South Windsor Vacations from $401

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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.
Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

3.5 out of 5
Price was $448, price is now $401 per person
$401
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.4/10 Very Good! (1,005 reviews)

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $575, price is now $498 per person
$498
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.6/10 Excellent! (1,105 reviews)
Great

Reviewed on Nov 5, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $667, price is now $583 per person
$583
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $576, price is now $509 per person
$509
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (1,002 reviews)

Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
Price was $490, price is now $449 per person
$449
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
The room was terrible, he had a weird smell and was Not clean. Maybe it was just my room but would not recommend

Reviewed on Nov 5, 2026

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Stay near popular South Windsor attractions

Shoppes at Buckland Hills

8.6/10 (72 reviews)
The Shoppes at Buckland Hills offers 100+ retailers across two levels in Manchester, Connecticut. Browse department stores and specialty shops, then enjoy various dining options from quick bites to full-service restaurants.
See properties

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
Fully refundable
$135 nightly
The price is $155 total per night from Nov 29 to Nov 30
$155 total
Nov 29 - Nov 30
Total with taxes and fees
Cambria Hotel Manchester South Windsor
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $105 total per night from Dec 6 to Dec 7
$105 total
Dec 6 - Dec 7
Total with taxes and fees
The Capitol Hotel
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way Springfield MA
$147 nightly
The price is $166 total per night from Nov 8 to Nov 9
$166 total
Nov 8 - Nov 9
Total with taxes and fees
MGM Springfield
See all 753 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.

Find the Best South Windsor Vacation Packages

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 $401 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.

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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.