Pittsford Vacations from $410

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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!

The Latest Pittsford vacation packages

Price found within the past 48 hours. Click for updated prices.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Rutland (RUT)
8.6/10 Excellent! (1,001 reviews)
We were only there for one night. Slept well. But the tv was unplugged and hard to reach outlet. Most disappointing was the closed pool. Had a kid who could have really used up some energy in there.

Reviewed on Jul 10, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Rutland (RUT)
7.2/10 Good! (1,003 reviews)
The hotel is in the midst of upgrading. I was disappointed that there was no swimming pool as I believed there was one. All of the attractions in the area were closed which disappointed my grandchildren and myself. The room was above and beyond excellent.

Reviewed on Jul 9, 2025

Rent An Inn! Takeover The Birch Ridge W/ Your Group. Mountain Lodge: 11 Rooms, Bar, Fireplace. 28ppl 11 Bedroom Home

Rent An Inn! Takeover The Birch Ridge W/ Your Group. Mountain Lodge: 11 Rooms, Bar, Fireplace. 28ppl 11 Bedroom Home

2 out of 5
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Rutland (RUT)
No reviews
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Rutland (RUT)
9/10 Wonderful! (43 reviews)
Very nice place only negative was the sauna did not work

Reviewed on Apr 28, 2025

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Rutland (RUT)
9.2/10 Wonderful! (813 reviews)
Great place to stay with kids. Our boys loved the pool and the games room.

Reviewed on Jul 11, 2025

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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
$125 nightly
The price is $138 total per night from Jul 20 to Jul 21
$138 total
Jul 20 - Jul 21
Total includes taxes and fees
8/10 Very Good! (1,003 reviews)
"the staff was great and the facility is very clean"

Reviewed on Jul 8, 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
$161 nightly
The price is $177 total per night from Aug 6 to Aug 7
$177 total
Aug 6 - Aug 7
Total includes taxes and fees
8.8/10 Excellent! (1,005 reviews)
"Highly recommended"

Reviewed on Jul 11, 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
$144 nightly
The price is $158 total per night from Jul 20 to Jul 21
$158 total
Jul 20 - Jul 21
Total includes taxes and fees
7.2/10 Good! (1,003 reviews)
"The hotel is in the midst of upgrading. I was disappointed that there was no swimming pool as I believed there was one. All of the attractions in the area were closed which disappointed my grandchildren and myself. The room was above and beyond excellent."

Reviewed on Jul 9, 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.

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

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Frequently asked questions

How much does a Pittsford vacation package cost?
You'll find cheap prices from $410 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.