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Windsor Vacation Packages

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Windsor Flight + Hotel Packages

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

Albany Airport Inn

2.5 out of 5
Price was $617, price is now $541 per person
$541
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Albany (ALB)
Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free parking, and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and MVP Arena are located nearby.
Airport shuttle

Reviewed on Oct 14, 2026

Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,583, price is now $1,243 per person
$1,243
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Book a stay at this golf hotel in Wilmington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and North Branch Deerfield River are located nearby.
Our weeklong trip meandering the roads of Vermont was made more memorable by our stay at the Brook Bound Inn! The property is gorgeous and impeccably maintained! Our room was clean and so quiet! The bed was comfortable, and the blackout window blinds allowed us to sleep a little later than normal. The bathroom was very clean with a large shower and great smelling body wash, shampoo, etc. Jake and Hope were so helpful before and during our stay. We also appreciated the robust WIFI. We didn’t try the amazing pool this time, but we will for sure on our next trip!

Reviewed on Aug 30, 2026

The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Price was $936, price is now $772 per person
$772
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Albany (ALB)
Book a stay at this business-friendly hotel in Schenectady. Enjoy free WiFi, free parking, and 5 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Schenectady Light Opera Performing Arts Center are located nearby.

Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

3 out of 5
Price was $6,787, price is now $5,808 per person
$5,808
per person
Dec 3 - Dec 8
found 2 days ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this cottage in Stephentown. Enjoy free parking, volleyball on site, and a pool table. Popular attractions Jiminy Peak Mountain Resort and Zema's Nursery are located nearby.

South Shire

South Shire

4 out of 5
Price was $1,450, price is now $1,247 per person
$1,247
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Stay at this B&B in Bennington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Bennington Arts Guild Gallery and Fiddlehead at Four Corners are located nearby.
We love it ♥️

Reviewed on Oct 6, 2026

The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

3 out of 5
Price was $3,328, price is now $2,883 per person
$2,883
per person
Dec 3 - Dec 8
found 2 days ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this cottage in Earlton. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Thunderhart Golf Course and Cairo Lockwood State Forest are located nearby.

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
Price was $703, price is now $611 per person
$611
per person
Nov 16 - Nov 21
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Book a stay at this ski hotel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bennington Museum and Fiddlehead at Four Corners are located nearby.
Located on the edge of the downtown area. Room was tastefully done with high ceilings and wood beams. Bathroom was nicely done with tile and large pedestal sink that easily held both of our things. Breakfast was included.

Reviewed on Oct 15, 2026

The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

4.5 out of 5
Price was $834, price is now $732 per person
$732
per person
Nov 16 - Nov 21
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Good

Reviewed on Oct 13, 2026

Windsor Vacation Packages 3-4 Night Stays

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

Albany Airport Inn

2.5 out of 5
Price was $617, price is now $541 per person
$541
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Albany (ALB)
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,583, price is now $1,243 per person
$1,243
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Nothside
Price was $936, price is now $772 per person
$772
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Albany (ALB)
South Shire

South Shire

4 out of 5
Price was $1,450, price is now $1,247 per person
$1,247
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)

Windsor Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
Price was $703, price is now $611 per person
$611
per person
Nov 16 - Nov 21
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

3 out of 5
Price was $6,787, price is now $5,808 per person
$5,808
per person
Dec 3 - Dec 8
found 2 days ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

3 out of 5
Price was $3,328, price is now $2,883 per person
$2,883
per person
Dec 3 - Dec 8
found 2 days ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Marriott Albany

Marriott Albany

3.5 out of 5
Price was $847, price is now $741 per person
$741
per person
Nov 16 - Nov 21
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)

Top Flight Deals

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

Allegiant Air
Sun, Oct 25 - Sun, Nov 1
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$172 Roundtrip, found 20 hours ago
$172
Roundtrip
found 20 hours ago
Select Allegiant Air flight, departing Sun, Oct 25 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Nov 1, priced at $172 found 20 hours ago
Bargain Flight
Sat, Oct 31 - Fri, Nov 13
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$289 Roundtrip, found 9 hours ago
$289
Roundtrip
found 9 hours ago
Select Bargain Flight flight, departing Sat, Oct 31 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Fri, Nov 13, priced at $289 found 9 hours ago
Bargain Flight
Wed, Dec 2 - Sat, Dec 12
TPA
Tampa Intl.
ALB
Albany Intl.
$293 Roundtrip, found 1 day ago
$293
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Dec 2 from Tampa Intl. to Albany Intl., returning Sat, Dec 12, priced at $293 found 1 day ago
Bargain Flight
Tue, Nov 3 - Sat, Nov 14
LAX
Los Angeles Intl.
ALB
Albany Intl.
$328 Roundtrip, found 1 day ago
$328
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Nov 3 from Los Angeles Intl. to Albany Intl., returning Sat, Nov 14, priced at $328 found 1 day ago