Pittsford Vacation Packages

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Your Pittsford Vacation

When a city adventure is calling, answer it with a Pittsford vacation package. With all your travel plans taken care of before you go, all you need to do here is focus on having a ball. Make your trip to Pittsford even more enjoyable by including some sightseeing. Rutland Country Club, New England Maple Museum and Lefferts Pond are some of the big attractions you'll want to explore. Expedia is here to help you escape the everyday. Tailor your vacation to Pittsford to match your travel style, whatever that may be!

Top Pittsford Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Vermont Inn

The Vermont Inn

3 out of 5
Price was CA $1,104, price is now CA $1,042 per person
CA $1,042
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Rutland (RUT)
9.2/10 Wonderful! (430 reviews)

The Landgrove

The Landgrove

3.5 out of 5
Price was CA $1,210, price is now CA $1,099 per person
CA $1,099
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Rutland (RUT)
10/10 Exceptional! (1 review)
Tammy, the assistant inn keeper and restaurant manager was fantastic. She was attentive to every need. The restaurant staff was phenomenal as well highly recommend, it’s a little hidden gem off the beaten path. I will definitely return. Had a fabulous time.

Reviewed on Jun 27, 2026

Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was CA $1,407, price is now CA $1,313 per person
CA $1,313
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Rutland (RUT)
9/10 Wonderful! (99 reviews)
The lock situation on the door to my cabin was concerning. The key was required to lock it from both the inside and the outside (presenting a hazard if I needed to escape quickly), and there was no deadbolt. There was another lock that had a keyhole on both the inside and outside, but my key did not work on it. As a single woman staying on the property entirely alone in the off season, I felt the need to barricade my door each night to ensure nobody could get in, since I couldn't deadbolt it.

Reviewed on Jun 18, 2026

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was CA $1,256, price is now CA $1,177 per person
CA $1,177
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Rutland (RUT)
9.2/10 Wonderful! (1,002 reviews)
Small, but great outdoor pool. On site restaurant was way better than expected with a nice range of food and drink choices. The rooms were good for this price point. Overall, a very solid option.

Reviewed on Jul 6, 2026

Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was CA $1,737, price is now CA $1,631 per person
CA $1,631
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Rutland (RUT)
9/10 Wonderful! (118 reviews)
This was our second time staying here and it never disappoints! I booked this trip during our kids' spring break for a quick getaway and to use the amazing heated outdoor pool. It's a great location convenient to all the amazing sites Vermont has to offer. Would love to go back again in the fall!

Reviewed on Apr 19, 2026

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Pittsford Hotel Deals

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Jul 12 to Jul 13
CA $208
CA $228 total
Jul 12 - Jul 13
includes taxes & fees
7.4/10 Good! (1,005 reviews)
"We had a great stay. The staff was nice and the property was awesome. The beds were super comfy and the rooms were clean.Close to everything."

Reviewed on Jul 5, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is CA $216 per night from Jul 13 to Jul 14
CA $216
CA $249 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Small, but great outdoor pool. On site restaurant was way better than expected with a nice range of food and drink choices. The rooms were good for this price point. Overall, a very solid option."

Reviewed on Jul 6, 2026

The Mountain Inn at Killington
Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square Middlebury VT
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Jul 7 to Jul 8
CA $169
CA $186 total
Jul 7 - Jul 8
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"This was the welcoming and friendly hotel that I have stayed. The room was perfect, and very well maintained."

Reviewed on Jul 4, 2026

Middlebury Inn
See all 1,799 properties in Pittsford
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.
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Stay near popular Pittsford attractions

New England Maple Museum

8.0/10 (11 reviews)
You can spend time studying the exhibits at New England Maple Museum during your travels in Pittsford. Discover the area's mountain views and charming coffeehouses.
See properties

Frequently asked questions

How much does a Pittsford vacation package cost?
Offering great value package deals from CA $1,042 on Expedia, you'll be surprised at how little a vacation to Pittsford costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Pittsford?
The off-season is the best time to head to Pittsford if you're trying to keep costs down. Another tip for finding cheap Pittsford vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Pittsford?
The ideal duration for your Pittsford vacation depends on what you'd like to do. Typically, a few days to a week will give you time to check out all the leading sights and explore some hidden treasures along the way.
How to find the best Pittsford package deals?
Start your search for a Pittsford package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Pittsford package deal right away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Pittsford adventure underway.
Is it cheaper to book a Pittsford vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still have the freedom to create a customized Pittsford vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Pittsford?
Secure amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Pittsford vacation.
How to plan a trip to Pittsford?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Pittsford.
  2. Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to activities and airfares. Your accommodations will probably be the largest expense during your trip to Pittsford.
  3. Decide how many days away: Start by making a list of all the attractions and activities you'd like to get to in Pittsford. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Pittsford vacation package.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.