Pillar Point Vacations from $440

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Your Pillar Point Vacation

Our Pillar Point vacation packages give you countless opportunities to indulge in new sights, sounds and activities. And with all your travel plans taken care of, you'll be free to enjoy your city adventure without a worry in the world. If sightseeing is on your list of things to do during your trip to Pillar Point, stop by famous attractions like Farmhouse Maple. That dream Pillar Point vacation is only clicks away. Explore airfares, hotels and more on Expedia for a getaway that's tailored just for you.

The Latest Pillar Point vacation packages

Price found within the past 48 hours. Click for updated prices.
Pleasant Night Inn

Pleasant Night Inn

2 out of 5
West Carthage
Price was $490, price is now $440 per person
$440
per person
Nov 7 - Nov 11
found 24 hours ago
Roundtrip flight included
Seattle (SEA) to Watertown (ART)
7.4/10 Good! (202 reviews)
The toilet hadn't been flushed. The shower wasn't clean. There was dirt on the bathroom floor.

Reviewed on Aug 11, 2025

The Roxy Cape Vincent

The Roxy Cape Vincent

2.5 out of 5
Price was $674, price is now $526 per person
$526
per person
Nov 7 - Nov 11
found 24 hours ago
Roundtrip flight included
Seattle (SEA) to Watertown (ART)
8.8/10 Excellent! (34 reviews)
Perfect location to experience the town!

Reviewed on Sep 28, 2025

Chateau Country Inn

Chateau Country Inn

2 out of 5
Price was $565, price is now $510 per person
$510
per person
Nov 7 - Nov 11
found 24 hours ago
Roundtrip flight included
Seattle (SEA) to Watertown (ART)
9.6/10 Exceptional! (118 reviews)
The breakfast was easily accessible. They had French toast which is my favorite. The room was clean and well organized. I enjoyed my stay and I appreciate that.

Reviewed on Sep 29, 2025

Candlewood Suites Watertown Fort Drum by IHG

Candlewood Suites Watertown Fort Drum by IHG

2.5 out of 5
Price was $550, price is now $502 per person
$502
per person
Nov 7 - Nov 11
found 24 hours ago
Roundtrip flight included
Seattle (SEA) to Watertown (ART)
8.4/10 Very Good! (481 reviews)
Everything was great and wonderful

Reviewed on Sep 29, 2025

Holiday Inn Express Hotel & Suites Watertown-Thousand Island by IHG

Holiday Inn Express Hotel & Suites Watertown-Thousand Island by IHG

2.5 out of 5
Price was $544, price is now $499 per person
$499
per person
Nov 7 - Nov 11
found 24 hours ago
Roundtrip flight included
Seattle (SEA) to Watertown (ART)
9.2/10 Wonderful! (1,002 reviews)
Hotel was very clean, the breakfast was very good as well.

Reviewed on Sep 28, 2025

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Pillar Point Hotel Deals

Modern Lakeside Retreat on Lake Ontario 4 bedroom/3 bath

Modern Lakeside Retreat on Lake Ontario 4 bedroom/3 bath

Dexter
Get rates
Modern Lakeside Retreat on Lake Ontario 4 bedroom/3 bath
Black Bay Chalet- Spectacular lake front location

Black Bay Chalet- Spectacular lake front location

Dexter
9.8/10 Exceptional! (17 reviews)
Relaxing week away
"We loved staying here! The home is beautiful, clean and updated. It is centrally located to many Thousand island towns, which we visited. We loved relaxing on the deck and the rocks for the waves, sunsets, and fishing. There was only one bad part having to leave! A grill, firepit and a raft would ..."

Reviewed on Jun 25, 2025

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Black Bay Chalet- Spectacular lake front location
Ramada by Wyndham Watertown/Thousand Islands NY

Ramada by Wyndham Watertown/Thousand Islands NY

2.5 out of 5
21000 NY State Rt 3, Watertown, NY
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $88 total per night from Oct 22 to Oct 23
$88 total
Oct 22 - Oct 23
Total with taxes and fees
7.8/10 Good! (1,056 reviews)
"Room clean and comfy. Staff very friendly and helpful."

Reviewed on Sep 30, 2025

Ramada by Wyndham Watertown/Thousand Islands NY
See all 277 properties in Pillar Point
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.

Pillar Point Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Watertown Intl. Airport (ART)

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Frequently asked questions

How much does a Pillar Point vacation package cost?
Offering great value package deals from $440 on Expedia, you'll be thrilled with how little a vacation to Pillar Point costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Pillar Point?
October, November and December are the best times to look for cheap Pillar Point vacation packages. Opting to travel in quieter months means you can generally find better prices on flights and accommodations.
How many days is enough for Pillar Point?
With a well-organized schedule, you can easily visit the top Pillar Point attractions in a handful of days. But if you prefer to discover lesser-known spots or go on day tours, consider booking your Pillar Point vacation for longer.
How to find the best Pillar Point package deals?
Start your search for a Pillar Point package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Pillar Point package deal straight away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Pillar Point adventure underway.
Is it cheaper to book a Pillar Point vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and stays separately. Better still, you can tailor your Pillar Point trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Pillar Point?
Secure amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Pillar Point adventure.
How to plan a trip to Pillar Point?

  1. Choose the perfect time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to travel to Pillar Point.
  2. Plan your budget wisely: In addition to the price of your stay, you'll need to consider other expenses too. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that may come up during your trip to Pillar Point.
  3. Discover Pillar Point using Expedia's trip planning tool: Gain insights into the top attractions and best stays for your trip to Pillar Point. You can also save your favorite locations, collaborate with friends and family and organize all your plans in one place.
  4. Decide how long to go for: Now that you're more familiar with Pillar Point, you can figure out the perfect length of your vacation. Put together a draft plan and give yourself enough time to get through everything on your must-do list.
  5. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a tailored Pillar Point vacation package.
  6. Add on experiences and excursions: Have a look at our dedicated travel guide to find some incredible things to do in Pillar Point. Book tickets or make reservations as soon as you can to save time and skip the hassle of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Pillar Point vacation packages?
Your Pillar Point trip is meant to be a relaxing escape from your busy life, not a source of money-related stress. So to give you that extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.