The Best Bachelorette Party Trips to Plan in Every Season

Photo courtesy of O2 Beach Club and Spa

Make your last fling before the ring as unique as each season with these unforgettable trips that are an easy jaunt from Westchester.

Today’s bachelorette parties are often a dime a dozen: tacky matching outfits, expensive dinners, and the same locations visited over and over (looking at you, Nashville). Take advantage of the season by planning a getaway that makes the most of your favorite time of the year. These four locales offer an experience guaranteed to be memorable — with or without matching outfits.



O2 Beach Club and Spa

Dover Road
St. Lawrence Gap, Bridgetown Christ Church, BB15020

beach bachelorette
Photo courtesy of O2 Beach Club and Spa

If white sands and blue waters are what your heart desires, O2 Beach Club and Spa in dreamy Barbados is your play. Have your own version of Bachelor in Paradise (minus the lame dudes) on this island oasis in an all-inclusive resort known for its modern elegance and breathtaking seascapes. Add a dash of adventure to your time on the island with O2’s complimentary “How To” daily lessons that explore all aspects of island living, from “How to Make Rum Punch” to “How to Kayak.” With live entertainment every night, there’s always an energetic backdrop for choosing how to spend your sundown hours. Take advantage of the offshore activities at your fingertips (or fins), such as snorkeling and boogie boarding.

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a relaxing resort
Your besties will adore this bachelorette trip destination. Photo courtesy of O2 Beach Club and Spa

If you’re more of a chill group who’d rather just lounge, the resort offers three pools, two swim-up bars, and access to pristine beaches. When it’s time to get all gussied up for the night, reserve your spot at Oro, the resort’s fine-dining, ninth-floor restaurant, boasting 260-degree views of the South Coast of the island. The a la carte menu is a fusion of Caribbean and European flavors that will have foodie bridesmaids floored. Finish the evening off sipping on a bevvy made with award-winning Foursquare Rum, a liquor indigenous to the island. Rates start at $584/night.


Jackson Hole

Hotel Terra

3335 West Village Drive, Teton Village, WY, 83025

cozy winter getaway
Photo courtesy of The Hotel Terra Jackson Hole

For a winter getaway that has activities to entertain even the pickiest bridesmaid, there’s the Hotel Terra in Wyoming’s Teton Village. As Jackson Hole’s reputation suggests, the Grand Teton mountains offer all the picturesque skiing and snowboarding trails a winter-sport-leaning bride and her gang could ask for. Immerse yourselves in the world’s first national park by taking a snowcoach tour of Yellowstone National Park or one of the many ranger-led programs. If your group is looking to snow bunny around, the lodge’s welcoming fireplace provides the perfect perch. Meander up to the rooftop spa (aptly named Chill Spa), complete with a hot tub and an infinity pool to recharge after a day of adventuring. Treatments include a CBD relief massage, vitamin C–boosting facial, and chakra-balancing journey. Turn to the restaurant Il Villagio Osteria for an upscale night cap (bonus points if you order one made with local spirits). Rates begin at $626/night. For larger parties, suites are available and advised.

a steamy resort pool
Winter views and a dip in the pool are perks at this bachelorette destination. Photo courtesy of The Hotel Terra Jackson Hole


The Hamptons

Wölffer Estate Vineyard

139 Sagg Road
Sagaponack, NY, 11962

Known for the beloved “Summer in Bottle” rosé, sip and swirl with your bridal party across the pristine Wölffer Estate Vineyard, located in Sagaponack, NY. Only a few hours from the Hudson Valley, the estate makes an excellent day-trip getaway or a marquee destination for a Hamptons weekend. Surrounded by lush vineyards, the rustic-chic tasting room offers samples of the estate’s crisp wines and flavorful ciders. Book a reservation to enjoy a seated experience at the tasting room and learn about and partake of the estate’s award-winning wines.

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wine bachelorette
Photo courtesy of Wölffer Estate Vineyard

And since wine is best enjoyed with something savory, the tasting room plates up a gourmet selection of small bites and charcuterie platters. To take your bachelorette to the next level by opting for the vineyard tour and tasting, a 45-minute guided tour of the tasting room and cellar, led by an expert sommelier, or the private pergola experience, for an intimate afternoon of wine and nosh ($250 deposit required for the pergola experience). For a souvenir of the day (or wedding favors if you’re up for a splurge), to-go wine is available even at the boutique across the road. Pro Tip: Wölffer is a classy place, and while enjoying yourself is encouraged, staff does not allow in-theme accessories or decor (think anything of the NSFW or glitter variety).

wine tasting
What bachelorette party is complete without a glass of wine? Photo courtesy of Wölffer Estate Vineyard



The Porches Inn At Mass MoCa

231 River St
North Adams, MA, 01247

Take leaf-peeping to a new level with this New England bungalow complex. Located in Massachusetts’ lush Berkshire valley, this boutique inn is the right balance of refined and rustic and the ideal setting for all autumnal activities. The scene from the rooms is unparalleled, with an expansive view of the monolithic Massachusetts Museum of Contemporary Art (MASS MoCA) from its porches. This strip of stunningly detailed 19th-century Victorian row houses pays homage to the generations of millworker families who once lived there. Waltz through MASS MoCA, the former textile mill itself, to be immersed in art forms from some of the world’s most evocative artists.

bachelorette inn
Photo courtesy of the Porches Inn

When leaving Porches, stroll around North Adams, a town that feels ripped from the set of Gilmore Girls. Speckled with hometown coffeeshops and local creameries, riffle through the community for antiquing or just a fresh cup of coffee. During peak leaf-peeping season, take an Insta-worthy guided hike through the Hoosac Range and leave all your wedding-day worries on the mountain. At night, cozy up in the fresh fall air by the inn bar’s fireplace, beverage in hand. Rates start at $219/night; suites are available for larger groups.

bachelorette getaway
Relaxation is easy at this bachelorette destination. Photo courtesy of the Porches Inn

Related: 6 New England Vacations to Take From Westchester

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