Title: Downtown Poughkeepsie Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $664 Expedia.ca

[Downtown Poughkeepsie Travel Guide](https://expedia.ca/Poughkeepsie-Downtown-Poughkeepsie.dx944697092109320192)[Hotels in Downtown Poughkeepsie](https://expedia.ca/Downtown-Poughkeepsie-Hotels.d944697092109320192.Travel-Guide-Hotels)[Flights to Poughkeepsie](https://expedia.ca/Cheap-Flights-To-Poughkeepsie.d6056317.Travel-Guide-Flights)[Things to do in Poughkeepsie](https://expedia.ca/Things-To-Do-In-Poughkeepsie.d6056317.Travel-Guide-Activities)[Downtown Poughkeepsie Car Rentals](https://expedia.ca/Car-Rentals-In-Downtown-Poughkeepsie.d944697092109320192.Car-Rental-Guide)

![](https://images.trvl-media.com/place/944697092109320192/28bf0e70-d274-45f1-b83f-0dad2ad39a5f.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Downtown Poughkeepsie Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
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## Top Holiday Package Deals in Downtown Poughkeepsie

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

![Hampton Inn & Suites Yonkers](https://images.trvl-media.com/lodging/3000000/2650000/2647900/2647825/e36e4673_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hampton Inn & Suites Yonkers

Northwest Yonkers

CA $664

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to White Plains (HPN)

8.2/10 Very Good! (1,621 reviews)

Partially friendly and professional staff. Rooms are subpar because carpets are worn and not steam cleaned properly. Had to change my room due to nasty stench. The other half of staff during the daytime hours have a “NY do it yourself” attitude.

Reviewed on Feb 5, 2026

![Hampton Inn White Plains/Tarrytown](https://images.trvl-media.com/lodging/1000000/30000/23300/23291/d5b0e16e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hampton Inn White Plains/Tarrytown

CA $670

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to White Plains (HPN)

8/10 Very Good! (1,264 reviews)

It was fine. Rooms were in ok condition; a bit older and need some remodelling. Staff was fine. Place needs a bit of a glow up.

Reviewed on Feb 2, 2026

![Tarrytown House Estate](https://images.trvl-media.com/lodging/1000000/50000/49700/49674/a89a02a1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Tarrytown House Estate

CA $750

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to White Plains (HPN)

8/10 Very Good! (1,001 reviews)

Unique place, very clean and well Maintained.

Reviewed on Feb 5, 2026

![Sleepy Hollow Hotel](https://images.trvl-media.com/lodging/1000000/10000/4000/3956/ee0f5c7a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sleepy Hollow Hotel

CA $828

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to White Plains (HPN)

6.8/10 (1,002 reviews)

Clean rooms and friendly staff

Reviewed on Jan 13, 2026

## Where to stay in Downtown Poughkeepsie

Find the best Downtown Poughkeepsie areas and neighborhoods for the activities you enjoy most. [Learn more about Downtown Poughkeepsie](https://expedia.ca/Poughkeepsie-Downtown-Poughkeepsie.dx944697092109320192)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Arlington

1 out of top 10 points of interest in this area

 You'll enjoy the coffeehouses and art galleries in Arlington. You might want to make time for a stop at Frances Lehman Loeb Art Center or Vassar Golf Course. 

[Find hotel + flight trips in Arlington](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Arlington&DestID=553248634999048383&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![view of the mid hudson bridge to poughkeepsie, new york from highland (suspension bridge over river crossing) scenic landmark](https://images.trvl-media.com/place/553248634999249867/f2c24c28-5e70-4413-8013-f4424bebc55d.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Crown Heights

 Visitors to Crown Heights enjoy its coffeehouses, and if you want to do some exploring, Hudson River is worth a stop. 

[Find hotel + flight trips in Crown Heights](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Crown%20Heights&DestID=553248634999249867&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Mid-Hudson Bridge featuring a bay or harbour, tranquil scenes and a sunset](https://images.trvl-media.com/place/6093747/4b1a6750-92e5-4848-a246-4eb589961272.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Poughkeepsie Waterfront

1 out of top 10 points of interest in this area

 You'll enjoy the restaurants and riverfront in Poughkeepsie Waterfront. You might want to make time for a stop at Mid-Hudson Bridge or Walkway Over the Hudson State Historic Park. 

[Find hotel + flight trips in Poughkeepsie Waterfront](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Poughkeepsie%20Waterfront&DestID=6338910&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![panoramic view of mid hudson bridge over hudson river valley](https://images.trvl-media.com/place/553248634998900489/43dfaefc-f04f-45b7-bc35-40574f714c7b.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Red Oaks Mill

 The river views, waterfalls, and breweries are just a few things travelers enjoy about Red Oaks Mill. If you want to experience more of the area, check out Locust Grove or Poughkeepsie Galleria. 

[Find hotel + flight trips in Red Oaks Mill](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Red%20Oaks%20Mill&DestID=553248634998900489&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![view of the mid hudson bridge to poughkeepsie, new york from highland (suspension bridge over river crossing) scenic landmark](https://images.trvl-media.com/place/907719581714612224/db4be363-892f-4ee6-b91a-2759dffb4f70.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Union Street Historic District

 When in Union Street Historic District, you can plan a visit to Mid-Hudson Civic Center and Bardavon 1869 Opera House, some noteworthy sights in the nearby area. 

[Find hotel + flight trips in Union Street Historic District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Union%20Street%20Historic%20District&DestID=907719581714612224&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Downtown Poughkeepsie Hotel Deals

![DoubleTree by Hilton Poughkeepsie Convention Center](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/acc87956_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

DoubleTree by Hilton Poughkeepsie Convention Center

40 Civic Center Plz Poughkeepsie NY

Fully refundableReserve now, pay when you stay

CA $139

CA $163 total

Feb 21 - Feb 22

includes taxes & fees

8.4/10 Very Good! (1,004 reviews)

Room was clean and comfortable. Staff was so friendly. Would definitely stay here again

Reviewed on Jan 29, 2026

[](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=14563&PinnedHotelID=14563&HadPinnedHotel=true&regionId=944697092109320192)

![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Courtyard by Marriott Poughkeepsie

2641 South Road/Route 9 Poughkeepsie NY

Fully refundableReserve now, pay when you stay

CA $144

CA $162 total

Feb 16 - Feb 17

includes taxes & fees

8.8/10 Excellent! (1,008 reviews)

Very friendly, kind staff and clean room

Reviewed on Feb 2, 2026

[](https://expedia.ca/Hotel-Search?startDate=16%2F02%2F2026&endDate=17%2F02%2F2026&selected=5910&PinnedHotelID=5910&HadPinnedHotel=true&regionId=944697092109320192)

![Residence Inn by Marriott Kingston](https://images.trvl-media.com/lodging/16000000/15720000/15715300/15715238/3f674783_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Residence Inn by Marriott Kingston

800 Frank Sottile Boulevard Kingston NY

Fully refundableReserve now, pay when you stay

CA $168

CA $188 total

Mar 1 - Mar 2

includes taxes & fees

8.8/10 Excellent! (833 reviews)

Have stayed here many times. they have done a really good job of keeping the property up to date. Very nice people.

Reviewed on Jan 25, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=15715238&PinnedHotelID=15715238&HadPinnedHotel=true&regionId=944697092109320192)

[See all 943 properties in Downtown Poughkeepsie](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&regionId=944697092109320192)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Downtown Poughkeepsie

![Springwood Estate - FDR Home](https://images.trvl-media.com/place/6156532/478bf03e-7c48-4738-a32e-08c4f77cf315.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Eleanor Roosevelt National Historic Site

You can find out about the history of Haviland with a stop at Eleanor Roosevelt National Historic Site. While you're in the area, stroll along the riverfront. 

[](https://expedia.ca/Eleanor-Roosevelt-National-Historic-Site-Poughkeepsie.d6156532.Vacation-Attraction)

### Things to do

![Bear Mountain State Park+ BeaconTown 1-Day Tour From NY](https://mediaim.expedia.com/localexpert/50302489/1ceb0837-f410-471c-80a4-908b6cbc0dd2.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Bear Mountain State Park+ BeaconTown 1-Day Tour From NY

CA $128

per adult

[](https://expedia.ca/things-to-do/bear-mountain-state-park-beacontown-1-day-tour-from-ny.a50302489.activity-details)

[See all activities in Poughkeepsie](https://expedia.ca/things-to-do/search?rid=944697092109320192)

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