Maryland / Local rental guide

Dumpster rental
in Chester.

Chester has no town hall, so Queen Anne's County sets the rules, and SHA District 2 controls MD 18, MD 552 and US 50/301. No County dumpster permit was found, so keep the bin on your own driveway. Any company collecting refuse for you needs the County's annual collection permit. The Batts Neck and Grasonville transfer stations take only a 55-gallon drum of remodel debris a week and turn away contractors, so for real renovation or storm cleanup a roll-off is the practical route off the island.

Sources checked November 14, 2026 · Guide updated November 14, 2026
Independent research · No paid placements · Research method

The first decision in Chester

Start with an eligible hauler.

Yard Works Plus (Easton) is the one to price against: it publishes flat rates of $449, $649 and $699 for 10-, 20- and 30-yard bins with 14 days and 1 or 3 tons included. Complete Rolloff Services (Kennedyville) publishes no prices but adds a 15-yard and a 40-yard box, also includes 14 days, and states its extra-day rate ($4 a day) and mattress and tire charges. Neither publishes an overweight rate, so get that in writing.

Your local checklist

Check your street sign before delivery: green means a County road, blue means a private road where your association decides, and a numbered route like MD 18 or MD 552 means SHA District 2.
Ask the roll-off company to confirm it holds a current Queen Anne's County solid waste collection permit from the Director of Public Works.
On a waterfront or low-lying Chester lot, have the bin set on boards on firm ground away from the shoreline and keep debris inside it, and tarp it when storms are forecast.

Plan a rental in Chester

Published details, side by side

2 researched options.

Listings are an editorial starting point, not a complete market ranking. Supplier-published amounts are not Dumpsterly quotes. Confirm address eligibility, material acceptance, dates and the full delivered total.

01 / SOURCE-CHECKED LISTING

Complete Rolloff Services

Published sizes: 10-yard (12 x 8 x 5 ft), 15-yard (15 x 8 x 4 ft), 20-yard (listed as 15 x 8 x 4 ft, the same as the 15-yard, apparently a copy error), 30-yard (21 x 8 x 5 ft) and 40-yard (21 x 8 x 7 ft)
Rental & weight terms: The home page says rentals include 14 days, then $4 a day; mattresses $30 each and tires from $15 each. Included weight and overweight charges are not published; request a written quote.
Price basis: Not published (the page advertises flat-rate local pricing with no long-distance delivery fee); quote by phone, 443-480-9623.

Family-owned roll-off company based at 10946 Kennedyville Road, Kennedyville, MD 21645 (Kent County). Its Kent Island page names Chester, saying it often offers next-day and sometimes same-day service to Stevensville, Chester and Romancoke. It is the only one of the two with a 40-yard box for a large renovation or teardown. It does not accept tires, vehicle or marine batteries, flammables, or liquid paint and fuels.

Sources: [15] · [16]Visit supplier website Direct link · No referral tracking

02 / SOURCE-CHECKED LISTING

Yard Works Plus

Published sizes: 10-yard (12 x 8 x 3.5 ft), 20-yard (16 x 8 x 6 ft) and 30-yard (22 x 8 x 6 ft)
Rental & weight terms: Flat rate includes delivery, pickup and a 14-day rental; included disposal weight is 1 ton for the 10-yard and 3 tons for the 20- and 30-yard. Overweight and extra-day charges are not published; call for longer rentals and request a written quote.
Price basis: Published on the Kent Island page: $449 (10-yard), $649 (20-yard), $699 (30-yard).

Family-owned Eastern Shore roll-off company dispatching from 28769 Llandaff Road, Easton, MD 21601, and saying it has served the Shore since 1998. Its Kent Island page names Chester, Stevensville and Kent Narrows as regular delivery areas. The page says private-property placement needs no permit and that public-road placement goes through the County Roads Division; it also notes HOA rules may apply. Confirm overage terms before booking. Phone 410-820-6414.

Sources: [17] · [18]Visit supplier website Direct link · No referral tracking

Get the missing numbers in writing.

Ask for delivery, pickup, included tons and days, per-ton overage, extra-day charges, fuel, tax, prohibited-item fees, swaps and blocked-trip charges. “Quote required” means the reviewed source did not establish a usable fixed total.

Compare the quotes you receive →

Chester dumpster: keep it on your lot; County right-of-way work needs a Roads Division permit; US 50/301, MD 18 and MD 552 are SHA District 2

Because Chester is unincorporated, Queen Anne's County governs a roll-off here. No County permit written specifically for a dumpster on a County road was found. The County's Public Works FAQ says construction, culvert installation or landscape changes in the County right-of-way need a Roads Division permit with a $500 review fee, and the Roads Division page offers only an entrance permit application; neither mentions containers. That is not the same as saying no permit is needed, so keep the bin on your own driveway or lot, and if it truly must sit on a County road call the Roads Division (410-758-0920, 312 Safety Drive, Centreville) first. Green street signs mark County roads and blue signs mark private roads, which are common in Chester's waterfront subdivisions; ask your association before placing a bin on a private road. Homes fronting a numbered route such as MD 18 (Main Street) or MD 552 (Dominion Road) are on State roads: the State Highway Administration requires a permit for activities in the State right-of-way, and Queen Anne's County is in its District 2, 615 Morgnec Road, Chestertown (410-810-3244).

Read the local government source

Open local permit instructions

What matters locally

Batts Neck and Grasonville transfer stations take household loads on a ticket, not contractor debris

Queen Anne's County runs five transfer stations for residents and property owners, all open 8 a.m. to 4 p.m. on set days. The two nearest Chester are Batts Neck, 422 Batts Neck Road, Stevensville (Wednesday, Friday, Saturday) and Grasonville, 401 Gravel Run Road, across Kent Narrows (Tuesday, Thursday, Saturday). You pay with a ticket book: 15 tickets for $60, one ticket per car, truck or trailer, with extra tickets for each tire (car and light-truck tires up to 17 inches, rims off) and ten extra for a refrigerator, freezer or other appliance with CFCs. Furniture and mattresses are accepted. Ticket books are for residential waste only; commercial users and contractors cannot use the stations. The Safeway at Routes 50 and 552 in Chester is one of the ticket-book outlets.

Check the source

Remodel debris: one 55-gallon drum a week at a transfer station, larger loads go off-island

The County's solid waste FAQ limits residents to one 55-gallon drum of construction and demolition debris a week at a transfer station. Larger loads go to private R.B. Baker in Queenstown or the Midshore Regional Landfill in Ridgely, Caroline County, and brick and concrete can go to Dependable Sand, Stone and Recycling in Wye Mills. Brush must be under 4 inches thick and 6 feet long, and residents may bring three pallets a week. For anything bigger than a drum's worth of drywall, flooring or decking, a roll-off is usually simpler than repeated trips off Kent Island.

Check the source

Before you book

Questions about renting in Chester.

Does Queen Anne's County make Chester residents use a particular hauler for a roll-off?

No County franchise or County curbside service was found on the County's solid waste pages. What the County Code does require is that every refuse collector apply to the Director of Public Works for an annual solid waste collection permit, issued after its equipment is inspected. The Code's definition of rubbish leaves out building and construction debris, and its small-container rules are written for household garbage set out for collection, so keep food waste out of an open roll-off.

Sources: [3] · [1] · [2] · [11]

Can I take my remodel debris to the Batts Neck transfer station instead of renting a dumpster?

Only in small amounts. The County lets residents bring one 55-gallon drum of construction and demolition debris a week to a transfer station, paid with tickets from a $60 book of 15, and contractors cannot use the stations at all. Larger loads have to go to R.B. Baker in Queenstown or the Midshore Regional Landfill in Ridgely, so for a kitchen, deck or flood cleanout a roll-off usually costs less time.

Sources: [7] · [6] · [5]

Check the right jurisdiction

More guides in Queen Anne's County, Maryland.

Working in another community? Check its own placement rules, disposal options and supplier coverage.

Sources & checked dates

These are supplier and government sources, not customer reviews. Published terms can change. Where a source is incomplete, we leave the detail unknown. Street guidance is a starting point; the responsible local authority decides what your address needs.

Flag a correction →

FIND YOUR DUMPSTER

Rent the right
dumpster.

Find a size starting point, placement guidance and supplier options for your Chester project.

Find my dumpster Free to use. No signup or sales calls.

ChesterYour project. Your plan.Find my dumpster