East Windham Vacations from $661

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The Latest East Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
Little Cat Lodge

Little Cat Lodge

2 out of 5
Price was $749, price is now $661 per person
$661
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Hudson (HCC)
9.4/10 Exceptional! (64 reviews)
Good sized room with a comfortable bed. Friendly staff and breakfast was nice. The area was rather odd. Far too expensive for what I got but prices were really high the night I stayed.

Reviewed on Dec 2, 2025

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

3 out of 5
Save 100% on your flight
Price was $2,742, price is now $2,298 per person
$2,298
per person
Mar 25 - Mar 29
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
No reviews
Deer Mountain Inn

Deer Mountain Inn

2 out of 5
Price was $1,469, price is now $1,246 per person
$1,246
per person
Mar 25 - Mar 29
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
9/10 Wonderful! (4 reviews)
I loved the guest room with the pool table and self attend bar.

Reviewed on Oct 22, 2024

The Haüs Windham

The Haüs Windham

2 out of 5
Price was $1,084, price is now $941 per person
$941
per person
Mar 25 - Mar 29
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
8.6/10 Excellent! (17 reviews)
I loved the view and the area

Reviewed on Jul 31, 2025

Eastwind Windham

Eastwind Windham

2 out of 5
Price was $981, price is now $865 per person
$865
per person
Mar 25 - Mar 29
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
9.2/10 Wonderful! (67 reviews)
This is one of the most amazing weekend vacations I have been on. I can’t complain about anything!

Reviewed on Jan 5, 2026

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East Windham Hotel Deals

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
$150 nightly
The price is $162 total per night from Jan 20 to Jan 21
$162 total
Jan 20 - Jan 21
Total with taxes and fees
9.4/10 Exceptional! (119 reviews)
I loved every single part of the stay

Reviewed on Jan 8, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296 Windham NY
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $172 total per night from Jan 20 to Jan 21
$172 total
Jan 20 - Jan 21
Total with taxes and fees
9.2/10 Wonderful! (740 reviews)
Nice rooms and continental breakfast. Very reasonable price.

Reviewed on Jan 13, 2026

Hotel Vienna
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
$163 nightly
The price is $176 total per night from Jan 22 to Jan 23
$176 total
Jan 22 - Jan 23
Total with taxes and fees
9/10 Wonderful! (842 reviews)
Sub par breakfast

Reviewed on Jan 11, 2026

Hunter Lodge, a Bluebird by Lark
See all 1,685 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.

Find the Best East Windham Vacation Packages

East Windham Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
30ºF
Max Temp Summer
75ºF

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Frequently asked questions

How much does an East Windham vacation package cost?
Offering excellent value package deals from $661 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.