Pittsford Vacations from $876

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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
Price was $956, price is now $876 per person
$876
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
8.6/10 Excellent! (1,012 reviews)
Room was clean and staff friendly. Did not use the pool but looked great.

Reviewed on Oct 23, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,045, price is now $929 per person
$929
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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

Sugar Hollow in Chittenden

Sugar Hollow in Chittenden

2 out of 5
Price was $2,385, price is now $2,139 per person
$2,139
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
No reviews
Hidden Kingdom in Plymouth

Hidden Kingdom in Plymouth

2 out of 5
Price was $1,908, price is now $1,716 per person
$1,716
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
No reviews
The Vermont Inn

The Vermont Inn

3 out of 5
Price was $1,046, price is now $958 per person
$958
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
9.2/10 Wonderful! (410 reviews)
Our room was clean and the bed was very comfortable. The Inn is for sale... which could explain the needed updates. I wish I could buy it! 🤗 We would stay here again.

Reviewed on Oct 23, 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
$130 nightly
The price is $143 total per night from Nov 2 to Nov 3
$143 total
Nov 2 - Nov 3
Total with taxes and fees
7.2/10 Good! (1,002 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

Killington Mountain Lodge, Tapestry Collection by Hilton
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr, Killington, VT
$130 nightly
The price is $143 total per night from Nov 9 to Nov 10
$143 total
Nov 9 - Nov 10
Total with taxes and fees
8.6/10 Excellent! (1,022 reviews)
The staff were nice. However, some simple upgrades would really have improved my stay. Things like coffee pot in the room, a larger tv, softer/nicer towels, better toiletries, etc.

Reviewed on Oct 18, 2025

North Star Lodge and Resort
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd, Killington, VT
$156 nightly
The price is $172 total per night from Oct 26 to Oct 27
$172 total
Oct 26 - Oct 27
Total with taxes and fees
9/10 Wonderful! (928 reviews)
Everything was great. I will definitely go back. Just next time I would pick a higher room it felt like a basement. But loved it other then that

Reviewed on Oct 20, 2025

The Mountain Inn at Killington
See all 1,705 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 $876 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.