($304+) Chesapeake, VA to Winston-Salem, NC Movers

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Background image of a moving truck moving from Chesapeake, VA to Winston-Salem, NC

Moving from Chesapeake, VA, to Winston-Salem, NC, runs anywhere from $295 for a DIY rental-truck move of a small home up to $5,980 for full-service movers handling a larger 4 - 5 bedroom household. The two cities sit about 264 miles apart, and a move on this route usually takes 1 to 4 days door to door. Use our moving cost calculator to compare estimates and options for your specific move.

  • Full-service moves for smaller spaces (studio apartments and 1-bedrooms) start around $895, while larger 4 - 5 bedroom relocations can reach $5,980 or more.
  • Moving containers run $906 - $2,742, and renting a moving truck from Budget or U-Haul is the cheapest route at $295 - $735.
  • Safeway Moving (4.9/5 stars) is our top recommendation for a move from Chesapeake, VA, to Winston-Salem, NC. They're known for transparent pricing, with 2-bedroom quotes starting around $1,522 on this route. They also throw in 30 days of free storage and have 24/7 customer support.

Compare moving options from Chesapeake, VA to Winston-Salem, NC

There are 3 main ways to move from Chesapeake to Winston-Salem: full-service movers, moving containers, and rental trucks. Full-service is the most expensive but covers everything from labor to transportation, with a 2-3 bedroom move on this route averaging $1,522 - $4,497. Containers cost roughly 30% less than full-service for the same home size, and rental trucks run about 60% less, though loading is on you with either DIY option. At 264 miles, expect 1 to 4 days in transit no matter which service you choose.

Here is how full-service movers, moving containers, rental trucks, and freight trailers compare on the 264-mile route from Chesapeake to Winston-Salem, broken down by home size:

Home size Full-service movers Moving container Rental truck Freight trailer
Studio / 1 bedroom $895 - $3,491 $906 - $1,550 $295 - $566 $753 - $1,450
2 - 3 bedrooms $1,522 - $4,497 $1,080 - $2,234 $343 - $663 $891 - $1,719
4+ bedrooms $2,034 - $5,980 $1,438 - $2,742 $412 - $735 $1,222 - $2,129

Pricing reflects moveBuddha's monthly dataset of 1,500+ live quotes across our vetted mover network. Last updated September 16, 2026.

Professional
Safeway Moving
star star star star star 4.9 / 5
Read our full Safeway review
Best overall value
Portion to charity
Veteran-owned
Container
Unlimited storage
3 container sizes
10% discount
Rental Truck
Budget Truck Rental
star star star star star 4.3 / 5
Read our full Budget review
Affordable pricing
Online estimates
Several discounts
Freight
MovingYourself
star star star star star 4.5 / 5
Read our full MovingYourself review
Fast delivery
Nationwide
100+ miles moves

Full-service moving costs from Chesapeake, VA to Winston-Salem, NC

For the 264-mile move from Chesapeake, Virginia, to Winston-Salem, North Carolina, full-service movers cost between $895 and $5,980. A long-distance moving company takes care of loading, hauling, and unloading. For an added cost of $288 - $1,920 (1 - 5+ bedrooms), crews will pack your boxes. The weight of your shipment and the mileage between the two cities are what drive your final cost. For scale, local movers in Chesapeake generally start around $290 plus $125 per hour, per mover.

Here's a breakdown of full-service moving costs by home size from Chesapeake to Winston-Salem:

  • Studio apartment / 1 bedroom: $895 - $3,491
  • 2 - 3 bedrooms: $1,522 - $4,497
  • 4+ bedrooms: $2,034 - $5,980

Packing, storage, shuttle fees, and added coverage can stack on top of the base price. See the full add-ons and specialty services table below for what each runs from Chesapeake to Winston-Salem.

The following are real quotes requested by moveBuddha readers in the past 90 days for moves from Virginia to North Carolina. Prices are based on 1,500+ monthly pricing data points collected across our network of vetted movers and updated monthly.

Pro tip: Avoiding peak moving season dates (May - September) is one of the easiest ways to reduce costs. Off-season moves typically come with lower pricing and more room to negotiate since movers have fewer bookings.

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Specialty moving services from Chesapeake, VA to Winston-Salem, NC

Specialty needs vary by market — 100% of Chesapeake movers offer storage-in-transit, compared to 85% nationally. In Winston-Salem, 90% of movers offer the same service.

Service When you need it Typical cost
Full packingFull crew packing100% of local movers$480 - $4,800
Storage in transitNew place not ready100% of local movers85% nationallyTop pick: TWO MEN AND A TRUCK$192 - $1,152/mo
Shuttle feeTruck can't reach door$288 - $2,304
Full-value protectionMore than $0.60/lb coverage43% of local movers$300 - $600 (1% - 2% of value)
Small movesUnder ~2,000 lbs62% of local movers$960 - $2,880
Office / commercialWorkplace relocation$2,400 - $9,600
Car shippingSecond vehicle$719 - $1,366
Antiques & fine artFragile, high-value items48% of local movers46% nationallyTop pick: Atlantic Beach Movers$960 - $2,400
PianoAny piano type81% of local movers71% nationallyTop pick: TWO MEN AND A TRUCK$768 - $3,360
Pool tableDisassembly & re-leveling29% of local movers$288 - $1,440
Hot tubHeavy, needs disconnect24% of local movers22% nationallyTop pick: Apple Moving $624 - $1,920
Wine collectionClimate-controlled transport$288 - $14,400+
Pet relocationGround, air, or concierge$288 - $3,360+

What are the best full-service movers from Chesapeake to Winston-Salem?

North Carolina Movers Association membership is a quick way to confirm a mover is legitimate in North Carolina, on top of the picks below.

  1. Safeway Moving (4.9/5 stars): Safeway Moving is the best overall value on this route. Flat-rate pricing means no surprise charges on moving day, and their support team is consistently rated among the most responsive in the industry.
  2. American Van Lines (4.9/5 stars): American Van Lines is the most experienced mover here, with 30+ years in business since 1995. AVL is one of the few national carriers that uses full-time in-house crews instead of contracted labor.
  3. Allied Van Lines (4.2/5 stars): Allied Van Lines is best for contents coverage, with fragile-only packing, 24/7 shipment monitoring, and an optional full-value protection plan that covers damage, loss, and breakage.

How much do local movers cost in Chesapeake, VA?

Based on recent quotes for this route, a 2-bedroom move from Chesapeake to Winston-Salem with a local mover averages $1,598 - $4,721. For moves under 500 miles, local moving companies in Chesapeake, VA can be a practical and cost-effective alternative to national carriers. Many price shorter moves using hourly or regional rates that may come in lower overall, with leaner operations and tighter service areas often translating to more flexible scheduling and a more personalized experience.

Keep in mind that not every local mover is authorized for moves that cross city or state lines. Always confirm interstate licensing and proper insurance before booking.

TWO MEN AND A TRUCK (4.56/5 stars) is the top overall local mover in Chesapeake, ranked #10 in Virginia, based on our analysis of feedback from 258 customers, 79.8% of which is positive.

Address: 4007 Seaboard Ct #7, Portsmouth, VA, 23701 | Founded: 2017

Moving container costs from Chesapeake, VA to Winston-Salem, NC

Moving containers from Chesapeake, Virginia, to Winston-Salem, North Carolina, cost between $906 and $2,742. You load everything on your own schedule (U-Haul gives you 3 days and PODS gives you 30). When you're ready, the company takes care of getting the container from point A to point B. Need more time than that? Extra storage in Chesapeake typically runs around $100/month.

Take a look at moving container pricing by home size from Chesapeake to Winston-Salem:

  • Studio apartment / 1 bedroom: $906 - $1,550
  • 2 - 3 bedrooms: $1,080 - $2,234
  • 4+ bedrooms: $1,438 - $2,742

What other costs come with moving containers?

  • Access: Most major container brands operate in both Chesapeake, VA and Winston-Salem, NC. Still, double-check that a nearby facility is available if you need to access your belongings before delivery.
  • Moving labor: Because containers are self-loaded, many customers hire hourly help. Two movers for about 5 hours typically cost around $672 in Chesapeake, VA, according to moveBuddha data. Compare the best labor-only movers nationwide
  • Storage: Monthly container rental after the first 30 days averages $72 for small units (7 - 8 feet) and about $144 for larger ones (12 - 16 feet).
  • Added contents protection: For more coverage beyond the standard minimum, full-value protection is the typical upgrade, generally 1% - 2% of your declared shipment value. On a $50,000 household, that's roughly $500 - $1,000 as a one-time fee.

Every price below reflects an actual quote from a moveBuddha reader planning a Virginia to North Carolina move in the past 90 days. Our pricing data is drawn from 1,500+ monthly data points across our vetted mover network and refreshed every month.

Pro tip: Before ordering moving containers, take a careful inventory of everything you're moving. A typical 1-bedroom home weighs around 3,000 pounds and fits in a single container starting at $906. Underestimating and needing 1 - 2 additional containers can push your total to $1,080 - $2,234, so getting your count right upfront saves you from a costly surprise.

What are the best moving containers Chesapeake to Winston-Salem?

  1. Units Moving and Portable Storage (4.3/5 stars)
  2. U-Pack (5.0/5 stars)
  3. MovingYourself (5.0/5 stars)

Want a hand without paying for full service? A container or truck move does not mean doing all the heavy lifting yourself. You can hire a labor-only crew in Chesapeake to load and unload while you handle the drive, then book full help later if you change your mind. Three top-rated local crews for labor-only help in Chesapeake:

  • TWO MEN AND A TRUCK (4.4/5), 9 years in business
  • Atlantic Beach Movers (4.7/5), 20 years in business
  • Tidal Town Moving (4.9/5), 6 years in business

Moving truck rental costs from Chesapeake, VA to Winston-Salem, NC

Truck rentals from Chesapeake, Virginia, to Winston-Salem, North Carolina, range from $295 - $735 for the 264-mile drive. You handle the loading, driving, and unloading yourself, plus these extra costs:

  • Fuel for the drive: $81 - $92
  • Daily insurance: $29/day
  • Equipment rentals: $7 - $19
  • Chesapeake daily rental rate: $19 - $39
  • Per-mile fee beyond your free allowance: $0.69 - $0.89
Home sizeTypical truck size
Studio / 1 bedroom10 - 12 ft
2 - 3 bedrooms15 - 17 ft
4+ bedrooms20 - 26 ft (typically requires diesel)

These are typical moving truck rental costs from Chesapeake to Winston-Salem based on home size:

  • Studio apartment / 1 bedroom: $295 - $566
  • 2 - 3 bedrooms: $343 - $663
  • 4+ bedrooms: $412 - $735

Pro tip: The base rate of $295 - $735 is just the starting point for a rental truck move from Chesapeake to Winston-Salem. Fuel ($81 - $92) , lodging at around $144/night, meals, and equipment rentals are all on top of that. Factor in an extra $600 - $1,200 to get a realistic picture of what the move will actually cost.

What other costs come with rental trucks?

  • Additional insurance: Supplemental coverage typically averages around $30 per day.
  • Lodging: Budget around $144 per night if your drive requires an overnight stop. Typically, you'll make 1 - 3 overnight stops, depending on move distance.
  • Moving labor: Bringing in professional loading help in Chesapeake, Virginia, usually costs about $672 for 2 movers and 5 hours of labor.
  • Gas: Fuel for the 264-mile drive falls between $81 and $92, depending on whether your truck runs on gas or diesel.
  • Equipment: Appliance dollies, moving pads, and vehicle trailers are easy to overlook but can add between $48 and $288 to your total.

What are the best moving truck rentals from Chesapeake to Winston-Salem?

  1. Budget Truck Rental (4.3/5 stars)
  2. Penske Truck Rental (4.0/5 stars)
  3. U-Haul Truck Rental (4.2/5 stars)

The best truck rental companies for this route, based on moveBuddha's ratings.

Freight trailer costs from Chesapeake, VA to Winston-Salem, NC

Freight trailers are well suited for larger moves from Chesapeake, Virginia, to Winston-Salem, North Carolina, when you want to do the loading yourself without having to drive a massive vehicle. The trailer is delivered, you pack it up, and the carrier handles the long haul.

What sets freight trailers apart is the pay-for-what-you-use pricing model. Each additional foot of trailer space you occupy adds to the cost. Overall pricing for a move of this size and distance typically lands around $891 and $1,719.

Take a look at freight trailer costs based on home size for moves from Chesapeake to Winston-Salem:

  • Studio apartment / 1 bedroom: $753 - $1,450
  • 2 - 3 bedrooms: $891 - $1,719
  • 4+ bedrooms: $1,222 - $2,129

Pro tip: Freight trailers offer generous space but reward good packing strategy. The 4-foot ramp can be challenging for large or heavy pieces, and using the full 8-foot height takes careful stacking. Because you're billed by the linear foot, maximizing vertical space keeps your costs lower.

What other costs come with freight trailers?

  • Demand cycles: Trailer costs climb during peak moving season, especially from mid-May through mid-September when demand is at its highest.
  • More space: You're billed only for the linear feet you use, but underestimating your inventory means paying for extra space, typically around $72 - $144 more per foot.
  • Moving labor: Freight trailers don't include loading crews. Two movers in Chesapeake, Virginia, for about five hours typically runs $672.

What are the best freight companies from Chesapeake to Winston-Salem?

  1. MovingYourself (5/5 stars): MovingYourself is best for large moves. Primarily known as a top moving container option for its DIY hybrid model where customers load and the company drives, MovingYourself also functions as a strong freight option thanks to its 53-foot trucks and pay-only-for-the-space-you-use pricing.
  2. U-Pack (5/5 stars): U-Pack is the best value freight trailer on this list. Best known for its container service, U-Pack also runs a top-notch freight trailer operation with the same no-deposit, pay-by-the-foot approach that keeps overall costs lower than most freight competitors.
  3. Sysco Hampton Roads, Inc. (4.58/5 stars): Sysco Hampton Roads, Inc. is the best locally owned freight company on this list. Locally owned facilities and accessible live support staff make scheduling and route coordination easier on local-area routes than what most national freight providers can offer.

Pro tip: If speed matters on your move from Chesapeake to Winston-Salem, freight trailers are one of the fastest interstate options available, second only to renting a truck and driving it yourself. The tradeoff is that freight works best when you're ready to receive your belongings on the other end. If your timeline is tight on the receiving side or you need a short storage buffer, a moving container might be a better fit.

Cost of living: Chesapeake, VA vs Winston-Salem, NC

The price of the move is only part of the picture. Here is how everyday costs compare once you are settled in Winston-Salem, side by side with Chesapeake on housing, income, and taxes.

Measure Chesapeake, VA Winston-Salem, NC
Cost of living index10484
Average rent$1,800/mo$1,300/mo
Median home value$359,218$208,184
Average income$94,189/yr$57,673/yr
Unemployment rate5.0%5.2%
State income taxUp to 5.75%Up to 4.5%
Walkability score21/10022/100
Safety index70.88/10067.33/100
Air qualityGoodGood

Cost of living index is relative to the U.S. average of 100. Figures reflect the latest available city and state data.

Moving the reverse route? We've got you covered with our Winston-Salem, NC to Chesapeake, VA guide.

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Our take

The 264-mile move from Chesapeake, VA, to Winston-Salem, NC, costs between $895 and $5,980 with full-service movers, $906 - $2,742 with a moving container, and $295 - $735 for a rental truck. Your budget and how much heavy lifting you want to do are the two biggest factors in choosing the right option. If you go with full-service movers, Safeway Moving is our top recommendation, with transparent flat-rate pricing starting around $1,522 for a 2-bedroom move, 30 days of free storage, and 24/7 customer support.

Beyond the move itself, people who've relocated to Winston-Salem tend to point to no traffic and friendly people, though summertime humidity and allergy-inducing pollen come up as common complaints. Major employers in the area include Wake Forest Baptist Medical Center and Novant Health.

FAQs: Moving from Chesapeake, VA, to Winston-Salem, NC

What are the best neighborhoods in Winston-Salem?

For families, Sherwood Forest, Ardmore, and Buena Vista are worth a look in Winston-Salem. If you're moving solo or without kids, West End, Ardmore, and Buena Vista tend to be popular picks instead.

What is the cheapest way to move from Chesapeake, VA to Winston-Salem, NC?

Renting a moving truck is almost always the most affordable option, since you handle the loading, driving, and unloading yourself. A 2-bedroom rental truck move on this route averages $343 - $663. See our cheapest truck rental recommendations for the lowest available rates on your DIY move.

Is Winston-Salem a safe place to live?

Winston-Salem has a safety index of 67.33 out of 100 and a crime index of 32.67, compared to 70.88 and 25.0 in Chesapeake. Neither figure tells the whole story on its own, so it's worth digging into specific neighborhoods before you commit to an address.

What size moving truck do I need for this route?

Rental trucks generally range from 10 to 26 feet. A 15- to 17-foot truck covers most 2-bedroom moves, while a smaller 10- to 12-foot truck works for a studio or 1-bedroom. Homes with 3 or more bedrooms usually need a 20- to 26-foot truck, and anything that size typically runs on diesel rather than gas.

What is the best time of year to move from Chesapeake, VA to Winston-Salem, NC?

Aim for a move between October and March, when demand drops and rates tend to be lower across all service types. Peak season runs mid-May through mid-September, and weekends and month-end dates are pricier regardless of season. North Carolina also has a hurricane season running June through November, worth factoring into your timing if you have flexibility. A midweek, mid-month date outside peak season is your best bet for saving money.

What percentage of Chesapeake movers handle specialty items like pianos or antiques?

About 81% of movers in Chesapeake handle piano moves, and 48% handle antiques and fine art, compared to 71% and 46% nationally.