Luxury Vacations in Connecticut 2026

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Flight and Luxury hotel deals in Connecticut

Price found within the past 48 hours. Click for updated prices.

J House Greenwich

CA $905

per person

Oct 10 - Oct 12

found 8 hours ago

Roundtrip flight included

Toronto (YYZ) to New York (JFK)

9/10 Wonderful! (1,002 reviews)

Hyatt Regency Greenwich

CA $940

per person

Nov 15 - Nov 18

found 12 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to White Plains (HPN)

8.8/10 Excellent! (1,131 reviews)

For a Hyatt Regency in Greenwich CT. You would expect so much more. It was average at best & the room was just very run down. Not what you would expect at all

Reviewed on Sep 6, 2026

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3 Night Luxury holidays in Connecticut

Price found within the past 48 hours. Click for updated prices.

Hyatt Regency Greenwich

CA $940

per person

Nov 15 - Nov 18

found 12 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to White Plains (HPN)

8.8/10 Excellent! (1,131 reviews)

For a Hyatt Regency in Greenwich CT. You would expect so much more. It was average at best & the room was just very run down. Not what you would expect at all

Reviewed on Sep 6, 2026

J House Greenwich

CA $972

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,002 reviews)

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4 Night Luxury holidays in Connecticut

Price found within the past 48 hours. Click for updated prices.

The Capitol Hotel

Downtown Hartford

CA $1,351

per person

Oct 15 - Oct 19

found 19 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Hartford (BDL)

7.4/10 Good! (1,512 reviews)

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What are some benefits when booking luxury Connecticut vacations?

When you book a luxury Connecticut vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Connecticut?

If you're looking for something luxurious in Connecticut, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $905, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 22. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Connecticut. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Connecticut?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Connecticut.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Connecticut. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Connecticut?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Connecticut or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Connecticut. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

Luxury Hotels in Connecticut

Mohegan Sun

1 Mohegan Sun Boulevard Montville CT

19 min drive from Foxwoods Resort Casino

CA $259

CA $339 total

Oct 1 - Oct 2

includes taxes & fees

Book a stay at this luxury resort in Montville. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in ...

9.2/10 Wonderful! (1,861 reviews)

"Great overnight to attend Matt Rife. Perfect fun filled day at the casino, yummy food and a clean bedroom to sleep in! No complaints!"

Reviewed on Sep 5, 2026

Rock Hall Luxe Lodging

19 Rock Hall Road Winsted CT

2 hours drive from Foxwoods Resort Casino

Book a stay at this luxury B&B in Winsted. Enjoy free breakfast, free parking, and a fitness center. Popular attractions Norfolk Historical Museum and Infinity ...

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Howard Johnson by Wyndham Mystic

253 Greenmanville Ave Mystic CT

17 min drive from Foxwoods Resort Casino

CA $118

CA $136 total

Sep 14 - Sep 15

includes taxes & fees

Book a stay at this business-friendly hotel in Mystic. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the pool and the helpful ...

6.6/10 (1,325 reviews)

"Clean room but tub and shower were old and moldy. Bed was comfortable and sheets and towels were very clean. Location is perfect!"

Reviewed on Sep 7, 2026

See all 4,152 properties in Connecticut

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.