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

New |   Pet Friendly   4 Bedrooms  2 Bathrooms  9 Guests
New Listing
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, 25‑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 325-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
marylandroadtripscom
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
noelleacrossthepondcom
blackwater distilling: sample craft spirits like rum, vodka, and whiskey with casual tours
livinginmarylandcom
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
visitmarylandorg
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
proptalkcom
stevensville crab shack: old-school steamed crabs, platters, and sides for grab-and-go feasts
laxhomescom
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 (eg 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 Kitchen, Air Conditioner, Parking, among other amenities. This House features Kitchen, Air Conditioner, Parking, 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.

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Chester, 21619, United States

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
  • Heating
  • Air conditioning
Bathrooms
  • Soap
  • Bathtub or shower
  • 2+ bathrooms
  • Toilet paper
  • Towels provided
  • Hair dryer
Bedroom
  • Bed sheets provided
  • 4 bedrooms
Kitchen
  • Oven
  • Stovetop
  • Microwave
  • Dishwasher
Laundry
  • Washing machine and dryer
  • Laundry facilities
Parking
  • Onsite parking
Pet Friendly
  • Pet friendly
  • 2 total pets
  • Welcoming cats and dogs only
Accessibility
  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Smoke-free property
  • No elevator (single level property)
Activities
  • Winery tours nearby
  • Golf nearby
  • Birdwatching nearby
  • Marina nearby
  • Fishing nearby
  • Kayaking 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

FAQ's

Is this Chester house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Chester house have a swimming pool?

No, this Chester house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Chester house?

Best-rates for the Chester house starts from $532 per night with includes Pet Friendly, TV, Balcony/Terrace, Bedding/Linens, Wellness Facilities, Child Friendly, Internet, Kitchen, Air Conditioner, Parking, Security/Safety, Fireplace/Heating, Laundry with all other facilities. PetFriendly is committed to making every traveler feel comfortable and have the best stay, whether they are traveling solo, with a date, with a pet, or as a family.

Is Chester house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Chester house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Chester house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Chester house?

Based on the information reported by the owner or manager, the Chester house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Chester house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Chester house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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US $532
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