Connecticut Luxury Vacations 2026

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Top Luxury vacation packages in Connecticut

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

Hyatt Regency Greenwich

$597

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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

Delamar Greenwich Harbor

Save 100% on your flight

$1,148

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

San Antonio (SAT) to White Plains (HPN)

9.4/10 Exceptional! (1,002 reviews)

Will be returning!

Reviewed on Sep 1, 2026

Mohegan Sun

$742

per person

Oct 14 - Oct 17

found 16 hours ago

Roundtrip non-stop flight included

Evansville (EVV) to Hartford (BDL)

9.2/10 Wonderful! (1,892 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

Madison Beach Hotel

Madison Center

$1,334

per person

Oct 15 - Oct 18

found 15 hours ago

Roundtrip flight included

Miami (MIA) to New Haven (HVN)

9.6/10 Exceptional! (385 reviews)

J House Greenwich

Save 100% on your flight

$1,033

per person

Nov 9 - Nov 14

found 6 hours ago

Roundtrip flight included

San Francisco (SFO) to New York (JFK)

9/10 Wonderful! (1,002 reviews)

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See all available trips from Columbus to Connecticut

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3 Night Luxury vacations in Connecticut

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

Hyatt Regency Greenwich

$597

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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

$647

per person

Nov 16 - Nov 19

found 21 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to New York (JFK)

9/10 Wonderful! (1,002 reviews)

Delamar Greenwich Harbor

$1,401

per person

Oct 11 - Oct 14

found 1 day ago

Roundtrip non-stop flight included

Cincinnati (CVG) to White Plains (HPN)

9.4/10 Exceptional! (1,002 reviews)

Will be returning!

Reviewed on Sep 1, 2026

Don't see what you're looking for?

See all available trips from Columbus to Connecticut

View all trips

4 Night Luxury vacations in Connecticut

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

Hilltop Inn and Suites, near Foxwoods Casino

$482

per person

Nov 20 - Nov 24

found 19 hours ago

Roundtrip flight included

Orlando (MCO) to Providence (PVD)

7.8/10 Good! (2,879 reviews)

J House Greenwich

$1,198

per person

Oct 8 - Oct 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (1,002 reviews)

Delamar Greenwich Harbor

Save 100% on your flight

$1,148

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

San Antonio (SAT) to White Plains (HPN)

9.4/10 Exceptional! (1,002 reviews)

Will be returning!

Reviewed on Sep 1, 2026

Don't see what you're looking for?

See all available trips from Columbus to Connecticut

View all trips

What can I expect from a luxury Connecticut vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Connecticut vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Connecticut?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Connecticut luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $482. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Connecticut?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Connecticut with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Connecticut?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Connecticut with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Connecticut with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.

Top Luxury Connecticut Hotels

Mohegan Sun

1 Mohegan Sun Boulevard Montville CT

19 min drive from Foxwoods Resort Casino

$213 nightly

$245 total

Oct 1 - Oct 2

Total with taxes and fees

Pamper yourself with a luxury stay at Mohegan Sun, where you can enjoy amenities like massage services, 24-hour room service, and more. Deluxe amenities at this ...

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

Discover luxurious lodging at Rock Hall Luxe Lodging, where you can enjoy amenities like fireplaces, plush bedding, and more. The outdoor tennis court, outdoor ...

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Howard Johnson by Wyndham Mystic

253 Greenmanville Ave Mystic CT

17 min drive from Foxwoods Resort Casino

$86 nightly

$98 total

Sep 14 - Sep 15

Total with taxes and fees

Howard Johnson by Wyndham Mystic offers a luxury stay. Popular amenities include an indoor pool, a restaurant, and a 24-hour fitness center.

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 4,137 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.