Windsor Vacations from $509

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Your Windsor Vacation

Enjoy amazing adventures when you reserve a Windsor vacation package. Whether you're a history buff, foodie or just a traveler who loves discovering new places, there's something for everyone in this awesome city. If seeing the sights is a priority during your trip to Windsor, make sure you swing by popular attractions like Wahconah Falls State Park and Bas Ridge Golf Course. No matter your travel plans or the size of your budget, organizing a tailored Windsor vacation is a walk in the park with Expedia.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Eastwind Oliverea Valley

Eastwind Oliverea Valley

2 out of 5
Price was $607, price is now $509 per person
$509
per person
May 28 - May 31
found 19 hours ago
Roundtrip flight included
Raleigh (RDU) to Albany (ALB)
9.4/10 Exceptional! (40 reviews)
Outstanding, beautifully designed boutique hotel with great amenities.

Reviewed on Mar 22, 2026

Urban Cowboy Lodge

Urban Cowboy Lodge

5 out of 5
Save 100% on your flight
Price was $992, price is now $730 per person
$730
per person
May 28 - May 31
found 19 hours ago
Roundtrip flight included
Raleigh (RDU) to Albany (ALB)
9.2/10 Wonderful! (212 reviews)
Staff was super sweet. But there should be some sort of service to take you to your room/bring you up to the main lodge for dinner. Maybe a front desk person with a golf cart. Pretty dangerous to walk down that path alone at night in the dark after some drinks at dinner. Otherwise, very chic and comfortable.

Reviewed on Mar 22, 2026

Hotel Trilogy Albany Airport, Tapestry Collection by Hilton

Hotel Trilogy Albany Airport, Tapestry Collection by Hilton

3.5 out of 5
Price was $894, price is now $772 per person
$772
per person
Jun 19 - Jun 21
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
8.6/10 Excellent! (1,002 reviews)
Great stay. Beautiful lobby, clean room, good price, and a solid location for those families of Siena students, I highly recommend it.

Reviewed on Mar 28, 2026

Hilton Albany

Hilton Albany

3.5 out of 5
Downtown Albany
Price was $712, price is now $618 per person
$618
per person
Jun 19 - Jun 21
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
7.2/10 Good! (1,005 reviews)
The hotel has a gorgeous location, modern renovation, relatively clean. But we noticed mice in the restaurant, there were not enough towels in the pool. But I liked the staff. In general, we are satisfied with the rest

Reviewed on Apr 5, 2026

Emerson Resort & Spa

Emerson Resort & Spa

3.5 out of 5
Price was $589, price is now $520 per person
$520
per person
May 28 - May 31
found 19 hours ago
Roundtrip flight included
Raleigh (RDU) to Albany (ALB)
9.4/10 Exceptional! (53 reviews)
The room is always clean and tidy. The hot tub in the room was nice as well. The staff are always nice. Hopefully they will add more items to their stores. I feel that the breakfast should be open longer.

Reviewed on Mar 27, 2026

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Windsor Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $141 total per night from Apr 12 to Apr 13
$141 total
Apr 12 - Apr 13
Total with taxes and fees
8.8/10 Excellent! (2,324 reviews)
Beds could be more updated

Reviewed on Apr 3, 2026

Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$127 nightly
The price is $142 total per night from May 4 to May 5
$142 total
May 4 - May 5
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Loud refrigerator overall 2.5 stars in terms of condition of the hotel Staff is friendly

Reviewed on Apr 5, 2026

Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from May 5 to May 6
$120 total
May 5 - May 6
Total with taxes and fees
9/10 Wonderful! (895 reviews)
Love that place. Does need a little sprucing up. Staff great and accomodating

Reviewed on Apr 5, 2026

Berkshire Mountain Lodge
See all 1,008 properties in Windsor
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 Windsor Vacation Packages

Windsor Essential Information

Language
English
Currency
U.S dollars
Population
890
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Colonial Theater, Barrington Stage Company and Berkshire Museum

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Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from $509 on Expedia, you'll be surprised at how little a vacation to Windsor costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Windsor?
October, November and December are the best times to look for cheap Windsor vacation packages. Opting to travel in quieter months means you'll typically find lower prices on flights and accommodations.
How many days is enough for Windsor?
With a well-planned schedule, you can easily hit the main Windsor attractions in a few days. But if you prefer to explore off the beaten track or go on day tours, think about booking your Windsor vacation for longer.
How to find the best Windsor package deals?
Use Expedia's filter tool to find some unbeatable Windsor package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Windsor package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and stays separately. Better still, you can customize your Windsor trip to fit your exact needs. 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 Windsor?
If you've got your Windsor vacation dates locked in, book early to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for impromptu escapes.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Your Windsor trip is meant to be a relaxing escape from your daily routine, not a source of money worries. So to give you a bit more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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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.