Pittsford Vacation Packages

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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!

Top Pittsford Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was CA $782, price is now CA $697 per person
CA $697
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
9.4/10 Exceptional! (809 reviews)
Room was clean and comfortable with lovely back deck overlooking the lake.

Reviewed on Aug. 12, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was CA $2,290, price is now CA $1,971 per person
CA $1,971
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Rutland (RUT)
8.6/10 Excellent! (1,000 reviews)
For the price it's not to bad, slightly dated interior in need of a facelift, but would go back based on the price.

Reviewed on Aug. 10, 2025

The Vermont Inn

The Vermont Inn

3 out of 5
Price was CA $1,806, price is now CA $1,640 per person
CA $1,640
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) 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

Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was CA $1,762, price is now CA $1,606 per person
CA $1,606
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Rutland (RUT)
9/10 Wonderful! (39 reviews)
We were able to have our amall dog with us.

Reviewed on Jul. 20, 2025

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was CA $1,569, price is now CA $1,440 per person
CA $1,440
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Rutland (RUT)
6.4/10 (1,004 reviews)
Clean and comfortable. Good value for what you get. Would stay again.

Reviewed on Aug. 18, 2025

Ready to book your vacation to Pittsford?

 

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Pittsford Hotel Deals

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
The price is CA $140 per night from Aug 24 to Aug 25
CA $140
CA $154 total
Aug 24 - Aug 25
includes taxes & fees
6.2/10 (1,005 reviews)
"Clean and comfortable. Good value for what you get. Would stay again."

Reviewed on Aug. 18, 2025

Days Inn by Wyndham Rutland/Killington Area
Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square, Middlebury, VT
The price is CA $206 per night from Sep 16 to Sep 17
CA $206
CA $227 total
Sep 16 - Sep 17
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"The oldest continuously operating hotel in the States but it doesn’t seem that way. The lobby is spacious, the staff friendly and helpful. The rooms are good sized, TV, WiFi, A/C, soft but comfy beds. We stayed in the original part of the hotel, but they also have newer buildings in back. There is ..."

Reviewed on Aug. 17, 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
The price is CA $146 per night from Aug 31 to Sep 1
CA $146
CA $160 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Great stay! Comfortable, clean and friendly. Would stay again."

Reviewed on Aug. 17, 2025

North Star Lodge and Resort
See all 1,709 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Pittsford vacation package cost?
Offering great value package deals from CA $697 on Expedia, you'll be surprised at how little a vacation to Pittsford costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Pittsford?
The off-season is the best time to head to Pittsford if you're trying to keep costs down. Another tip for finding cheap Pittsford vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Pittsford?
The ideal duration for your Pittsford vacation depends on what you'd like to do. Typically, a few days to a week will give you time to check out all the leading sights and explore some hidden treasures along the way.
How to find the best Pittsford package deals?
Start your search for a Pittsford package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Pittsford package deal right away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Pittsford adventure underway.
Is it cheaper to book a Pittsford vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still have the freedom to create a customized Pittsford vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Pittsford?
Secure amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Pittsford vacation.
How to plan a trip to Pittsford?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Pittsford.
  2. Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to activities and airfares. Your accommodations will probably be the largest expense during your trip to Pittsford.
  3. Decide how many days away: Start by making a list of all the attractions and activities you'd like to get to in Pittsford. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Pittsford vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.