See all properties
Entire home

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

Choose dates to view prices

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

Relax in Adirondack chairs along the serene lakeside, with a boat available for recreation.
Property video
Relax in a serene outdoor setting with Adirondack chairs and a rustic fire pit.
Relax by the pool surrounded by lush greenery and comfortable seating.
Set amidst a lush lawn, this charming house offers a serene retreat.

Entire home

5 bedrooms5 bathroomsSleeps 106000 sq ft

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 neighborhood

Sherwood

Located within a leisurely stroll of Goat Island, this vacation home is within a 10-minute drive of Back Creek Community Park. The vacation home includes a private pool, a kitchen, and a patio.
View more Vacation Homes in SherwoodOpens in a new window

What's nearby

  • Tilghman Watermen’s Museum - 9 min drive - 5.1 miles
  • St. Michaels Marina - 25 min drive - 14.1 miles
  • Chesapeake Bay Maritime Museum - 25 min drive - 14.1 miles
  • St. Michaels Winery - 26 min drive - 14.5 miles
  • Saint Michaels Village - 28 min drive - 15.3 miles

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.



The vacation home is air-conditioned and features a kitchen, 4.5 bathrooms, and a patio. There's space to spread out with 5 bedrooms and a dining area. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a private pool, a washing machine, and a coffee maker.

Property manager

Marissa

Languages

English

Similar properties

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

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

  • Pool
  • Kitchen
  • Washer
  • Dryer
10.0 out of 10, 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

  • This property doesn't allow pets

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
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 30

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector and a smoke detector.

Frequently asked questions

What is there to do near this vacation home?

This vacation home is located in Sherwood within a short 13-minute walk of Goat Island. You'll also find Tilghman Watermen’s Museum and Tilghman Island Marina within a short drive.

Is parking available on site at this vacation home?

Yes, there is electric car charging available.

Is this vacation home next to a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home; however, the accommodation features a private pool.

Is Heated pool, sandy beach, pier, and playground set punch point apart! a good place to stay for couples?

Amenities that appeal to couples at this waterfront vacation home include a private pool, a kitchen, and a smart TV.

Are there hot tubs at Heated pool, sandy beach, pier, and playground set punch point apart!?

No, but guests can enjoy a heated pool at this vacation home.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Are there connecting rooms at this vacation home?

No, this vacation home doesn't feature connecting guestrooms.

What is the closest airport to this vacation home?

The closest major airport to this vacation home is Easton, MD (ESN-Easton - Newnam), which is 22.4 mi away (33 minutes by car).

Can I book a room with a balcony at Heated pool, sandy beach, pier, and playground set punch point apart!?

Yes, every accommodation at Heated pool, sandy beach, pier, and playground set punch point apart! comes with a deck with some featuring water views.

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