Recognition
Celebrating two Trailstead homes recognized in the Paradiso Homes luxury collection: The Evergreen (opens in a new tab) in Somers, Montana and The Scottsdale Social (opens in a new tab) in Scottsdale. Explore the recognition and plan your stay.
Photo 1 of 8. The Tamarack — living room with vaulted ceiling, large windows, brown leather sofas, coffee table, and stone fireplace
1/8Trailstead Stays
Scottsdale & Flathead Lake vacation rentals
Four group homes across two very different settings — desert Arizona and Montana's Flathead Lake valley. Compare them here, then see dates and your full stay total.
Two-home stays
One trip. Two homes. Room for your people.
Planning around an offsite wedding, reunion, or group weekend? Compare two separate homes in one destination, then check each home’s calendar and rules for the guests staying there.
Dates still open
Planning fall, the holidays or a longer Montana stay?
The Scottsdale Social
The Evergreen
The Tamarack
Exact dates are confirmed on each home's official booking page.
Check the calendar
Pick your dates. We'll take them to the booking page.
Choose a destination, your nights and your group size. Every home carries those details to its official booking page, where you can see available dates and your full stay total.
These are suggested dates around the event you picked — the night before through two nights after. Availability is not confirmed here. Adjust the dates and group size, then check each home’s official booking page.
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.
Scottsdale, Arizona
The Sunkiss
Sleeps up to 16
Scottsdale, Arizona
The Scottsdale Social
Sleeps up to 18
Somers, Montana
The Evergreen
Sleeps up to 10
Lakeside, Montana
The Tamarack
Sleeps up to 10
Choose in 30 seconds
Two quick choices, then jump straight to the matching homes below.
Worth a trip
Upcoming dates worth planning around
Confirmed home dates from official Arizona schedules. Pick one and we'll suggest a stay window in the planner above — availability is still confirmed on each home's own booking page.
Oct 24
Arizona State vs. Kansas State
Mountain America Stadium
Oct 25 · 1:05 PM
Arizona Cardinals vs. Denver
State Farm Stadium
Nov 4 · tip time: see suns.com
Phoenix Suns home game
Mortgage Matchup Center
Nov 5 · tip time: see suns.com
Phoenix Suns home game
Mortgage Matchup Center
Nov 6–15
Canal Convergence
Scottsdale Waterfront
Nov 7 · tip time: see suns.com
Phoenix Suns home game
Mortgage Matchup Center
Dates come from each organiser’s official schedule and can change; the organiser always controls. Availability is never confirmed here. See the full Scottsdale calendar.
Arizona or Montana?
Two destinations, two very different trips.
Scottsdale suits warm-weather group trips built around a pool, a sport court, golf and Old Town evenings — best in the cooler months. Montana's Flathead Lake valley suits lake days, Glacier planning, larch-season fall and ski weekends, with a hot tub and sauna waiting at the end of the day. Pick the setting first; each home below is on that destination's page too.
Scottsdale, Arizona
Scottsdale
Desert light, long pool days, and easy group logistics.
- — Two Trailstead homes in one metro, so a large group can split across houses while keeping each stay separate.
- — 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.
- The Sunkiss — Serve. Swim. Stay awhile.
- The Scottsdale Social — Made to play. Built to gather.
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.
- The Evergreen — Room to reconnect. Montana to explore.
- The Tamarack — Adventure out. Exhale in.
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 Scottsdale
Serve. Swim. Stay awhile.
Featured in The STR Report
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.
View detailsSee dates and your full stay total(opens the The Sunkiss booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
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.
View detailsSee dates and your full stay total(opens the The Scottsdale Social booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
Somers, Montana
The Evergreen at Flathead Lake
Room to reconnect. Montana to explore.
Featured by Travel Curator
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.
View detailsSee dates and your full stay total(opens the The Evergreen booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
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.
View detailsSee dates and your full stay total(opens the The Tamarack booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
Seasonal property films
See each home in its season.
Four short property portraits: fall in Montana and evenings in Scottsdale. Use the filters to compare one region at a time.
Runtime 0:22 · Flathead Valley, Montana
The Evergreen — Fall
A fall-season portrait of The Evergreen in Montana's Flathead Valley.
What this film shows (text alternative)
- No narration or dialogue. Ambient audio only.
- Fall exterior of The Evergreen in Somers, Montana, with autumn colour in the surrounding trees.
- The hot tub and barrel sauna outside.
- Interior of the speakeasy and the game room.
- Closing wide shot of the house at golden hour. No on-screen text.
Seasonal visualization created from the actual property; weather, foliage, sky or lighting may be digitally enhanced.
View The EvergreenCheck dates(opens the The Evergreen booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
Runtime 0:22 · Flathead Valley, Montana
The Tamarack — Fall
A fall-season portrait of The Tamarack in Montana's Flathead Valley.
What this film shows (text alternative)
- No narration or dialogue. Ambient audio only.
- Fall exterior of The Tamarack in Lakeside, Montana, with autumn colour in the surrounding trees.
- The hot tub and stone fire pit, then the sauna.
- Interior of the game room and the main gathering space.
- Closing wide shot of the house and driveway. No on-screen text.
Seasonal visualization created from the actual property; weather, foliage, sky or lighting may be digitally enhanced.
View The TamarackCheck dates(opens the The Tamarack booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
Runtime 0:22 · Scottsdale, Arizona
The Scottsdale Social — Snookball After Dark
An after-dark look at The Scottsdale Social's Snookball setup and blue-and-red game court.
What this film shows (text alternative)
- No narration or dialogue. Ambient audio only.
- Evening exterior of The Scottsdale Social's backyard under house lighting.
- The Snookball table in its fixed position along the wall behind the seating area.
- The blue-and-red game court, then the pool and hot tub after dark.
- Closing shot of the seating area and fire feature. No on-screen text.
Visualization created from the actual property; sky, lighting or aerial perspective may be digitally enhanced.
View The Scottsdale SocialCheck dates(opens the The Scottsdale Social booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
Runtime 0:22 · Scottsdale, Arizona
The Sunkiss — Blue Hour
A blue-hour portrait of The Sunkiss and its orange-and-yellow sport court.
What this film shows (text alternative)
- No narration or dialogue. Ambient audio only.
- Blue-hour exterior of The Sunkiss, with the house and backyard lit as the sky darkens.
- The pool and hot tub, then the fire pit lounge.
- The orange-and-yellow sport court, set up for pickleball and basketball.
- Closing wide shot of the backyard at dusk. No on-screen text.
Visualization created from the actual property; sky, lighting or aerial perspective may be digitally enhanced.
View The SunkissCheck dates(opens the The Sunkiss booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
Seasonal conditions and availability vary; confirm current dates on the official booking page.
Plan your holidays
Thanksgiving, Christmas and New Year in Arizona or Montana.
Start with meals, packing and one realistic outing, then choose the home that fits. Open a panel for concise ideas and follow the full guide for changing conditions and official sources.
The Sunkiss, Scottsdale
Arizona
Scottsdale holidays
Build the week around shared meals, comfortable outdoor hours and one flexible local outing. Confirm pool heat, house rules and every changing detail before the trip.
Thanksgiving
Choose cooking, prepared pickup or dining out before arrival. Assign the grocery run, confirm holiday opening hours directly and pack layers for cooler desert evenings.
Christmas
Keep one day intentionally light: a shared meal, time at the house and an optional outing. Check organiser hours and ticket requirements before adding any seasonal activity.
New Year
Plan transport and the return to the house before choosing an evening outing. These are guest homes, not event venues, so review occupancy and gathering rules on the booking page.
Plan for The Sunkiss
Check current dates — The Sunkiss(opens the The Sunkiss booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
Plan for The Scottsdale Social
Check current dates — The Scottsdale Social(opens the The Scottsdale Social booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
The Evergreen, Flathead Valley
Montana
Flathead Valley holidays
Plan for short daylight, changing road conditions and more time together indoors. Treat weather, access, operations and seasonal programming as details to verify close to travel.
Thanksgiving
Do the main grocery shop on arrival, organise the meal before the travel day and carry warm, waterproof layers for any outdoor time. Check roads and local opening hours directly.
The Evergreen Thanksgiving inspiration film
The Evergreen, Flathead Valley. Gathering and decor shown are an illustrative AI visualisation, not promised amenities or availability. Check current dates and group size on the official booking page.
View this film on Instagram(opens in a new tab)Christmas
Build each day around one main outing and a flexible return before dark. Glacier's winter access is limited and changeable, so use the park's current guidance rather than assumptions.
New Year
Keep evening plans adaptable to roads and weather. Confirm restaurant or activity operations with the provider, then leave room for meals and games together at the house.
Plan for The Evergreen
Check current dates — The Evergreen(opens the The Evergreen booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
Plan for The Tamarack
Check current dates — The Tamarack(opens the The Tamarack booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
Official planning sources
Check current dates and group size on each home’s official booking page. That page confirms availability, full fees, minimum stays, occupancy and house rules; this planner does not.
Compare at a glance
Compare the stays
Use the trip fit and sleeping notes to narrow the four homes. Then open the home's details and check dates and group size on its official booking page, where full fees, minimum stays, policies and house rules are confirmed.
The Sunkiss
- Where
- Scottsdale, Arizona
- Best for
- Golf and pickleball groups, Family and multigenerational trips, Cooler-season desert escapes
- Bedrooms and group size
- Sleeps up to 16. Five bedrooms, eight beds and three bathrooms. Maximum 16 guests overnight.
The Scottsdale Social
- Where
- Scottsdale, Arizona
- Best for
- Group celebrations and reunions, Golf trips, Holiday gatherings
- Bedrooms and group size
- Sleeps up to 18. Five bedrooms, nine beds and three bathrooms. Maximum 18 guests overnight.
The Evergreen
- Where
- Somers, Montana
- Best for
- Multigenerational family trips, Flathead Lake and Glacier planning, Fall and winter gatherings
- Bedrooms and group size
- Sleeps up to 10. Six bedrooms, ten beds and 3.5 bathrooms. Maximum 10 guests overnight per local regulations.
The Tamarack
- Where
- Lakeside, Montana
- Best for
- Lake trips, Group retreats, Ski and winter weekends
- Bedrooms and group size
- Sleeps up to 10. Six bedrooms, nine beds plus trundle and 4.5 bathrooms. Maximum 10 guests overnight.
| Stay | Where | Best for | Bedrooms and group size | Booking |
|---|---|---|---|---|
| The Sunkiss | Scottsdale, Arizona | 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. | |
| The Scottsdale Social | Scottsdale, Arizona | Group celebrations and reunions, Golf trips, Holiday gatherings | Sleeps up to 18. Five bedrooms, nine beds and three bathrooms. Maximum 18 guests overnight. | |
| The Evergreen | Somers, Montana | 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. | |
| The Tamarack | Lakeside, Montana | 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. |
Open a home’s details to compare the verified fit, then check dates and group size on its official booking page. Review the full fees, minimum stay, policies and house rules before booking.
Plan together
Planning a holiday, a group trip or a stay of 30+ nights? Tell us your dates.
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.
Check current dates — The Sunkiss(opens the The Sunkiss booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
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.
Check current dates — The Scottsdale Social(opens the The Scottsdale Social booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
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.
Check current dates — The Sunkiss(opens the The Sunkiss booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
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.
- Scottsdale events and seasonal planning
- Spring training and sports trips
- Concerts, festivals and major events
Check current dates — The Scottsdale Social(opens the The Scottsdale Social booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
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.
Check current dates — The Evergreen(opens the The Evergreen booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
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.
Check current dates — The Tamarack(opens the The Tamarack booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
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.
Check current dates — The Evergreen(opens the The Evergreen booking page in a new tab)Book direct on our Guesty booking portal: no Airbnb or VRBO service fees + 5% off.
The official path
One portfolio. Four distinct stays. One clear way to plan.
Trailstead Stays helps you compare the portfolio, carry your dates and group size to the official booking page, and see dates and your full stay total there.
Availability, rates, fees, minimum stays, policies, and final occupancy are confirmed on the Trailstead booking calendar for each home.
Choose your stay.
Four homes. Two destinations. One clear next step.
Plan your trip
- Barrett-Jackson Scottsdale 2027
- Things to do in Glacier National Park
- Montana in October and November
- Fall vacation ideas for groups and families
- Ski Whitefish, stay by Flathead Lake
- A warm-weather winter trip to Scottsdale
- Flathead Lake vacation rentals for groups
- When does Going-to-the-Sun Road open?
- Summer on Flathead Lake