage

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

9.6 out of 10, Exceptional, (19)
"The house was just as it was listed!! Our annual family vacation was so much fun here! Plenty of room, very clean, and fully stocked! Peddle boats, kayaks, and pool used daily!! Fire every night!!! Thank you for the wonderful hospitality!!!"
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

9.8 out of 10, Exceptional, (9)
"I loved this sweet A frame home! Celebrated my 48th birthday with a girls' trip and we all loved it. Enjoyed fires and Christmas movies each night. House has a lot of space and is so comfortable. Loved the views of the Bay, particularly from the sunroom and porch. Found quite a bit of sea glass on the neighborhood beach, as well as at the house beach during low tide. Owner was incredibly responsive and went above and beyond. Great place. Would highly recommend. "
Beachy Maryland A-Frame: Steps to Chesapeake Bay!

The Blackwater refuge country house on a quiet 12 acres

9.8 out of 10, Exceptional, (9)
"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

Riverside House w/ Kayaks, Piano & Fireplace

9.0 out of 10, Wonderful, (12)
"This house is well-maintained and my business associates enjoy staying here. We will book this house every time it comes available."
Riverside House w/ Kayaks, Piano & Fireplace

Bayfront Gem w/ Amazing Water Views + Pond!

10.0 out of 10, Exceptional, (12)
"Wonderful house with great views of water. Everything was as advertised and we had a very relaxing stay. Will definitely consider returning. "
Bayfront Gem w/ Amazing Water Views + Pond!

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

Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy

9.4 out of 10, Exceptional, (3)
"We were in town for a reunion and this was a nice alternative to the local hotels. Updates to the house were nicely done and I love that checkout was simplified to two to three tasks, not a whole laundry list. If I had two suggestions, one would be that the plug-ins were too many and too strong - we considered opening a window for some relief but did not since we were out at the reunion most of the day. But only one per floor would likely be enough although the house is so clean (five stars!)...
Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy

3 Bedrooms Relaxing Rustic House on Saint Thomas CreeK

3 Bedrooms Relaxing Rustic House on Saint Thomas CreeK
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 property types in Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (65)
"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

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.