South Windsor Vacations from $433

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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.
Liberty Inn

Liberty Inn

2 out of 5
Price was $520, price is now $433 per person
$433
per person
Jul 1 - Jul 6
found 22 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
7.6/10 Good! (648 reviews)
Perfect clean and safe for a quick overnight stay. Owner is very nice and polite. There are no amenities. Only complaint I have is that is if right on I-95 and is noisy.

Reviewed on May 25, 2026

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $603, price is now $447 per person
$447
per person
Aug 27 - Aug 30
found 21 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
8/10 Very Good! (1,000 reviews)
Comfortable for a nights stay. Close to nice restaurants and shopping.

Reviewed on May 21, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $2,559, price is now $1,918 per person
$1,918
per person
Aug 12 - Aug 16
found 19 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
No reviews
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $849, price is now $677 per person
$677
per person
Jul 23 - Jul 26
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Price was $1,131, price is now $912 per person
$912
per person
Jul 23 - Jul 26
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.6/10 Exceptional! (73 reviews)
I had a great stay at this property overall. The room was clean, comfortable, and well-maintained, which made it easy to relax after a long day. The staff was friendly and helpful, always willing to answer questions and make sure everything was taken care of. The kitchen was stocked with the basics needed for cooking, which was convenient during the stay. Parking was also easy to access and felt safe, which was a big plus. The location was convenient, close to nearby attractions, restaurants, and stores. If I had to mention one thing for improvement, it would be minor updates to some areas to make the space feel a bit more modern. Overall, I would definitely recommend this property and would consider staying here again in the future.

Reviewed on May 5, 2026

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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 acclaimed theater scene 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 great live music or attend a sporting event.

Nomads Adventure Quest

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
$178 nightly
The price is $204 total per night from Jun 28 to Jun 29
$204 total
Jun 28 - Jun 29
Total with taxes and fees
9.2/10 Wonderful! (965 reviews)
"We have stayed here before and loved it so we booked again. This time we got a room on the first floor next to the ice machine. A wedding party was going on which was excessively noisy but honestly the ice machine was the bigger issue. Couldn't Believe it was across the hall from us. To top it off ..."

Reviewed on May 31, 2026

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
$107 nightly
The price is $123 total per night from Jun 14 to Jun 15
$123 total
Jun 14 - Jun 15
Total with taxes and fees
7.4/10 Good! (1,346 reviews)
"The overall experience was good, however a fire alarm woke us up at 6:30 in the morning. Unfortunately we stayed at the top floor and my partner on a walker would not have been able to negotiate the fire stairs. I had indicated with the reservation that I am traveling with a handicapped person and ..."

Reviewed on Jun 1, 2026

The Capitol Hotel
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way Springfield MA
$198 nightly
The price is $224 total per night from Jun 7 to Jun 8
$224 total
Jun 7 - Jun 8
Total with taxes and fees
9/10 Wonderful! (1,543 reviews)
"Clean room, staff was very helpful and accommodating."

Reviewed on Jun 1, 2026

MGM Springfield
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.

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 $433 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.