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Trailstead Stays
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The portfolio

Every Trailstead stay, in one place.

Four homes today, with cabins and outdoor stays added only when real, bookable inventory exists.

Check dates

Start with the destination, dates and group size.

Choose Scottsdale or Flathead Valley, then carry your dates and group size to each home's official booking page. That is where current availability, full fees, minimum stays, policies and house rules are confirmed.

Eligible results carry your dates and full group size to the home’s official booking page. See available dates and your full stay total there, along with minimum stays and guest limits.

Compare the collection

Two Scottsdale homes. Two Flathead Valley homes.

The Sunkiss is the play-focused Scottsdale choice; The Scottsdale Social centers shared gathering space and games. The Evergreen suits larger Montana groups under one roof; The Tamarack suits lake, retreat and winter plans. Open each home's details before checking its calendar.

Filter by destination

Scottsdale, Arizona

The Sunkiss Scottsdale

Serve. Swim. Stay awhile.

5 bedrooms · 8 beds · 3 baths · 4.93 (60) · checked 23 Sep 2026

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 up to 16. Five bedrooms, eight beds and three bathrooms. Maximum 16 guests overnight.

Scottsdale, Arizona

The Scottsdale Social

Made to play. Built to gather.

5 bedrooms · 9 beds · 3 baths · 4.92 (71) · checked 23 Sep 2026

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. Five bedrooms, nine beds and three bathrooms. Maximum 18 guests overnight.

Somers, Montana

The Evergreen at Flathead Lake

Room to reconnect. Montana to explore.

6 bedrooms · 10 beds · 3.5 baths · 4.98 (42) · checked 23 Sep 2026

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, near Flathead Lake and Glacier Country.

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

Sleeps up to 10. Six bedrooms, ten beds and 3.5 bathrooms. Maximum 10 guests overnight per local regulations.

Lakeside, Montana

The Tamarack

Adventure out. Exhale in.

6 bedrooms · 9 beds plus trundle · 4.5 baths · 5.0 (12) · checked 23 Sep 2026

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

Sleeps up to 10. Six bedrooms, nine beds plus trundle and 4.5 bathrooms. Maximum 10 guests overnight.

Questions travelers ask

Straight answers to the questions groups ask before they choose a home. Availability, rates, fees, minimum stays and final guest limits are always confirmed on the official booking calendar.

What is the best Scottsdale vacation rental for a large group?

Trailstead Stays offers two large Scottsdale homes. Choose The Sunkiss for four king bedrooms plus a bunk room, a private pool and hot tub, and a sport court set up for pickleball and basketball. Choose The Scottsdale Social for five bedrooms, nine beds, a private pool and hot tub, a putting green, and more than 15 games.

Confirm dates, rates and the final guest limit on the official booking calendar.

Which Scottsdale house has an onsite sport court, and which has Snookball, a pool and a hot tub?

The Scottsdale Social has a private pool, hot tub, Snookball, putting green and a broad indoor and outdoor game collection. Pickleball for guests of The Scottsdale Social is offsite, not an onsite amenity.

The Sunkiss has the onsite orange-and-yellow sport court set up for pickleball and basketball. Amenity lists are the ones verified on each property site; confirm anything you are planning around on the official booking calendar.

Where should a multigenerational family stay near Old Town Scottsdale?

The Sunkiss is a strong fit because it combines four king bedrooms, a bunk room, three bathrooms, a long dining table and a private backyard with pool, hot tub, fire pit and sport court.

Old Town is a short drive, not promised walking distance. The final guest limit and house rules are on the live calendar.

What Scottsdale house works for golf, spring training, concerts or a local staycation?

Both Scottsdale homes work as group bases. The Sunkiss suits king-room and sport-court groups; The Scottsdale Social suits nine-bed, game-focused groups.

Start with the event and experience guides for the weeks that move demand, then continue to each home's official calendar.

Where can a large group stay near Flathead Lake and Glacier National Park?

The Evergreen in Somers and The Tamarack in Lakeside are six-bedroom homes near public Flathead Lake recreation and regional drives into Glacier Country.

The Evergreen has six bedrooms, a speakeasy, game room, hot tub and barrel sauna. It sleeps up to 10. The Tamarack has nine beds, 4.5 baths, hot tub, sauna, fire pit and game room, and sleeps up to 10.

Neither home includes private, deeded or property-specific lake access; the lake is reached through public beaches, ramps, marinas and parks.

What Montana vacation rental is best for fall foliage or a winter ski trip?

The Tamarack fits gear-heavy Lakeside groups, with garage and driveway parking, hot tub, sauna, fire pit and game room. The Evergreen fits Somers family and wellness groups, with a barrel sauna, hot tub, speakeasy and large game room.

Weather, roads, resort operations and Glacier access vary by season; check the official sources linked in the Flathead Valley winter guide before you travel.

Which Montana house has a sauna, hot tub, game room and space for a reunion or retreat?

Both do. The Evergreen has six bedrooms and adds a speakeasy, and sleeps up to 10. The Tamarack sleeps up to 10 and adds a fire pit plus garage and driveway parking.

These are residential stays run under house rules, not event venues. Confirm the guest limit and gathering rules on the official booking calendar before planning around a headcount.