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Trailstead Stays

Guide

Eating out and booking experiences around Scottsdale

Ten people, one dinner reservation, and nobody wants to make the calls.

Plan two dinners out, not five

Large parties are the hardest reservation in any restaurant town. The pattern that works is one or two nights out for the whole group, booked weeks ahead, with the rest cooked at the house — both Scottsdale homes have kitchens and outdoor space set up for it.

Old Town Scottsdale is about ten minutes from both houses and holds the widest concentration of restaurants, bars and galleries, so a single drive covers the evening.

Booking a table for a group

Call the restaurant directly for parties above six; most large-party bookings are not offered through the online widget. Ask about a set menu, an automatic service charge and the cancellation window in the same call.

We do not hold tables, have no restaurant partnerships and receive nothing from any venue. Every link below goes to an official source.

Experiences worth booking ahead

Tee times, pickleball courts, hot-air balloon flights, desert jeep tours and guided hikes all sell out on cool-season weekends. Book directly with the operator and confirm the group minimum and cancellation terms before you collect money from anyone.

For hiking, check trailhead parking and any heat restrictions with the city or preserve on the morning you go, not the week before.

Last reviewed 2026-09-05 · Maintained by Trailstead Stays content team

Related stays

Homes mentioned in this guide

Scottsdale, Arizona

The Sunkiss

Serve. Swim. Stay awhile.

5 bedrooms · 3 baths · 4.93 (58)

A Scottsdale home shaped around outdoor time. Four king bedrooms and a bunk room, a private pool and hot tub, and a sport court set up for pickleball and basketball. It suits groups who want to play during the day and stay in for a long evening together.

  • Golf and pickleball groups
  • Family and multigenerational trips
  • Cooler-season desert escapes

Five bedrooms with sleeping arrangements for 16+. Final guest limits are confirmed on the booking calendar.

Scottsdale, Arizona

The Scottsdale Social

Made to play. Built to gather.

5 bedrooms · 9 beds · 3 baths · 4.91 (68)

The larger of the two Scottsdale houses, built around shared time. Five bedrooms and nine beds, a private backyard with pool, hot tub and putting green, and more than fifteen games for the evenings nobody wants to go out.

  • Group celebrations and reunions
  • Golf trips
  • Holiday gatherings

Five bedrooms and nine beds, with sleeping arrangements for up to 18. Final guest limits are confirmed on the booking calendar.