Windsor Vacations from $627

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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.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $857, price is now $627 per person
$627
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
9.4/10 Exceptional! (10 reviews)
Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,169, price is now $698 per person
$698
per person
Oct 2 - Oct 5
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
9/10 Wonderful! (2 reviews)
Prospect was a wonderful stay with very friendly staff. The property is very well maintained. We had a great time with the all the lake activities. Would definitely recommend for a quick getaway

Reviewed on Jun 23, 2025

The Perch Hotel

The Perch Hotel

2 out of 5
Save 100% on your flight
Price was $2,282, price is now $1,386 per person
$1,386
per person
Oct 2 - Oct 5
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
9/10 Wonderful! (14 reviews)
Exceptional view. The sunrise from the valley view is incredible

Reviewed on Aug 16, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Price was $917, price is now $659 per person
$659
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
7.4/10 Good! (512 reviews)
When we arrived the front desk had 2 people working with numerous check ins as there was a convention checking in as well as other guests. They were understaffed in many departments. The elevator rug needed replacement as it was dirty and worn. The side entrances were full of large spider webs and debris all the time it appeared no one every cleaned them. It was the disabled entrance. Our bathroom had a serious outdated issue. The hand rails in the tub were rusty and full of soap scum. The outside was in need of a refresh as well most of the iconic green shutters were broken/falling off. It just felt off from the beautiful iconic Equinox Inn of old when the owners took extreme pride in the quality of their quests experiences and comforts.

Reviewed on Aug 21, 2025

The Old Catskill Game Farm Inn

The Old Catskill Game Farm Inn

3.5 out of 5
Save 100% on your flight
Price was $3,102, price is now $2,289 per person
$2,289
per person
Oct 2 - Oct 5
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
9.6/10 Exceptional! (23 reviews)
I loved everything about this place ! The room the giraffe house it’s so gorgeous ! Sean the man who takes care of and manages the property is so knowledgeable. He gave my boyfriend and I a tour around the whole property with his goats and when I tell you this man knows the property HE KNOWS THE PROPERTY & history of the area. The experience wouldn’t have been the same with out him.

Reviewed on Jan 11, 2025

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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
$130 nightly
The price is $145 total per night from Aug 27 to Aug 28
$145 total
Aug 27 - Aug 28
Total with taxes and fees
8.6/10 Excellent! (1,957 reviews)
"A rare, affordable place in the Berkshires! The scenery is stunning, and we loved the pools (both indoor and out) and fire pit. The staff was friendly, and our room was spacious but dated: the blinds were broken, the doors stuck, the walls were paper thin and our king-size mattress had clearly seen ..."

Reviewed on Aug 18, 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $96 total per night from Sep 22 to Sep 23
$96 total
Sep 22 - Sep 23
Total with taxes and fees
8.8/10 Excellent! (581 reviews)
"Enjoyed the room, towels and kitchen. I can recommend."

Reviewed on Aug 18, 2025

Berkshire Mountain Lodge
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $160 total per night from Sep 22 to Sep 23
$160 total
Sep 22 - Sep 23
Total with taxes and fees
8.6/10 Excellent! (999 reviews)
"Great stay. Well balanced, clean, friendly."

Reviewed on Aug 20, 2025

Hotel Downstreet, Ascend Hotel Collection
See all 981 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.

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Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from $627 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.