Enjoy up to 5 nights at this beautiful 6 bedroom home in the stunning, natural beauty of Jackson Hole, with access to Grand Teton and Yellowstone National Park. Some of the most extraordinary fly-fishing in the United States can be found in nearby, pristine waters, most notably, the Snake River.

One room features bunks for 6 which makes it perfect families with kids. Perfect for one or more families to have an unforgettable getaway.

Dates will need to be mutually agreed upon by the winner and the generous donor.

Spend three nights and four days relaxing at the Bahia Hotel and Beach Club. Located in the historic Medano Beach District- in the heart of Cabo San Lucas- the Bahia Hotel and Beach Club is a chic, modern boutique hotel just steps from Medano beach. Set in a seaside pedestrian village, Bahias urban setting offers privacy and relaxation as well as the opportunity to enjoy the excitement of downtown Cabo restaurants, shopping and nightlife. The Bahia's signature Bar Esquina Restaurant has been described by locals and tourists as the hippest gathering in town and is know for its vibrant atmosphere, delicious menu, live music and prime downtown location. Valid through September 26th, 2019 to September 24th 2019. Some blackout dates apply.

Spend four nights and five days on the beautiful Maine coast in a waterfront home with a guest house on twenty-plus private acres. Enjoy spectacular views from every room or while relaxing on the large wraparound deck. Use the dock as a launching pad to explore the river by canoe and kayak or venture to nearby Damariscotta to browse the shops and galleries. To the south, visit Wiscasset (15 minutes), Boothbay Harbor (30 minutes), Portland (1 hour) and Kennebunkport (1.5 hours) To the north, Camden (45 minutes), Rockland (45 minutes), and Acadia National Park (2.5 hours) The home has four bedrooms, four and a half baths, full kitchen, open and airy living space with a fireplace, and wraparound deck. The guest house has a private outdoor patio, two living spaces, a full kitchen, one bedroom, and one bath, limit 8 guests. Available between September and mid-June. Some blackout dates apply. Limit of 8 people. Valid through December 2020.

Spend six nights and seven days in the the little corner of Wyoming that some say is "heaven on earth". This cozy western style well appointed 3 bedroom, 3 bath condominium three bedroom condominium at Teton Pines can accommodate 6-8 guests and is ideally located for a spectacular summer or winter adventure! Just fifteen minutes from the Jackson Hole ViIlage and 3 miles form Teton Village Ski Resort, this vacation home is nestled on stunning ranch land neighboring the majestic Teton Mountain Range. Teton Pines is in close proximity to two of the nation's premier national parks, Grand Teton and Yellowstone. From Teton Pines, the southern-most entrance to Grand Teton is only 5 miles north on the Moose-Wilson Road while the south entrance of Yellowstone is 55 miles north via Grand Teton National Park. Available year round with the exception of Christmas week.

Two round trip seats on the Tradewind Shuttle to either:

Nantucket or Martha's Vineyard from Teterboro Airport of Westchester County Airport

Stowe from Westchester County Airport

St Barths from San Juan, St Thomas or Antigua

Anguilla from San Juan

Blackout Dates Apply - 11/22/19 - 12/2/19, 12/15/19 - 1/7/2019, 2/14/2020 - 2/24/2020. 3/13/2020 - 3/23/2020, 4/9/2020 - 4/13/2020