Dumpster Rental in Windsor, VA
Fast, flat-rate roll-off dumpster rental for Windsor homes, contractors and businesses — delivered from our nearby Portsmouth yard, often the same day.
Your Windsor Dumpster Rental Company
Portsmouth Dumpster Rental Group delivers roll-off dumpsters out to Windsor, the small Isle of Wight County town sitting on the US-460 corridor between Suffolk and Smithfield. Our flat-rate pricing means delivery, pickup, and disposal are all baked into one number. Whether it is a farmhouse cleanout or a renovation off Windsor Boulevard, we bring the right container to this rural stretch.
Windsor is a compact railroad-and-highway town surrounded by the farmland and timberland of western Isle of Wight County. Its housing is a mix of older homes near the center along Windsor Boulevard, scattered rural farmhouses, and a few newer subdivisions on the edges of town. The terrain is flat, open coastal plain with farm fields and wooded parcels, and the Blackwater River basin lies nearby. Big rural lots and long driveways make it easy to place 30- and 40-yard roll-offs for barn, outbuilding, and estate cleanouts. We take the bulky farm and renovation debris that small-town curbside pickup cannot handle.
Call (757) 337-2599

Dumpster Delivery Across Windsor
We deliver to homes and businesses throughout Windsor, from established blocks to newer developments. A few of the areas we serve:
- Downtown Windsor
- Holland Meadows
- Shiloh
- Church Street
- Duke Street
- Carrsville Highway corridor
Don't see your street? We cover all of Windsor — just give us a call.
Near the Places That Make Windsor Home
Being a local company means we know Windsor well. We deliver near landmarks and spots residents know, including:
- Windsor Town Hall
- Windsor High School
- Windsor Boulevard (US-460)
- Courthouse Highway (SR-258)
- Georgie D. Tyler Middle School
- Windsor Town Center
Getting to you: Drivers run the VA-164 Western Freeway to US-58, then cut over to US-460 (Windsor Boulevard) and head west straight into Windsor and the surrounding country roads.

Full-Service Dumpster Rental for Windsor
Whatever your Windsor project — farmhouse and outbuilding cleanouts — we have the right container and an honest flat price.
Dumpster Sizes Available in Windsor
From compact 10-yard bins to 30-yard construction containers — delivered to Windsor and placed on protective boards.
| Dumpster | Volume | Holds | Best For | Weight Incl. |
|---|---|---|---|---|
| 10 Yard | 10 yd³ | ≈ 3 pickup loads | Small cleanouts, bathroom remodels, yard debris | 2 tons |
| 15 Yard | 15 yd³ | ≈ 4–5 pickup loads | Flooring, roofing, medium renovations | 2–3 tons |
| 20 Yard | 20 yd³ | ≈ 6 pickup loads | Large remodels, whole-room cleanouts, decking | 3 tons |
| 30 Yard | 30 yd³ | ≈ 9 pickup loads | New construction, major demolition, commercial | 4 tons |

Why Windsor Chooses Portsmouth Dumpster Rental Group
- Local knowledge. We know Portsmouth's permit rules, tight streets and disposal facilities — so drop-off and pickup go smoothly.
- On-time, every time. Same-day and next-day delivery windows we actually keep, because your project can't wait.
- Honest flat rates. One transparent price covers delivery, pickup, rental period and disposal up to your weight limit.
- Driveway-friendly. We protect your surfaces with boards and place the dumpster exactly where you need it.
Windsor Dumpster Rental FAQs
Do you deliver dumpsters to Windsor, VA?
Yes — Windsor is one of our core service areas. Located west of Portsmouth along the US-460 corridor, about 35 minutes, so we deliver quickly and reliably, often with same-day availability. Call (757) 337-2599 to schedule.
How much does a dumpster rental cost in Windsor?
Rentals in Windsor are flat-rate, typically $325–$575 depending on the size, rental length and debris type. Your quote includes delivery, pickup, the rental period and disposal up to the weight limit — no hidden fees. We'll give you an exact price when you call.
Will a large dumpster fit on a Windsor farm property?
Almost always. Windsor's rural lots have long driveways and open yard space, so a 30- or 40-yard roll-off fits comfortably for barn, shed, and whole-property cleanouts. The main thing we check is ground firmness, since a fully loaded truck needs stable footing on dirt or gravel. Pick a level spot near the road or a solid drive, and we will set the container exactly where you want it to work.
What size dumpster should I rent in Windsor?
It depends on your project. Small cleanouts and heavy debris suit a 10-yard; medium remodels a 15-yard; large renovations and cleanouts a 20-yard; and construction or demolition a 30-yard. Describe your Windsor project and we'll size it right.
We Also Serve These Hampton Roads Neighborhoods
Get a Dumpster Delivered in Windsor Today
Skip the online forms — one quick call gets you a flat quote and a delivery time that works for your Windsor project, often the same day.
(757) 337-2599