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Plan Your Winter Staycation on Long Island, New York

When you think of a winter getaway you’re probably picturing warm sun and beaches. After all, don’t people want to get away from the cold when they take a winter vacation? I’m actually a fan of colder weather, it’s the heat I’m not crazy about. That’s why I think a winter staycation on Long Island, NY is the perfect getaway! There’s so much to do and you’ll be so busy you probably won’t even notice the cold.

Long Island Winter Vacation

Where you stay will make or break your getaway. There are many Long Island hotels offering special hotel packages that combine a stay with several fun options. You could book a romantic and relaxing package that include spa services; or bring the family for a weekend that combines admission tickets to the local aquarium or children’s museum.

Winter Wine Tasting & Spa Getaways on Long Island

Wine tasting. Photo: Discover Long Island
Wine tasting. Photo: Discover Long Island

The wineries are open year-round and a trip to wine country is a great way to explore that region before the summer crowds come pouring in. Many hotels offer overnight stays that include a wine tour and tastings.

Want to get away with some friends and hit the spa? Book a Spa-jama Getaway at the Inn and Spa at East Wind. The package includes

  • Balancing Facial or Essentials Massage (50 min)
  • luxury overnight accommodations
  • spa lunch at Desmond’s Restaurant
  • a round of cocktails at Desmond’s Lounge
  • and breakfast at Myra’s Coffee Shop

Consider a Wine Country Getaway at the Hilton Garden Inn in Riverhead. You’ll receive

  • luxury transportation to visit three select wineries
  • complimentary tastings at each location
  • boxed lunch or a food voucher at a local vineyard
  • and a farm to table breakfast.
Inn and Spa at East Wind Photo: Discover Long Island
Inn and Spa at East Wind Photo: Discover Long Island

The Inn and Spa at East Wind offers an East End Wine Tour getaway that includes

  • transportation and tasting at three Long Island Vineyards
  • luxurious overnight accommodations in a Deluxe Double Queen Room
  • picnic lunch to go
  • dinner in Desmond’s Restaurant and a bottle of wine
  • breakfast in Myra’s Café
  • and à la carte services in the Spa & Salon – $50 value per person.

Long Island Vacation with Kids

If you’re booking a stay with your family or children, you could also consider a hotel that includes a visit to local attractions like Spring Hill Suites Aquarium Experience, which includes admission to the Long Island Aquarium in Riverhead.

Long Island aquarium. Photo: Discover Long Island
Long Island aquarium. Photo: Discover Long Island

Enjoy luxury accommodations and two tickets to Long Island’s Aquarium and Exhibition Center. The aquarium is only five minutes away. If you’re interested in purchasing extra tickets just ask the front desk. Extend the activities by visiting Tanger Outlets, which is located directly across from the hotel. You’ll also receive a complimentary coupon book for Tanger that offers over $1,600 in savings.

The Hampton Inn Garden City Family Fun Package for Four includes four tickets to the Long Island Children’s Museum, located just one mile from the Hampton Inn Garden City, and overnight accommodations.

Long Island for your Romantic Getaway

A winter hike to the Fire Island lighthouse (open year-round). Photo: Sean Mills
A winter hike to the Fire Island lighthouse (open year-round). Photo: Sean Mills

Make some time for a romantic getaway with the Inn at Fox Hollow’s Suite Surrender package, which includes

  • overnight stay in a luxury suite
  • champagne
  • roses and chocolates
  • dinner for two at Volpe restaurant at the Fox Hollow
  • and breakfast for two at the Inn at Fox Hollow.

The Hyatt Place East End’s Romance in Riverhead package includes overnight accommodations for two

  • $60 Gift Card to a local restaurant
  • chocolate-covered strawberries and sparkling wine
  • complimentary breakfast for two
  • early check-in/late check-out when available.

Long Island with Pets

Want to bring your pet along on a getaway? The Andrew Hotel in Great Neck has a special ‘Pampered Pet Package,’ which includes

  • luxury accommodations for you and your pet
  • a special welcome pet amenity
  • complimentary dog walks
  • and turn-down service with treats for you and your pet.
Mill House B&B in the Hamptons. Photo: Discover Long Island
Mill House B&B in the Hamptons. Photo: Discover Long Island

There are a lot of events still going on at local Long Island museums. There’s a Norman Rockwell era exhibit at the Heckscher Museum, a Long Island in the 60s exhibit at the LI Museum and a photography exhibit at the Nassau Museum of Art. Or you can plan an evening out at one of the local theaters and music halls where you’ll find everything from great comedy and live music performances.

17 Comments

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  1. I love all of the great ideas – this is a wonderful resource for travelling that you have created! This is a great list of relaxing ideas to do in Long Island!

  2. i hope we can plan something like this on winter, but we are loaded of works during winter haha lol. but Long Island, NY is really a nice place!

  3. I didn’t know that Long Island had wineries! I absolutely love the New York City area. I will have to check this out the next time I’m there!

  4. oh, I’ve always wanted to stay at a B&B, I have to make that happen… looks like a great place for a staycation! (esp the spa and the hike to the fire island lighthouse!)

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Written by Amber

Amber is a 30 something country girl who is a habitual optimist, animal lover, reluctant foodie, and adventure seeker.