Rutland Flight + Hotel Packages

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

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

$578

per person

Sep 21 - Sep 24

found 4 hours ago

Roundtrip non-stop flight included

San Diego (SAN) to Rutland (RUT)

Stay at this resort in Brownsville. Enjoy a business center, a fireplace in the lobby, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions Mount Ascutney and Mt Ascutney State Park are located nearby.

Bentley House Bed and Breakfast

$614

per person

Sep 21 - Sep 24

found 4 hours ago

Roundtrip non-stop flight included

San Diego (SAN) 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.

Owners are very nice and friendly. Property /room is clean. Breakfast is ok. Will recommend to stay here.

Reviewed on Aug 18, 2026

The Mountain Inn at Killington

$664

per person

Oct 3 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

San Diego (SAN) 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.

Didn’t stay

Reviewed on Aug 20, 2026

Comfort Inn Rutland - Killington

$655

per person

Sep 21 - Sep 24

found 4 hours ago

Roundtrip non-stop flight included

San Diego (SAN) 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 breakfast and the helpful staff in our reviews. Popular attractions Vermont State Fairgrounds and Green Mountain Shopping Plaza are located nearby.

The Landgrove

$619

per person

Oct 3 - Oct 5

found 1 day 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 Hapgood Pond and Wild Wings Ski Touring Center are located nearby.

North Star Lodge and Resort

$699

per person

Oct 3 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

San Diego (SAN) 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.

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

$739

per person

Sep 21 - Sep 24

found 4 hours 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.

Nice area, clean and kitchen was well equipped. We used the air fryer for dinner one night.

Reviewed on Aug 15, 2026

Emrose Luxury Cabins

$601

per person

Oct 3 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

San Diego (SAN) to Rutland (RUT)

Book a stay at this family-friendly hotel in Brandon. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Otter Valley Winery and Stephen A Douglas Birthplace are located nearby.

The property is beautiful loved the heated pool and outdoor activities .

Reviewed on Aug 19, 2026

Rutland Vacation Packages 3-4 Night Stays

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