South Windsor Vacations from $301

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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.
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was $363, price is now $301 per person
$301
per person
Apr 3 - Apr 6
found 9 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
8/10 Very Good! (1,457 reviews)
its ok great for 1 night needs to be updated I dont think i would stay in another best western

Reviewed on Jan 27, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $497, price is now $377 per person
$377
per person
Apr 3 - Apr 6
found 9 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Great location to explore Yale. Quiet, comfortable & smartly appointed.

Reviewed on Jan 25, 2026

Landing Modern 2bd, Gym

3 out of 5
West New Haven
Save 100% on your flight
Price was $531, price is now $404 per person
$404
per person
Feb 27 - Mar 2
found 2 hours ago
Roundtrip flight included
West Palm Beach (PBI) to New Haven (HVN)
No reviews
Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
Price was $865, price is now $677 per person
$677
per person
Apr 3 - Apr 6
found 9 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
9.4/10 Exceptional! (21 reviews)
Very quiet, clean and peaceful accommodation. Enjoyed our stay here. Very spacious apartment with everything you need for a comfortable stay. Felt right at home - away from home. Highly recommend.

Reviewed on Jan 7, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Save 100% on your flight
Price was $546, price is now $431 per person
$431
per person
Mar 20 - Mar 22
found 24 hours ago
Roundtrip flight included
Myrtle Beach (MYR) to New Haven (HVN)
9.6/10 Exceptional! (60 reviews)
Cleaning good although some of the furniture and carpets show a lot of wear for a new building. Definitely would stay there again.

Reviewed on Jan 12, 2026

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Discover the most popular places to visit in South Windsor

Shoppes at Buckland Hills

4/5(32 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.

Shoppes at Buckland Hills

Promenade Shops at Evergreen Walk

4.5/5(6 reviews)

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

Promenade Shops at Evergreen Walk

Nomads Adventure Quest

4.5/5(7 reviews)

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

Cambria Hotel Manchester South Windsor

Cambria Hotel Manchester South Windsor

3 out of 5
1000 Long Leaf Lane South Windsor CT
Fully refundable
$131 nightly
The price is $151 total per night from Feb 22 to Feb 23
$151 total
Feb 22 - Feb 23
Total with taxes and fees
9.2/10 Wonderful! (869 reviews)
Was a wonderful stay from beginning to end

Reviewed on Jan 19, 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
$88 nightly
The price is $102 total per night from Jan 29 to Jan 30
$102 total
Jan 29 - Jan 30
Total with taxes and fees
7.4/10 Good! (1,156 reviews)
Breakfast was delicious. Maybe some more toppings for waffles

Reviewed on Jan 21, 2026

The Capitol Hotel
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way Springfield MA
$145 nightly
The price is $165 total per night from Feb 23 to Feb 24
$165 total
Feb 23 - Feb 24
Total with taxes and fees
8.8/10 Excellent! (1,470 reviews)
everything was perfect!

Reviewed on Jan 26, 2026

MGM Springfield
See all 700 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 $301 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.