South Windsor Vacations from $455

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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.

The Latest South Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $637, price is now $455 per person
$455
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.2/10 Very Good! (1,008 reviews)
Type of room booked was not available at check in

Reviewed on Oct 3, 2025

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Save 100% on your flight
Price was $808, price is now $528 per person
$528
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.6/10 Excellent! (1,128 reviews)
Staff was very nice and accommodating. Beyond 5 stars if it were possible

Reviewed on Oct 5, 2025

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $864, price is now $585 per person
$585
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (1,002 reviews)
Super clean, friendly staff, fast elevators and easy parking. A no brainer for staying in New Haven.

Reviewed on Oct 7, 2025

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $1,942, price is now $1,325 per person
$1,325
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (316 reviews)
the staff was exceptional and our dinner was very good

Reviewed on Sep 17, 2025

Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $686, price is now $529 per person
$529
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.6/10 Excellent! (570 reviews)
It was a perfect place to stay for a wedding weekend. Great family and dog friendly accommodations.

Reviewed on Sep 30, 2025

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Discover the most popular places to visit in South Windsor

Shoppes at Buckland Hills

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.

Shoppes at Buckland Hills

Promenade Shops at Evergreen Walk

You can find the perfect gifts to bring home at Promenade Shops at Evergreen Walk during your stay in South Windsor. Experience the acclaimed theater scene and great live music in this family-friendly area.

Promenade Shops at Evergreen Walk

Nomads Adventure Quest

You can enjoy the entertainment at Nomads Adventure Quest during your trip to South Windsor. Experience the area's acclaimed theater scene or attend a sporting event.

Nomads Adventure Quest

South Windsor Hotel Deals

The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $118 total per night from Oct 9 to Oct 10
$118 total
Oct 9 - Oct 10
Total with taxes and fees
7.4/10 Good! (1,011 reviews)
"Friendly staff!"

Reviewed on Oct 7, 2025

The Capitol Hotel
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way, Springfield, MA
$179 nightly
The price is $203 total per night from Nov 2 to Nov 3
$203 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,427 reviews)
"had the best nites sleep on the bed at the hotel. the room was gorgeous"

Reviewed on Oct 6, 2025

MGM Springfield
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

2 out of 5
185 Ella Grasso Turnpike, Windsor Locks, CT
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $77 total per night from Nov 2 to Nov 3
$77 total
Nov 2 - Nov 3
Total with taxes and fees
6.6/10 (1,586 reviews)
"This is one of the cleanest hotels I have ever stayed at. The restaurant staff extremely kind the food that is prepared is done in excellence. The check-in staff at the desk are always available and friendly. The cleaning crew was professional. whenever I’m in the area I will always stay at this ..."

Reviewed on Oct 6, 2025

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
See all 635 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.

South Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
24,400
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Broad Brook Opera House, Nomads Adventure Quest and Lutz Childrens Museum

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Frequently asked questions

How much does a South Windsor vacation package cost?
You'll find cheap prices from $455 on Expedia for your South Windsor escape. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to South Windsor costs.
What are the cheapest months to go to South Windsor?
If you're looking to book a cheap South Windsor vacation package, consider visiting in December, January and February. You're likely to find lower rates on airfares and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for South Windsor?
With around 2 days, you'll have plenty of time to visit popular neighborhoods such as Central Manchester and Manchester Center during your South Windsor vacation. Be sure to also add Promenade Shops at Evergreen Walk and Wood Memorial Library & Museum to your sightseeing list. Up for some more adventures? Consider exploring outside of South Windsor on day trips and tours.
Is it worth booking a vacation package to South Windsor?
Boasting a host of highlights starting with its excellent history, South Windsor is a good vacation destination. Whether you'd like to explore sights 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 start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for South Windsor package deals in the off-season. Play around with your travel dates and you may score even better 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 South Windsor vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and accommodations separately. Better still, you can personalize your South Windsor trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to South Windsor?
If you're considering an impromptu South Windsor vacation, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later South Windsor vacation packages?
Your South Windsor getaway should be an escape from your daily routine, not a source of money worries. So to give you a little more flexibility, we've partnered with online lender Affirm to bring you 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 are no late payment fees or hidden costs to worry about.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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