Entire home

Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails

Vacation home in Chester with kitchen

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Photo gallery for Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails

Fridge, microwave, oven, stovetop
Game room
Exterior
Smart TV
Dining

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathrooms2000 sq ft

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Outdoor Space
  • Kitchen
  • Air conditioning

Explore the area

View in a map
Chester, MD
  • Place, Matapeake State Park
    ‪7 min drive‬
  • Place, Chesapeake Bay Bridge
    ‪11 min drive‬
  • Place, Sandy Point State Park
    ‪14 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪47 min drive‬

Room options

About the neighborhood

Chester

This vacation home places you within a 10-minute drive of Chesapeake Exploration Center and Island Dog Park. The vacation home includes a kitchen, a refrigerator, and a microwave.

What's nearby

  • Paul Reed Smith Guitars - 4 min drive - 2.2 miles
  • Matapeake State Park - 7 min drive - 4.5 miles
  • Chesapeake Bay Bridge - 11 min drive - 8.2 miles
  • Sandy Point State Park - 14 min drive - 10.1 miles
  • U.S. Naval Academy - 25 min drive - 18.1 miles

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 28 min drive

Restaurants

  • ‪Chick-fil-A - ‬4 min drive
  • ‪McDonald's - ‬8 min drive
  • ‪Pour House Pub - ‬6 min drive
  • ‪McDonald's - ‬5 min drive
  • ‪Cracker Barrel - ‬8 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.

Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails

Charming Kent Island Retreat – 4 BR • 2.5 BA • Pool Table • Near the Water ""Brand New Construction""
Escape to the Eastern Shore with this spacious and comfortable 4‑bedroom, 2.5‑bath haven—perfect for family getaways, reunions, or remote work retreats.

The Space
Bedrooms: Four bright, well-appointed rooms — one king, two queens, and one room with a bunk bed (twin and a double) ideal for kids or extra guests.

Bathrooms: Two full bathrooms (one with a bathtub) plus a handy half bath—a great fit for groups and families.

Top Amenities
Game room fun: Challenge your crew to a match on the pool table, perfect for evenings in.

Climate control: Central A/C keeps things comfortable year-round.

Connectivity: Fast, reliable Wi‑Fi—ideal for streaming or remote working.

Essentials provided: Full washer and dryer, hair dryer, plus plush towels and linens.

Comfort & Space
With over 2,000 sq ft of open living space, vaulted ceilings, and a bright layout, there’s plenty of room to gather, unwind, or just spread out in peace and comfort.

Location Perks
Just a short drive to the water, with easy access to boating, beaches, seafood spots, and wildlife watching.

Conveniently located only two exits from the Bay Bridge, making day trips to Annapolis, St. Michaels, Baltimore, and Washington, D.C. a breeze.

Ideal For
Multi-generational families

Groups seeking water access + indoor entertainment

Remote workers needing reliable Wi‑Fi and comfort

All You Can Do on Kent Island:

Outdoor & Water Adventures:

Terrapin Nature Park: Explore 276 acres of wetlands, sandy beaches, and a 3.25-mile trails system—great for hiking, beachcombing, and wildlife watching, with stunning Bay Bridge views

Matapeake State Park: Relax on this former ferry landing beach with picnic spots and scenic Chesapeake Bay views

Cross Island & South Island Trails: Bike or stroll along flat, scenic trails—6–7 miles crisscrossing farms, woodlands, and bay shoreline

Kayak, Paddleboard & Canoe: Launch at CBEC, Ferry Point Park, or along Kent Narrows—plenty of waterways and guided options available

Fishing & Crabbing: Visit Romancoke Pier or charter a fishing trip for rockfish, sea trout, bluefish—or join a crabbing adventure

Nature & Wildlife:

Chesapeake Bay Environmental Center (CBEC): A 500‑acre wildlife preserve offering guided hikes, birdwatching, kayaking, and educational programs

Birdwatching & Nature Trails: Spot herons, swans, turtles along trails and boardwalks on Bayfront reserves

Cruises & Historical Sites:

Cruise or Bridge Gazing: Admire the Chesapeake Bay Bridge from the water or waterfront locations—it’s an iconic island landmark
marylandroadtrips.com

Historic Tours: Visit Cray House, Stevensville Post Office, Christ Church (1880), Stevensville Bank, Train Depot, and the Kirwan House & Store, all part of self-guided or docent-led tours on the first Saturday

Food & Drink Experiences:

Wine & Spirits
Cascia/Mark Cascia Vineyards: Tour and taste local wines on a waterfront vineyard
noelleacrossthepond.com

Blackwater Distilling: Sample craft spirits like rum, vodka, and whiskey with casual tours
livinginmaryland.com

Dockside Dining & Tiki Bars: Enjoy steamed crabs, rockfish, cocktails, live music at spots like The Jetty, Bridges, Kentmorr, Libbey’s, and Dirty Dave’s Tiki Bar
visitmaryland.org

Casual Eateries & Coffee:

Waterman Joe Coffee Truck: Early morning favorite for coffee, tea, and protein shakes near exit 37

Dessert First: Dockside coffee and treats in Kent Narrows
proptalk.com

Stevensville Crab Shack: Old-school steamed crabs, platters, and sides for grab-and-go feasts
laxhomes.com

Shopping & Culture:

Stevensville Arts & Entertainment District: Monthly events, antiques, galleries, local shops, and charming cafés

Boutiques & Vintage Finds: Ophiuroidea, DejaBlu Vintage, Anchors & Oars, and local artist galleries for unique beach-themed treasures

Experiences & Tours:

Working Seafood Facility Tour: Witness Maryland watermen and shuckers at a local seafood processing house (e.g., Harris Seafood)

Guided Fishing & Oyster Tours: Charter boat trips for fishing, oyster harvesting, or bow-fishing adventures .

Watermen’s Heritage Trail: Learn about Chesapeake Bay’s watermen with monuments, boat basins, and heritage signage
The vacation home is air-conditioned and features a kitchen and 2.5 bathrooms, and there's space to spread out with 4 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a coffee maker, and an ironing board.

Similar properties

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Onsite parking options include a garage

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Smart TV

Outdoor areas

  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Service animals only (pets not 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.
  • Handrails in stairways
  • Hardwood flooring in public areas
  • Thin carpet in public areas
  • Upper floors accessible by stairs only
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near an outlet shopping mall
  • Near the marina

Things to do

  • Billiards/pool table
  • Birdwatching nearby
  • Fishing nearby
  • Golfing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Winery tours nearby

Safety features

  • No carbon monoxide detector or gas appliances (host has indicated there are no carbon monoxide detectors or gas appliances on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Deadbolt lock

General

  • Garden
  • Unit size: 2,000 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 18

Check-out

Check-out before 11:00 AM
Contactless check-out available

Special check-in instructions

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

Check-out instructions

The host requires you complete the following before checking out:
Gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights
Used towels can be gathered and placed on laundry room on floor.
Failure to complete these may result in a negative review from the host.

Pets

  • Service animals exempt from fees

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 are no carbon monoxide detectors or gas appliances on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a first aid kit and a deadbolt lock
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: 18

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 smoke detector, a first aid kit, and a deadbolt lock.

Additional information about polices, regulations, and more:

  • There are no elevators.

Frequently asked questions

What is there to do within easy reach of this vacation home?

This vacation home is located in Chester, close to Matapeake State Park, Chesapeake Bay Environmental Center, and Love Point State Park. You'll also find Chesapeake Bay and Paul Reed Smith Guitars within a short drive.

Will I be able to park at this vacation home?

Yes, there is a garage.

Is this vacation home associated with 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.

What amenities will couples enjoy at Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails?

Couples staying at this vacation home will appreciate amenities like a kitchen and a smart TV as well as a garden.

Are there hot tubs at Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails?

No, there isn't a spa tub at this vacation home.

Does this vacation home include breakfast service?

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 though service animals are welcome.

Does this vacation home have connecting rooms?

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

Where is the closest airport to this vacation home?

The closest major airport to this vacation home is Easton, MD (ESN-Easton - Newnam), which is 24 mi away (28 minutes by car). Another top airport is Baltimore Washington Intl. Airport (BWI), which is around 24.6 mi away.

Can I book a room with a balcony at Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails?

No, there aren't any accommodations with balconies at Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails.