Pittsford Vacations from $301

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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!

The Latest Pittsford vacation packages

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

Align Inn Vermont

2.5 out of 5
Price was $373, price is now $301 per person
$301
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Rutland (RUT)
9.4/10 Exceptional! (1,017 reviews)
The most beautiful scenic views!

Reviewed on Nov 30, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
Price was $955, price is now $702 per person
$702
per person
Feb 12 - Feb 15
found 15 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
7.4/10 Good! (1,003 reviews)
It’s a small beautiful cabin like/feel hotel and they have everything you need and most esp a quick drive to Killington resort Their food is also very good and well prepared.

Reviewed on Nov 30, 2025

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Save 100% on your flight
Price was $1,504, price is now $1,110 per person
$1,110
per person
Feb 12 - Feb 15
found 15 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
No reviews
Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $1,384, price is now $1,041 per person
$1,041
per person
Feb 12 - Feb 15
found 15 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
No reviews
The Vermont Inn

The Vermont Inn

3 out of 5
Price was $935, price is now $737 per person
$737
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)
9.2/10 Wonderful! (412 reviews)
Great experiment. Very accommodating stuff and environment.

Reviewed on Nov 29, 2025

Don't see what you're looking for?
See all available trips from Columbus to Pittsford
View all trips

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

Discover the most popular places to visit in Pittsford

New England Maple Museum

4/5(8 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.

New England Maple Museum

Proctor-Pittsford Country Club

5/5(3 reviews)

Enjoy a round of golf in Pittsford at Proctor-Pittsford Country Club. Discover the area's museums and shops.

Proctor-Pittsford Country Club

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
$147 nightly
The price is $161 total per night from Dec 7 to Dec 8
$161 total
Dec 7 - Dec 8
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
Great staff and a beautiful place to stay

Reviewed on Nov 17, 2025

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
$209 nightly
The price is $230 total per night from Dec 3 to Dec 4
$230 total
Dec 3 - Dec 4
Total with taxes and fees
9/10 Wonderful! (949 reviews)
The front desk staff are patient and enthusiastic.

Reviewed on Nov 24, 2025

The Mountain Inn at Killington
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr Killington VT
$117 nightly
The price is $129 total per night from Dec 3 to Dec 4
$129 total
Dec 3 - Dec 4
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
Go to Mid-Week Ski stay . Good Beds & Continental Breakfast wou

Reviewed on Nov 23, 2025

North Star Lodge and Resort
See all 1,747 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.

Find the Best Pittsford Vacation Packages

Pittsford Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rutland Southern Vermont Regional Airport (RUT)
Population
740
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Pico Mountain at Killington Ski Resort, Paramount Theater and Gifford Woods State Park

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Pittsford vacation package cost?
You'll find cheap prices from $301 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?
If you're looking to score a cheap Pittsford vacation package, consider traveling in April, May and June. You'll typically find lower prices on accommodations and flights during these months — ideal for a budget-friendly break.
How many days is enough for Pittsford?
With a well-organized schedule, you can easily hit the main Pittsford sights in a handful of days. But if you prefer to discover lesser-known spots or go on day trips, think about booking your Pittsford vacation for longer.
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.
Does Expedia offer Book Now, Pay Later Pittsford vacation packages?
Your Pittsford trip is meant to be an escape from your daily routine, not a reason for money worries. So to allow you that extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden 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.