Pittsford Vacations from $883

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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.
The Vermont Inn

The Vermont Inn

3 out of 5
Price was $1,071, price is now $883 per person
$883
per person
Dec 19 - Dec 25
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
9.2/10 Wonderful! (408 reviews)
Needed an update on the outside Property being sold

Reviewed on Oct 6, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,709, price is now $1,313 per person
$1,313
per person
Dec 19 - Dec 25
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
8.6/10 Excellent! (1,003 reviews)
Pleasant check in. My room was adequate. Everything basically worked but was worn.

Reviewed on Oct 9, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,384, price is now $1,079 per person
$1,079
per person
Dec 19 - Dec 25
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
7.4/10 Good! (1,004 reviews)
Best place in Killington!

Reviewed on Sep 30, 2025

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,639, price is now $1,323 per person
$1,323
per person
Dec 19 - Dec 25
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
9.2/10 Wonderful! (891 reviews)
View ok ‚ room noisy

Reviewed on Oct 10, 2025

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $1,146, price is now $926 per person
$926
per person
Dec 19 - Dec 25
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
6.4/10 (1,005 reviews)
Good bfast old facility. Needs updating.

Reviewed on Oct 9, 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

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
$156 nightly
The price is $172 total per night from Oct 19 to Oct 20
$172 total
Oct 19 - Oct 20
Total with taxes and fees
9/10 Wonderful! (908 reviews)
"Amazing area!"

Reviewed on Oct 7, 2025

The Mountain Inn at Killington
Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $152 total per night from Nov 6 to Nov 7
$152 total
Nov 6 - Nov 7
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
"Our room was updated with a jacuzzi! Staff was very polite and welcoming. They were very helpful with information about the area. Had a great stay!"

Reviewed on Oct 7, 2025

Middlebury Inn
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
$130 nightly
The price is $143 total per night from Oct 15 to Oct 16
$143 total
Oct 15 - Oct 16
Total with taxes and fees
8.6/10 Excellent! (1,006 reviews)
"Off season, so lounge/cafe closed. However plenty of brewed coffee availary 0500 to 11 am. Dining options a few minutes away. Great bed."

Reviewed on Oct 6, 2025

North Star Lodge and Resort
See all 1,693 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.

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 $883 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.