Pittsford Trips (flight + hotel)

Photo by Benny Goh

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Top hotels in Pittsford

Middlebury Inn
Middlebury Inn
3 out of 5
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
The price is P9,179 per night from Jul 9 to Jul 10
P9,179
P10,097 total
Jul 9 - Jul 10
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Wonderful place to stay in quaint Middlebury. Historic inn and very nice, clean rooms. Love the rocking chairs on the front porch."

Reviewed on Jun 18, 2025

Middlebury Inn
Comfort Inn Rutland - Killington
Comfort Inn Rutland - Killington
2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is P7,461 per night from Jun 24 to Jun 25
P7,461
P8,207 total
Jun 24 - Jun 25
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"Quiet and comfortable"

Reviewed on Jun 16, 2025

Comfort Inn Rutland - Killington
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 P7,961 per night from Jun 29 to Jun 30
P7,961
P8,757 total
Jun 29 - Jun 30
includes taxes & fees
7.2/10 Good! (1,002 reviews)
"Pleasant stay"

Reviewed on Jun 20, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
See all 1,729 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.

Frequently asked questions

How much does a Pittsford vacation package cost?
You'll find cheap prices on Expedia for your Pittsford getaway. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Pittsford costs.
What are the cheapest months to go to Pittsford?
To score cheap Pittsford vacation packages, plan your getaway outside of busy periods such as school holidays. You'll generally find lower prices and better availability for hotels and flights.
How many days is enough for Pittsford?
Generally, a handful of days is enough to see the top sights during your Pittsford vacation. But if you prefer to have more time to rest or go on day tours, consider extending your trip.
How to find the best Pittsford package deals?
Start your search for a Pittsford package deal by entering your destination and travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Pittsford package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Pittsford escape underway.
Is it cheaper to book a Pittsford vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Pittsford vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Pittsford?
If you have your Pittsford travel dates locked in, book as soon as you can to grab some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Pittsford?

  1. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to visit Pittsford.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and food to activities and airfares. Your accommodations will likely be the largest expense during your trip to Pittsford.
  3. Decide how long to go away for: Now that you know more about Pittsford, you can work out the right length of your break. Pull together a rough itinerary and allocate enough time to cover everything you want to see.
  4. Combine your airfare and accommodations: After you've settled on your dates and duration, lock in the right Pittsford vacation package for you.

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