East Windham Vacations from $943

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The Latest East Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
Price was $1,015, price is now $943 per person
$943
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Hudson (HCC)
9.2/10 Wonderful! (314 reviews)
Excellent location , great staff and clean room. Very happy with our stay.

Reviewed on Jan 6, 2026

The Haüs Windham

The Haüs Windham

2 out of 5
Save 100% on your flight
Price was $2,170, price is now $1,703 per person
$1,703
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Hudson (HCC)
8.6/10 Excellent! (17 reviews)
I loved the view and the area

Reviewed on Jul 31, 2025

Hunter Mountain Ski House - Tesla Charger

Hunter Mountain Ski House - Tesla Charger

2 out of 5
Price was $3,646, price is now $3,301 per person
$3,301
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Hudson (HCC)
No reviews
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,036, price is now $948 per person
$948
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Hudson (HCC)
8.8/10 Excellent! (80 reviews)
Very nice hotel. Exactly what we needed.

Reviewed on Jan 2, 2026

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
Price was $1,140, price is now $1,083 per person
$1,083
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Hudson (HCC)
9.2/10 Wonderful! (808 reviews)
Great location, very nice common rooms, friendly staff

Reviewed on Jan 8, 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
$169 nightly
The price is $183 total per night from Jan 14 to Jan 15
$183 total
Jan 14 - Jan 15
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
$159 nightly
The price is $172 total per night from Jan 12 to Jan 13
$172 total
Jan 12 - Jan 13
Total with taxes and fees
9.2/10 Wonderful! (735 reviews)
We stay here often and always have a great experience. Clean room,super comfortable bed and friendly staff (especially the sweet blonde lady that works Sunday night and Monday morning-it skipped my mind to ask what her name was but she is very nice every time).

Reviewed on Jan 5, 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
$174 nightly
The price is $188 total per night from Jan 19 to Jan 20
$188 total
Jan 19 - Jan 20
Total with taxes and fees
9.2/10 Wonderful! (837 reviews)
Clean room, cozy atmosphere, great restaurant, friendly staff.

Reviewed on Jan 1, 2026

Hunter Lodge, a Bluebird by Lark
See all 1,676 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 $943 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.