South Windsor Vacation Packages

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Your South Windsor Vacation

Lock in a South Windsor vacation package that includes everything you need and no unnecessary extras. Great for shopping, families and festivals, think about basing yourself in the neighborhood of Downtown Hartford. Make your trip to South Windsor even more fun by including some sightseeing. Shoppes at Buckland Hills, Promenade Shops at Evergreen Walk and Broad Brook Opera House are among the most popular attractions you'll want to explore. Whoever you're taking time off with and whatever the size of your budget, your dream South Windsor vacation is just clicks away with Expedia.

Top South Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was CA $814, price is now CA $678 per person
CA $678
per person
Aug 24 - Aug 27
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
9.2/10 Wonderful! (2,191 reviews)
Easy check-in and helpful staff. Only there over night as family member in Yale Hospital. Paring easy as was check out. Needs more charging ports.

Reviewed on Jul 3, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was CA $1,373, price is now CA $1,112 per person
CA $1,112
per person
Aug 24 - Aug 27
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

Landing Furnished Apartment Near Yale University

Landing Furnished Apartment Near Yale University

3 out of 5
Downtown New Haven
Price was CA $942, price is now CA $806 per person
CA $806
per person
Aug 24 - Aug 27
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
2/10 (1 review)
Was unable to enter the unit as the key was not available in the Lockbox. Landing (the rental company) was unable to locate the key, which was apparently with the cleaning staff, who were unavailable. We ended up having to rent another property for our visit.

Reviewed on Jun 2, 2026

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was CA $858, price is now CA $740 per person
CA $740
per person
Aug 24 - Aug 27
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
8.6/10 Excellent! (1,316 reviews)
Great stay! Breakfast was fresh. Bed was amazing!

Reviewed on Jul 3, 2026

La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
Long Wharf
Price was CA $793, price is now CA $697 per person
CA $697
per person
Sep 7 - Sep 10
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to New Haven (HVN)
6/10 (1,289 reviews)
Not very clean, barley swept and the bathroom has hair everywhere

Reviewed on Jul 3, 2026

Ready to book your vacation to South Windsor?

 

Choose your dates

South Windsor Hotel Deals

Cambria Hotel Manchester South Windsor

Cambria Hotel Manchester South Windsor

3 out of 5
1000 Long Leaf Lane South Windsor CT
The price is CA $254 per night from Jul 5 to Jul 6
CA $254
CA $292 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (984 reviews)
"This is by far one of the best hotels that I have visited!! The location was great, property outside was clean and well kept. Parking lot was right in front of the property. Went in and the receptionist was very welcoming, sweet and informative. The room was well designed, modern, clean and bright ..."

Reviewed on Jul 1, 2026

Cambria Hotel Manchester South Windsor
Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

2 out of 5
1341 Silas Deane Hwy Wethersfield CT
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Jul 20 to Jul 21
CA $105
CA $121 total
Jul 20 - Jul 21
includes taxes & fees
7/10 Good! (1,207 reviews)
"Great price, service and cleanliness for a motel. Would definitely come back again."

Reviewed on Jul 3, 2026

Motel 6 Wethersfield, CT - Hartford
Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

2.5 out of 5
185 Brainard Rd Hartford CT
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Aug 2 to Aug 3
CA $147
CA $169 total
Aug 2 - Aug 3
includes taxes & fees
7.8/10 Good! (1,087 reviews)
"Place was a dump. Floors were vaccum. We wrote our shoes in the room to not stand on bare floor, the soap was opened and used in the shower. The hallways smelled and the rooms smelled. Not work more than $20 a night"

Reviewed on Jun 29, 2026

Best Western Hartford Hotel & Suites
See all 706 properties in South 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular South Windsor attractions

Shoppes at Buckland Hills

8.6/10 (72 reviews)
You can do some window-shopping at Shoppes at Buckland Hills during your stay in South Windsor. Experience the great live music or attend a sporting event in this family-friendly area.
See properties

Frequently asked questions

How much does a South Windsor vacation package cost?
Offering great value package deals from CA $678 on Expedia, you'll be thrilled with how little a vacation to South Windsor costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to South Windsor?
You can usually find lower prices and greater availability in February, July and December. Check out our cheap South Windsor vacation packages and you could get some excellent off-season deals.
How many days is enough for South Windsor?
We'd recommend booking a South Windsor vacation for around 2 days. This will give you time to visit top attractions including Broad Brook Opera House and Nomads Adventure Quest, and explore neighbourhoods like Central Manchester and Manchester Centre. You could even squeeze in a day trip outside of South Windsor.
Is it worth booking a vacation package to South Windsor?
Boasting a host of highlights starting with its amazing history, South Windsor is a good vacation destination. Whether you'd like to discover attractions such as Shoppes at Buckland Hills and Promenade Shops at Evergreen Walk or venture off the beaten track, you'll have loads to keep you busy during your South Windsor vacation.
How to find the best South Windsor package deals?
Use Expedia's filters to find some great South 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 break for midweek, or browse for South Windsor package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a South Windsor vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and hotels individually. Better still, you can personalize your South Windsor trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to South Windsor?
If you have your South Windsor travel dates locked in, book as early as you can to bag some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for quick escapes.
How to plan a trip to South Windsor?

  1. Choose your dates: The things you want to do in South Windsor and your preferred season will help you decide when to get away.
  2. Plan your budget wisely: Besides the price of your accommodations, you'll need to consider other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that could arise during your trip to South Windsor.
  3. Decide how long to go for: Now that you're up to speed on South Windsor, you can work out the ideal length of your break. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored South Windsor vacation package.

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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.