Cute Vacation Dresses
Pack your bags, babe, because the ultimate getaway just got a whole lot cuter with our collection of cute vacation dresses! Whether you're jet-setting to a tropical paradise or planning a chic city escape, these dresses are your passport to turning heads and stealing hearts. Designed for sunshine-filled days and dreamy sunset strolls, each piece is ready to make you feel like the main character in your own travel story. So slip into something fabulous and let those vacay vibes flow—adventure awaits, and you're dressed to impress!
$36.90
A denim satin mini dress with a ruched wrap silhouette and spaghetti straps for a chic look.
$32.90
A sultry pink mesh mini dress with adjustable straps and ruched seams for a chic night out.
$36.90
An elegant pink off-the-shoulder midi dress with a stretchy knit fabric and flared hem.
$40.90
A black glitter mini dress with a halter cowl neckline and side ruched seams.
$37.90
A denim satin strapless mini dress with a pleated bust and flattering bodycon silhouette.
$68.90
A chic mauve skater dress featuring floral jacquard satin, a corset bodice, and lace-up back.
$46.90
A brown woven midi dress with a ditsy floral pattern, corset bodice, and high front slit.
$44.90
A red floral print mesh maxi dress with a sleeveless sweetheart neckline and bodycon silhouette.
$46.90
A vibrant yellow skater dress with a ruffled design, halter tie-back, and smocked high waist.
$44.90
A red glitter knit mini dress with a pleated cowl neckline and asymmetric wrap-front design.
$49.90
A sleeveless black skater dress featuring sheer lace, a V-neckline, and adjustable spaghetti straps.
$38.90
A white eyelet knit skater dress featuring a sleeveless square neckline and adjustable spaghetti straps.
$35.90
A pink sleeveless bodycon midi dress with a square neckline and stretchy knit fabric.
$19.97 $44.90 56% off
A white floral skater dress with a strappy tie-back and ruffled mini-length hem.
$59.90
A light blue woven midi dress featuring a corset bodice and charming lace-up back detail.
$48.90
A breezy white eyelet knit mini skater dress with a flirty tie-back and ruffled hem.
$44.90
A gold metallic knit maxi dress featuring a plunge cowl halter neckline and adjustable strappy open back.
$39.90
A brown mesh mini dress featuring a strapless neckline, side cutout, and ruffle-trim slit.
$20.97 $46.90 55% off
An abstract red knit maxi dress featuring a cowl neckline, hoop trims, strappy back, and high side slit.
$42.90
An ivory lace mini dress featuring a tie-front bust, ruffled hem, and adjustable spaghetti straps.
$59.90
An ivory A-line maxi dress featuring gauze fabric, sheer lace insets, and a faux leather belt.
$34.90
A black rib-knit maxi dress featuring a crew neck and form-hugging, stretchy silhouette for versatile styling.
$39.90
A strapless black and white striped mini dress with a cutout bodice and bodycon silhouette.
$42.90
A navy blue paisley skater dress with a halter V-neckline and playful tie-back design.
$39.90
A sheer white crochet knit cover-up dress with long sleeves, plunge neckline, and chic hoop insert.
$9.97 $42.90 77% off
A slate A-line mini dress with a V-neckline and ruffled hem in soft knit fabric.
$39.90
An eyelet lace mini dress in white with ruffled straps and a ruched sweetheart neckline.
$49.90
A brown mesh maxi dress featuring a bold floral print, cowl halter neckline, and curve-hugging fit.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.
$44.90
A taupe paisley skater dress with a halter V-neck and stretchy smocked bodice.
$38.90
A vibrant pink mini dress featuring a leopard snake print, mesh fabric, side cutout, and ruffled slit.
$9.97 $46.90 79% off
A blue gauze skater dress featuring a halter neckline, cutout bodice, and ruffled mini hem.
$19.97 $39.90 50% off
A natural paisley-print maxi dress in mesh with a bodycon fit, square neckline, and high side slit.
$36.90
A heather grey knit mini dress with an off-the-shoulder neckline and A-line silhouette.
$19.97 $34.90 43% off
A yellow striped knit mini dress featuring a twisted strapless neckline and flattering bodycon silhouette.
$38.90
A black mesh-lined bodycon mini dress featuring short puff sleeves, a sweetheart neckline, and side cutouts.
$44.90
A natural-colored knit mini dress with an off-the-shoulder neckline and twist popover accent.
$36.90
A black nylon mini dress featuring a fitted A-line silhouette, square neckline, and hidden shorts.
$44.90
A green mini dress with a sleeveless square neckline, cap-like sleeves, and ruched detailing.
$46.90
An adorably chic taupe skater dress with a plaid print and strapless sweetheart neckline.
$52.90
A pink skater dress with puff sleeves, lace trim, and a playful bubble hem.
$89.90
A playful pink A-line short dress featuring lace trim, adjustable straps, and hidden side pockets.
$25 $34.90 28% off
A grey plaid strapless mini dress with a pleated hem and form-hugging knit fabric.
$35.90
A burgundy plaid mini dress with lace trim, spaghetti straps, and a form-hugging silhouette.
$19.97 $36.90 46% off
A sultry tan knit mini dress featuring strapless cutouts, hoop inserts, and a flattering bodycon silhouette.
$59.90
A pink woven mini dress featuring a tie-front design, pleated hem, and spaghetti strap ties.
$26.90
A taupe plaid mini dress with a V-neckline, spaghetti straps, and a side slit.
$6.97 $29.90 77% off
A taupe ribbed knit bodycon mini dress with spaghetti straps and a scoop neckline.
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This adorable strapless A-line mini dress is so your vibe! Designed with a stretchy lined knit fabric, it features a strapless straight-across neckline, chic pleated detailing at the bust, and a flirty flowy A-line silhouette on the mini-length hem. Style for a girl's night with statement earrings and strappy mules. Fit & FeaturesStretchy knit fabric with knit lining, Strapless straight neckline, no-slip strip, Pleated bust, A-line fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Your Vibe Strapless A-line Mini Dress in Light Blue | Size: L | Knit Fabric
Bring on the cute attitude in this ponte mini skort brings featuring a flattering high-rise waist, and a skirt overlay designed with dual front slits along the form-hugging fit. Fit & FeaturesSmooth ponte knit fabric, minimal stretch, High-rise waist, Skirt overlay, dual front slits, Form-hugging silhouette, Mini-length hem, Shorts lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cute Attitude Ponte Slit Mini Skort in Black | Size: L | Knit Fabric
A fashionista like you will adore this basic mini skirt for creating your day and night looks! Featuring an elasticized high-rise waistband, bodycon silhouette, and a flirty front hem slit on stretchy and smooth knit fabric. Style with a corset top and heels. Fit & FeaturesHigh-rise elasticized waistband, Bodycon silhouette, Front hem slit, Mini-length hem, Stretchy and smooth knit fabric, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Get Down With Basic Slit Mini Skirt in Black | Size: M | Knit Fabric
This satin mini dress will be your favorite for celebrations, events, and date nights! Sleek and smooth satin shapes this off-the-shoulder dress, which features a flattering A-line silhouette perfect for styling with heels. Fit & FeaturesSmooth and sleek satin fabric, stretchy knit lining, Off-the-shoulder neckline, Short sleeve cuffs, A-line silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Classics Lover Off-The-Shoulder Satin A-Line Mini Dress in Pink | Size: S | Knit Fabric/Satin Fabric
A true showstopper of a mini dress perfect for adding a touch of sparkle to any occasion. The short-length rhinestone dress features a square neckline and adjustable spaghetti straps, while the A-line silhouette flatters your figure down to the uneven-cut hem. Complete the look in platform sandals for a dressy night out! Fit & FeaturesSleeveless square neckline, Adjustable spaghetti straps, Back zipper and hook-eye closure, A-line silhouette, Mini-length hem, uneven cut design, Rhinestone-embellished, mesh fabric, stretchy knit lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sparkling Perfection Rhinestone A-Line Mini Dress in Pink | Size: XS | Knit Fabric/Rhinestone/Mesh Fabric
Capture all the attention with your sultry allure in the Paige rhinestone formal bodycon mini dress! She features a sleeveless cowl neckline, adjustable spaghetti straps for a customized fit, all-over rhinestone embellishments for that total glam girl vibe, a mini-length hem, and a bodycon silhouette to hug your gorgeous curves. The slinky knit fabric offers plenty of stretch. Style this mini dress with metallic heels for your next dressy night out! Fit & FeaturesSleeveless cowl neckline, Adjustable spaghetti straps, All-over rhinestone embellishments, Mini-length hem, bodycon silhouette, Slinky knit fabric, full-length knit lining, plenty of stretch, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Paige Rhinestone Formal Bodycon Mini Dress in Light Blue | Size: M | Knit Fabric/Rhinestone
Windsor Brenda Low Back Bow Taffeta Skater Dress in Black
$19.97 $64.90
69% off
Chat, dance, and twirl the night away in the Brenda taffeta skater dress! The short dress is ready to party with a voluminous silhouette and a stunning low-cut back with a statement bow. Fit & FeaturesTaffeta fabric lined with tulle, stretchy knit fabric, Tank shoulder straps, Low back with bow, Skater silhouette, Short-length hem, Runs true to size, Where to Wear:Prom, brides, weddings, bridesmaids, fancy date nights, dinner parties, cocktail events Free Shipping on All Orders Over $75. | Windsor Brenda Low Back Bow Taffeta Skater Dress in Black | Size: XS | Knit Fabric
A sassy mini dress to slip on when the sun goes down and the beat is calling you to the dancefloor! This dress is featured in a sultry bodycon silhouette with a halter neckline accented with hoop inserts. Fit & FeaturesAbstract print, stretchy knit fabric, Cowl halter neckline, hoop accents, Bodycon silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sun Goes Down Halter Abstract Bodycon Mini Dress in Brown | Size: S | Knit Fabric
Here comes the sun and you radiating trendy vibes in this strapless mini dress perf for casual plans! The ruched sides and ruffled hem add a playful touch to the bodycon silhouette. Fit & FeaturesDouble-lined brushed knit fabric, moderate stretch, Strapless straight neckline, Ruched side seams, Bodycon silhouette, Mini-length tiered ruffled hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Here Comes The Sun Strapless Ruffled Mini Dress in Brown | Size: S | Knit Fabric
Prance around like the cutie you are in this off-the-shoulder mini dress! The playful ruffles add movement and feminine charm while the flattering form-hugging silhouette showcases your curves. Fit & FeaturesWoven smocked stretchy fabric, Ruffle off-the-shoulder neckline, Form-hugging silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Definition Of Cute Off-The-Shoulder Mini Dress in Black | Size: XS | Stretchy Fabric
Cute Vacation Dresses
Let’s be real: planning a getaway is basically an excuse to unleash your inner main character, and nothing says “lead role energy” like leveling up your suitcase with cute vacation dresses that do the most. Whether you’re jetting off for a girls’ trip, booking a spontaneous baecation, or just living your best life on a weekend staycation, the right dress is your secret weapon. Think about it: you want something that looks effortless, but also makes you feel like you just stepped off a Pinterest board. From flirty minis that are perfect for rooftop brunches to breezy midis made for golden hour strolls, Windsor vacation dresses are all about capturing those “wish you were here” vibes. And let’s not forget about the details—flowy fabrics that catch the breeze, bold prints that pop in every photo, and silhouettes that make you want to twirl until your phone dies from too many Boomerangs. When you’re packing for your next adventure, versatility is key. You want pieces that can slay at a fancy dinner and still look fire thrown over your swimsuit by the pool. That’s where these dresses for vacation come in clutch—they’re made for mixing, matching, and making memories. Don’t be surprised if your travel bestie “accidentally” borrows one for her own Insta moment.
Gifting a cute vacation dress? You’re officially the MVP of the friend group. There’s something iconic about giving the gift of a getaway-ready look, whether it’s for a birthday, a bridal shower, or just because. Imagine your bestie unwrapping a dress that practically screams “passport required”—it’s the kind of present that says, “I see you, globe-trotter, and I’m here to hype you up.” And let’s be honest, everyone has that one friend who always shows up overdressed for airport security (in the best way)—she’ll live for a windsor vacation dress that’s equal parts comfy and chic. If you’re shopping for yourself, don’t be afraid to step outside your comfort zone. Try a bold color you’ve never worn, or a cut that makes you feel like you could flirt your way into first class. The best vacation looks are the ones that make you feel unstoppable, whether you’re exploring a new city or dancing barefoot on the beach. And for all the planners out there, don’t sleep on spring vacation dresses—they’re perfect for layering, so you’re ready for anything your trip throws at you, from chilly plane rides to sun-soaked adventures.
No matter where your wanderlust takes you, Windsor has your back (and your fit). Our collection is curated for the girl who wants every moment to be a photo op, the one who’s always down for a spontaneous road trip or a last-minute flight. We know that the right dress isn’t just an outfit—it’s a whole mood, a confidence boost, and sometimes, the best souvenir. Ready to start packing? Check out our full collection of Women's Vacation Dresses and get ready to turn every getaway into a runway.