Entire home

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

Waterfront holiday home with private pool and kitchen

Exterior - Heated pool, sandy beach, pier, and playground set punch point apart! (Sherwood)

Fridge, microwave, oven, stovetop - Heated pool, sandy beach, pier, and playground set punch point apart! (Sherwood)

A heated pool - Heated pool, sandy beach, pier, and playground set punch point apart! (Sherwood)

Punch Point in St. Michaels, MD offers a fresh take on luxury rentals. This vibrant space boasts two islands, refrigerators, and game rooms to encourage community and fun. Lounge by the heated pool or relax with loved ones at the firepit after launching kayaks from your own sandy beach.

Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 10557 sq m

Popular amenities

Dryer
Pool
Washer
Barbecue grill
Parking available
Outdoor space

Add dates for prices

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 amenities

Beach

Beach nearby
Beach loungers
Beach towels

Pool/Spa

Heated pool
Private pool

Internet

Available in the house: Free WiFi

Parking and transport

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
Hob
Ice maker
Kitchen island
Microwave
Oven
Paper towels
Refrigerator
Spices
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

Smoke-free property

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

Similar properties

Pool
Kitchen
Washer
Dryer

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

Information provided by the property may be translated using automated translation tools

Rules

Once confirmed you will be required to sign our rental agreement prior to occupying the property

A picture ID of the guest executing the property's terms and conditions is required prior to check-in

NO EVENTS. NO WEDDINGS. 10 guest maximum at all times. There are no additional guests permitted. Please adhere to the posted occupancy.

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

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

On-site parties or group events are strictly prohibited

Host has indicated that there is a carbon monoxide detector on the property

Host has indicated that 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

About the area

Sherwood, MD

What's nearby

Knapp's Narrows Marina & Inn - 6 min drive - 6.2 km
Back Creek Community Park - 6 min drive - 6.2 km
Tilghman Island Marina - 7 min drive - 7.2 km
Phillips Wharf Environmental Center - 8 min drive - 7.2 km
Tilghman Watermen’s Museum - 8 min drive - 8.2 km

Getting around

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

Restaurants

‪Carpenter Street Saloon - ‬19 min drive
‪Chesapeake Landing - ‬14 min drive
‪Ava's Pizzeria & Wine Bar - St Michaels - ‬20 min drive
‪Two if by Sea - ‬8 min drive
‪Talbot St. Tavern - ‬19 min drive

Frequently asked questions

Does Heated pool, sandy beach, pier, and playground set punch point apart! have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Heated pool, sandy beach, pier, and playground set punch point apart! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Heated pool, sandy beach, pier, and playground set punch point apart!?

On-site parking is available at the property.

What time is check-in at Heated pool, sandy beach, pier, and playground set punch point apart!?

Check-in begins at 4:00 PM.

What time is check-out at Heated pool, sandy beach, pier, and playground set punch point apart!?

Checkout is at 11:00 AM.

Where is Heated pool, sandy beach, pier, and playground set punch point apart! located?

This family-friendly Sherwood holiday home is located on the waterfront, 0.7 mi (1.1 km) from Goat Island, and within 6 mi (10 km) of Phillips Wharf Environmental Center and Back Creek Community Park. Kronsberg Park and Wittman Park are also within 6 miles (10 km).

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

10

Exceptional

10

Cleanliness

10

Location

10/10 Excellent

Chris S.

30 Jul 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful property with everything you would need to have a great family vacation. Marissa was a great hostess!

Stayed 7 nights in Jul 2025

10/10 Excellent

Ashley C.

16 Jul 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Adrienne N.

11 Aug 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family trip

We had a wonderful time. The home was perfect. There were so many areas in the home to keep both the children and adults happy. The kitchen was amazing. The owner was very helpful. We would definitely enjoy renting with them again.

Stayed 4 nights in Aug 2025

10/10 Excellent

Daniel M.

3 Aug 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Our family of ten throughly enjoyed our stay. There were lots of activities for the young children. The pool was great. The accommodations were spacious and immaculate. There was enough room, so that one group could work on a puzzle while others played kids card games and others were in the pool. the chefs of the family enjoyed the high end kitchen appliances.

Stayed 9 nights in Jul 2025

10/10 Excellent

Jackie C.

11 Oct 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Julia G.

10 Nov 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Michael G.

6 Jul 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Martha B.

5 Dec 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Gaston S.

13 Jun 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

10/10 Excellent

Celia M.

25 Apr 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

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