Top Luxury vacation packages in Niagara Wine Region

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

Woodbourne Inn

St. Davids

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Toronto (YYZ)

9.8/10 Exceptional! (490 reviews)

The attention to detail at the property was excellent. The grounds were peaceful. The breakfast was phenomenal. The room was lacking. Not worth the money for the room itself. We couldn't get a good night's sleep. It was definitely a very small space. We felt claustrophobic. We paid for a room with Queen bed (per Expedia description) and got a double instead that you could barely walk around in. Tiny room.. I would be open to their other options, but would never consider room #6 again. Everything else was great.

Reviewed on Aug 12, 2025

Oban Inn

Old Town Historic District

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Toronto (YYZ)

9.2/10 Wonderful! (1,000 reviews)

We were only there for a night. Staff very friendly and the room was lovely. We’d go back.

Reviewed on Aug 12, 2025

124 on Queen Hotel & Spa

Old Town Historic District

per person

Oct 18 - Oct 20

found 14 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Toronto (YYZ)

9.4/10 Exceptional! (1,004 reviews)

A fabulous boutique Hotel located in the heart of Niagara on the Lake. The staff exceeded my expectations and the room was very well appointed. You will not be disappointed!

Reviewed on Aug 17, 2025

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3 Night Luxury vacations in Niagara Wine Region

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

Oban Inn

Old Town Historic District

per person

Oct 27 - Oct 29

found 18 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Toronto (YYZ)

9.2/10 Wonderful! (1,000 reviews)

We were only there for a night. Staff very friendly and the room was lovely. We’d go back.

Reviewed on Aug 12, 2025

Woodbourne Inn

St. Davids

Save 100% on your flight

per person

Sep 18 - Sep 21

found 7 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Toronto (YYZ)

9.8/10 Exceptional! (490 reviews)

The attention to detail at the property was excellent. The grounds were peaceful. The breakfast was phenomenal. The room was lacking. Not worth the money for the room itself. We couldn't get a good night's sleep. It was definitely a very small space. We felt claustrophobic. We paid for a room with Queen bed (per Expedia description) and got a double instead that you could barely walk around in. Tiny room.. I would be open to their other options, but would never consider room #6 again. Everything else was great.

Reviewed on Aug 12, 2025

124 on Queen Hotel & Spa

Old Town Historic District

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip non-stop flight included

Indianapolis (IND) to Toronto (YYZ)

9.4/10 Exceptional! (1,004 reviews)

A fabulous boutique Hotel located in the heart of Niagara on the Lake. The staff exceeded my expectations and the room was very well appointed. You will not be disappointed!

Reviewed on Aug 17, 2025

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4 Night Luxury vacations in Niagara Wine Region

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

Woodbourne Inn

St. Davids

Save 100% on your flight

per person

Sep 18 - Sep 22

found 8 hours ago

Roundtrip non-stop flight included

Nashville (BNA) to Toronto (YYZ)

9.8/10 Exceptional! (490 reviews)

The attention to detail at the property was excellent. The grounds were peaceful. The breakfast was phenomenal. The room was lacking. Not worth the money for the room itself. We couldn't get a good night's sleep. It was definitely a very small space. We felt claustrophobic. We paid for a room with Queen bed (per Expedia description) and got a double instead that you could barely walk around in. Tiny room.. I would be open to their other options, but would never consider room #6 again. Everything else was great.

Reviewed on Aug 12, 2025

124 on Queen Hotel & Spa

Old Town Historic District

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Tulsa (TUL) to Toronto (YYZ)

9.4/10 Exceptional! (1,004 reviews)

A fabulous boutique Hotel located in the heart of Niagara on the Lake. The staff exceeded my expectations and the room was very well appointed. You will not be disappointed!

Reviewed on Aug 17, 2025

Riverbend Inn and Vineyard

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Toronto (YYZ)

9.4/10 Exceptional! (1,000 reviews)

Beautiful property with wonderful views and friendly staff. Shuttle is extremely convenient and helpful to get too and from town. Front desk staff were very friendly and helpful. Special shout out to Laura or being exceptionally helpful and welcoming.

Reviewed on Aug 17, 2025

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What can I expect from a luxury Niagara Wine Region vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Niagara Wine Region 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 Niagara Wine Region?

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 Niagara Wine Region 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 $456. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Niagara Wine Region?

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 Niagara Wine Region 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 Niagara Wine Region?

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 Niagara Wine Region 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 Niagara Wine Region 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 Niagara Wine Region Hotels

Greaves Sweet Escape

55 Queen Street, Niagara-on-the-Lake, ON

7 min walk from Shaw Festival Theatre

Be treated to deluxe lodging at this apartment, where you'll find deep soaking bathtubs and Egyptian cotton sheets.

9.8/10 Exceptional! (21 reviews)

"The apartment was the smallest ame asthe photos on the website. Great location, being in the middle of the old town was an easy walk to all of the shops and the theatre. Highly recommend this place for a visit to Niagara on the Lake and the surronding wine country"

Reviewed on Nov 24, 2024

Woodbourne Inn

214 Four Mile Creek Rd, St. Davids, Niagara-on-the-Lake, ON

17 min drive from Shaw Festival Theatre

Pamper yourself with a luxury stay at Woodbourne Inn, where you can enjoy amenities like pillowtop beds, Egyptian cotton sheets, and more.

9.8/10 Exceptional! (492 reviews)

"The attention to detail at the property was excellent. The grounds were peaceful. The breakfast was phenomenal. The room was lacking. Not worth the money for the room itself. We couldn't get a good night's sleep. It was definitely a very small space. We felt claustrophobic. We paid for a room with ..."

Reviewed on Aug 12, 2025

Riverbend Inn and Vineyard

16104 Niagara River Pkwy, Niagara-on-the-Lake, ON

18 min walk from Shaw Festival Theatre

Treat yourself to some luxurious accommodations at Riverbend Inn and Vineyard, where you can enjoy amenities like Frette Italian sheets, pillowtop beds, and ...

9.2/10 Wonderful! (1,003 reviews)

Gorgeous views of winery

"Beautiful scenery overlooking the winery. Our room was quite large and beautiful. Love the bubbly at check-in and the bikes. It was perfect."

Reviewed on Aug 15, 2025

See all 1,254 properties in Niagara Wine Region

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.