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Middlebury Vacation Packages

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Middlebury Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Stowe Motel & Snowdrift

Stowe Motel & Snowdrift

2 out of 5
Price was $613, price is now $493 per person
$493
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Burlington (BTV)
Book a stay at this ski hotel in Stowe. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Stowe Mountain Resort and Alchemist Brewery are located nearby.

Green Mountain Inn

Green Mountain Inn

3.5 out of 5
Price was $977, price is now $705 per person
$705
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Burlington (BTV)
Book a stay at this ski resort in Stowe. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Straw Corner Shops and Vermont Ski Museum are located nearby.
Loved the location, people and how quaint this hotel

Reviewed on Sep 23, 2026

Club Wyndham Smugglers’ Notch Vermont

Club Wyndham Smugglers’ Notch Vermont

3.5 out of 5
Price was $906, price is now $683 per person
$683
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Burlington (BTV)
Book a stay at this ski hotel in Jeffersonville. Enjoy free parking, an outdoor pool, and 9 restaurants. Popular attractions Stowe Mountain Resort and Smugglers Notch are located nearby.

The Essex Resort & Spa

The Essex Resort & Spa

4 out of 5
Price was $911, price is now $689 per person
$689
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Burlington (BTV)
Book a stay at this spa hotel in Essex Junction. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions The Links at Lang Farm and Essex Outlets are located nearby.

Vermont Suites

Vermont Suites

2 out of 5
Price was $717, price is now $545 per person
$545
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Burlington (BTV)
Stay at this motel in South Burlington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Church Street Marketplace and Waterfront Park are located nearby.

von Trapp Family Lodge & Resort

von Trapp Family Lodge & Resort

3.5 out of 5
Price was $1,180, price is now $906 per person
$906
per person
Dec 4 - Dec 7
found 14 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Burlington (BTV)
Book a stay at this ski lodge in Stowe. Enjoy an outdoor pool, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Stowe Mountain Resort and von Trapp Brewing are located nearby.
The setting and gardens were fabulous, as was the food and dining experience in the main dining room. The rooms and furniture in the lounge are a bit dated, has that 80's feel. Could use a bit of updatig. Can't say enough about the overall setting, views and dining...

Reviewed on Sep 23, 2026

Valcour Inn & Boathouse

Valcour Inn & Boathouse

3 out of 5
Price was $699, price is now $563 per person
$563
per person
Dec 4 - Dec 7
found 14 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Burlington (BTV)
Stay at this guesthouse in Peru. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Ausable Chasm and Baggs' Landing are located nearby.
Great peaceful place to spend time. Loved the waterfront and you can watch the sunset while enjoy your quiet time

Reviewed on Sep 11, 2026

Outbound Stowe

Outbound Stowe

3.5 out of 5
Price was $726, price is now $586 per person
$586
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Burlington (BTV)
Stay at this hotel in Stowe. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Stowe Mountain Resort and West Branch Gallery & Sculpture Park are located nearby.

Middlebury Vacation Packages 3-4 Night Stays

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

Vermont Suites

2 out of 5
Price was $717, price is now $545 per person
$545
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Burlington (BTV)
Green Mountain Inn

Green Mountain Inn

3.5 out of 5
Stowe Village Historic District
Price was $977, price is now $705 per person
$705
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Burlington (BTV)
Club Wyndham Smugglers’ Notch Vermont

Club Wyndham Smugglers’ Notch Vermont

3.5 out of 5
Price was $906, price is now $683 per person
$683
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Burlington (BTV)
The Essex Resort & Spa

The Essex Resort & Spa

4 out of 5
Price was $911, price is now $689 per person
$689
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Burlington (BTV)

Middlebury Vacation Packages 5-7 Night Stays

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

Vermont Suites

2 out of 5
Price was $754, price is now $593 per person
$593
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Burlington (BTV)
The Essex Resort & Spa

The Essex Resort & Spa

4 out of 5
Price was $862, price is now $626 per person
$626
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Burlington (BTV)
Green Mountain Inn

Green Mountain Inn

3.5 out of 5
Stowe Village Historic District
Save 100% on your flight
Price was $1,102, price is now $808 per person
$808
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Burlington (BTV)
Club Wyndham Smugglers’ Notch Vermont

Club Wyndham Smugglers’ Notch Vermont

3.5 out of 5
Price was $919, price is now $714 per person
$714
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Burlington (BTV)

Top Flight Deals

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

Breeze Airways
Wed, Oct 21 - Tue, Oct 27
TPA
Tampa Intl.
BTV
Burlington Intl.
$229 Roundtrip, just found
$229
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Oct 21 from Tampa Intl. to Burlington Intl., returning Tue, Oct 27, priced at $229 just found
Bargain Flight
Fri, Oct 16 - Wed, Oct 21
ATL
Hartsfield-Jackson Atlanta Intl.
BTV
Burlington Intl.
$292 Roundtrip, found 3 hours ago
$292
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Fri, Oct 16 from Hartsfield-Jackson Atlanta Intl. to Burlington Intl., returning Wed, Oct 21, priced at $292 found 3 hours ago
American Airlines
Mon, Oct 19 - Sat, Oct 31
DCA
Ronald Reagan Washington National
BTV
Burlington Intl.
$299 Roundtrip, just found
$299
Roundtrip
just found
Select American Airlines flight, departing Mon, Oct 19 from Ronald Reagan Washington National to Burlington Intl., returning Sat, Oct 31, priced at $299 just found
Delta
Sun, Dec 20 - Sat, Dec 26
JFK
John F. Kennedy Intl.
BTV
Burlington Intl.
$309 Roundtrip, found 13 hours ago
$309
Roundtrip
found 13 hours ago
Select Delta flight, departing Sun, Dec 20 from John F. Kennedy Intl. to Burlington Intl., returning Sat, Dec 26, priced at $309 found 13 hours ago