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Randolph Vacation Packages

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Randolph Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Killington Haus

Killington Haus

2 out of 5
Price was $562, price is now $541 per person
$541
per person
Oct 22 - Oct 25
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Stay at this guesthouse in Killington. Enjoy free WiFi, free parking, and a restaurant. Popular attractions Killington Resort and Black Dog Sports are located nearby.

Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $836, price is now $700 per person
$700
per person
Oct 22 - Oct 25
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Th

Reviewed on Sep 19, 2026

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was $661, price is now $584 per person
$584
per person
Oct 22 - Oct 25
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Okay for a night stay.....

Reviewed on Sep 20, 2026

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $659, price is now $605 per person
$605
per person
Oct 22 - Oct 25
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Old and run down. Won’t be returning

Reviewed on Sep 16, 2026

Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $735, price is now $699 per person
$699
per person
Oct 22 - Oct 25
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this family-friendly hotel in Brandon. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Stephen A Douglas Birthplace and Judith Reilly Gallery are located nearby.
I thought the cabins were very unique and very nicely done. Everything was clean when we arrived. It was a little confusing about the check-in, but someone came to our aid. We enjoyed our stay. One thing that was wrong. Was we came home at night after dinner out and we were planning to take a shower and the water was trickling and cold. It was like there was no water on the property. It was already late so we did not contact anyone and the next morning, the water was working. This is a problem that needs to be looked at.

Reviewed on Sep 20, 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 $700, price is now $672 per person
$672
per person
Oct 22 - Oct 25
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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

Randolph Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was $661, price is now $584 per person
$584
per person
Oct 22 - Oct 25
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $836, price is now $700 per person
$700
per person
Oct 22 - Oct 25
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $659, price is now $605 per person
$605
per person
Oct 22 - Oct 25
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)