Guys' trips · Eastern Shore Maryland
Twelve guys. One house. Six bedrooms. Boat ramp four minutes away.
A 6-bedroom Chesapeake Bay water-view estate with a smoker on the rear deck, a fire pit out back, and two 75-inch TVs for split game days.
10-car driveway · 1.2 private acres · no neighbors visible.
Bay View
Pergola
Flex Barn
Kitchen
Anti-resort · straight talk · real amenities
You don't need a resort. You need a base with the right stuff.
Six bedrooms — nobody on a couch, nobody fighting for the master. Ten-car driveway for the trucks + trailers + boats. A real smoker on the rear deck (not a kettle). Two 75-inch TVs in different living rooms so the fantasy draft and the playoff game can run at the same time.
Hoopersville Boat Ramp is four minutes away. The crab traps off the front-yard ditch work April through mid-December. Rippons Brothers Seafood is two miles for live crabs. Old Salty's is 3.6 miles for legendary Maryland crab feasts.
Maybe you've been the one organizing this trip every year for a decade. Or maybe this is the year you decide to be the guy who finally sends the text — "Block the second weekend of September. I've got the house." Either way, the part that always trips up guys' trips — finding the place that fits everyone — is already handled.
Honest about what we aren't: no hot tub. No pool. No nightclub scene on the island. Quiet hours 10 PM–8 AM are real because it's a working watermen community. If those rules out your trip, we'd rather tell you now.
What kind of trip
Pick your weekend.
The day your crew actually lives
Here's what the weekend looks like.
5 AM (fishing crews only)
Coffee in the kitchen, trucks rolling at 5:15.
Hoopersville Ramp is 4 minutes door-to-trailer. While the rentals 30 minutes away are still launching, you're already on the chum slick. Working watermen community — nobody around here is bothered by 5 AM noise.
Mid-afternoon
Cold beer on the front deck, watching the watermen come in.
Front deck rocking chairs. Bay view. Cargo ships drifting past on the horizon — sometimes a cruise ship. The crab traps in the front-yard ditch get pulled. Whatever you didn't catch out there, you caught right here.
Sundown
Smoker fires up. Old Salty's is 7 minutes away if you didn't catch enough.
Rear-deck smoker handles a 10-person brisket or two pork shoulders. Or run to Rippons Brothers Seafood (2 mi) for live crabs + Old Bay and steam them at the house. Either way, you're eating outdoors and the sunset's putting on a show.
Game day
Two 75-inch TVs. Split-window NFL works.
Downstairs living room is the bigger party room. Upstairs is the quieter second-screen zone. Both have a 75-inch Smart TV — fantasy draft, playoff games, college football Saturdays — run two at once without anyone fighting the remote.
After dark
Fire pit. Long stories. Honest conversations.
The fire pit becomes the late-night room. The kind of conversation that only happens with the people who knew you in college, or in service, or in your first job. Music wraps at 10 (watermen community quiet hours) but the fire and the talk keep going.
Slow morning
Rear deck. Coffee. Birds. The hangover cure that actually works.
Purple martins flipping for bugs over the lawn. Sometimes a blue heron at the marsh edge. An osprey overhead. If you're stealthy enough, a deer at the feeder. The kind of quiet that resets the brain — the thing the resort weekend never delivered.
Explore the Property
Every room, at the scale a group uses it
Why You'll Love It Here
Curated highlights for your stay
Panoramic Bay Views
Watch cargo ships, cruise ships & sailboats drift across the Chesapeake — the view shifts all day long from every front window and the second-floor rooms are stunning
Flex Barn (1,600 sqft)
16-ft ceilings, 16-ft sliding barn door, step-free ramps in and out — 'the yes space' for families, strategy room for teams, yoga studio, storage for boats & gear. No extra cost.
Three Living Spaces + Two 75" TVs
Two large living rooms (upstairs + downstairs), each with a 75" TV, plus a downstairs sitting room with a smaller TV above the decorative fireplace — the upstairs has a kids' play area, a card table with chairs, and a bay-view work-from-home nook perfect for a quiet morning coffee or a focused work session
Pergola · Fire Pit · Hammock · Picnic Table
Seats 20 at the lighted pergola, 6 at the convertible picnic table, 2 in the hammock under the tree canopy — every inch of the backyard is designed for lingering
10-Car Parking + Boat/Gear Storage
About 10 cars comfortably, more with careful parking, and room for a boat trailer. The Flex Barn can be driven into for unloading and takes overflow cars when it isn't in use. No permit needed
4-Load Laundry
Two full-size washers and two full-size dryers — ideal for extended stays, fishing trips, or large groups doing same-day turnover
Rear Deck Grill-Smoker + Outdoor Dining
Grill-smoker combo with outdoor dining set for 6 on the rear deck — cook your catch right there or go low-and-slow for the group
Pet-Friendly
Up to 2 dogs, $150 per stay. No cats.
About 110–125 miles from major metros
No surprises at checkout
What it actually costs.
One price covers the whole house, the Flex Barn and every bedroom, for up to 24 people. Here is everything that goes into it.
$1,161
2 nights for the whole house, cleaning and Maryland tax included. The cheapest 2 nights still open are Mon 7 Dec to Wed 9 Dec.
30% deposit at booking for stays 14+ days out, balance 3 days before check-in; closer in, paid in full.
Full refund if cancelled 14+ days before check-in.
Check-in 4 PM · Check-out 10 AM. No early check-in or late check-out.
Quiet hours 10 PM–8 AM; sound carries over the water out here. No events beyond the people staying unless the owner approves them, and only on stays booked here. Up to 50 people on the property, including the 24 staying the night during an approved event. Ask before check-in — there is no fixed number of days — and the owner's approval must be in writing.
Same nightly rate as our Evolve listing. You just don't pay a booking platform's service fee on top.
What Guests Say
"We had such a fantastic stay! The house truly lived up to the listing—tons of space for our group of 20, and the layout made it easy for everyone to relax and enjoy. The host was amazing: super responsive, thoughtful, and proactive with details and local tips. The property itself is beautiful and private, with a great backyard and a huge flex barn. The kitchen had everything we needed, and all the linens were spotless. We'd absolutely come back for another stay!"
Smitha Ann
Group trip · July 2026
Verified review — see it on Airbnb"This is great property for folks looking for accessibility - there's a ramp and primary bedroom / bath are on the main floor. This was a must for us as we were traveling with elderly parents with limited mobility. The setting is scenic but the location is more remote than some — so good for those looking for a quiet and relaxing time. We enjoyed nearby restaurant called "Old Salty's." We appreciated how responsive the host was to our suggestions and questions. We appreciated small details, like laundry baskets in the rooms as well as Tupperware in the kitchen, puzzles and card games in the sitting area. I believe the host is continuing to add more amenities as guests send more suggestions!"
Anoka F.
Stayed 6 nights in Jul 2026 · Traveled with family and young children
Verified review — see it on Vrbo"We absolutely loved our stay. [The] house was beautiful, the amenities were excellent, and we loved the crabs!! We went for a family weekend (mix of 18 kids and adults) and it was very spacious and comfortable for everyone. The pergola in the back was an especially big hit! We highly recommend and would stay again."
Bridget C.
Stayed 2 nights in Aug 2026 · Traveled with family and young children
Verified review — see it on Vrbo"I stayed here during the long Memorial Day weekend with 6 couples and 4 children. The place was large enough to accommodate us all for sleeping arrangements. The views were very nice. The place was very clean and looked new. We had a wonderful time. The host was very accommodating and responsive. I highly recommend."
Andrew
Herndon, VA · Group trip · May 2026
Verified review — see it on Airbnb"We had a wonderful experience staying at this beautiful house. Kitchen was fully equipped, bathrooms were clean with enough towels and toiletries and bed was very comfortable. Host was very responsive to answer questions via chat and was checking regularly everything was going well. I would recommend this place to others and will stay there again in the future."
Siva
East Brunswick, NJ · Group trip · July 2026
Verified review — see it on Airbnb"The house was perfect for a large family get away. It was quiet and private enough that we had a great sense of privacy and comfort while still being not too far from stores, restaurants, and other things to do if you want to get outside. The views on the drive in and over the water were incredible"
Esli
Chicago, IL · Group trip · August 2026
Verified review — see it on Airbnb"Very peaceful with great views. The host was very kind and helpful."
Koo
Boyds, MD · Stayed with kids · July 2026
Verified review — see it on AirbnbWould rather book somewhere you have used before? The same house and the same dates are on Airbnb and VRBO. Each site shows its own total at its own checkout.
Real questions
What you're probably wondering.
Have a question we didn't answer? The AI concierge in the bottom-right knows the property inside out.
Pick the weekend. Get the crew. Done.
Pay by card and it's saved at booking; nothing charged until the owner personally approves your request. 30% deposit on approval and the balance 3 days before check-in, for stays 14+ days out; closer in, paid in full on approval. Free cancellation 14+ days out. No platform fees. Pet-friendly.