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Pittsford Vacation Packages

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Pittsford Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $1,047, price is now $866 per person
$866
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip non-stop flight included
San Diego (SAN) 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.

The Landgrove

The Landgrove

3.5 out of 5
Price was $1,037, price is now $886 per person
$886
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip non-stop flight included
San Diego (SAN) to Rutland (RUT)
Book a stay at this family-friendly inn in Londonderry. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bromley Mountain Ski Resort and Hapgood Pond are located nearby.
Lots to like about this Inn: Accurate web descriptions including of their many tasty breakfast options; Very clean, Comfortable mattress with quality linens, Great bath products, Hot showers, Individual temp controls for room, Tasty tap water, Pretty landscaping. Every staff member is very pleasant – shout out to Audrey. Other things to expect: Bring a sleep mask if sensitive to light, no cell service nearby but inn offers unsecured Wi-Fi; stairs to 2nd flr rooms are shallow & steep-typical for age of building; and its easy to take country walks on the road.

Reviewed on Sep 1, 2026

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $1,099, price is now $973 per person
$973
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip non-stop flight included
San Diego (SAN) to Rutland (RUT)
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Whale Dance Sculpture and Montague Golf Club are located nearby.
Liked: Welcome staff. Clear explanations @ check in. The room was immaculate and had all amenities I needed. It was quite difficult finding how to get there. My GPS did not recognize the address given on the website and on the confirmation email.

Reviewed on Sep 13, 2026

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $908, price is now $874 per person
$874
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip non-stop flight included
San Diego (SAN) to Rutland (RUT)
Book a stay at this ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage I are located nearby.
It was pet friendly and also was quite and relaxing

Reviewed on Sep 8, 2026

Pittsford Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $1,047, price is now $866 per person
$866
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip non-stop flight included
San Diego (SAN) to Rutland (RUT)
The Landgrove

The Landgrove

3.5 out of 5
Price was $1,037, price is now $886 per person
$886
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip non-stop flight included
San Diego (SAN) to Rutland (RUT)
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $1,099, price is now $973 per person
$973
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip non-stop flight included
San Diego (SAN) to Rutland (RUT)
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $908, price is now $874 per person
$874
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip non-stop flight included
San Diego (SAN) to Rutland (RUT)