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Heated pool, sandy beach, pier, and playground set punch point apart!

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Relax in Adirondack chairs along the serene lakeside, with a boat available for recreation.
Property video
Relax by the pool surrounded by lush greenery and comfortable seating.
Staircase leads to an upper level, with a console table and artwork on display.
Relax in a serene outdoor setting with Adirondack chairs and a rustic fire pit.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 10

Popular amenities

  • Dryer
  • Washer
  • Pool
  • Parking available
  • Barbecue grill
  • Outdoor space

Explore the area

Map
Sherwood, MD
  • St. Michaels Marina
    ‪25 min drive‬
  • Chesapeake Bay Maritime Museum
    ‪25 min drive‬
  • St. Michaels Winery
    ‪26 min drive‬
  • Easton, MD (ESN-Easton - Newnam)
    ‪50 min drive‬

Room options

About the area

Sherwood

On waterfront.You'll be within 2 miles (3 km) of Goat Island and 6 miles (10 km) of Back Creek Community Park with a stay here. Knapp's Narrows Marina & Inn and Phillips Wharf Environmental Center are also within 6 miles (10 km).
View more Vacation homes in SherwoodOpens in a new window

What's nearby

  • Tilghman Watermen’s Museum - 9 min drive - 8.2 km
  • St. Michaels Marina - 25 min drive - 22.6 km
  • Chesapeake Bay Maritime Museum - 25 min drive - 22.6 km
  • St. Michaels Winery - 26 min drive - 23.3 km
  • Saint Michaels Village - 28 min drive - 24.7 km

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 33 min drive

Restaurants

  • ‪Chesapeake Landing Restaurant - ‬14 min drive
  • ‪The Blue Crab - ‬19 min drive
  • ‪Carpenter Street Saloon - ‬19 min drive
  • ‪Ava's Pizzeria & Wine Bar - St Michaels - ‬19 min drive
  • ‪Justine's Ice Cream Parlour - ‬19 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Heated pool, sandy beach, pier, and playground set punch point apart!

TREMEZZO STAY - PUNCH POINT
Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury rental experiences in St. Michaels, MD.

If you do not see availability for your dates or are looking to sleep more or less than 10, please visit our 3 additional exclusive listings!!
Chesapeake Mansion (sleeps 12):
https://www.vrbo.com/2207416?unitld=2771970
Ranch at Royal Oak (sleeps 12):
https://www.vrbo.com/2697100?unitld=3267863
Spencer Creek Cabin (sleeps 8):
https://www.vrbo.com/1342430?unitld=1900766

Welcome to Punch Point! The years of design work for our guests have culminated with this new listing. The rehab mission being; provide our guests with more. Not 1 but 2 islands, not 1 but 2 refrigerators, not 1 but 2 game rooms, not 1 but 2 sets of washer and dryers... and on and on the list goes! It is a fresh, fun, and vibrant space that encourages community. There is an abundance of comfortable areas to lounge, both indoors and out. Enjoy the heated pool. Launch the kayaks from our eastern shore-style sandy beach. Smile at your loved ones by the firepit. Take it all in and share the love we have for St. Michaels.
*With this being a brand new listing we would invite you to look at reviews for any of our other properties for the time being. You will see that we are locked in our guests needs.



Property manager

Marissa

Languages

English

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Relax by the serene lake with a stroll along the pier and unwind in the adjacent lounge chairs.

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  • Pool
  • Kitchen
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5.0 out of 5, Exceptional, 34 reviews
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Electric car charging station on site
  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 4.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Books
  • Games
  • Smart TV

Outdoor areas

  • Barbecue grill
  • Firepit
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Concierge services
  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near the bay
  • Near the marina
  • On the waterfront

Things to do

  • Arcade/game room
  • Bicycles
  • Billiards/pool table
  • Foosball table
  • Golf
  • Heated pool
  • Kayak
  • Table tennis
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Kayaking nearby
  • Motor boating nearby
  • Swimming nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • Bicycles
  • Electric car charging station
  • Garden
  • Unit size: 6,000 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 30

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in each accommodation.

Heated pool, sandy beach, pier, and playground set punch point apart! Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 7 out of 7 reviews
Rating 8 - Good. 0 out of 7 reviews
Rating 6 - Okay. 0 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Ashley C.

Liked: Cleanliness

Wonderful Stay!

We had a wonderful stay! The home has plenty of room, it is clean, quiet and fully stocked. Property management is very responsive and helpful. The activities available at the home and in nearby St. Michael's made our trip especially memorable!
Stayed 4 nights in Jul 2025

10/10 Excellent

Michael G.

Liked: Cleanliness

Fantastic Stay

This is the second time we have stayed at one of the Tremezzo Stay properties and once again it was spectacular. Punch Point is better than advertised. The interior is bright, airy and immaculate. So many great amenities for our kids. The perfect place to have kids of any ages. Every detail was thought out from the fully stocked kitchen to the fire pit with smores. The kids spent hours in the pool. Best vacation home we’ve stayed in. Looking forward to coming back.
Stayed 4 nights in Jul 2025

10/10 Excellent

Celia M.

Liked: Cleanliness

Absolute perfection!

From start to finish, everything was perfect! This home just shows that the owners have thought of everything to embrace a memorable stay! We are a family of 10, ranging from 10 months to 83, and everyone had a wonderful time..Marissa was a pleasure to work with and was always ready to answer any questions promptly. The home was exactly like shown and the location is just amazing! Plenty of space for all! Thank you so much for sharing this gem with our family....
Stayed 5 nights in Apr 2025

10/10 Excellent

Martha B.

Liked: Cleanliness

Perfection!

Everything about this property was perfect for our family of 10 ranging in age from 79 to 2.5. The children loved the indoor and outdoor play areas, and it was hard to drag them away from the house for Thanksgiving dinner. The location was excellent for access to St Michael's and other spots on the eastern shore. The owner even helped us find a place to get fresh local oysters and shucking them was a family affair.
Stayed 5 nights in Nov 2024

10/10 Excellent

Julia G.

Liked: Cleanliness

Family Weekend

We had a wonderful and serene stay. We were traveling with our 9 month old and the play mat and toy area were so convenient. The renter also provided a crib and high chair. It’s an amazing home and view.
Stayed 3 nights in Nov 2024

10/10 Excellent

Jackie C.

Liked: Cleanliness

Wonderful bday celebration

Beautifully decorated, peaceful, well appointed home for our girls bday celebration. Highly recommend.
Stayed 3 nights in Sep 2024

10/10 Excellent

Gaston S.

Liked: Cleanliness

Tastefully remodeled house on beautiful property

I stayed on this property with my family (parents in their 70s, wife and i in our 30s, and a 3.5 and 1 year old) and everyone had a wonderful time. The house is gorgeous and very well decorated. Theres plenty to do on the property and plenty of unique spaces around the house, all of which have a stunning view of the water. The hosts were great and responsive. I would recommend this property/host to everyone.
Stayed 5 nights in May 2024