East Side Luxury Vacations

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Flight and Luxury hotel deals in East Side

Price found within the past 48 hours. Click for updated prices.
The Kitano Hotel New York

The Kitano Hotel New York

Manhattan
CA $941
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to New York (JFK)
9.4/10 Exceptional! (2,354 reviews)
Great Location and very good hosts

Reviewed on Sep 1, 2026

Lotte New York Palace

Lotte New York Palace

Manhattan
CA $1,473
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9/10 Wonderful! (2,187 reviews)
Had a wonderful stay with an incredible view of St Patrick’s Cathedral from our upgraded room. Location perfect for us. Staff were so helpful, professional and friendly. Housekeeping were great especially Diana. Highly recommend.

Reviewed on Sep 2, 2026

The Shelburne Sonesta New York

The Shelburne Sonesta New York

Manhattan
CA $1,383
per person
Nov 2 - Nov 6
found 8 hours ago
Roundtrip flight included
Seattle (SEA) to New York (JFK)
9/10 Wonderful! (2,044 reviews)
⭐⭐⭐⭐ Great Value, Comfortable Beds & Convenient Location We stayed at the Shelburne Sonesta from Aug 28–Sept 1 in a double queen room with a kitchenette. Overall, we had a great stay and felt it was well worth the price. Check-in was quick and easy, and our room was clean and spacious. The sheets were soft and the beds were VERY comfortable after long days exploring New York. A fun bonus was choosing two treats from the hotel’s snack stash each night, including chips, Gatorade, pop, water, juice and cookies. It was a simple perk, but we really enjoyed it! The location was convenient, with the subway nearby, easy Uber access and taxis generally available out front. Many main attractions were also within walking distance. The attached restaurant offers room service, but we ate there instead and enjoyed fries, wings and drinks. Everything was great, and the hotel staff were very helpful throughout our stay. A couple of things to note: the TV didn’t support streaming apps, so we were limited to regular cable. The phone in our room also didn’t work properly, meaning we had to call the front desk using speakerphone. The room was clean overall, though it didn’t feel deeply cleaned. A little more attention to detail would have helped, but it didn’t affect our stay. Overall, we enjoyed the comfortable beds, convenient location, helpful staff and kitchenette. For the price, it was definitely worth it, and we would stay again.

Reviewed on Sep 2, 2026

Hotel Park Ave NYC

Hotel Park Ave NYC

Manhattan
CA $1,146
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,675 reviews)
The Renwick

The Renwick

Manhattan
CA $1,245
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,690 reviews)
Great location

Reviewed on Sep 2, 2026

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5* Luxury holidays in East Side

Price found within the past 48 hours. Click for updated prices.
The Marmara Park Avenue

The Marmara Park Avenue

Manhattan
CA $1,099
per person
Nov 9 - Nov 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,004 reviews)
The pool and Turkish bath are a real treat. This was a nice staycation for myself.

Reviewed on Aug 30, 2026

The Lowell

The Lowell

Manhattan
CA $4,079
per person
Nov 10 - Nov 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.6/10 Exceptional! (229 reviews)
Loews Regency New York Hotel

Loews Regency New York Hotel

Manhattan
CA $1,970
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to New York (JFK)
9.2/10 Wonderful! (1,014 reviews)
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3 Night Luxury holidays in East Side

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

The Lombardy Hotel

Manhattan
CA $1,064
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,581 reviews)
Room was clean, and very quiet. The highlight of the trip was the staff - front desk, doormen and maintenance were always friendly and welcoming, especially with our daughter. Wonderful stay.

Reviewed on Sep 1, 2026

The Shelburne Sonesta New York

The Shelburne Sonesta New York

Manhattan
CA $1,094
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,044 reviews)
⭐⭐⭐⭐ Great Value, Comfortable Beds & Convenient Location We stayed at the Shelburne Sonesta from Aug 28–Sept 1 in a double queen room with a kitchenette. Overall, we had a great stay and felt it was well worth the price. Check-in was quick and easy, and our room was clean and spacious. The sheets were soft and the beds were VERY comfortable after long days exploring New York. A fun bonus was choosing two treats from the hotel’s snack stash each night, including chips, Gatorade, pop, water, juice and cookies. It was a simple perk, but we really enjoyed it! The location was convenient, with the subway nearby, easy Uber access and taxis generally available out front. Many main attractions were also within walking distance. The attached restaurant offers room service, but we ate there instead and enjoyed fries, wings and drinks. Everything was great, and the hotel staff were very helpful throughout our stay. A couple of things to note: the TV didn’t support streaming apps, so we were limited to regular cable. The phone in our room also didn’t work properly, meaning we had to call the front desk using speakerphone. The room was clean overall, though it didn’t feel deeply cleaned. A little more attention to detail would have helped, but it didn’t affect our stay. Overall, we enjoyed the comfortable beds, convenient location, helpful staff and kitchenette. For the price, it was definitely worth it, and we would stay again.

Reviewed on Sep 2, 2026

Lotte New York Palace

Lotte New York Palace

Manhattan
CA $1,473
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9/10 Wonderful! (2,187 reviews)
Had a wonderful stay with an incredible view of St Patrick’s Cathedral from our upgraded room. Location perfect for us. Staff were so helpful, professional and friendly. Housekeeping were great especially Diana. Highly recommend.

Reviewed on Sep 2, 2026

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4 Night Luxury holidays in East Side

Price found within the past 48 hours. Click for updated prices.
Hotel 32 32

Hotel 32 32

Manhattan
CA $1,115
per person
Nov 10 - Nov 14
found 3 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to New York (JFK)
8/10 Very good! (2,550 reviews)
Staff were all friendly and helpful! We got King Superior room. Bed were so comfortable. Kitchen was clean and there were 2 small fridges. Great location for tourists as the subway its on the same block. There is a great hole on the wall breakfast place on the same block that was so convenience and pretty cheap, nice cafe next door. It's located in the Korea Town -- Restaurants selections are amazing. Don'd forget to stop by the Food Court in a couple of blocks away on 32nd street.

Reviewed on Sep 1, 2026

Lotte New York Palace

Lotte New York Palace

Manhattan
CA $1,999
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
9/10 Wonderful! (2,187 reviews)
Had a wonderful stay with an incredible view of St Patrick’s Cathedral from our upgraded room. Location perfect for us. Staff were so helpful, professional and friendly. Housekeeping were great especially Diana. Highly recommend.

Reviewed on Sep 2, 2026

The Shelburne Sonesta New York

The Shelburne Sonesta New York

Manhattan
CA $1,383
per person
Nov 2 - Nov 6
found 8 hours ago
Roundtrip flight included
Seattle (SEA) to New York (JFK)
9/10 Wonderful! (2,044 reviews)
⭐⭐⭐⭐ Great Value, Comfortable Beds & Convenient Location We stayed at the Shelburne Sonesta from Aug 28–Sept 1 in a double queen room with a kitchenette. Overall, we had a great stay and felt it was well worth the price. Check-in was quick and easy, and our room was clean and spacious. The sheets were soft and the beds were VERY comfortable after long days exploring New York. A fun bonus was choosing two treats from the hotel’s snack stash each night, including chips, Gatorade, pop, water, juice and cookies. It was a simple perk, but we really enjoyed it! The location was convenient, with the subway nearby, easy Uber access and taxis generally available out front. Many main attractions were also within walking distance. The attached restaurant offers room service, but we ate there instead and enjoyed fries, wings and drinks. Everything was great, and the hotel staff were very helpful throughout our stay. A couple of things to note: the TV didn’t support streaming apps, so we were limited to regular cable. The phone in our room also didn’t work properly, meaning we had to call the front desk using speakerphone. The room was clean overall, though it didn’t feel deeply cleaned. A little more attention to detail would have helped, but it didn’t affect our stay. Overall, we enjoyed the comfortable beds, convenient location, helpful staff and kitchenette. For the price, it was definitely worth it, and we would stay again.

Reviewed on Sep 2, 2026

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Plan the perfect luxury East Side vacation with Expedia

What are some benefits when booking luxury East Side vacations?

When you book a luxury East Side 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 East Side?

If you're looking for something luxurious in East Side, 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 $941, 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 East Side. 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 East Side?

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 East Side.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in East Side. 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 East Side?

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 East Side 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 East Side. 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 East Side

Lotte New York Palace

Lotte New York Palace

455 Madison Ave New York NY
  • 5 min walk from Grand Central Terminal
Book a stay at this luxury hotel in New York. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
9/10 Wonderful! (2,233 reviews)
"Had a wonderful stay with an incredible view of St Patrick’s Cathedral from our upgraded room. Location perfect for us. Staff were so helpful, professional and friendly. Housekeeping were great especially Diana. Highly recommend."

Reviewed on Sep 2, 2026

Lotte New York Palace
Waldorf Astoria New York

Waldorf Astoria New York

301 Park Avenue New York NY
  • 4 min walk from Grand Central Terminal
Book a stay at this luxury hotel in New York. Enjoy free WiFi, a full-service spa, and 3 restaurants. Popular attractions Grand Central Terminal and 5th Avenue ...
9.8/10 Exceptional! (84 reviews)
"Great Job"

Reviewed on Aug 30, 2026

Waldorf Astoria New York
InterContinental New York Barclay by IHG

InterContinental New York Barclay by IHG

111 East 48th Street New York NY
  • 3 min walk from Grand Central Terminal
Book a stay at this luxury hotel in New York. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
InterContinental New York Barclay by IHG
See all 1,679 properties in East Side
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.

Things to do

Edge Immersive Observation Deck Ticket

Edge Immersive Observation Deck Ticket

CA $60
per adult
96% of travellers recommend
Edge Immersive Observation Deck Ticket
American Dream: SEA LIFE New Jersey Aquarium

American Dream: SEA LIFE New Jersey Aquarium

CA $46
per traveller
88% of travellers recommend
American Dream: SEA LIFE New Jersey Aquarium
Statue of Liberty & Ellis Island Sunset Cruise

Statue of Liberty & Ellis Island Sunset Cruise

CA $35
per adult
78% of travellers recommend
Statue of Liberty & Ellis Island Sunset Cruise
See all activities in East Side

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.