Title: Sterling Vacation Packages & Trips 2026 from CA $647 | Expedia.ca [Hotels in Sterling](https://expedia.ca/Sterling-Hotels.d55983.Travel-Guide-Hotels)[Vacation Rentals in Sterling](https://expedia.ca/Sterling-Vacation-Rentals.d55983.Travel-Guide-VacationRentals)[Sterling Car Rentals](https://expedia.ca/Car-Rentals-In-Sterling.d55983.Car-Rental-Guide) ![](https://images.trvl-media.com/place/55983/bacffede-53cd-4c76-b34b-7a6670c74699.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Sterling 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 Sterling Vacation Our Sterling vacation packages offer countless opportunities to discover new sights, sounds and sensations. And with all the planning taken care of, you can relax and enjoy your city break in the way that you deserve. [Tower Hill Botanic Garden](https://www.expedia.ca/Tower-Hill-Botanic-Garden-Boylston.d553248621532666810.Vacation-Attraction), [Museum of Russian Icons](https://www.expedia.ca/Museum-Of-Russian-Icons-Clinton.d553248621532667011.Vacation-Attraction) and [Dexter Drumlin](https://www.expedia.ca/Dexter-Drumlin-Lancaster.d553248621532667013.Vacation-Attraction) are just a few of the sights worth exploring during your trip to Sterling. Expedia is here to help you escape the everyday. Tailor your vacation to Sterling to suit your style of travel, whatever that may be. ## Top Sterling Vacation Deals Price found within the past 48 hours. Click for updated prices. ![The Cove at Yarmouth by Westgate Resorts](https://images.trvl-media.com/lodging/1000000/10000/4400/4331/ac25d19b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Cove at Yarmouth by Westgate Resorts CA $647 per person May 15 - May 18 found 21 hours ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.2/10 Wonderful! (254 reviews) From the moment we arrived, we was welcomed with warm hospitality and genuine friendliness The room was spotless, comfortable, and beautifully maintained, and I especially appreciated the attention to detail throughout the property. The indoor pool a plus in these cold months - The location was perfect as well—close to everything I wanted to explore, yet peaceful and relaxing. Your staff went above and beyond to ensure a pleasant experience, and it did not go unnoticed. It’s clear that you take great pride in providing exceptional service, and it made my trip all the more memorable. Thank you for such a wonderful stay. I will absolutely be recommending your hotel to friends and family, and I look forward to returning in the future. Reviewed on Mar 29, 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 $1,337 per person Jun 12 - Jun 15 found 14 hours ago Roundtrip non-stop flight included Toronto (YTO) to Boston (BOS) 8.8/10 Excellent! (1,426 reviews) Location, location, location! Breakfast is top notch. The entire staff was helpful and friendly. Reviewed on Apr 3, 2026 ![Raffles Boston](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/f081d391_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Raffles Boston Back Bay CA $2,977 per person Jun 16 - Jun 19 found 4 hours ago Roundtrip flight included Toronto (YYZ) to Boston (BOS) 9.6/10 Exceptional! (248 reviews) The photos doesn’t give this place justice. Reviewed on Mar 24, 2026 ![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/54f3deb7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Boston Downtown Boston CA $2,429 per person Jun 12 - Jun 15 found 14 hours ago Roundtrip non-stop flight included Toronto (YTO) to Boston (BOS) 9.6/10 Exceptional! (1,004 reviews) The rooms were very clean, beds were comfortable, staff friendly and great amenities (I wish the pool was open until 10 pm). Reviewed on Apr 4, 2026 ![The Westin Boston Seaport District](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/b920b61e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Boston Seaport District Seaport District CA $1,051 per person Jun 12 - Jun 15 found 14 hours ago Roundtrip non-stop flight included Toronto (YTO) to Boston (BOS) 9.2/10 Wonderful! (2,404 reviews) Excellent front desk staff. All staff were polite and welcoming and very helpful. Clean spacious room. Just wish the restaurabt offered a few simpler meal options Reviewed on Apr 5, 2026 ## Ready to book your vacation to Sterling? Choose your dates ## Sterling Hotel Deals ![Chocksett Inn and Restaurant](https://images.trvl-media.com/lodging/2000000/1210000/1202200/1202140/2e99d26e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chocksett Inn and Restaurant 59 Laurelwood Road Sterling MA Fully refundableReserve now, pay when you stay CA $222 CA $248 total May 3 - May 4 includes taxes & fees 8.8/10 Excellent! (151 reviews) Although we had to cancel our reservation, everyone we spoke with on the telephone was professional, understanding, and kind. Reviewed on Feb 17, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F05%2F2026&endDate=04%2F05%2F2026&selected=1202140&PinnedHotelID=1202140&HadPinnedHotel=true®ionId=55983) ![Embassy Suites by Hilton Boston Marlborough](https://images.trvl-media.com/lodging/1000000/30000/23000/22959/2c252d7a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Boston Marlborough 123 Boston Post Rd W Marlborough MA CA $219 CA $245 total Apr 12 - Apr 13 includes taxes & fees 9.2/10 Wonderful! (1,008 reviews) love this place, wonderful with everything Reviewed on Apr 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=22959&PinnedHotelID=22959&HadPinnedHotel=true®ionId=55983) ![Great Wolf Lodge Boston / Fitchburg, MA](https://images.trvl-media.com/lodging/9000000/8460000/8458800/8458771/08aa09e5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Great Wolf Lodge Boston / Fitchburg, MA 150 Great Wolf Dr Fitchburg MA CA $220 CA $245 total May 3 - May 4 includes taxes & fees 8.6/10 Excellent! (1,003 reviews) Was great Reviewed on Apr 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F05%2F2026&endDate=04%2F05%2F2026&selected=8458771&PinnedHotelID=8458771&HadPinnedHotel=true®ionId=55983) [See all 393 properties in Sterling](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=06%2F04%2F2026&endDate=07%2F04%2F2026®ionId=55983) 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) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app