Wyndham Route 66 Grand-Mother Roadtrip Sweepstakes

Posted Date: April 28, 2026

Win a seven-night Route 66 road trip for you and a grandparent with lodging, travel funds, $15,000 payment, Wyndham Diamond status, and swag.

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Prize Description:

Win a 7-night Route 66 road trip for you and a grandparent-ish guest!

Trip includes Wyndham hotel stays, travel funds, $15,000 cash, one-year Wyndham Diamond status, and branded swag, worth $21,600!

Includes travel

Entry Frequency: Single Entry

Total Prizes: 1

Grand Prize ARV: $21,600

All Prizes ARV: $21,600

Start Date: April 7, 2026

End Date: May 1, 2026

Eligible States:
All states

All states

Quick Take!

Oh my gosh, how sweet is this for grandparents and grandkids, right? I love that it’s a one-and-done creative entry, just a short video or essay via email. The prize is truly generous for a single entry, but remember it’s judged so put a little effort into your story. Great for anyone who wants a memorable multi-day adventure with a grandparent, skip it if you don’t want to document the trip.

How to Enter:

Email Entry to roadtrip@wyndham.com with a short video or short essay showing why you and your grandparent (or similar) want to take this trip together along Route 66.

Entries are judged – See official rules for exact requirements and judging criteria.

All Prizes

Grand Prize:

Seven (7) nights of lodging at various hotels within the Wyndham portfolio (one room per night) provided as Wyndham Rewards points deposited into the winning Entrant’s account
$15,000 USD paid to the winning Entrant for completion of Independent Contractor Agreement obligations
$5,000 USD paid to the winning Entrant to cover travel related expenses excluding lodging (two roundtrip economy airfare tickets, one economy or compact car rental for eight days, gas, tolls, daily meals, and activities)
Wyndham Rewards Diamond level status upgrade for one year for both members of the Entrant Pair
Wyndham branded swag for both members of the Entrant Pair (approx. $200 ARV)

ARV: $21,600

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Good to Know:

One entry per entrant, trip travel is U.S. domestic and winner pays taxes, winner must document the trip and complete deliverables.

Frequently Asked Questions:

Is this sweepstakes free to enter?

Sure is! This sweepstakes includes a free entry option and purchases never improve your odds.

How and when will the winner be notified?

Winners will be contacted by email and/or phone using the contact information provided on or around 06/02/26; potential winners must respond within 48 hours and complete required paperwork and verifications.

Not sure what a real winner notification looks like? See real examples of actual sweepstakes winner emails on our How to Know If You Won page.

Is this sweepstakes legitimate?

Yes, this sweepstakes is legitimate, it is sponsored by Wyndham Hotel Group and governed by the official rules posted by the sponsor and administrator.

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