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Roxbury Vacation Packages

Build your package with 2 more options

Roxbury Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Windham NY Escape

Windham NY Escape

3 out of 5
Price was $1,790, price is now $1,575 per person
$1,575
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Hudson (HCC)
Stay at this cabin in Hensonville. Enjoy free WiFi, free parking, and an in-room coffeemaker. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.
The best

Reviewed on Oct 6, 2025

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

3 out of 5
Save 100% on your flight
Price was $8,857, price is now $7,106 per person
$7,106
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Hudson (HCC)
Stay at this cottage in Hensonville. Enjoy free parking, volleyball on site, and a pool table. Popular attractions Hunter Mountain and Windham Mountain Resort are located nearby.

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

3 out of 5
Save 100% on your flight
Price was $8,483, price is now $6,815 per person
$6,815
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Hudson (HCC)
Stay at this cottage in Hensonville. Enjoy free parking and air conditioning. Popular attractions Hunter Mountain and Windham Mountain Resort are located nearby.

The Haüs Windham

The Haüs Windham

2 out of 5
Price was $2,040, price is now $1,764 per person
$1,764
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Hudson (HCC)
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.
Firstly I would like to say communication with the staff is extremely difficult. Constantly having to call multiple times to get to someone. For example, the code given for room wasn’t correct and communication took forever. There was no toiletries whatsoever and since communication was so hard it forced us to buy our own paper towels, towels, rags, etc. The property was nice but it was clear no housekeeping had been in there before we came. The nature was probably the only thing that made up for all the inconveniences.

Reviewed on Aug 13, 2026

Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

3 out of 5
Price was $4,250, price is now $4,082 per person
$4,082
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Hudson (HCC)
Book a stay at this business-friendly cottage in Windham. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Windham Country Club and Windham Vineyards and Winery are located nearby.

Roxbury Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Windham NY Escape

Windham NY Escape

3 out of 5
Price was $1,790, price is now $1,575 per person
$1,575
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Hudson (HCC)
Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

3 out of 5
Save 100% on your flight
Price was $8,857, price is now $7,106 per person
$7,106
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Hudson (HCC)
Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

3 out of 5
Save 100% on your flight
Price was $8,483, price is now $6,815 per person
$6,815
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Hudson (HCC)
The Haüs Windham

The Haüs Windham

2 out of 5
Price was $2,040, price is now $1,764 per person
$1,764
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Hudson (HCC)

Top Flight Deals

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

Allegiant Air
Thu, Sep 17 - Sun, Sep 20
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$136 Roundtrip, found 2 hours ago
$136
Roundtrip
found 2 hours ago
Select Allegiant Air flight, departing Thu, Sep 17 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Sep 20, priced at $136 found 2 hours ago
Breeze Airways
Sat, Oct 3 - Sat, Oct 3
TPA
Tampa Intl.
SWF
Stewart Intl.
$150 Roundtrip, found 1 day ago
$150
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Oct 3 from Tampa Intl. to Stewart Intl., returning Sat, Oct 3, priced at $150 found 1 day ago
Allegiant Air
Thu, Sep 3 - Sun, Sep 6
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$298 Roundtrip, found 6 days ago
$298
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Thu, Sep 3 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Sep 6, priced at $298 found 6 days ago
Bargain Flight
Thu, Oct 29 - Mon, Nov 9
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$302 Roundtrip, just found
$302
Roundtrip
just found
Select Bargain Flight flight, departing Thu, Oct 29 from Dallas-Fort Worth Intl. to Albany Intl., returning Mon, Nov 9, priced at $302 just found