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Round Top Vacation Packages

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Round Top Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,388, price is now $1,229 per person
$1,229
per person
Oct 9 - Oct 12
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Hudson (HCC)
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.

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
Price was $6,578, price is now $5,385 per person
$5,385
per person
Oct 9 - Oct 12
found 1 hour ago
Roundtrip flight included
Dallas (DFW) 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
Price was $6,204, price is now $5,085 per person
$5,085
per person
Oct 9 - Oct 12
found 1 hour ago
Roundtrip flight included
Dallas (DFW) 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 $1,654, price is now $1,332 per person
$1,332
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) 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

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

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.

Round Top Vacation Packages 3-4 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 $994, price is now $894 per person
$894
per person
Oct 9 - Oct 12
found 1 hour ago
Roundtrip flight included
Dallas (DFW) 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
Price was $6,578, price is now $5,385 per person
$5,385
per person
Oct 9 - Oct 12
found 1 hour ago
Roundtrip flight included
Dallas (DFW) 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
Price was $6,204, price is now $5,085 per person
$5,085
per person
Oct 9 - Oct 12
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Hudson (HCC)
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,388, price is now $1,229 per person
$1,229
per person
Oct 9 - Oct 12
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Hudson (HCC)

Round Top Vacation Packages 5-7 Night Stays

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

The Haüs Windham

2 out of 5
Price was $1,654, price is now $1,332 per person
$1,332
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Hudson (HCC)
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)
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)