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

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A two-story house with a swimming pool, outdoor seating, and a well-maintained lawn.
A lakeside setting with four Adirondack chairs and a canoe on the sand.
A large house with a swimming pool, surrounded by a well-maintained lawn and trees.
A modern kitchen with a large island, wooden bar stools, and a view of the living area.
A modern kitchen with a central island, wooden dining table, and chairs.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 106000 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Sherwood, MD
  • Place, Knapp's Narrows Marina & Inn
    ‪6 min drive‬
  • Place, Tilghman Island Marina
    ‪7 min drive‬
  • Place, Northern Chesapeake Bay
    ‪7 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪42 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

  • Knapp's Narrows Marina & Inn - 6 min drive - 3.9 miles
  • Back Creek Community Park - 6 min drive - 3.9 miles
  • Tilghman Island Marina - 7 min drive - 4.7 miles
  • Northern Chesapeake Bay - 7 min drive - 4.7 miles
  • Tilghman Watermen’s Museum - 8 min drive - 5.1 miles

Getting around

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

Restaurants

  • ‪Chesapeake Landing - ‬14 min drive
  • ‪Talbot St. Tavern - ‬19 min drive
  • ‪Ava's Pizzeria & Wine Bar - St Michaels - ‬20 min drive
  • ‪Big Mack's Kitchen & Dock Bar - ‬7 min drive
  • ‪Gina’s @ The Bridge - ‬7 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 rentals in St. Michaels, MD. We also own Tilghman Island Inn, a waterfront destination specializing in group retreats, weddings, and private events.

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.

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  • Pool
  • Kitchen
  • Washer
  • Dryer
8.2 out of 10, Very good, 122 reviews
$193 nightly
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Nov 22 - Nov 23
Total with taxes and fees
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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
  • Wheelchair-accessible parking available
  • 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
  • Bed sheets 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

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No elevator
  • Null
  • Wheelchair-accessible parking
  • 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)
  • Fire extinguisher

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 10:00 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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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
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
Safety features at this property include a fire extinguisher
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: 10:00 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, a fire extinguisher, and a smoke detector.

Additional information about polices, regulations, and more:

  • There are no elevators.

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 Knapp's Narrows Marina & Inn and Tilghman Island Marina within a short drive.

Is there parking available at Heated pool, sandy beach, pier, and playground set punch point apart!?

Yes, there is an electric car charging station and wheelchair-accessible parking 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.

What amenities will couples enjoy at Heated pool, sandy beach, pier, and playground set punch point apart!?

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 this vacation home does have a heated pool.

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

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).

Are there rooms with balconies at Heated pool, sandy beach, pier, and playground set punch point apart!?

Yes, every house at Heated pool, sandy beach, pier, and playground set punch point apart! comes with a patio and some offer water views.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 14 out of 14 reviews
Rating 8 - Good. 0 out of 14 reviews
Rating 6 - Okay. 0 out of 14 reviews
Rating 4 - Poor. 0 out of 14 reviews
Rating 2 - Terrible. 0 out of 14 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A secluded and quiet setting with lots of amenities to keep us occupied. The kitchen was well stocked and had everything we needed. We appreciated the heated pool which was very clean. If older folks are staying here, be aware that there are no railings on outdoor stairs - might be something for the owners to consider in the future. We had no maintenance problems and had a relaxing stay.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
It's a great family get-together house. The beds were very comfortable, the kitchen is large and easy for multiple cooks, and there is plenty of room to spread out. The pool, play area, game garage, fire pit and water access are really nice for a family with kids of all ages. We are a family of 9 with 6 adults and 3 kids and it worked very well for us. Many thanks, we had a great family vacation!
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 9 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 6 nights in Aug 2025