South Windsor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
per person
Jul. 26 - Jul. 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7/10 Good! (804 reviews)
The area was safe and quiet and it was right off the higway. There were places to eat and shop near by The room smelled of cleaning products and the rooms were dated however we were only spending a night in a budget hotel so you get what you pay for the room had two beds and one had a stain on the sheet so we slept in the other and that one had a stain on the comforter the breakfast was continental so recommend eating someplace else. breakfast was in a brown bag and was a donut and a granola bar a fruit cup and a fruity drink if you are looking for no frills budget stay I would recommend staying here however I would check the sheets or bring your own

Reviewed on May 17, 2024

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
per person
Jul. 26 - Jul. 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.4/10 Exceptional! (1,000 reviews)
A short weekend away with my 8 year old. As a single mom, I look for value, easy and location. This was amazing all around! Loved the indoor and outdoor pools, local towns and state parks recommended by the hotel staff all amazing!

Reviewed on May 27, 2024

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4 out of 5
Old Saybrook Center
per person
Jul. 26 - Jul. 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.4/10 Exceptional! (7 reviews)
Near nice shops and restaurants

Reviewed on May 26, 2024

The Niantic Inn

The Niantic Inn

2 out of 5
per person
Jul. 26 - Jul. 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.6/10 Exceptional! (15 reviews)
Very nice accommodations.

Reviewed on May 19, 2024

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
per person
Jul. 26 - Jul. 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7.6/10 Good! (775 reviews)
Just what you need for a quick stay. Really great breakfast option across the street. Hard to get anything late.

Reviewed on May 27, 2024

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 refundableReserve now, pay when you stay
The price is CA $207 per night from Jun. 9 to Jun. 10
CA $207
CA $238 total
includes taxes & fees
Jun 9 - Jun 10
9.2/10 Wonderful! (385 reviews)
"It was amazing"

Reviewed on May 20, 2024

Cambria Hotel Manchester South Windsor
Holiday Inn Express Southington, an IHG Hotel
Holiday Inn Express Southington, an IHG Hotel
2.5 out of 5
120 Laning St, Southington, CT
Fully refundable
The price is CA $196 per night from May 29 to May 30
CA $196
CA $226 total
includes taxes & fees
May 29 - May 30
8.4/10 Very Good! (1,007 reviews)
"The property was well kept and clean"

Reviewed on May 26, 2024

Holiday Inn Express Southington, an IHG Hotel
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 $138 per night from Jun. 3 to Jun. 4
CA $138
CA $159 total
includes taxes & fees
Jun 3 - Jun 4
7.8/10 Good! (1,002 reviews)
"Great breakfast and attentive associates"

Reviewed on May 14, 2024

Best Western Hartford Hotel & Suites
See all 571 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

Frequently asked questions

How much does a South Windsor vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in South Windsor from just CA $512. And the more you bundle, the more you save. The getaway of your dreams has never been more affordable.
How do I get a cheap travel package to South Windsor?
Just imagine all the thrilling things you could do in South Windsor with extra cash in your pocket. Watch your savings stack up when you bundle your travel bookings into a South Windsor vacation package. You have plenty of choice with Expedia too. In fact, you can take your pick of over 550 air carriers and 1,000,000 hotel options globally. Whether you’re taking off with the entire family or surprising your special someone, planning a trip to South Windsor is better with a package.
Where should I stay in South Windsor?
Stay where the action happens. Many visitors book hotels within easy reach of top attractions, such as Shoppes at Buckland Hills, Promenade Shops at Evergreen Walk and Nomads Adventure Quest.
How far in advance should I book my South Windsor vacation?
To land cheap prices, book nice and early. Air carriers typically release tickets, along with some of the lowest fares, around a year ahead of time. Hotels, experiences and car rental should also be booked well in advance to avoid disappointment. If you’re in need of a last-minute getaway to South Windsor, there are always lots of great deals to be had on Expedia. Book something in today!
What does an Expedia South Windsor travel package include?
It all comes down to what type of escape you’re contemplating. South Windsor vacation deals can include hotels, flights and car rentals. You can mix and match to find the travel package that works for you! You can also add on experiences and activities after you’ve booked to pick up even bigger discounts.
What should I know before booking a South Windsor travel package?
Bundling your bookings into a South Windsor vacation package is the most convenient way to organize your trip. Not only that, you’ll save when you combine your flights, hotels and car rentals. Once you’ve booked, why not add on an activity or a tour?
Can I choose my airline with a South Windsor Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you’re looking to fly to South Windsor in first class or coach, simply select from the available airline options. Expedia has access to more than 550 partner airlines around the world.
If I'm not able to travel, can I cancel my South Windsor vacation package?
Plans can change without warning, so yes, you can. You may be able to cancel and rebook your South Windsor vacation package at no cost if you’ve booked in the last 24 hours. For older bookings, you can still make changes, but your airline, hotel or car rental company may impose a fee. Looking for more information? Visit our Customer Service Portal. We’re here to help make sure your trip goes off without a hitch.

Discover the most popular places to visit in South Windsor

Image for Shoppes at Buckland Hills

Shoppes at Buckland Hills

4/5(2 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
Image for Promenade Shops at Evergreen Walk

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
Image for Nomads Adventure Quest

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