Pittsford Vacations from $404

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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 Putney Inn

The Putney Inn

2.5 out of 5
Price was $508, price is now $404 per person
$404
per person
Sep 29 - Oct 3
found 19 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
8.4/10 Very Good! (1,005 reviews)
My stay here was perfect for what I was looking for, just a one night stay in the area. The property is dated but the accommodations are clean and the surrounding area is extremely quiet and secluded, but the parking lot is well lit and safe. I would stay here again if I needed a short term accommodation.

Reviewed on Aug 22, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,622, price is now $1,274 per person
$1,274
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
8.6/10 Excellent! (1,006 reviews)
Every person here was extremely polite and welcoming.They were a very welcoming group.Room was clean. It is disappointing the breakfast area and the bar are closed in the summer.I understand why the bar is closed, since less people stay in the summer, but they could provide a little more then coffee, even just donuts.

Reviewed on Aug 22, 2025

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $555, price is now $444 per person
$444
per person
Sep 29 - Oct 3
found 19 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
6.4/10 (1,005 reviews)
Clean and comfortable. Good value for what you get. Would stay again.

Reviewed on Aug 18, 2025

The Vermont Inn

The Vermont Inn

3 out of 5
Price was $1,124, price is now $939 per person
$939
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
9.2/10 Wonderful! (407 reviews)
Was a wonderful little bed and breakfast. Will stay here again.

Reviewed on Jul 23, 2025

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $639, price is now $537 per person
$537
per person
Sep 29 - Oct 3
found 19 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
9.4/10 Exceptional! (814 reviews)
Room was clean and comfortable with lovely back deck overlooking the lake.

Reviewed on Aug 12, 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
$131 nightly
The price is $144 total per night from Aug 27 to Aug 28
$144 total
Aug 27 - Aug 28
Total with taxes and fees
9/10 Wonderful! (874 reviews)
We’ll be back.
"Beautiful area, outside of facility looks dated, but that’s not realistic to change. Inside has had a nice update. The staff is very friendly and helpful. We had an inconsiderate and noisy person upstairs over us, just a matter of who is there. We would surely stay here again."

Reviewed on Aug 23, 2025

The Mountain Inn at Killington
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $121 total per night from Aug 27 to Aug 28
$121 total
Aug 27 - Aug 28
Total with taxes and fees
6.2/10 (1,001 reviews)
"Had all we needed"

Reviewed on Aug 21, 2025

Days Inn by Wyndham Rutland/Killington Area
Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $186 total per night from Aug 27 to Aug 28
$186 total
Aug 27 - Aug 28
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
"Old style quaintness."

Reviewed on Aug 22, 2025

Middlebury Inn
See all 1,714 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.

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Frequently asked questions

How much does a Pittsford vacation package cost?
You'll find cheap prices from $404 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.