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Windham Vacation Packages

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Windham Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
per person
Jun 5 - Jun 7
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 Fire Tower are located nearby.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
per person
Jun 5 - Jun 7
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Stay at this 3.5-star beach lodge in Bomoseen. Enjoy free parking, an outdoor pool, and a private beach. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Prospect Bay Country Club and Lake Bomoseen are located nearby.
Golden Stage Inn B&B

Golden Stage Inn B&B

3.5 out of 5
per person
Jun 5 - Jun 7
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Stay at this 3.5-star B&B in Cavendish. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
The Vermont Inn

The Vermont Inn

3 out of 5
per person
Jun 5 - Jun 7
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Stay at this 3-star family-friendly B&B in Rutland. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Killington Resort and Golden Express Quad are located nearby.
Greenbrier Inn

Greenbrier Inn

2 out of 5
per person
Jun 5 - Jun 7
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 Pico Mountain at Killington Ski Resort are located nearby.
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
per person
Jun 5 - Jun 7
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
per person
Jun 5 - Jun 7
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Stay at this 3-star 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.
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
per person
Jun 5 - Jun 7
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Stay at this 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.

Windham Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
per person
May 23 - May 26
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
per person
May 23 - May 26
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
per person
May 23 - May 26
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
per person
May 23 - May 26
found 8 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, Mar 18 - Sat, Mar 22
LGA
LaGuardia
RUT
Rutland Southern Vermont Regional
$388 Roundtrip, found 4 days ago
$388
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Mar 18 from LaGuardia to Rutland Southern Vermont Regional, returning Sat, Mar 22, priced at $388 found 4 days ago
JetBlue Airways
Wed, Mar 19 - Sat, Mar 22
LGA
LaGuardia
RUT
Rutland Southern Vermont Regional
$396 Roundtrip, found 4 days ago
$396
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Mar 19 from LaGuardia to Rutland Southern Vermont Regional, returning Sat, Mar 22, priced at $396 found 4 days ago
JetBlue Airways
Tue, Mar 18 - Mon, Mar 24
LGA
LaGuardia
RUT
Rutland Southern Vermont Regional
$398 Roundtrip, found 4 days ago
$398
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Mar 18 from LaGuardia to Rutland Southern Vermont Regional, returning Mon, Mar 24, priced at $398 found 4 days ago
JetBlue Airways
Mon, Mar 17 - Fri, Mar 21
LGA
LaGuardia
RUT
Rutland Southern Vermont Regional
$426 Roundtrip, found 4 days ago
$426
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, Mar 17 from LaGuardia to Rutland Southern Vermont Regional, returning Fri, Mar 21, priced at $426 found 4 days ago