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

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

A modern kitchen with white cabinetry, a central island, and a dining area with a bench.
A staircase with dark wood steps and a black balustrade, leading to an upper floor.
A modern living room with a sectional sofa, a small coffee table, and a dining area with a white table and chairs.
A modern kitchen with white cabinets, stainless steel appliances, and a central island with stools.
A two-story building with a yellow and white facade, a blue door, and a sign that reads "Avery's Bar & Grill."

Reviews

9.4 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Garage parking available
    Enjoy the convenience of garage parking - a rare offering in the area.
4 bedrooms2+ bathroomsSleeps 9

Popular amenities

  • Garage parking available
  • Kitchen
  • Washer
  • Air conditioning
  • Garden
  • Free WiFi

Explore the area

View in a map
Chester, MD
  • Place, Island Dog Park
    ‪4 min drive‬
  • Place, Paul Reed Smith Guitars
    ‪5 min drive‬
  • Place, Chesapeake Exploration Center
    ‪7 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪60 min drive‬

Rooms & beds

4 bedrooms (sleeps 9)

Bedroom 1- Master bedroom

1 King Bed

Bedroom 2

1 Large Twin Bunk Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Toilet · Hair dryer

Bathroom 2

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet

Bathroom 3

Soap · Toilet

Spaces

Kitchen
Garden

About this property

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
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed, service animals permitted
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Smoking

Smoking is not permitted

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.

Important information

You need to know

Property # 4667874
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

About the neighborhood

Chester

Chester is home to this vacation home. Shoppers can check out Annapolis City Dock, while everyone can enjoy the natural beauty of Chesapeake Bay and Sandy Point State Park. Paul Reed Smith Guitars and Rufus M and Loraine Hall Todd Performing Arts Center are also worth visiting. Looking to get your feet wet? Kayaking, motor boating and fishing adventures can be found near the property.
Map
Chester, MD

What's nearby

  • Island Dog Park - 4 min drive - 3.8 km
  • Paul Reed Smith Guitars - 5 min drive - 4.9 km
  • Chesapeake Exploration Center - 7 min drive - 5.6 km
  • Matapeake State Park - 8 min drive - 9.0 km
  • Love Point State Park - 9 min drive - 10.3 km

Getting around

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

Restaurants

  • ‪Chick-fil-A - ‬4 min drive
  • ‪McDonald's - ‬5 min drive
  • ‪McDonald's - ‬8 min drive
  • ‪Starbucks - ‬5 min drive
  • ‪Hardee's - ‬5 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.

How much does it cost to stay at Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails?

As of Aug 29, 2026, prices found for a 1-night stay for 2 adults at Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails on Aug 31, 2026 start from $766, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available 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?

Check-out is at 11:00 AM.

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

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

About the host

Hosted by Kim Newkirk

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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