East Windham Vacations from $296

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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
Save 100% on your flight
per person
Oct 11 - Oct 14
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) 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

AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Save 100% on your flight
per person
Oct 4 - Oct 8
found 6 hours ago
Roundtrip flight included
Tampa (TPA) to Hudson (HCC)
9/10 Wonderful! (409 reviews)
It was good expensive overall, but they can do better

Reviewed on Aug 7, 2025

Coldbrook Bed and Breakfast

Coldbrook Bed and Breakfast

4 out of 5
Save 100% on your flight
per person
Oct 11 - Oct 14
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) 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
per person
Oct 4 - Oct 8
found 5 hours ago
Roundtrip flight included
Tampa (TPA) to Hudson (HCC)
No reviews
Cortland by Avantstay Charming Heritage Estate w/ Private Lake & Pool

Cortland by Avantstay Charming Heritage Estate w/ Private Lake & Pool

3.5 out of 5
Save 100% on your flight
per person
Oct 4 - Oct 8
found 2 hours ago
Roundtrip flight included
Tampa (TPA) to Hudson (HCC)
9/10 Wonderful! (2 reviews)
Fine, elegant, house. A great departure from one’s daily life. Great layout but could use more lighting. There were old quirks about the house but it made it more unique. Some doors don’t shut and will rattle when windows are open. Could use a griddle or larger pans/more baking sheets. The property is gorgeous and the crisp air was refreshing. Lovely experience and would book again!

Reviewed on Apr 7, 2024

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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
Fully refundableReserve now, pay when you stay
$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! (734 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
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $140 total per night from Sep 8 to Sep 9
$140 total
Sep 8 - Sep 9
Total includes taxes and fees
9.2/10 Wonderful! (616 reviews)
"Great hotel"

Reviewed on Aug 12, 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 18 to Aug 19
$220 total
Aug 18 - Aug 19
Total includes taxes and fees
9.4/10 Exceptional! (56 reviews)
"What I like about the property that is was a beautiful area to recharge and refresh your mind, getting away from the city side was soo peaceful I would recommend going back again. The thing I don’t like the cabin that I was staying the stovetop wasn’t working to it’s full potential but it worked ..."

Reviewed on Aug 13, 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 $296 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.