Title: Cuttyhunk Vacation Packages & Trips 2026  | Expedia.ca

[Cuttyhunk Travel Guide](https://expedia.ca/Cuttyhunk.dx3000441000)[Hotels in Cuttyhunk](https://expedia.ca/Cuttyhunk-Hotels.d3000441000.Travel-Guide-Hotels)[Vacation Rentals in Cuttyhunk](https://expedia.ca/Cuttyhunk-Vacation-Rentals.d3000441000.Travel-Guide-VacationRentals)[Flights to Cuttyhunk](https://expedia.ca/Cheap-Flights-To-Cuttyhunk.d3000441000.Travel-Guide-Flights)[Cuttyhunk Car Rentals](https://expedia.ca/Car-Rentals-In-Cuttyhunk.d3000441000.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Cuttyhunk Vacation Packages

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

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

## Ready to book your vacation to Cuttyhunk?

Choose your dates

## Cuttyhunk Hotel Deals

![Mansion House Inn And Spa](https://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/e86ce24b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Mansion House Inn And Spa

9 Main Street Vineyard Haven MA

CA $239

CA $288 total

Dec 18 - Dec 19

includes taxes & fees

9.2/10 Wonderful! (999 reviews)

Perfect as always

Reviewed on Dec 10, 2025

[](https://expedia.ca/Hotel-Search?startDate=18%2F12%2F2025&endDate=19%2F12%2F2025&selected=2182094&PinnedHotelID=2182094&HadPinnedHotel=true&regionId=3000441000)

![Hampton Inn by Hilton New Bedford/Fairhaven](https://images.trvl-media.com/lodging/1000000/60000/55000/54948/647c4f15_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hampton Inn by Hilton New Bedford/Fairhaven

1 Hampton Way Fairhaven MA

Fully refundableReserve now, pay when you stay

CA $131

CA $146 total

Jan 5 - Jan 6, 2026

includes taxes & fees

8.8/10 Excellent! (1,001 reviews)

The hot chocolate bar is top notch!

Reviewed on Dec 13, 2025

[](https://expedia.ca/Hotel-Search?startDate=05%2F01%2F2026&endDate=06%2F01%2F2026&selected=54948&PinnedHotelID=54948&HadPinnedHotel=true&regionId=3000441000)

![New Bedford Harbor Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/24000000/23260000/23251300/23251279/76e173eb_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

New Bedford Harbor Hotel, an Ascend Collection Hotel

222 Union St New Bedford MA

Fully refundable

CA $151

CA $169 total

Jan 5 - Jan 6, 2026

includes taxes & fees

8.2/10 Very Good! (1,002 reviews)

Clean room and friendly staff

Reviewed on Dec 14, 2025

[](https://expedia.ca/Hotel-Search?startDate=05%2F01%2F2026&endDate=06%2F01%2F2026&selected=23251279&PinnedHotelID=23251279&HadPinnedHotel=true&regionId=3000441000)

[See all 1,214 properties in Cuttyhunk](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025&regionId=3000441000)

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)

## Frequently asked questions

### Can I cancel my flight booking to Cuttyhunk due to COVID-19?

### What's the best way to find cheap flights to Cuttyhunk that have flexible change policies?

### What are some of the general tips for travelers to Cuttyhunk during the COVID-19 outbreak?

> - Investigate if any travel restrictions apply to your destination and origin before locking in your flight. Also check if there are any requirements you'll have to follow on arrival, such as health testing.
> - Keep your face mask on during airport screening. A TSA officer will ask you to adjust your mask to verify your identity.
> - To reduce the likelihood of cross-contamination, position your boarding pass on the reader yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA officer.
> - One liquid hand sanitizer container is now allowed in your carry-on bag. It must be no larger than 12 oz (350 ml), and you'll need to take it out of your bag for scanning.
> - To minimize handling during screening, put items such as your keys, wallet, phone and belt into your carry-on rather than into the bins.
> - Transport all food items in a clear plastic bag and also put them in a screening bin. Keeping your food separate from your carry-on means it's less likely a TSA agent will need to open and touch your bag for inspection.

### Which airlines fly to Cuttyhunk?

### How can I find cheap tickets to Cuttyhunk?

### How much is a flight to Cuttyhunk?

### What are the most popular airports to fly into in Cuttyhunk?

### When is the cheapest time to fly to Cuttyhunk?

### How much is a plane ticket to Cuttyhunk?

### Which airlines with flights to Cuttyhunk employ COVID-19 cleanliness policies?

> - Cape Air - this airline is known for providing passenger masks and cleaning with disinfectant.
> - JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
> - Tradewind Aviation - this airline is known for providing passenger masks and cleaning with disinfectant.

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

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