Pillar Point Vacations from $400

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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.
Quality Inn & Suites Watertown Fort Drum

Quality Inn & Suites Watertown Fort Drum

2.5 out of 5
per person
Aug 30 - Sep 1
found 1 day ago
Roundtrip flight included
New York (NYC) to Watertown (ART)
8.2/10 Very Good! (1,004 reviews)
Our stay was very nice.

Reviewed on Jun 28, 2025

Thousand Island Hart House

Thousand Island Hart House

2 out of 5
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Brownsville (BRO) to Watertown (ART)
10/10 Exceptional! (9 reviews)
Charming b and b with exceptional service. Great breakfast and lovely walk to Boldt Yacht House.

Reviewed on May 12, 2025

Ramada by Wyndham Watertown/Thousand Islands NY

Ramada by Wyndham Watertown/Thousand Islands NY

2.5 out of 5
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Brownsville (BRO) to Watertown (ART)
8/10 Very Good! (1,004 reviews)
Quiet and friendly staff

Reviewed on Jun 28, 2025

The Roxy Cape Vincent

The Roxy Cape Vincent

2 out of 5
per person
Aug 30 - Sep 1
found 1 day ago
Roundtrip flight included
New York (NYC) to Watertown (ART)
8.4/10 Very Good! (16 reviews)
The Roxy Hotel in Cape Vincent is beautiful with Celtic carvings on the entrance way, and beautiful wooden details in the rooms.

Reviewed on May 19, 2025

Pleasant Night Inn

Pleasant Night Inn

2 out of 5
West Carthage
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Brownsville (BRO) to Watertown (ART)
7.6/10 Good! (194 reviews)
Very unspectacular. Dated and dingy. Nothing was horrendous, but nothing stood out either. Mattress was old and lumpy. A few small stains on the bedspread. Slightly musty smell in the room but not overwhelming. Spartan and utilitarian. Fine for a night, decent value for the price.

Reviewed on Jun 24, 2025

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Pillar Point Hotel Deals

Black Bay Chalet- Spectacular lake front location
Black Bay Chalet- Spectacular lake front location
Dexter
9.8/10 Exceptional! (16 reviews)
Perfect Destination for Relaxation , Comfort & Fun
"Traveled from California to New York for son’s graduation and post family vacation . This was one of our stops for half of us which we thoroughly enjoyed . Beautiful lake views with all the comforts of home . Would definitely come back again !"

Reviewed on May 17, 2025

Get rates
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
$69 nightly
The price is $77 total per night from Jul 1 to Jul 2
$77 total
Jul 1 - Jul 2
Total includes taxes and fees
8/10 Very Good! (1,003 reviews)
Highly recommend, right off 81 near EVERYTHING A++
"Second time here and again, can't complain at all... Chad was also excellent and helpful, very kind!! Highly recommend and right off 81... near Walmart and many other shops restaurants"

Reviewed on Jun 27, 2025

Ramada by Wyndham Watertown/Thousand Islands NY
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
1290 Arsenal St, Watertown, NY
Fully refundable
$122 nightly
The price is $135 total per night from Jul 6 to Jul 7
$135 total
Jul 6 - Jul 7
Total includes taxes and fees
9.2/10 Wonderful! (1,003 reviews)
"Breakfast. Beds Pleasant employees"

Reviewed on Jun 25, 2025

Holiday Inn Express Hotel & Suites Watertown-Thousand Island by IHG
See all 276 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.

Find the Best Pillar Point Vacation Packages

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 $400 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.