Title: South Windsor Vacation Packages & Trips 2026 from CA $605 | Expedia.ca

[South Windsor Travel Guide](https://expedia.ca/South-Windsor.dx6175902)[Hotels in South Windsor](https://expedia.ca/South-Windsor-Hotels.d6175902.Travel-Guide-Hotels)[Vacation Rentals in South Windsor](https://expedia.ca/South-Windsor-Vacation-Rentals.d6175902.Travel-Guide-VacationRentals)[Flights to South Windsor](https://expedia.ca/Cheap-Flights-To-South-Windsor.d6175902.Travel-Guide-Flights)[South Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-South-Windsor.d6175902.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# South Windsor Vacation Packages

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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](https://www.expedia.ca/Shoppes-At-Buckland-Hills-South-Windsor.d6178496.Vacation-Attraction), [Promenade Shops at Evergreen Walk](https://www.expedia.ca/Promenade-Shops-At-Evergreen-Walk-South-Windsor.d6178499.Vacation-Attraction) and [Broad Brook Opera House](https://www.expedia.ca/Broad-Brook-Opera-House-Broad-Brook.d553248621561886423.Vacation-Attraction) 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.

![Liberty Inn](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/8ac8989f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Liberty Inn

CA $605

per person

Jun 19 - Jun 22

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to New Haven (HVN)

7.6/10 Good! (641 reviews)

Centrally located for the area.

Reviewed on Oct 31, 2025

![Madison Beach Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/1ec18076_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Madison Beach Hotel

Madison Center

CA $2,020

per person

Jun 19 - Jun 22

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to New Haven (HVN)

9.4/10 Exceptional! (347 reviews)

beautiful room and views

Reviewed on Dec 13, 2025

![James Pharmacy Bed & Breakfast](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/w848h631x48y3-ad11e9c5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### James Pharmacy Bed & Breakfast

Old Saybrook Center

CA $1,117

per person

Jun 19 - Jun 22

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to New Haven (HVN)

9/10 Wonderful! (23 reviews)

Room was pleasant and clean, although small. Bathroom fixtures all new and very clean and functional. Firm bed, which I appreciated. The stairs are steep though there is a firm railing. I didn't realize that we would get a breakfast voucher as opposed to a true B&B experience. The restaurant provided was friendly and the food all looked great but unfortunately didn't have much flavor. The Paperback Cafe nearby had tastier choices. Make sure that you get their email about how to get in because there is no one on site and when we arrived after dark, the front of the building wasn't lit because the entry is in the back. On our first morning, we got a text about our credit card payment not going through. The owner and manager were both responsive but given that they weren't on site, a friendlier tone (i.e., assuming that there might've been a mistake in their information, which there was!) would've been appreciated. It's a lovely place in an excellent location but perhaps slightly expensive given that they are not providing a full B&B experience.

Reviewed on Oct 6, 2025

![Westbrook Inn B&B](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/62eddf34_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Westbrook Inn B&B

Westbrook Center

CA $984

per person

Jun 19 - Jun 22

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to New Haven (HVN)

9.8/10 Exceptional! (179 reviews)

Our stay was amazing! All the staff were so accommodating and kind. The inn has a rustic charm and was so festive for the holidays! Rooms are a good size, clean, and have everything you need. The breakfast was delicious and they even had free tea/coffee/cookies for all guests to enjoy :)

Reviewed on Dec 21, 2025

![Tower Inn And Suites Of Guilford - Madison](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/7368827e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Tower Inn And Suites Of Guilford - Madison

CA $754

per person

Jun 19 - Jun 22

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to New Haven (HVN)

7.4/10 Good! (240 reviews)

The room was clean, the place could use some updates, the 1 chair next to the table had some nasty stains on the fabric

Reviewed on Mar 2, 2026

## Ready to book your vacation to South Windsor?

Choose your dates

## South Windsor Hotel Deals

![Cambria Hotel Manchester South Windsor](https://images.trvl-media.com/lodging/41000000/40600000/40596000/40595943/8714e74b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Cambria Hotel Manchester South Windsor

1000 Long Leaf Lane South Windsor CT

Fully refundable

CA $191

CA $220 total

Apr 19 - Apr 20

includes taxes & fees

9.2/10 Wonderful! (903 reviews)

Very nice hotel in a nice area. Would stay again

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=40595943&PinnedHotelID=40595943&HadPinnedHotel=true&regionId=6175902)

![The Capitol Hotel](https://images.trvl-media.com/lodging/1000000/10000/6800/6777/2c26b973_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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The Capitol Hotel

440 Asylum St Hartford CT

Fully refundableReserve now, pay when you stay

CA $122

CA $140 total

Apr 1 - Apr 2

includes taxes & fees

7.6/10 Good! (1,207 reviews)

yes

Reviewed on Mar 23, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&selected=6777&PinnedHotelID=6777&HadPinnedHotel=true&regionId=6175902)

![MGM Springfield](https://images.trvl-media.com/lodging/28000000/27670000/27664900/27664860/6589d0b2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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MGM Springfield

One MGM Way Springfield MA

CA $204

CA $263 total

Apr 5 - Apr 6

includes taxes & fees

9/10 Wonderful! (1,506 reviews)

Excellent modern facility. Lots of options for things to do. Gambling, bowling, movies and plenty of food options.

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=27664860&PinnedHotelID=27664860&HadPinnedHotel=true&regionId=6175902)

[See all 723 properties in South Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F03%2F2026&endDate=26%2F03%2F2026&regionId=6175902)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

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