Entire home·Private host

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

Holiday home in Chester with kitchen

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

Fridge, microwave, oven, stovetop
Smart TV
Smart TV
Exterior
Games room
Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails provides amenities, such as a garden and laundry facilities. Stay connected with free in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathrooms186 sq m

Popular amenities

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

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.

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

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • 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
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near an outlet shopping centre
  • 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

Similar properties

Policies

Check-in

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

Check-out

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

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 to complete the following before checking out:
Gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
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

Pets not allowed (service animals are welcome, and are exempt from fees)

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a first aid kit and a deadlock
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

We should mention

This property does not have any lifts

About the area

Map
Chester, MD

What's nearby

  • Paul Reed Smith Guitars - 4 min drive - 3.5 km
  • Matapeake State Park - 7 min drive - 7.3 km
  • Chesapeake Bay Bridge - 11 min drive - 13.2 km
  • Sandy Point State Park - 14 min drive - 16.3 km
  • U.S. Naval Academy - 25 min drive - 29.1 km

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

Frequently asked questions

Is Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails pet-friendly?

No, only service animals are welcome at the property.

What time is check-in at Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails?

Check-in begins at 4:00 PM.

What time is check-out at Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails?

Checkout is at 11:00 AM.

Where is Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails located?

Situated in Chester, this holiday home is within 6 miles (10 km) of Island Dog Park, Chesapeake Exploration Center and Paul Reed Smith Guitars. Chesapeake Bay and Northern Chesapeake Bay are also within 6 miles (10 km).

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Reviews

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

10

Exceptional

10

Cleanliness

10

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

Reviews

10/10 Excellent

pat l.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a beautiful home with plenty of space for an entire family. I couldn’t have asked for a better process start to finish.
Stayed 2 nights in Oct 2025

10/10 Excellent

Sara N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We stayed at Kim’s place for the weekend as a group of three couples and a baby. The home is brand new and has such a fun living space with a spacious family room, large dining table and kitchen, and even a pool table. Kim was very helpful with providing rental companies that delivered baby gear to the house. The house is also conveniently located and we were able to get ubers to kent narrows which was only about a 10 minute drive. We loved it and will be back again!
Stayed 2 nights in Jul 2025