2019 Heartland Pioneer
$90 a night listed, rated 5.0 from 4 reviews
Travel trailer · Towable · Sleeps 4
Pick up in Chesapeake
Delivery up to 100 mi
$90 / night listed, before fees
On Nov 8, 2026, 6 RVs were listed within 25 miles of Windsor across Outdoorsy. Half of listed rates fell between $100 and $115 per night, before fees. You book with the listing site.
Dates are optional. Without dates you can browse every listing; add them to see each rental's calendar.
Chosen from listing facts (rating, reviews, size, delivery, pet policy), never by commission.
$90 a night listed, rated 5.0 from 4 reviews
Travel trailer · Towable · Sleeps 4
Pick up in Chesapeake
Delivery up to 100 mi
$90 / night listed, before fees
Owner delivers up to 50 mi, so no towing yourself
Travel trailer · Towable · Sleeps 10
Pick up in Newport News
Delivery up to 50 mi · Pets allowed
$135 / night listed, before fees
Listing allows pets; sleeps 8
Travel trailer · Towable · Sleeps 8
Pick up in Chesapeake
Delivery up to 50 mi · Pets allowed
$105 / night listed, before fees
Half of listed nightly rates near Windsor fall between $100 and $115. 67% of listings add a cleaning fee (median $75); 100% ask for a refundable deposit (median $500), which you get back and is not a rental cost.
| Vehicle type | Typical listed rate / night | Listed | Drive or tow | Search |
|---|---|---|---|---|
| Travel trailer | $107 ($100–$115) | 6 | Tow | See 6 travel trailers near Windsor |
Listings from Outdoorsy (6) within 25 miles (straight-line) of Windsor, read Nov 8, 2026. Typical rate is the median listed nightly rate, with the middle half in brackets. Rates are before cleaning, mileage, generator and service fees and taxes. Counts are listings, not availability. RV rental cost guide
6 rentals are listed within 25 miles of Windsor, so here are 12 more from 25 to 60 miles away (straight-line). They aren't counted in the figures on this page.
25 mi from Windsor
Travel trailer · Towable · Sleeps 6
Pick up in Newport News
Delivery up to 45 mi · Pets allowed
$124 / night listed, before fees
28 mi from Windsor
Travel trailer · Towable · Sleeps 6
Pick up in Chesapeake
Delivery up to 150 mi · Pets allowed
$110 / night listed, before fees
29 mi from Windsor
Travel trailer · Towable · Sleeps 8
Pick up in Norfolk
Delivery up to 150 mi · Pets allowed
$125 / night listed, before fees
29 mi from Windsor
Fifth wheel · Towable · Sleeps 5
Pick up in Norfolk
Delivery up to 50 mi
$159 / night listed, before fees
29 mi from Windsor
Class C motorhome · Drivable · Sleeps 7
Pick up in Norfolk
Delivery up to 50 mi · Pets allowed
$199 / night listed, before fees
31 mi from Windsor
Class C motorhome · Drivable · Sleeps 8
Pick up in Virginia Beach
Delivery up to 100 mi
$285 / night listed, before fees
31 mi from Windsor
Travel trailer · Towable · Sleeps 6
Pick up in Chesapeke
Delivery up to 25 mi · Pets allowed
$99 / night listed, before fees
33 mi from Windsor
Travel trailer · Towable · Sleeps 5
Pick up in Virginia Beach
Delivery up to 20 mi · Pets allowed
$125 / night listed, before fees
33 mi from Windsor
Travel trailer · Towable · Sleeps 6
Pick up in Williamsburg
Delivery up to 150 mi · Pets allowed
$99 / night listed, before fees
33 mi from Windsor
Class C motorhome · Drivable · Sleeps 5
Pick up in Virginia Beach
Delivery up to 30 mi · Pets allowed
$285 / night listed, before fees
36 mi from Windsor
Travel trailer · Towable · Sleeps 2
Pick up in Virginia Beach
Delivery up to 267 mi
$115 / night listed, before fees
36 mi from Windsor
Travel trailer · Towable · Sleeps 7
Pick up in Virginia Beach
Delivery up to 120 mi
$145 / night listed, before fees
Trailers need a tow vehicle unless the owner delivers and sets up. 6 listed near Windsor, typical listed rate $107 a night, about 27 ft long on average.
Travel trailer · Towable · Sleeps 10
Pick up in Newport News
Delivery up to 50 mi · Pets allowed
$135 / night listed, before fees
Travel trailer · Towable · Sleeps 8
Pick up in Chesapeake
Delivery up to 50 mi · Pets allowed
$105 / night listed, before fees
Travel trailer · Towable · Sleeps 4
Pick up in Chesapeake
Delivery up to 100 mi
$90 / night listed, before fees
Travel trailer · Towable · Sleeps 5
Pick up in Chesapeake
Delivery up to 151 mi · Pets allowed
$100 / night listed, before fees
Travel trailer · Towable · Sleeps 7
Pick up in Suffolk
Delivery up to 50 mi · Pets allowed
$115 / night listed, before fees
Travel trailer · Towable · Sleeps 4
Pick up in Chesapeake
Delivery up to 50 mi · Pets allowed
$100 / night listed, before fees
Owners list their RVs for pickup in Chesapeake (4), Suffolk (1), Newport News (1). 6 listings offer delivery; the typical listed delivery radius is 50 miles, up to 151 miles. Fees and distance are set by each owner.
See Windsor RVs that deliver · then check that the owner's radius reaches your campground on the listing.
| Campground | Distance | Hookups | Max RV length |
|---|---|---|---|
| Solitude at Thornton Farm | 18 mi | Full | 40 ft |
| Chippokes State Park | 23 mi | Water & electric | 50 ft |
| The Pines Horse Farm | 32 mi | Water & electric | 45 ft |
| Machicomoco State Park | 36 mi | Water & electric | 60 ft |
| Camp Cardinal - Gloucester Point | 37 mi | Full | 45 ft |
| Camp Cardinal RV Resort | 37 mi | Full | 45 ft |
| Jellystone Park™ Williamsburg | 38 mi | Full | 75 ft |
| The Oysterhouse Landing | 38 mi | Water & electric | 45 ft |
Campgrounds with electric hookups within 60 miles (straight-line), nearest first. Open a campground to check site fit for your RV's length and availability for your dates. All campgrounds
Listed nightly rates near Windsor run from $90 to $130; half fall between $100 and $115 (median $107). Travel trailer: median $107. Cleaning fees, mileage and taxes are extra and vary by owner; refundable deposits are not part of the rental cost.
6 rentals with photos and a nightly rate were listed within 25 miles of Windsor on Outdoorsy as of Nov 8, 2026. That is a listing count, not availability for any dates.
6 listings (100%) offer delivery, typically up to 50 miles; the owner sets the distance and fee.
5 listings (83%) say pets are allowed. Pet fees are set per listing.
0% of rentals near Windsor are drivable motorhomes or vans. Trailers need a tow vehicle unless the owner delivers and sets up.
Also near Windsor: campgrounds · glamping & cabins · RV rentals in Virginia