Pittsford Vacations from $752

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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.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $920, price is now $752 per person
$752
per person
Jan 9 - Jan 13
found 24 hours ago
Roundtrip flight included
Miami (MIA) to Rutland (RUT)
6.4/10 (1,009 reviews)
The breakfast selection was good with eggs, sausage, toast, bagels, waffles, fresh fruit, cereal, yogurt. The room was clean however the bathroom could use updating but was adequate.

Reviewed on Oct 27, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,380, price is now $1,081 per person
$1,081
per person
Jan 9 - Jan 13
found 24 hours ago
Roundtrip flight included
Miami (MIA) to Rutland (RUT)
7.4/10 Good! (1,000 reviews)
Great place to stay! The balcony was definitely nice to have as an option. The Mountain View were phenomenal. Highly recommend staying at this facility.

Reviewed on Oct 18, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,122, price is now $903 per person
$903
per person
Jan 9 - Jan 13
found 24 hours ago
Roundtrip flight included
Miami (MIA) to Rutland (RUT)
8.6/10 Excellent! (1,012 reviews)
Location was great and was clean but the facility and room is old. Needs a major face lift.

Reviewed on Oct 27, 2025

Mt Green 2-e06 in Killington

Mt Green 2-e06 in Killington

2 out of 5
Price was $1,535, price is now $1,309 per person
$1,309
per person
Jan 9 - Jan 13
found 24 hours ago
Roundtrip flight included
Miami (MIA) to Rutland (RUT)
No reviews
Summit Lodge

Summit Lodge

3 out of 5
Price was $1,041, price is now $894 per person
$894
per person
Jan 9 - Jan 13
found 24 hours ago
Roundtrip flight included
Miami (MIA) to Rutland (RUT)
8.6/10 Excellent! (393 reviews)
An experience…a journey..breakfast was pathetic..but we didn’t thought abt staying in this heritage property for breakfast…rest all was good and memorable.

Reviewed on Oct 30, 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

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
$130 nightly
The price is $143 total per night from Nov 16 to Nov 17
$143 total
Nov 16 - Nov 17
Total with taxes and fees
7.2/10 Good! (1,001 reviews)
very nice place

Reviewed on Oct 22, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
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
$110 nightly
The price is $121 total per night from Nov 5 to Nov 6
$121 total
Nov 5 - Nov 6
Total with taxes and fees
8/10 Very Good! (1,007 reviews)
Staff was pleasant, room appeared clean, the only issue I had was that there was a really strong smell like cat urine on the entire level I was on and in my room. I bought some spray air freshener at a local CVS and and was able to sleep, otherwise everything else was good.

Reviewed on Oct 29, 2025

Comfort Inn Rutland - Killington
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
$133 nightly
The price is $146 total per night from Nov 27 to Nov 28
$146 total
Nov 27 - Nov 28
Total with taxes and fees
9/10 Wonderful! (929 reviews)
The staff is super friendly and helpful. Their service is outstanding.

Reviewed on Oct 29, 2025

The Mountain Inn at Killington
See all 1,726 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 $752 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.