A comparison by MoneyLion, using Claude's web search capabilities, analyzed lodging costs for group trips to Nantucket, Massachusetts, and Healdsburg, California. For a beach trip for four women to Nantucket from July 19–26, 2026, booking two hotel rooms with two queen beds each was cheaper than an equivalent Airbnb in all but the luxury category. The Beachside at Nantucket, a midrange hotel, was the lowest price at about $1,225 per person for seven nights, while an affordable Airbnb with each traveler getting their own bedroom cost roughly $1,825 per person. The luxury White Elephant Hotel cost about $1,600 per night, or $5,600 per person, compared to a comparable four-bedroom waterfront home at about $5,000 per person. However, when the group size increased to eight travelers, pricing shifted significantly in favor of Airbnbs across every category. For a romantic, wine-focused weekend for two couples in Healdsburg, California, from July 19–26, 2026, Airbnbs were the more affordable option in every category. The most affordable short-term rental, a two-bedroom cottage, would cost about $825 per person, while the Harmon Guest House hotel ran about $1,225 per person. The luxury Montage Healdsburg cost about $3,990 per person, while a high-end private villa cost about $3,750 per person