Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails | House in Chester

10.0 (1 Review) |   Pet Friendly   4 Bedrooms  2 Bathrooms  9 Guests
Chester House | Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails

4 Bedroom House in Chester

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

Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails is located in Chester. Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails provides accommodation, featuring Parking, Pet Friendly, Security/Safety, among other amenities. This House features Parking, Pet Friendly, Security/Safety, to make your stay a comfortable one.

Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails has 4 Bedrooms , 2 Bathrooms, and max occupancy of 9 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Chester has interesting places to visit. If you want to learn more about the House in Chester, such as places to visit and things to do nearby, you can check below to learn more.

Show more
OneKey Logos

This Property is OneKey Eligible

Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.

JOIN TODAY

Amenities

Air Conditioner
Parking
Pet Friendly
TV
Balcony/Terrace
Security/Safety
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
  • Heating
Bathrooms
  • Bathtub or shower
  • 2+ bathrooms
  • Toilet paper
  • Hair dryer
  • Soap
  • Towels provided
Bedroom
  • Bed sheets provided
  • 4 bedrooms
Kitchen
  • Microwave
  • Stovetop
  • Dishwasher
  • Oven
Laundry
  • Laundry facilities
  • Washing machine and dryer
Parking
  • Onsite parking
Pet Friendly
  • Pet friendly
  • Welcoming cats and dogs only
  • 2 total pets
Accessibility
  • No elevator (single level property)
  • Smoke-free property
  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
Activities
  • Marina nearby
  • Winery tours nearby
  • Kayaking nearby
  • Birdwatching nearby
  • Golf nearby
  • Fishing nearby
  • Power boating nearby
Entertainment
  • Smart TV
General
  • Unit size: 2000 sq ft (186 sq m)
  • English
  • Near outlet shopping
Internet
  • WiFi available
Outdoors
  • Garden
Security/Safety
  • No carbon monoxide detector (host has indicated there is no carbon monoxide detector or gas appliances on the property)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)

Policies

Check-in
Check-in time starts at 4:00 pm minimum check-in age: 18
Check-out
Check-out before 11:00 am
Child Policy
Children are welcome.
Event Policy
Events allowed: family gatherings, birthday parties, weddings;maximum event attendees: 20
Pet Policy
2 total pets pets allowed service animals are welcome, and are exempt from fees welcoming dogs and cats only
Smoking Policy
Smoking is not permitted

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 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 parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 20 special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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 House Availability
Nightly rates from:
USD US $620
You will be redirected to  
Hot Deal - It has been viewed 60 times today
Not the right fit? Check out our other properties in Chester
Property Image From US $165
         

|
9.4 (641 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $210
         

|
8.9 (100 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $165
         

10.0 (103 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • TV
Property Image From US $951
         

New
House
  • Parking
  • Pet Friendly
  • Security/Safety
Property Image From US $163
         

10.0 (42 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • TV
Property Image From US $167
         

9.0 (359 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $443
         

10.0 (24 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Property Image From US $179
         

10.0 (4 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Property Image From US $117
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $796
         

New
House
  • Air Conditioner
  • Parking
  • TV
Property Image From US $703
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV