Pittsford Vacations from $1,170

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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 $1,252, price is now $1,170 per person
$1,170
per person
Sep 21 - Sep 24
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) to Rutland (RUT)
6.6/10 (1,001 reviews)
Clean, good condition, staff very helpful.

Reviewed on Jun 28, 2026

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $1,311, price is now $1,196 per person
$1,196
per person
Sep 21 - Sep 24
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) to Rutland (RUT)
9.4/10 Exceptional! (944 reviews)
The room was clean and comfortable. Very convenient to all the places we visited. Staff was wonderful and the property is just wonderful.

Reviewed on Jun 25, 2026

Golden Stage Inn B&B

Golden Stage Inn B&B

3.5 out of 5
Price was $1,358, price is now $1,266 per person
$1,266
per person
Sep 21 - Sep 24
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) to Rutland (RUT)
10/10 Exceptional! (44 reviews)

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,310, price is now $1,227 per person
$1,227
per person
Sep 21 - Sep 24
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) to Rutland (RUT)
9.2/10 Wonderful! (1,013 reviews)
I really enjoyed the heated pool

Reviewed on Jun 29, 2026

Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was $1,253, price is now $1,205 per person
$1,205
per person
Sep 21 - Sep 24
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) to Rutland (RUT)
9.4/10 Exceptional! (681 reviews)

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Stay near popular Pittsford attractions

New England Maple Museum

8.0/5 (11 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.
See properties

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 Jul 7 to Jul 8
$143 total
Jul 7 - Jul 8
Total with taxes and fees
7.4/10 Good! (1,000 reviews)
"We loved the large beautiful hot tub outside and the firepit. We spent a lot of time there. Staff was amazing food was good."

Reviewed on Jun 23, 2026

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
$146 nightly
The price is $161 total per night from Jul 1 to Jul 2
$161 total
Jul 1 - Jul 2
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
"I really enjoyed the heated pool"

Reviewed on Jun 29, 2026

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
$122 nightly
The price is $134 total per night from Jul 8 to Jul 9
$134 total
Jul 8 - Jul 9
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"Power went out for 3hrs 7am-10am. Asked at front desk about partial compensation, desk person said management was going to send email, but haven't heard back"

Reviewed on Jun 29, 2026

Middlebury Inn
See all 1,804 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 $1,170 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.