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Gaysville Vacation Packages

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Gaysville Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $768, price is now $643 per person
$643
per person
Nov 16 - Nov 21
found 6 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Very unique house with lovely furnishings. Owners were very helpful and breakfast was delicious.

Reviewed on Oct 9, 2026

Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $5,576, price is now $3,997 per person
$3,997
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this business-friendly apartment in Killington. Enjoy free WiFi, free parking, and in-room washers/dryers. Popular attractions Killington Resort and Black Dog Sports are located nearby.
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.

Reviewed on Jan 28, 2026

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Save 100% on your flight
Price was $4,880, price is now $3,515 per person
$3,515
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.

The Landgrove

The Landgrove

3.5 out of 5
Price was $914, price is now $696 per person
$696
per person
Nov 16 - Nov 21
found 6 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
WONDERFUL! Wonderful! Wonderful!

Reviewed on Oct 12, 2026

The Vermont Inn

The Vermont Inn

3 out of 5
Price was $2,288, price is now $1,843 per person
$1,843
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this family-friendly B&B in Rutland. Enjoy free WiFi, free parking, and a conference center. Popular attractions Killington Resort and Golden Express Quad are located nearby.
Such a disappointment. The standard of amenities was very poor. Manager was very very helpful and welcoming but this did not make up for the poor plumbing ,lack of amenities

Reviewed on Oct 13, 2026

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was $2,237, price is now $1,804 per person
$1,804
per person
Dec 24 - Dec 31
found 1 day 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.
Extremely Friendly Staff. Very clean and comfortable room. Convenient location. Highly recommend

Reviewed on Oct 13, 2026

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,739, price is now $1,448 per person
$1,448
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.

Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was $2,111, price is now $1,806 per person
$1,806
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
I would highly recommend this inn. Its small

Reviewed on Oct 10, 2026

Gaysville Vacation Packages 3-4 Night Stays

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

The Landgrove

3.5 out of 5
Price was $682, price is now $568 per person
$568
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Save 100% on your flight
Price was $1,253, price is now $619 per person
$619
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,750, price is now $1,415 per person
$1,415
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was $704, price is now $605 per person
$605
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)

Gaysville Vacation Packages 5-7 Night Stays

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

Lake Bomoseen Lodge

3.5 out of 5
Price was $743, price is now $561 per person
$561
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $5,576, price is now $3,997 per person
$3,997
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Save 100% on your flight
Price was $4,880, price is now $3,515 per person
$3,515
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
The Landgrove

The Landgrove

3.5 out of 5
Price was $914, price is now $696 per person
$696
per person
Nov 16 - Nov 21
found 6 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)

Top Flight Deals

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

JetBlue Airways
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$399 Roundtrip, found 1 day ago
$399
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $399 found 1 day ago
JetBlue Airways
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$409 Roundtrip, found 1 day ago
$409
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $409 found 1 day ago
JetBlue Airways
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$419 Roundtrip, found 1 day ago
$419
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $419 found 1 day ago
JetBlue Airways
Mon, Nov 16 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$440 Roundtrip, found 1 day ago
$440
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Nov 16 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $440 found 1 day ago