South Windsor Holidays from £1,191

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Your South Windsor Holiday

Lock in a South Windsor holiday package that includes everything you need and no unnecessary extras. Great for shopping, families and festivals, think about basing yourself in the neighbourhood 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 holiday is just clicks away with Expedia.

Top South Windsor Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Head of Pond House

Head of Pond House

3 out of 5
Price was £1,313, price is now £1,191 per person
£1,191
per person
11 Jan - 17 Jan
just found
Return flight included
London (LON) to New Haven (HVN)
10/10 Exceptional! (18 reviews)
Monika is a warm, energetic and helpful host at every turn while granting your privacy . The rooms were immaculate and beautifully designed with comfortable mattress, thick towels, lovely sheets, a reading chair with ottoman, good lighting , an antique sturdy writing desk. Thick bathrobes and a great bathroom along with excellent controls for setting AC or heat too. Breakfasts were delicious with juice, fresh fruit, homemade scones and muffins, pastries, and yogurt , granola, one morning,a quiche with excellent tea and coffee offerings ( including cappuccinos , latte). The large property with lovely landscaping , a big back terrace , a pool , huge trees overlooks the pond which at sunset is spectacular. And very conveniently located near Hampton jitney stops and local beaches and sightseeing at at venues and shopping. Calling an Uber was simple and fast though in the high summer season it may take longer than 3 minutes. . I recommend Head of Pond House very highly ( I’ve traveled for 30 years worldwide with stays at b&b’s and high end hotels).

Reviewed on 12 Oct 2026

South Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
24,400
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Nomads Adventure Quest, Broad Brook Opera House and Scantic River State Park

Top hotels in South Windsor

Cambria Hotel Manchester South Windsor

Cambria Hotel Manchester South Windsor

3 out of 5
1000 Long Leaf Lane South Windsor CT
Fully refundable
The price is £124 per night from 30 Nov to 1 Dec
£124
30 Nov - 1 Dec
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Beautiful room, easy check in service!"

Reviewed on 7 Nov 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
The price is £84 per night from 11 Nov to 12 Nov
£84
11 Nov - 12 Nov
includes taxes & fees
The Capitol Hotel
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way Springfield MA
The price is £124 per night from 24 Nov to 25 Nov
£124
24 Nov - 25 Nov
includes taxes & fees
9/10 Wonderful! (1,554 reviews)
"Great"

Reviewed on 9 Nov 2026

MGM Springfield
See all 745 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 Holidays
All Inclusive Holidays
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Beach Holidays
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Family Friendly Holidays

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 speciality shops, then enjoy various dining options from quick bites to full-service restaurants.
See properties

Frequently asked questions

How much does a South Windsor travel package cost?
Perhaps less than you might think — from just £1,191, as a matter of fact! By combining flights, hotels and car rentals into your own custom-made travel package, your South Windsor escape is only clicks away.
If I'm not able to travel, can I cancel my South Windsor travel package?
It's difficult to predict what tomorrow might bring, so it's good to know that you can cancel or change your South Windsor travel package. If you booked in the last 24 hours, you may be entitled to a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to find out more.
How do I get a cheap travel package to South Windsor?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we've got it all. Select the combination that suits you and watch your savings pile up. We know a travel package is never one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 hotels around the globe, which lets you customize your South Windsor adventure.
Does Expedia offer Book Now, Pay Later South Windsor holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has come up with a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a fantastic getaway without drying up your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your break. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds best for you, Klarna offers just that! Paying in easy monthly instalments will make that dream holiday possible.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan with Klarna.

Where should I stay in South Windsor?
With so much to discover in South Windsor, we suggest you secure a room in a hotel close to its attractions. Shoppes at Buckland Hills, Promenade Shops at Evergreen Walk and Nomads Adventure Quest are some fascinating ones to add to your to-do list.
What are the top hotels in South Windsor?
Sheraton Hartford Hotel at Bradley Airport and Courtyard By Marriott Hartford/Windsor Airport are a couple of the most popular properties in South Windsor. Why not have a look at the rates and facilities at each and then decide?
How far in advance should I book my South Windsor holiday?
Smart travellers often reserve their seats as early as possible. You can usually browse through international airfares on Expedia up to 12 months before your flight. If you're booking last minute, don't stress. Cheap prices occasionally occur just weeks before departure dates.
What does an Expedia South Windsor travel package include?
With Expedia, you can select a combination of car rentals, hotels and flights to create your ideal South Windsor travel package. Once you've made your booking, you can add on fun stuff like tours and experiences. Remember, the more you bundle, the more deals you'll score!
What should I know before booking a South Windsor travel package?
So many places to go, so many things to do. With a package, you can tick more of them off your list. Combine your flights, rental cars and hotels and land big savings.
Can I choose my airline with a South Windsor Expedia travel package?
Yes, and with over 550 airlines to pick from worldwide, you have loads of choice. Browse the available options and find out which airline best suits your needs and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.