East Windham Vacations from $321

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The Latest East Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
The Hidden Inn

The Hidden Inn

4 out of 5
Price was $413, price is now $321 per person
$321
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Hudson (HCC)
9.4/10 Exceptional! (37 reviews)
Great restaurant right downstairs. Quiet little town. Will be going back.

Reviewed on Aug 13, 2025

Coldbrook Bed and Breakfast

Coldbrook Bed and Breakfast

4 out of 5
Save 100% on your flight
Price was $649, price is now $447 per person
$447
per person
Oct 9 - Oct 12
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
10/10 Exceptional! (7 reviews)
Superbly designed B&B where comfort is found in every detail - from the beds to the fire pit with s'mores kits to the breakfast choices. Amazing experience - the modern, fresh and inviting design of this B&B is nestled in the woods with views of the mountains. We spent a long weekend here, exploring the local towns and trails by day, happy to come home to this lovely B&B every evening. We'll be back!

Reviewed on Aug 4, 2025

Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

3 out of 5
Save 100% on your flight
Price was $4,004, price is now $3,050 per person
$3,050
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Hudson (HCC)
No reviews
Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Save 100% on your flight
Price was $1,275, price is now $972 per person
$972
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Hudson (HCC)
9.4/10 Exceptional! (164 reviews)
Loved everything about it, especially large deck with view of waterfall. Interiors were beautiful and contemporary in a very convenient and comfortable way. No negatives.

Reviewed on Aug 18, 2025

Hotel Vienna

Hotel Vienna

2.5 out of 5
Save 100% on your flight
Price was $548, price is now $418 per person
$418
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Hudson (HCC)
9.4/10 Exceptional! (605 reviews)
Friendly staff , direct access to states trails.very nice !

Reviewed on Aug 16, 2025

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East Windham Hotel Deals

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St, Hunter, NY
$169 nightly
The price is $183 total per night from Sep 11 to Sep 12
$183 total
Sep 11 - Sep 12
Total includes taxes and fees
9.2/10 Wonderful! (736 reviews)
"Nice lodge with a great view. Staff was very friendly."

Reviewed on Aug 16, 2025

Hunter Lodge, a Bluebird by Lark
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
$134 nightly
The price is $145 total per night from Aug 27 to Aug 28
$145 total
Aug 27 - Aug 28
Total includes taxes and fees
9.2/10 Wonderful! (618 reviews)
"Hotel was very clean, grounds looked great and the owner/manager was constantly waiting on guests."

Reviewed on Aug 16, 2025

Hotel Vienna
Postcard Cabins Eastern Catskills

Postcard Cabins Eastern Catskills

2 out of 5
282 Cairo Junction Rd, Catskill, NY
$204 nightly
The price is $220 total per night from Aug 20 to Aug 21
$220 total
Aug 20 - Aug 21
Total includes taxes and fees
9.4/10 Exceptional! (58 reviews)
Peaceful
"Amazing little cozy retreat with beautiful surroundings! Everything you need for a perfect visit with nature - firewood, s’mores kit, coffee. The views were great!"

Reviewed on Aug 17, 2025

Postcard Cabins Eastern Catskills
See all 1,643 properties in East Windham
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Frequently asked questions

How much does an East Windham vacation package cost?
Offering excellent value package deals from $321 on Expedia, you'll be thrilled with how little a vacation to East Windham costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to East Windham?
If you'd like to score a cheap East Windham vacation package, consider visiting in December, January and February. You'll usually find better prices on hotels and airfares during these months — ideal for travelers wishing to save money.
How many days is enough for East Windham?
With a well-organized travel plan, you can easily tick off the main East Windham attractions in a handful of days. But if you prefer to explore off the beaten track or go on day trips, consider booking your East Windham vacation for longer.
How to find the best East Windham package deals?
Start your search for an East Windham package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal East Windham package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your East Windham escape underway.
Is it cheaper to book an East Windham vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and accommodations individually. Better still, you can personalize your East Windham getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to East Windham?
If you're considering an impromptu East Windham trip, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later East Windham vacation packages?
Set off on your perfect trip to East Windham with Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait for the next payday — we've joined forces with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.