Vacation rentals in Hoopersville

4.98 out of 5 average rating, 123 reviews

Home in Church Creek

Church Creek Charm (close to Blackwater Refuge)

Charming Eastern Shore home built in 1900, located in CHURCH CREEK, MD, less than 10-15 mins from Cambridge, Blackwater National Wildlife Refuge & the Harriet Tubman Underground Railroad museum. Ideal spot for cycling, birding, fishing, canoeing, relaxing, or exploring the many cute towns of Maryland's Eastern Shore. Just over an hour from Ocean City & Assateague Nat'l Seashore. Pet-friendly with a fenced backyard. The Eastern Shore is famous for its seafood, history, nature & fresh produce!

4.98 out of 5 average rating, 196 reviews

Farm stay in Madison

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 345 reviews

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 50 lb. weight limit total, can be split up between 2 small dogs or 1 at 50lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

4.98 out of 5 average rating, 198 reviews

Tiny home in Cambridge

The Little House on the Farm, Water Access

Peaceful, Quaint & located on the Little Blackwater River, & 1.5 miles from the Blackwater National Wildlife Refuge & The Harriet Tubman Underground Railroad State Park & Museum. A bird watching, kayaking, and bicycling paradise awaits. Perfect for a couples retreat, girls getaway or a solo vacation to relax & unwind. Hunters and Fishermen are welcome also! Route 50 & downtown Cambridge are 10 mins away for local eateries and shopping! This is the perfect location to explore the Eastern Shore!

4.96 out of 5 average rating, 189 reviews

Cottage in Leonardtown

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

4.78 out of 5 average rating, 373 reviews

Farm stay in Cambridge

Blackwater & Snakehead Farm "She Shed" Tiny House

The "She Shed" Tiny House is the best bargain & unique stay around! This Tiny House is made from a traditional 10'x18' shed and is solar powered! It's surprisingly spacious with a full size bathroom, kitchenette, lofted twin bed, day bed & trundle bed! The home borders a sheep pasture, farm barn, goat pasture & chicken coop! Snakehead fishing is just a short walk away! Kayacks & creek launch on site! Just a 5 minute drive from Blackwater Refuge! Relax and enjoy country living on the farm!

Apartment in Lexington Park

4.97 out of 5 average rating, 566 reviews

Historic St. Mary's City, MD

1,000 square foot two-bedroom, one bath waterfront apartment features separate entrance and a screened-in porch overlooking the St. Mary’s River. Property has a large dock and a small private beach. Jellyfish, crabs, and oysters make swimming challenging, although many swim off the dock in the deeper water. No Diving! Dogs are welcome. We just ask that they be on a leash. The apartment is attached to part of the house where we reside, although it is sealed off and nothing is shared.

Apartment in Lexington Park

4.97 out of 5 average rating, 130 reviews

Serene setting great location surrounded by woods

The one-bedroom apartment will sleep 2 adults and 1 child under 18. In a serene setting with woods, a fish pond, and a comfortable patio. Separate code lock entrance. Well-equipped kitchen. Free WiFi, two TVs with Netflix and Amazon Prime. There is also a cedar sauna. Parking is on the property. Apartment situated near shops, restaurants, St. Mary's College and the Patuxent River Naval Air Station. 15 minutes from Chesapeake Bay, 1 hour to DC beltway. French and German also spoken.

5 out of 5 average rating, 110 reviews

Home in Dameron

Peace Point - Waterfront, Secluded, Home w/hot tub

Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

Apartment in Lexington Park

5 out of 5 average rating, 381 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

4.75 out of 5 average rating, 206 reviews

Guest suite in Crisfield

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

4.97 out of 5 average rating, 235 reviews

Cottage in California

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has an open floor plan that allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum featuring live concerts by top name bands.

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Other great vacation rentals in Hoopersville

4.92 out of 5 average rating, 12 reviews

Home in Lancaster

Waterfront Fishing, Game Room, Kayaks, Firepit

TracyRating, 5 stars7 months ago

This house was absolutely gorgeous! It has everything you need ! It was clean and the beds were so comfortable. The view every morning was beautiful. We had so much fun and it was so peaceful. We will be back for sure

4.89 out of 5 average rating, 64 reviews

Home in Lusby

Beachfront Oasis with Amazing Views

NguyetRating, 5 stars2 weeks ago

We had such a wonderful stay! The kitchen was incredibly well stocked—honestly better than my own at home—with 5-6 large pots, an Instant Pot, every spice you could think of,peelers (which saved me!), and both a NutriBullet and a regular blender. It made cooking for the family a breeze. The kid had a blast on the trampoline, and we all loved the easy beach access with calm waters perfect for swimming all day and kayaking. The beach was also perfect for a peaceful morning run, and at night we could see the lighthouse light on the water. The porch quickly became our favorite spot—we gathered there to watch a rainstorm and were treated to a stunning double rainbow. The sky was full of stars at night, creating such a peaceful atmosphere. The grill on the porch made cooking super convenient. We enjoyed being close to a large park where we played pickleball. The beds were large and comfortable—everyone slept really well. Michael was a fantastic host—very attentive and accommodating.

4.88 out of 5 average rating, 100 reviews

Home in Deale

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

CourtneyRating, 5 stars2 months ago

This air b&b is in a beautiful setting with plenty to do (kayaking, hot tub, fire pits, bird watching, etc). It's also very centrally located so we could easily get to more populated areas in no time. The most stunning part of the house is the master suite in my opinion which is on the upper level (the upper level is shared with another apartment, but you don't really hear the air b&b tenants of this suite and it's completely separate with a separate entrance). Stunning views from both the master bedroom and the bath tub in the master suite! The downstairs is also quite lovely with two regular bedrooms, one small bedroom, and a sun room that has a pull out couch (we didn't use it). It's a lovely house to entertain in. It has personal photographs to the owner downstairs that speak to the family's history. The owner is communicative. The overall experience was quite lovely. We'd be happy to return.

4.96 out of 5 average rating, 27 reviews

Home in Solomons

Solomons Yellow House - Waterfront

SheilaRating, 5 stars5 months ago

Really enjoyed holiday get away . Place was located near water with great views. We enjoyed walking around the neighborhood was quaint. The town was was pretty with water on each side with the Christmas lights at night . We truly enjoyed our relaxing stay . Would definitely book again

4.98 out of 5 average rating, 128 reviews

Home in Cambridge

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

AnneRating, 5 stars1 month ago

This was a great house for our teammates to stay in for the weekend!

4.88 out of 5 average rating, 234 reviews

Home in Montross

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

KelliRating, 5 stars1 month ago

I can't express enough how wonderful this home is. We loved it so much that we extended our stay by an extra day! The location was absolutely perfect and met all our family's needs. The private dock quickly became a family favorite, along with the hot tub. It's a quiet, peaceful retreat and the ideal place to recharge with your loved ones. We will definitely be back!

4.83 out of 5 average rating, 172 reviews

Cabin in Lusby

2-bedroom lake-house with a magnificent view

MohamedRating, 5 stars1 month ago

Beautiful house and beautiful view. Outdoor jacuzzi with the view is not to be missed! Gorgeous and clean home. The private site made it an amazing getaway from busy life. Thank you, we will be back soon!!!