10 Best October Vacations

When the seasons are changing, and the days are getting  shorter, why not throw on a cozy sweater and start thinking about a new place to explore?  Fall can be the perfect time for a vacation. The summer crowds are gone, and you don’t have to worry about winter weather delays. There are also often great deals to be had, so here is a list of the 10 best October vacations.

vermont october vacationsVermont

When the northern forests of New England explode in color, covering the Green Mountains in a tweed-like pattern of bright reds, yellows and oranges, it is the best time of the year to visit Vermont. Pack warm sweaters, comfortable jeans and walking shoes, and head out for a hike through one of the many state forests.

Montreal, Canada

For a beautiful leaf-peeping vacation with a bit of a European twist, head north of the border to Montreal. The city itself is beautiful, with vibrant French culture, world class restaurants and chic shopping, and the lovely Laurentian Mountains are only a half hour’s drive from downtown.

Paris, France

October is one of the loveliest times to visit Paris. The tourists have all gone home, so you have the museums and shops to yourself, and it’s not impossible to find an excellent table with a view at a chic café. As well, the Jardin de Luxembourg and the Bois de Bologne are resplendent in fall color.

Munich, Germany

One of the 10 best October vacations in Europe, and indeed the world, is in Munich. The city’s annual Oktoberfest is an 18-day party and one of the world’s largest fairs. More than five million people head to Germany for Oktoberfest every year to celebrate the excellent beer brewed in Munich, to sing, and to eat.  A lot.


Chicago may be a little windier in October, but it’s a perfect time of year to see this city. There are plenty of indoor activities to enjoy, including the Field Museum , the Shedd Aquarium , and the Chicago Art Institute . If the Chicago Bears are at home, spend the perfect autumn Sunday at a game at Soldier Field .

Tofino, Canada

While many people try to get away from stormy weather, on the West Coast of Vancouver Island in British Columbia the majesty and power of nature is embraced. People come from the world around for the region’s “storm tourism”, watching the massive waves smash into the picturesque beach in Tofino.


Cool - but not too cool - weather, light crowds, and fun Halloween events make Orlando a great destination in October. If you can get your kids out of school for a long weekend, they'll never forget a family trip to see Mickey Mouse. Disney's a fun destination for lovebirds, too. 

painted desert phoenix october vacationPhoenix

With the temperatures starting to cool, Phoenix is a perfect fall destination. From the majesty of Grand Canyon to the many colors of the Painted Desert and the sprawling vistas of Monument Valley , the weather is still comfortable enough to enjoy a hike through some of the most beautiful vistas in North America.

Churchill, Canada

For a truly unique fall vacation, travel to Churchill Manitoba on Canada’s Arctic Circle . October is polar bear season, when the bears are close to town waiting for the ice to form on the northern ocean. Hop a massive tundra buggy and get as close to wild polar bears as you ever want to get.


For the spookiest of the 10 best October vacations, head to Salem, Massachusetts, home of the famous witch trials. The city celebrates its supernatural past with a whole month’s worth of Halloween activities, from ghost walks to haunted harbor cruises.


Vacation Rentals in Vermont

Private Home In The Woods On 3 Acres (2 Mi. From Town, W/in 10 Mi To The Mtn)

Start the day with a cup of joe in the kitchen enjoying views of Mt. Mansfield. The house has three levels, you have the option of staying in two or three during your stay. The main level includes a master suite with a full bath and whirl pool tu...

2 bedroom Greenspring unit with great view of Mount Snow - 28B Greenspring

2 bedroom, 3 bathroom unit in the sought after Greenspring community. Winter shuttle to the mountain and amenity center in walking distance to this unit. Amenities include indoor pool and hot tub, exercise room, lounge, and tennis courts. Views of...

Killington, Vermont-Northside Condominium #01

Killington, Vermont- North Side Condos The region's best kept secret, the North Side Condominiums are located in a private setting directly across from the Pico Ski Area! In addition to a great location, for skiing, hiking, and local activities ...

Killington, Vermont- Sunrise East Glade D2

Killington, Vermont- Sunrise Complex Enjoy one of Killington’s few Ski on Ski off developments. As a guest put it “Staying at Sunrise you can have it all.” Sunrise is an ideal area for families, couples, and groups who want to get away from the ...

523 Stratton Arlington Road: 3 BR / 3 BA in Stratton, Sleeps 8

3 bedroom, 2 bath. Located between Mount Snow and Stratton. Have the best of both worlds. Winter Seasonal Rental Rate: $17,000.00 The rental rate does not include cleaning, security deposit, utilities, or amenity center fees if applicable. Dates...

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