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Rutland Vacation Packages

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Rutland Flight + Hotel Packages

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

Emrose Luxury Cabins

2 out of 5
Price was $1,149, price is now $1,031 per person
$1,031
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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 Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,386, price is now $1,139 per person
$1,139
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop 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.

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 $1,387, price is now $1,140 per person
$1,140
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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.
Beautiful place! In the middle of no where but everything you need is only 10 mins away

Reviewed on Aug 12, 2026

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,397, price is now $1,159 per person
$1,159
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Stay at this condo in Killington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Killington Resort and Killington School for Tennis are located nearby.

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $1,278, price is now $1,089 per person
$1,089
per person
Sep 28 - Oct 4
found 1 day 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.

Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was $1,236, price is now $1,063 per person
$1,063
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Stay at this hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Killington Resort and Gifford Woods State Park are located nearby.
Nice place. Rooms are large, and there is ample space in the common areas. Breakfast was simple but sufficient. My room had a small balcony.

Reviewed on Aug 3, 2026

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,386, price is now $1,232 per person
$1,232
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop 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.
It was amazing my favorite place to go

Reviewed on Aug 13, 2026

Silver Bay YMCA Inn and Conference Center

Silver Bay YMCA Inn and Conference Center

2 out of 5
Price was $1,260, price is now $1,131 per person
$1,131
per person
Sep 28 - Oct 4
found 19 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Stay at this hotel in Silver Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Lake George and Jabe Pond are located nearby.
Would’ve been nice to know that we didn’t have air-conditioning in our room. The food was just mediocre at the buffet next-door and quite expensive for what you received.

Reviewed on Aug 13, 2026

Rutland Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Trout House Village Resort

Trout House Village Resort

3 out of 5
Price was $631, price is now $610 per person
$610
per person
Oct 17 - Oct 19
found 10 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Rutland (RUT)
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,037, price is now $973 per person
$973
per person
Oct 2 - Oct 5
found 17 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Chateau Rooms

Chateau Rooms

4.5 out of 5
Price was $829, price is now $780 per person
$780
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $700, price is now $670 per person
$670
per person
Oct 17 - Oct 19
found 10 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Rutland (RUT)

Rutland Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $1,278, price is now $1,089 per person
$1,089
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,386, price is now $1,139 per person
$1,139
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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 $1,387, price is now $1,140 per person
$1,140
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,397, price is now $1,159 per person
$1,159
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$495 Roundtrip, found 2 days ago
$495
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $495 found 2 days ago
Delta
Tue, Sep 15 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$501 Roundtrip, found 22 hours ago
$501
Roundtrip
found 22 hours ago
Select Delta flight, departing Tue, Sep 15 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $501 found 22 hours ago
Delta
Sat, Sep 12 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$504 Roundtrip, found 22 hours ago
$504
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, Sep 12 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $504 found 22 hours ago
American Airlines
Sun, Sep 13 - Sat, Sep 26
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$660 Roundtrip, found 4 days ago
$660
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Sep 13 from McClellan-Palomar to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $660 found 4 days ago