Pickleball · group-sport reunion · Eastern Shore
The off-court base camp for the pickleball squad.
A 6-bedroom Eastern Shore Maryland base for a 6-12-player pickleball group. Cambridge YMCA + community courts 29 mi away (~40 min).
Honest: NO court on the property. The property is the off-court hangout.
Bay View
Pergola
Flex Barn
Kitchen
No pickleball court on the property. The 1.2-acre lot is open lawn — no marked court, no nets installed. Guests drive to Cambridge (~29 mi, ~40 min) to play at the YMCA or community courts. The property is the base camp for the off-court part of the trip. If you need an on-property court, this isn't the venue — we'd rather tell you up front.
The on-court hours are the headline · the off-court hours are the trip
For the doubles squad that finally schedules the trip.
Most pickleball groups play 4-6 hours a day max. The other 18 hours are the trip — the carb-loading breakfast, the long lunch, the post-court recovery soak in the master tub, the fire pit conversation that goes till 10 PM, the early-morning coffee on the front-deck rocking chairs before round two.
Cambridge (~29 miles, ~40 min) has the YMCA + community courts. Easton (~44 miles) has the higher-tier pickleball scene including Easton Premier Pickleball Club. Most groups do morning + evening sessions at Cambridge, eat lunch + dinner at the property, and rotate.
Six bedrooms = no air mattresses. A step-free main level and main-level master = real comfort for the 50-70 demographic. Freestanding soaking tub for the post- court recovery. Pet-friendly. 1.2 private acres.
What's the squad
Pick the sport reunion.
A day in the life of a pickleball weekend
Honest: the courts are 40 minutes away. The rest of the day lives here.
6:45 AM
Front-deck coffee before the 8 AM court reservation
Bay glowing, mourning doves, the squad in various states of awake-ness. Front-deck rocking chairs, the carb-loading breakfast laid out on the breakfast room table. The ritual that turns a trip into a tradition.
8 AM – noon
Cambridge courts (~29 mi, ~40 min)
Honest: the property does NOT have a pickleball court. Cambridge YMCA has dedicated courts plus several community courts in town. Easton (44 mi) is the higher-tier scene if you want a destination day. Drop-in fees $5–$15 per session.
12:30 PM
Lunch back at the house — full kitchen
Drive back, eat together, actually rest. Granite island for the build-your-own sandwich bar, breakfast room for the casual eaters, formal dining if someone made a real spread. Beats restaurant lunch between sessions, every time.
2 PM
Flex Barn mobility + movie break
1,600 sqft of rubber floor for the post-court stretch + foam-roll session. Sliding door open for the breeze. Or skip the movement and project a movie on the wall while the morning warriors nap. Either is the right call.
Sunset
Pergola — beers, the day's bracket, the bay going gold
Pergola string lights, the cold drinks (alcoholic or not — your call), the conversation about which doubles partner needs to get traded next time. The off-court half of the trip is the trip.
10 PM
Fire pit + real sleep before tomorrow's matches
Six bedrooms means no air mattresses, no roommate situation. Step-free master with the freestanding soaking tub for the post-court recovery. Quiet enforced 10 PM. Wake up actually ready for round two.
Explore the Property
Every room, at the scale a group uses it
Why You'll Love It Here
Curated highlights for your stay
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.
Full Kitchen for a Crowd
Large oven, island seating for 4, full breakfast room — built for group cooking and water view feasts
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
Step-Free Main Level
Both decks have ramps and French door entry. The Flex Barn has ramps in and out. Three bedrooms, including the master with its soaking tub, are on the main level and take no stairs to reach. The other three bedrooms are upstairs by a standard staircase and there is no chair lift
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
Pet-Friendly
Up to 2 dogs, $150 per stay. No cats.
Front Deck with Rocking & Gliding Chairs
Watch the Bay change from morning mist to golden hour from your own private rocking chairs — the front deck is where the day starts and ends
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.
Pickleball-trip 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 dates. The off-court base is ready.
Pay by card and it's saved at booking — nothing charged until the owner personally approves your dates and (if you ask) confirms what court availability looks like for your weekend. 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 OTA fees, no resort fees. Step-free main level. Pet-friendly.