Search Deals onPittsford Vacation Packages
Pittsford Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Harvest Barn Inn
Price was $515, price is now $454 per person
$454
per person
Oct 2 - Oct 5
found 9 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Stay at this B&B in Bellows Falls. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast in our reviews. Popular attractions North Walpole Village Park and Bellows Falls Opera House are located nearby.
Delicious breakfast and great communication throughout! Had a very lovely stay at the Harvest Barn Inn
Reviewed on Jul 22, 2026
Pointe at Castle Hill Resort
Price was $1,105, price is now $888 per person
$888
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Rutland (RUT)
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Golden Stage Inn B&B
Price was $933, price is now $762 per person
$762
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Rutland (RUT)
Stay at this B&B in Cavendish. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Julie and Mike were the nicest most amazing hosts! The breakfast was fantastic, the atmosphere was perfect for rest and relaxation. Our room was clean and cool and cozy, the bathroom was nice and the bath products were great, and sold on sight. We had such a nice time! We will definitely be back!
Reviewed on Jul 6, 2026
The Mountain Inn at Killington
Price was $705, price is now $610 per person
$610
per person
Oct 2 - Oct 5
found 9 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
This property is liking being home. Everyone was very helpful and welcoming. I needed to call the desk twice for something and they were at my room with what I needed in minutes. The one thing I would let others know is it is an older building so no elevator. It was a bit of a struggle for this 68 year old to lug my bags up three flights of steps especially since I was exhausted from my seven hour drive to get here from Pennsylvania. E still very much enjoyed our stay and the morning continental breakfast and readily available free bottles of water.
Reviewed on Jul 23, 2026
Castle Hill Resort And Spa
Price was $1,509, price is now $1,310 per person
$1,310
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Rutland (RUT)
Book a stay at this luxury hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
North Star Lodge and Resort
Price was $760, price is now $671 per person
$671
per person
Oct 2 - Oct 5
found 9 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Killington Resort and Killington School for Tennis are located nearby.
Bentley House Bed and Breakfast
Price was $695, price is now $620 per person
$620
per person
Sep 21 - Sep 25
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
Book a stay at this golf B&B in Poultney. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Poultney Public Library and Slate Quarry Park are located nearby.
Great place, friendly owners. I will be coming back.
Reviewed on Jul 11, 2026
Days Inn by Wyndham Rutland/Killington Area
Price was $753, price is now $691 per person
$691
per person
Aug 27 - Aug 30
found 6 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Green Mountain Shopping Plaza and Spartan Arena are located nearby.
It was ok
Reviewed on Jul 25, 2026
Pittsford Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Pittsford Vacation Packages 5-7 Night Stays
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