Hoopers Island Vacation Rentals

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Vacation Rentals in Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (54)
"We have stayed at this property twice and love it. Very peaceful, clean, and comfortable."
Waterfront Cottage in Beautiful Hoopers Island
The Schultz Estate
Outdoor dining
The Schultz Estate
9.6 out of 10, Exceptional, (5)
"This house is great for large groups with plenty of comfortable bedrooms, three bathrooms (note one is only a tub, no shower), and loads of outdoor seating and fire options. This is an old farmhouse, so quirks of an old wooden house on the Eastern shore come with that. Personal bug spray at this property is essential as the mosquitos are very intense. The owner did stop by to give us a lawn spray for them but we did not use it as I am a master naturalist and community garden manager who is...
The Schultz Estate
Historic Hoopersville Getaway on Chesapeake Bay!
Fridge, microwave, stovetop, dishwasher
Historic Hoopersville Getaway on Chesapeake Bay!
9.6 out of 10, Exceptional, (9)
"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!
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Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly
Pool
Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly
9.8 out of 10, Exceptional, (117)
"Overall the place was great, clean, and comfortable for 8 adults & 3 kids. There were 4 kayaks & 2 bikes we used & a small swing set that was perfect for the kids (all under 5). Kitchen and grill worked well for what we needed & the location next to Old Saltys was great to listen to music in the back yard! One important thing to note is that it isn’t really waterfront - more water adjacent. You have a clear view to the bay, but there is not any beach area for kids & you can’t access the dock...
The price is CA $731
CA $1,353 total
includes taxes & fees
Jun 13 - Jun 14
Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly
Sunrise Cottage on Hoopers Island. Fish, crab, boat, relax! Pet friendly.
Exterior
Sunrise Cottage on Hoopers Island. Fish, crab, boat, relax! Pet friendly.
10.0 out of 10, Exceptional, (42)
"My husband and I loved our visit to Sunrise Cottage! Everything was perfect and we can't wait to return."
Sunrise Cottage on Hoopers Island. Fish, crab, boat, relax! Pet friendly.
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
3 bedrooms, desk, iron/ironing board, free WiFi
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, (102)
"Loved the house!"
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Private Beach Front Getaway at The Sunshine Beach Cottage.
On the beach, sun loungers, beach towels
Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, (46)
"Comfortable, clean home directly on the Chesapeake Bay."
Private Beach Front Getaway at The Sunshine Beach Cottage.
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Beach
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
10.0 out of 10, Exceptional, (4)
"We were in town for a friends wedding. This was the perfect location as it was right in between the Catholic Church for the nuptial mass and the reception site. This place certainly did not disappoint. There was plenty of space for our large family, the home was well equipped and stocked with the necessary items. It was a relatively short stay, but I wish we had a bit more time and better weather to enjoy the use of kayaks - our one free morning was a bit chilly for us Florida folks, and we had...
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Beach
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
10.0 out of 10, Exceptional, (51)
"What a fantastic property! We loved staying here and our family had such a great time exploring. Sadly it was a drizzly, dreary weekend but we had one nice day to go down to the beach and the kids enjoyed playing in the water. We loved the variety of porches to sit on and have different views and there was plenty of room for the kids to play indoors when it was raining. Overall a great experience. Thank you!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (4)
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Waterfront House with Dock, Kayaks, & Sailboat!
View from property
Waterfront House with Dock, Kayaks, & Sailboat!
9.4 out of 10, Exceptional, (23)
"The house was nice and the property is spacious. Great views from the dining room table. A little steep heading down to the dock but not terrible. Very private setting, but also only 5 mins away from pretty much anything you could need. Some nice restaurants just across the bridge in Solomons Island. Would love to return in warmer weather to take advantage of the kayaks and water."
Waterfront House with Dock, Kayaks, & Sailboat!
Soul Oasis - home on the Chesapeake Bay
Sun loungers, beach towels
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, (6)
"Pleasant relaxing time. We were pleased and impress to locate this property"
The price is CA $178
CA $396 total
includes taxes & fees
Jun 10 - Jun 11
Soul Oasis - home on the Chesapeake Bay
Maryland Vacation Rental w/ Private Pool & Dock
Property grounds
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (4)
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock
Stunning River Front Home - Private Dock - 90 minutes from Washington DC
Fridge, microwave, oven, stovetop
Stunning River Front Home - Private Dock - 90 minutes from Washington DC
9.8 out of 10, Exceptional, (14)
"We booked a long weekend for our daughter’s graduation from St Mary’s. The house was beautiful and so spacious for our adult children and grandchildren to all be in one location without feeling cramped. We loved having the fire pit and room to throw a football around. Thank you for sharing your home Victoria!"
Stunning River Front Home - Private Dock - 90 minutes from Washington DC
Quaint Island Getaway
Beach nearby, sun loungers
Quaint Island Getaway
10.0 out of 10, Exceptional, (11)
"This is a charming place, full of really nice interior touches. The location gives you access to some great marshland so you are treated to a daily dose of great bird sightings, including ospreys, red-winged blackbirds, herons and others. The house has everything you need. The only advice I would give - to remind guests to clean off the grill when they are done using it. We had to clean it thoroughly as it had obviously not been cleaned in awhile. I suggest you add that to the short list of...
Quaint Island Getaway
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (29)
"👍👍"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Fridge, microwave, oven, stovetop
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (171)
"Groomsmen stayed here for wedding. Great experience in a beautiful location. Swimming and kayaking right out the back door. Owners were very kind and helpful. Definitely recommend this beautiful spot."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Beautiful Waterfront Retreat in Cambridge!
Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (17)
"We had a very enjoyable and relaxing stay here for Mother's Day weekend, coming in from DC. The property is in a great spot on the water and is a short ride into town. The house itself is cozy, clean, and welcoming with everything you need (including the crab house out back, which our four year old loved!) Rebecca is a thoughtful and accommodating host, too. She gave us several recommendations for food in the area and we really enjoyed her suggested restaurants in Cambridge and in Easton on the...
The price is CA $399
CA $691 total
includes taxes & fees
Jun 16 - Jun 17
Beautiful Waterfront Retreat in Cambridge!
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, (31)
"One of the best properties I have stayed at. With all the amenities, you never need to leave the home. We enjoyed the views, the quietness of the area, and the wildlife. We nicknamed two beautiful ducks…Sonny and Cher! The house is very clean, the checkin checkout procedures were very easy. The host communicated all the details plus additional suggestions. We are definitely returning very soon."
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
Beach umbrellas, beach towels
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
9.4 out of 10, Exceptional, (9)
"The cabin itself was lovely with a southwestern feel. Very clean when we arrived and met our expectations. The outside space was the best! Even though it was a rainy weekend, we were able to take the kayaks out on the lake during a break in the rain. Unfortunately the weather prohibited us from visiting the beach but the property was close to Solomon's Island where there is plenty of shopping and dining. My only complaint was the mattress in the master bedroom. It felt wore out and we kind of...
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
Don't see what you're looking for?
See all available properties in 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.

Hoopers Island Vacation Rental Travel Info

Popular accommodation
Hoopers Island private vacation homes
International airport
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)

Other types of properties in Hoopers Island you may be interested in

Waterfront Cottage in Beautiful Hoopers Island
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (54)
"We have stayed at this property twice and love it. Very peaceful, clean, and comfortable."
Waterfront Cottage in Beautiful Hoopers Island
The Schultz Estate
Outdoor dining
The Schultz Estate
9.6 out of 10, Exceptional, (5)
"This house is great for large groups with plenty of comfortable bedrooms, three bathrooms (note one is only a tub, no shower), and loads of outdoor seating and fire options. This is an old farmhouse, so quirks of an old wooden house on the Eastern shore come with that. Personal bug spray at this property is essential as the mosquitos are very intense. The owner did stop by to give us a lawn spray for them but we did not use it as I am a master naturalist and community garden manager who is...
The Schultz Estate
Waterfront Farmhouse, Hoopers Island. Relax, boat, crab, and fish. Pet friendly!
Exterior
Waterfront Farmhouse, Hoopers Island. Relax, boat, crab, and fish. Pet friendly!
10.0 out of 10, Exceptional, (36)
"Owners attenuative to texts for any needs. We arrived very late to property d/t I95 bridge being rerouted and it was no big deal with Toby the owner. Its a Quaint clean home with all needed amenities. Great kitchen. My husband and I love to cook. Be aware that main bedrooms are upstairs and bathroom is downstairs r/t toilet use at night/ small children. Property was well manicured with fabulous Chesapeake Bay views. Awesome dock for everything. Owner provided crab traps!!! Bring couple steaks...
Waterfront Farmhouse, Hoopers Island. Relax, boat, crab, and fish. Pet friendly!
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . Seeing all the best attractions is bound to make you fall in love with Hoopers Island. Who knows, you may even be tempted to extend your vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Recent reviews of Hoopers Island properties
Expedia verified reviews

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

5/5 Excellent
"Gorgeous property!"
A verified traveller stayed at Hyatt Regency Chesapeake Bay
Posted 3 days ago
Hyatt Regency Chesapeake Bay