Pittsford Vacations from $1,032

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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.
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $1,223, price is now $1,032 per person
$1,032
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
9/10 Wonderful! (65 reviews)
It was a great low t

Reviewed on Dec 2, 2025

Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,769, price is now $1,293 per person
$1,293
per person
Feb 23 - Feb 28
found 1 day ago
Roundtrip flight included
Grand Rapids (GRR) to Rutland (RUT)
No reviews
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,795, price is now $1,397 per person
$1,397
per person
Feb 23 - Feb 28
found 1 day ago
Roundtrip flight included
Grand Rapids (GRR) to Rutland (RUT)
No reviews
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,519, price is now $1,211 per person
$1,211
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
7.4/10 Good! (1,003 reviews)
Wonderful experience definitely would stay again.

Reviewed on Dec 16, 2025

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Save 100% on your flight
Price was $1,735, price is now $1,421 per person
$1,421
per person
Jan 22 - Jan 25
found 21 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
9/10 Wonderful! (53 reviews)
Clean room and everything I expected it to be. Will definitely book again!

Reviewed on Dec 15, 2025

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Discover the most popular places to visit in Pittsford

New England Maple Museum

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

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
$211 nightly
The price is $232 total per night from Jan 13 to Jan 14
$232 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
7.2/10 Good! (1,006 reviews)
Hotel staff was top shelf!!! Ate at the bar. Flatbread was great! And beer was ice cold !!! Great hotel definitely will stay here again!!

Reviewed on Dec 15, 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
$272 nightly
The price is $299 total per night from Dec 23 to Dec 24
$299 total
Dec 23 - Dec 24
Total with taxes and fees
9/10 Wonderful! (961 reviews)
Staff was very friendly and helpful. Room was clean. On site restaurant was wonderful.

Reviewed on Dec 15, 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
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $176 total per night from Jan 4 to Jan 5
$176 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
Location is very convenient. Service as described online.

Reviewed on Dec 6, 2025

North Star Lodge and Resort
See all 1,771 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 $1,032 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.