Deciding where to stay in the Hamptons reveals more about your intentions than your budget. The 13-room historic inn versus the 158-room oceanfront resort. The sharehouse split eight ways versus the $200,000 seasonal rental. Each choice signals something different about what you’re actually seeking from a Hamptons visit.

This guide covers the full spectrum: the trophy hotels everyone recognizes, the boutique properties insiders prefer, and the rental strategies that can save thousands or cost you opportunities depending on execution. Understanding the differences helps you match accommodation to actual goals rather than defaulting to whatever has availability.

The Trophy Hotels

These properties define Hamptons hospitality at its most visible. Reservations here make statements before you arrive.

Gurney’s Montauk Resort and Seawater Spa

The only year-round resort in the Hamptons operates 158 oceanfront rooms, suites, and cottages along 2,000 feet of private beach. Gurney’s has anchored Montauk’s hospitality scene for decades, evolving from modest origins into a full-service destination that defines East End luxury.

The Seawater Spa spans 30,000 square feet with indoor and outdoor treatment rooms, steam facilities, four bathing pools, and the only ocean-fed saltwater pool in North America. Five restaurants and bars range from elegant seasonal dining to casual beachfront fare. The Beach Club offers on-beach dining service unavailable anywhere else in the Hamptons.

Weekend rates during peak summer start around $800 per night and climb substantially for oceanfront accommodations. The property attracts a mix of couples seeking spa retreats, families wanting beach access, and weekend visitors drawn to the poolside DJ scene.

What Gurney’s signals: You’re here for the full resort experience, comfortable with visibility, and willing to pay premium prices for comprehensive amenities.

Topping Rose House

The Hamptons’ only full-service luxury hotel occupies a strategic position in Bridgehampton, equidistant from Southampton, East Hampton, and Sag Harbor. The property offers 16 guest rooms and 6 one-bedroom suites across a restored estate with contemporary interiors.

Jean-Georges Vongerichten operates the on-site restaurant, providing farm-to-table dining that draws guests and locals year-round. The spa, pool, and health facilities complete the package. Town cars shuttle guests around the area, eliminating transportation logistics that complicate other Hamptons stays.

Rates start around $600 per night during season, with suites commanding significantly more. The property attracts design-conscious travelers, culinary enthusiasts, and those who prefer refined understatement over resort scale.

What Topping Rose signals: You prioritize quality over quantity, appreciate thoughtful design, and value location flexibility over beachfront access.

Montauk Yacht Club

The 107-room resort on Star Island opened in 1927 and has hosted Vanderbilts, Morgans, Fords, and Lindbergh. Safe Harbor Marinas acquired the property in 2023 for $149 million, the largest real estate transaction in Hamptons history. Following extensive renovation, the club reopened for summer 2025 with refreshed “barefoot luxury” positioning.

The 16-acre property includes world-class spa facilities, tennis and paddle courts, two outdoor pools, an indoor pool, private beach access, and a marina accommodating super-yachts up to 300 feet. Chef Jarad McCarroll leads Ocean Club Montauk, the resort’s acclaimed seafood restaurant.

What Montauk Yacht Club signals: You appreciate maritime heritage, belong to the sailing set, or want the prestige that comes with a century of elite guests.

The Boutique Properties

These smaller hotels offer personality and intimacy unavailable at larger resorts. They’re where regulars stay when they want service over spectacle.

The Hedges Inn

The 2025 season marked a transformation for this historic 13-room property at 74 James Lane in East Hampton Village. Andrew and Sarah Wetenhall, owners of Palm Beach’s Colony Hotel, purchased the 1873 inn and introduced Swifty’s, the beloved restaurant that generated a 1,000-person waitlist within weeks of opening.

Located between Main Street and Main Beach, the Hedges occupies perhaps the most strategic position in East Hampton Village. The inn offers butler service, beach provisions, and a fleet of electric Volvos for guest transportation. Sunday trivia nights, imported from the Colony’s Palm Beach success, have already become appointment viewing.

Room rates during season reach $1,500 per night and higher. The Wetenhalls also acquired the adjacent house at 5 Hook Pond Lane for guests seeking longer stays or enhanced privacy.

What the Hedges signals: You understand the difference between staying somewhere and being part of something. You want the social scene, the restaurant access, and the community integration that boutique properties enable.

Baron’s Cove

This Sag Harbor waterfront property combines nautical charm with modern sophistication. Spacious rooms and suites feature private terraces overlooking the harbor. The on-site restaurant serves locally sourced seafood and seasonal fare with views that justify the prices.

The outdoor pool provides a gathering point without the scene-seeking atmosphere of larger resorts. Location steps from Sag Harbor’s boutiques, galleries, and year-round cultural venues makes Baron’s Cove ideal for guests who want village immersion rather than beach isolation.

What Baron’s Cove signals: You prefer Sag Harbor’s year-round creative community over Southampton’s social stratification or East Hampton’s celebrity culture.

The Maidstone Hotel

This East Hampton boutique hotel blends Scandinavian design sensibilities with traditional Hamptons aesthetic. The property occupies a prime village location with beautiful gardens and intimate scale that larger properties can’t replicate.

The unique design approach attracts guests who notice such things. The tranquil atmosphere appeals to those escaping rather than seeking the Hamptons social whirl.

Marram Montauk

Design-forward and deliberately peaceful, Marram offers a Tulum-meets-Montauk aesthetic with surf lessons, fire pits, and carefully considered interiors. Adjacent to Shadmoor State Park, the property encourages hiking, surfing, and coastal exploration.

Wellness programming includes yoga, meditation, tarot readings, and stargazing. The approach attracts visitors seeking restoration over stimulation, nature over nightlife.

What Marram signals: You’re here for the landscape, the wellness, and the design. The scene matters less than the experience.

The Historic Inns

For visitors who appreciate heritage, these properties connect contemporary stays to Hamptons history.

The 1770 House

Steps from Southampton Village shops and restaurants, this 250-year-old property offers historic charm with modern comforts. The dual dining concept provides both casual and refined options without leaving the grounds.

The American Hotel

Sag Harbor’s legendary property dates to the village’s whaling era. The Drew Room provides discretion for those requiring it. The wine list has achieved near-mythical status among collectors. The atmosphere rewards those who understand what they’re walking into.

The Baker House 1650

This East Hampton bed-and-breakfast occupies a beautifully preserved historic property with guest rooms featuring fireplaces and private gardens. The indoor pool and spa provide amenities unusual for properties of this scale. Personalized service and attention to detail attract repeat visitors seeking intimacy over resort anonymity.

The Summer Rental Strategy

Hotels represent one approach to where to stay in the Hamptons. Rentals represent another, with different economics, social dynamics, and lifestyle implications.

The 2026 Market Reality

The Hamptons rental market has fundamentally shifted since COVID’s peak. Summer rental prices dropped 15-25% from pandemic highs. Inventory surged past 3,500 listings. Properties that would have been locked up by February now remain available through May, giving renters negotiating leverage they haven’t had since 2019.

According to industry reports, 75% of pandemic-era buyers are now renting their properties rather than selling, flooding the market with inventory. The Memorial Day to Labor Day full-season lease is fading as renters prefer flexibility through platforms like Airbnb, VRBO, and StayMarquis.

Pricing by Village

Southampton maintains its position as the top-dollar rental market, commanding 10-20% premiums over comparable East Hampton properties. A quality 4-bedroom property in Southampton Village runs $85,000-$120,000 per month during peak season.

East Hampton has absorbed the largest inventory increase. Properties commanding $100,000+ in Southampton price at $65,000-$85,000 for East Hampton equivalents. The trade-off: different social dynamics, more casual atmosphere, stronger arts and gallery scene.

Amagansett maintains slightly bohemian reputation with creative-class appeal. Pricing lands between East Hampton Village and Springs, typically $55,000-$85,000 per month for quality 4-bedroom properties.

Springs offers the East End’s best value-to-location ratio. Properties price 30-40% below East Hampton Village for comparable square footage. The trade-off: less walkable village access, more car-dependent lifestyle.

Sag Harbor rental pricing has remained stickier than other markets. The year-round appeal with restaurants, shops, and cultural venues operating beyond summer creates sustained demand that other villages lack.

Timing Strategies

July now outperforms August in rental activity, a shift from traditional patterns. This creates strategic opportunities for flexible renters.

Properties listed at $200,000 for the season in February are negotiable at $160,000-$175,000 by June. Landlords with unrented properties drop prices 10-20% as summer approaches. The leverage shifts toward renters willing to wait.

The Sharehouse Calculation

Splitting a rental among friends reduces individual costs while introducing social dynamics that can enhance or destroy the experience depending on participant compatibility.

A $100,000 monthly rental split eight ways costs $12,500 per person per month. Weekend-only shares reduce exposure further. The economics make Hamptons access possible for professionals who couldn’t afford solo rentals.

The trade-off: shared spaces, coordinated schedules, and the reality that sharehouse quality varies enormously based on who’s participating. The best sharehouses create communities. The worst create conflicts.

The Wellness Retreats

A growing segment of Hamptons accommodations focuses on restoration rather than socializing.

Shou Sugi Ban House

Southampton’s first award-winning luxury wellness retreat and spa prioritizes relaxation over beach access. Daily wellness classes including yoga, pilates, breathwork, sound meditation, and strength training come included with stays.

A saltwater pool, house Tesla, organic bath products, biodynamic wines, and Michelin-starred cuisine reinforce the sustainability and wellness positioning. This is where you stay when the goal is leaving better than you arrived.

Matching Accommodation to Goals

The question of where to stay in the Hamptons depends entirely on what you’re actually trying to accomplish.

For Beach Access

Gurney’s Montauk provides 2,000 feet of private beach. Baron’s Cove offers harbor proximity. Most boutique hotels require transportation to beaches and navigation of the permit system.

For Social Scene

The Hedges Inn now anchors East Hampton Village dining. Gurney’s pool scene attracts weekend crowds. Southampton rentals provide geographic access to the village’s established social infrastructure.

For Business Networking

Topping Rose House’s central location enables access to multiple villages without committing to any single social ecosystem. The Jean-Georges restaurant draws decision-makers. The town car service eliminates transportation friction.

For Family Visits

Larger rental properties provide space, kitchens, and flexibility hotels can’t match. Montauk Yacht Club offers family-friendly amenities at resort scale. The state park beaches in Montauk provide less complicated access than village beaches.

For Wellness Retreat

Shou Sugi Ban House exists specifically for this purpose. Marram Montauk combines design with wellness programming. Gurney’s spa provides restoration within a resort context.

For Budget Optimization

Hampton Bays and Westhampton offer lower price points than the prestige villages. Off-season visits (May, September) provide similar experiences at reduced rates. Sharehouse participation trades privacy for access. The Hamptons Hopper and free shuttles reduce transportation costs once you arrive.

The New Properties

2025 brought several additions worth noting for 2026 planning.

The Sagaponack Hotel

Newly opened on seven acres, this 30-key property includes standard rooms and detached bungalows with kitchenettes. The location enables easy access to multiple Hamptons villages. Beach passes and lockers address the access complications that plague visitors at other properties.

The Reformed Hedges Inn

The Wetenhall transformation of the Hedges represents the most significant Hamptons hospitality development in years. Swifty’s has already become the summer’s most sought-after reservation. The planned fall restoration will upgrade guest rooms and grounds for the 2026 season, with extended or year-round operation under consideration.

Booking Strategy

Premium Hamptons hotels book months in advance for summer weekends. February reservations secure July 4th accommodations. March bookings capture August availability. Waiting until June means accepting whatever remains.

Rental booking traditionally begins after Presidents Day, with early birds starting in January. The 2025-2026 market softening has extended booking windows, but desirable properties in prestige locations still move quickly.

Shoulder season (May, September) offers availability, reduced rates, and experiences that summer crowds prevent. The weather cooperates more than you’d expect. The beaches remain beautiful. The restaurants remain open.

Social Life Magazine has covered Hamptons hospitality for over two decades. Our perspective reflects actual stays, real relationships with properties, and understanding of what different accommodations actually deliver.

Plan your Hamptons experience:

Related Reading: