Title: Holliston Vacation Packages & Trips 2026 from CA $1,348 | Expedia.ca

[Hotels in Holliston](https://expedia.ca/Holliston-Hotels.d3000441122.Travel-Guide-Hotels)[Vacation Rentals in Holliston](https://expedia.ca/Holliston-Vacation-Rentals.d3000441122.Travel-Guide-VacationRentals)[Holliston Car Rentals](https://expedia.ca/Car-Rentals-In-Holliston.d3000441122.Car-Rental-Guide)

![](https://images.trvl-media.com/place/3000441122/35da3236-2b70-4f1a-92a2-795066688911.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Holliston 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

#### Your Holliston Vacation

Enjoy unforgettable adventures when you lock in a vacation package to Holliston. Whether you're a foodie, history buff or just a traveler who loves experiencing new places, there's something for everyone in this lively city. Make your trip to Holliston even more fulfilling by going sightseeing. [Ashland State Park](https://www.expedia.ca/Ashland-State-Park-Ashland.d553248633992331328.Vacation-Attraction), [Pinecrest Golf Club](https://www.expedia.ca/Pinecrest-Golf-Club-Holliston.d553248633992334149.Vacation-Attraction) and [Stoddard Park](https://www.expedia.ca/Stoddard-Park-Holliston.d553248635983992555.Vacation-Attraction) are among the popular attractions you'll want to explore. No matter your travel plans or the size of your budget, putting together a tailored Holliston vacation is a cinch with Expedia.

## Top Holliston Vacation Deals

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

![The Westin Waltham-Boston](https://images.trvl-media.com/lodging/1000000/30000/23200/23129/8fb4c64c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Westin Waltham-Boston

CA $1,348

per person

Jun 13 - Jun 17

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

8.8/10 Excellent! (1,095 reviews)

Good service , Clean rooms

Reviewed on Mar 30, 2026

![The Inn at Hastings Park, Relais & Chateaux - Boston](https://images.trvl-media.com/lodging/8000000/7990000/7980700/7980601/8dcd0e80_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Inn at Hastings Park, Relais & Chateaux - Boston

CA $1,570

per person

Jun 13 - Jun 17

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

9.6/10 Exceptional! (252 reviews)

Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

![Eurostars The Boxer](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/ee935931_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Eurostars The Boxer

West End

CA $1,466

per person

May 21 - May 27

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Boston (BOS)

8.6/10 Excellent! (1,395 reviews)

Great hotel, in the middle of downtown, walking distance from td garden, friendly staff and great amenities, will be back for sure

Reviewed on Mar 30, 2026

### Luxury 2BR near Cambridge

Prospect Hill

CA $2,395

per person

Jun 13 - Jun 17

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

No reviews

![The Inn on Arsenal](https://images.trvl-media.com/lodging/1000000/860000/856000/855968/e8e47dc8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Inn on Arsenal

CA $1,667

per person

Jun 13 - Jun 17

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

8.2/10 Very Good! (84 reviews)

It was a great place to stay for the night. Clean and professional. The only complaint is that the bathroom door didn’t close completely and the heater was really loud.

Reviewed on Mar 28, 2026

## Ready to book your vacation to Holliston?

Choose your dates

## Holliston Hotel Deals

![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/57348ff5_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

citizenM Boston Back Bay

408 Newbury street Boston MA

Fully refundableReserve now, pay when you stay

CA $242

CA $282 total

Apr 5 - Apr 6

includes taxes & fees

9.4/10 Exceptional! (2,498 reviews)

Amazing views from our room. clean room comfortable bed

Reviewed on Mar 31, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=96998829&PinnedHotelID=96998829&HadPinnedHotel=true&regionId=3000441122)

![Sheraton Boston, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/30000/22100/22046/19346b33_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Sheraton Boston, a Marriott Hotel

39 Dalton St Boston MA

Fully refundableReserve now, pay when you stay

CA $375

CA $436 total

Apr 5 - Apr 6

includes taxes & fees

8.6/10 Excellent! (1,794 reviews)

Good hotel! Very bad and old towels! Didn’t like the breakfast! Comfortable bed and helpful staff

Reviewed on Mar 30, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=22046&PinnedHotelID=22046&HadPinnedHotel=true&regionId=3000441122)

![The Midtown Hotel MOD Collection by Sonesta](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/e1e25d35_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Midtown Hotel MOD Collection by Sonesta

220 Huntington Avenue Boston MA

Fully refundableReserve now, pay when you stay

CA $263

CA $307 total

Apr 5 - Apr 6

includes taxes & fees

8.6/10 Excellent! (144 reviews)

The location was very convenient and front desk staff were very friendly and helpful.

Reviewed on Mar 30, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=2898&PinnedHotelID=2898&HadPinnedHotel=true&regionId=3000441122)

[See all 2,174 properties in Holliston](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&regionId=3000441122)

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)

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