Pittsford Vacations from $482

Book a Hotel + Flight or Car together to unlock savings

Photo by Benny Goh
    deals illustration
    Better together
    Save up to $1,045 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    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.
The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

2.5 out of 5
per person
Aug 29 - Sep 1
just found
Roundtrip non-stop flight included
Richmond (RIC) to Rutland (RUT)
8.4/10 Very Good! (644 reviews)
Very friendly staff. Enjoyed my stay.

Reviewed on Jun 25, 2025

The Vermont Inn

The Vermont Inn

3 out of 5
per person
Sep 25 - Sep 28
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
9.2/10 Wonderful! (402 reviews)
Excellent. Jeanine was so kind and helpful. Really cute sitting room. Sauna was awesome. Quiet and clean!

Reviewed on May 25, 2025

Golden Stage Inn B&B

Golden Stage Inn B&B

3.5 out of 5
per person
Sep 25 - Sep 28
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
10/10 Exceptional! (26 reviews)
Family run B&B close to Okemo. Wonderful hosts.

Reviewed on Jan 22, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Rutland (RUT)
7.2/10 Good! (1,003 reviews)
Located not very far from the main road, very peaceful. So grateful that they are a pet friendly resort.

Reviewed on Jul 1, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
per person
Sep 25 - Sep 28
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
8.6/10 Excellent! (1,001 reviews)
Good value hotel in an excellent location.

Reviewed on Jun 29, 2025

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

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

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
$131 nightly
The price is $144 total per night from Jul 10 to Jul 11
$144 total
Jul 10 - Jul 11
Total includes taxes and fees
8/10 Very Good! (1,000 reviews)
"I believe I already submitted a review, but this was a great place to stay, convenient, clean, and friendly."

Reviewed on Jun 26, 2025

Comfort Inn Rutland - Killington
Middlebury Inn
Middlebury Inn
3 out of 5
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $186 total per night from Jul 8 to Jul 9
$186 total
Jul 8 - Jul 9
Total includes taxes and fees
8.8/10 Excellent! (1,000 reviews)
"Conveniently located in Middlebury, loved porches - we sat outside on the side porch and had desert from the restaurant."

Reviewed on Jun 30, 2025

Middlebury Inn
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
$139 nightly
The price is $152 total per night from Jul 13 to Jul 14
$152 total
Jul 13 - Jul 14
Total includes taxes and fees
7.2/10 Good! (1,001 reviews)
"Located not very far from the main road, very peaceful. So grateful that they are a pet friendly resort."

Reviewed on Jul 1, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
See all 1,730 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 $482 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.