Town of Pines Holidays from NZ$3,258

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The Latest Town of Pines Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
NZ$3,258
per person
14 Oct - 18 Oct
found 10 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.2/10 Very good! (2,992 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
NZ$3,767
per person
14 Oct - 18 Oct
found 10 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
Everything was great

Reviewed on 2 Sept 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
NZ$3,863
per person
14 Oct - 18 Oct
found 10 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
NZ$3,588
per person
14 Oct - 18 Oct
found 10 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (556 reviews)
Loved the hotel, super nice and clean! Felt like home away from home!

Reviewed on 1 Sept 2026

Level Chicago - River North

Level Chicago - River North

Downtown Chicago
NZ$3,588
per person
14 Oct - 18 Oct
found 10 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,064 reviews)

Town of Pines Holiday

Our pick of the best Town of Pines Hotel Deals

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

11111 Wilson Road New Buffalo MI
NZ$192
10 Sept - 11 Sept
includes taxes & fees
9.4/10 Exceptional! (2,167 reviews)
"I booked my trip through you guys. I set the dates paid for it and it changed the dates so I canceled the trip then I got charged for a hotel for a trip that I never went very bad experience not really happy. Don’t know if I’ll ever use you again, cause now, I gotta fight the charge on my credit ..."

Reviewed on 2 Sept 2026

Four Winds Casino Resort – New Buffalo
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

777 Blue Chip Drive Michigan City IN
Fully refundableReserve now, pay when you stay
NZ$212
28 Sept - 29 Sept
includes taxes & fees
Blue Chip Casino Hotel and Spa
Quality Inn Near Interstate I94

Quality Inn Near Interstate I94

18830 Laporte Rd New Buffalo MI
NZ$168
23 Sept - 24 Sept
includes taxes & fees
8.4/10 Very good! (1,288 reviews)
"For what we needed, this fit the bill. It was a last minute trip to New Buffalo and we didn't want to break the bank for an overnight. Staff was accomodating and friendly. The room & property was clean and we were allowed to bring our ebikes inside at night - a bit of piece of mind. I would stay ..."

Reviewed on 2 Sept 2026

Quality Inn Near Interstate I94
See all 1,613 properties in Town of Pines
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Town of Pines attractions

Pines Park

After visiting Pines Park, make a plan to see the other sights and activities in Town of Pines. While you're in the area, stroll along the beaches.
See properties

Frequently asked questions

How much does a Town of Pines holiday package cost?
You'll find cheap prices from NZ$3,258 on Expedia for your Town of Pines getaway. However, factors like your choice of hotel, the season and length of stay will influence how much your holiday to Town of Pines costs.
What are the cheapest months to go to Town of Pines?
Travel in the low season and you're likely to score cheap Town of Pines holiday packages. Keep in mind that school holiday periods and major events and festivals can have an impact on prices, so do a little research before you go.
How many days is enough for Town of Pines?
The ideal length of your Town of Pines holiday depends on what you'd like to do. Usually, a few days to a week will give you time to hit all the leading sights and explore some hidden gems along the way.
Is it worth booking a holiday package to Town of Pines?
It's no wonder a Town of Pines holiday is on the to-do list of many travellers. Major attractions like Lake View Beach are just the start of things to keep you busy here.
How to find the best Town of Pines package deals?
Start your search for a Town of Pines package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Town of Pines package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Town of Pines adventure underway.
Is it cheaper to book a Town of Pines holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component individually. And you'll still have the freedom to create a customised Town of Pines holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Town of Pines?
Secure incredible discounts by booking your flights early with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Town of Pines trip.
How to plan a trip to Town of Pines?
  1. Pick your travel dates: The things you plan to do in Town of Pines and your preferred season will help you decide when to go.
  2. Set your budget: Consider expenses like flights, food and transportation when calculating how much to put aside for your trip to Town of Pines. Then, select a property that fits your budget, whether that's a wallet-friendly stay or a more upscale getaway.
  3. Decide how long to go away for: Now that you know more about Town of Pines, you can figure out the perfect length of your holiday. Create a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customised Town of Pines holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.