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The Tamarack — living room with vaulted ceiling, large windows, brown leather sofas, coffee table, and stone fireplace

Scottsdale · Flathead Valley · More to come

Find the stay that fits the trip.

Remarkable group homes and outdoor stays, brought together for easier planning and a clearer path to booking direct.

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Check the calendar

Pick your dates. We'll take them to the booking page.

Choose a destination, your nights and your party size. Every home carries those details straight through to its official booking calendar, where live availability and pricing are confirmed.

Your dates and party size travel with you to each home’s official booking page, where live availability, rates, fees and minimum stays are confirmed.

Choose the setting

Two destinations, two very different trips.

Start with where you want to wake up. Each destination page explains what the area really gives a group, season by season.

The Sunkiss — family sitting around a modern fire pit on an outdoor patio at dusk

Scottsdale, Arizona

Scottsdale

Desert light, long pool days, and easy group logistics.

  • — Two Trailstead homes in one metro, so a large party can split across houses and still gather.
  • — A dependable warm-weather season when much of the country is cold.
  • — Golf, pickleball, hiking and dining are all within a normal drive of a single home base.
  • — Close enough for Phoenix-area locals to book as a staycation, with everything worth doing already in the backyard.
  • — A long cool season that suits snowbirds, Canadian winter regulars and international visitors staying weeks rather than nights.
Plan Scottsdale
The Tamarack — rear view of multi-level lodge featuring fire pit seating, patio, and upper deck at dusk

Northwest Montana

Flathead Valley

Lake days, forest quiet, and a practical base for Glacier Country.

  • — Two large homes built for groups that want one roof rather than several hotel rooms.
  • — Flathead Lake is close, and the valley's towns are an easy drive for supplies and dinners.
  • — Four genuinely distinct seasons, so the same house supports very different trips.
Plan Flathead Valley

Find your fit

Four homes, each suited to a different kind of trip.

Details, amenities and policies live on each property's own site. Start here to narrow the choice.

Scottsdale, Arizona

The Sunkiss

Serve. Swim. Stay awhile.

5 bedrooms · beds · 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

Sleeps 16+. Final guest limits are confirmed on the official booking page.

Tour this home(opens this Trailstead home’s own website in a new tab)Check availability(continues to the Trailstead booking calendar for this home, in a new tab)

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

Sleeps up to 18. Final guest limits are confirmed on the official booking page.

Tour this home(opens this Trailstead home’s own website in a new tab)Check availability(continues to the Trailstead booking calendar for this home, in a new tab)

Somers, Montana

The Evergreen

Room to reconnect. Montana to explore.

6 bedrooms · 10 beds · 3.5 baths · 4.97 (39)

A six-bedroom Montana home for groups that want one roof instead of several. A private hot tub and barrel sauna outside, a speakeasy and game room inside, and Flathead Lake a short drive away with Glacier Country under an hour on.

  • Multigenerational family trips
  • Flathead Lake and Glacier planning
  • Fall and winter gatherings

Six bedrooms and ten beds. Montana rules govern how overnight occupancy is advertised, so we publish a maximum of ten — the same number shown on the home's own site. Travelling with more? Ask on the booking page before you book.

Tour this home(opens this Trailstead home’s own website in a new tab)Check availability(continues to the Trailstead booking calendar for this home, in a new tab)

Lakeside, Montana

The Tamarack

Adventure out. Exhale in.

6 bedrooms · 9 beds · 4.5 baths · 5.0 (12)

A six-bedroom Montana lodge for groups that plan to be outside most of the day. Hot tub, sauna, fire pit and game room, room for gear and vehicles, and a setting built for golden-larch fall drives and winter ski days.

  • Lake trips
  • Group retreats
  • Ski and winter weekends

Six bedrooms and nine beds. Montana rules govern how overnight occupancy is advertised, so we publish a maximum of ten — the same number shown on the home's own site. Travelling with more? Ask on the booking page before you book.

Tour this home(opens this Trailstead home’s own website in a new tab)Check availability(continues to the Trailstead booking calendar for this home, in a new tab)

Looking somewhere else?

Started with Bozeman, Big Sky, Whitefish, Phoenix or Tucson?

Those are good searches. Here is an honest comparison with where our homes actually are, so you can decide before you book anything.

Bozeman or Big Sky

Southwest Montana, built around Yellowstone and one big ski resort. The Flathead Valley is the lake-and-Glacier side of the state.

Compare honestly →

Whitefish

The valley's busiest town. A Lakeside or Somers base trades main-street walking for the lake and quieter evenings.

Compare honestly →

Phoenix

Same metro. Scottsdale is the side of it where group houses with private pools actually sit.

Compare honestly →

Tucson

Quieter and two hours south. Scottsdale wins on flights and on how much sits within a short drive.

Compare honestly →

Start with the trip

What kind of trip are you planning?

Golf and pickleball

Scottsdale is easy to plan around when the trip revolves around a tee time and a court.

See the stays →

Family and group travel

One roof, several generations, and a plan that survives contact with a real family.

See the stays →

Flathead Lake and Glacier

A Somers–Lakeside base keeps the lake close and Glacier Country within a day's drive.

See the stays →

Fall and winter stays

Quieter valley, shorter days, and trips that are mostly about being indoors together.

See the stays →

Compare at a glance

Compare the stays

Only verified portfolio-level facts appear here. Sleeping arrangements, fees and policies are confirmed on each official booking page.

The Sunkiss

Where
Scottsdale, Arizona
Best for
Golf and pickleball groups, Family and multigenerational trips, Cooler-season desert escapes
Occupancy
Sleeps 16+. Final guest limits are confirmed on the official booking page.
Tour this home(opens this Trailstead home’s own website in a new tab)Check availability(continues to the Trailstead booking calendar for this home, in a new tab)

The Scottsdale Social

Where
Scottsdale, Arizona
Best for
Group celebrations and reunions, Golf trips, Holiday gatherings
Occupancy
Sleeps up to 18. Final guest limits are confirmed on the official booking page.
Tour this home(opens this Trailstead home’s own website in a new tab)Check availability(continues to the Trailstead booking calendar for this home, in a new tab)

The Evergreen

Where
Somers, Montana
Best for
Multigenerational family trips, Flathead Lake and Glacier planning, Fall and winter gatherings
Occupancy
Six bedrooms and ten beds. Montana rules govern how overnight occupancy is advertised, so we publish a maximum of ten — the same number shown on the home's own site. Travelling with more? Ask on the booking page before you book.
Tour this home(opens this Trailstead home’s own website in a new tab)Check availability(continues to the Trailstead booking calendar for this home, in a new tab)

The Tamarack

Where
Lakeside, Montana
Best for
Lake trips, Group retreats, Ski and winter weekends
Occupancy
Six bedrooms and nine beds. Montana rules govern how overnight occupancy is advertised, so we publish a maximum of ten — the same number shown on the home's own site. Travelling with more? Ask on the booking page before you book.
Tour this home(opens this Trailstead home’s own website in a new tab)Check availability(continues to the Trailstead booking calendar for this home, in a new tab)

The official path

One portfolio. Four distinct stays. One clear way to plan.

Trailstead Stays helps you explore the portfolio and then continue to the property's official booking partner. We do not run a separate booking engine, and we make no claims about price advantages.

Availability, rates, fees, minimum stays, policies, and final occupancy are confirmed on the Trailstead booking calendar for each home.

Plan the destination

Guides written for group trips.

Practical planning, with official sources linked for anything that changes.

The Sunkiss vs. The Scottsdale Social: choosing a Scottsdale group stay

A side-by-side look at Trailstead's two Scottsdale homes and which kind of group trip each one suits.

A practical Scottsdale golf-and-pickleball group itinerary

How to structure a play-focused Scottsdale weekend that a real group will actually follow.

Planning a multigenerational Scottsdale stay

What to settle before you book when the party spans three generations.

All guides

See the stays

Tours, details and destination notes.

Walk the homes on video

Property tours and “which stay fits?” comparisons live on the Trailstead Stays channel.

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From the feed

Destination notes, seasonal planning windows and details from the homes.

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About

A small portfolio, built around gathering.

Trailstead Stays brings together distinctive group homes and outdoor stays in destinations worth travelling for. We keep the portfolio small enough to know each home well.

More about Trailstead Stays

Choose your stay.

Four homes. Two destinations. One clear next step.

Explore the staysScottsdaleFlathead Valley