Pittsford Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Benny Goh

Top hotels in Pittsford

Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
The price is 3.787.372 ₫ per night from 10 Aug to 11 Aug
3.787.372 ₫
4.165.873 ₫ total
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"This inn was great! I loved all the historical pieces that are shown around the inn. It is close enough to be able to walk to all the little shops and cafes in town. The staff were wonderful and super friendly. The food in the restaurant was amazing!"

Reviewed on 5 Aug 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
8.4/10 Very Good! (1,000 reviews)
"Great little place. Very friendly and clean."

Reviewed on 31 Jul 2025

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North Star Lodge and Resort
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 2.651.344 ₫ per night from 18 Aug to 19 Aug
2.651.344 ₫
2.916.478 ₫ total
18 Aug - 19 Aug
includes taxes & fees
6.2/10 (1,006 reviews)
"Older property but rooms were just redone in Spring 2025. Very clean and comfortable, bathrooms still a bit on the older side but clean...water pressure was low but still usable. Overall, I would come back."

Reviewed on 3 Aug 2025

Days Inn by Wyndham Rutland/Killington Area
See all 1,725 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.

Popular places to visit

New England Maple Museum

You can spend time browsing the exhibits at New England Maple Museum during your trip to Pittsford. Discover the area's mountain views and cosy cafes.

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

Frequently asked questions

How much does a Pittsford holiday package cost?
You'll find cheap prices 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 holiday to Pittsford costs.
What are the cheapest months to go to Pittsford?
To score cheap Pittsford holiday packages, plan your getaway outside of busy periods such as school holidays. You'll generally find lower prices and better availability for hotels and flights.
How many days is enough for Pittsford?
Generally, a handful of days is enough to see the top sights during your Pittsford holiday. But if you prefer to have more time to rest or go on day tours, consider extending your trip.
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 holiday as a package?
Expedia holiday 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 personalised Pittsford holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday 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.
How to plan a trip to Pittsford?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to visit Pittsford.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and food to activities and airfares. Your accommodation will likely be the largest expense during your trip to Pittsford.
  3. Decide how long to go away for: Now that you know more about Pittsford, you can work out the right length of your break. Pull together a rough itinerary and allocate enough time to cover everything you want to see.
  4. Combine your airfare and accommodation: After you've settled on your dates and duration, lock in the right Pittsford holiday package for you.