Title: Middlesex County Vacations & Trips 2026 | Expedia.ca [Middlesex County Hotels](https://expedia.ca/Destinations-In-Middlesex-County.d553248635976431666.Hotel-Destinations)[Vacation Rentals in Middlesex County](https://expedia.ca/Destinations-In-Middlesex-County.d553248635976431666.Vacation-Rental-Destinations)[Middlesex County Car Rentals](https://expedia.ca/Destinations-In-Middlesex-County.d553248635976431666.Car-Rental-Destinations) ![](https://images.trvl-media.com/place/6130104/4e848a7e-8caf-4a0b-b226-eef5d20a8152.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Middlesex County Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Dawn Johnson - ## 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 Middlesex County Vacation Leave all the planning to us with a Middlesex County vacation package. With everything organized before you leave, the only thing left to do is sit back, relax and experience this destination's countless delights. Begin your trip to Middlesex County with a couple of nights in [Old Saybrook](https://www.expedia.ca/Old-Saybrook.d6057199.Destination-Travel-Guides) visiting popular sights like Westbrook Town Beach and Clinton Crossing Premium Outlets. [East Hampton](https://www.expedia.ca/East-Hampton.d6341064.Destination-Travel-Guides) is another city that lures crowds from near and far. TPC River Highlands and Brownstone Exploration & Discovery Park are two of the top places to see here. Expedia is a one-stop shop when it comes to planning your Middlesex County vacation. From accommodations and flights, to car rentals and activities, we're here to help you curate a travel experience like no other. ## Top vacation destinations in Middlesex County ![Essex showing a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94231-Essex.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Essex [](https://expedia.ca/Essex.d183061.Destination-Travel-Guides) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_553248635976431666) ## Middlesex County Hotel Deals ![Inn at Middletown](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/4e71c540_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Inn at Middletown 70 Main Street Middletown CT Fully refundableReserve now, pay when you stay 8.8/10 Excellent! (554 reviews) The hotel staff and accommodations were great. I would highly recommend it. Reviewed on Jan 17, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=6747876&PinnedHotelID=6747876&HadPinnedHotel=true®ionId=553248635976431666) [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=6747876&PinnedHotelID=6747876&HadPinnedHotel=true®ionId=553248635976431666) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Water's Edge Resort & Spa 1525 Boston Post Road Westbrook CT Fully refundableReserve now, pay when you stay CA $266 CA $330 total Feb 24 - Feb 25 includes taxes & fees 8.8/10 Excellent! (1,003 reviews) Great amenities, Beautiful view, and Caring Staff. Reviewed on Feb 12, 2026 [](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%2F02%2F2026&selected=9679841&PinnedHotelID=9679841&HadPinnedHotel=true®ionId=553248635976431666) ![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pier Blue Inn Old Saybrook - Essex 1430 Boston Post Rd Old Saybrook CT Fully refundableReserve now, pay when you stay CA $87 CA $100 total Feb 16 - Feb 17 includes taxes & fees 7.8/10 Good! (1,001 reviews) Room was clean and warm and the staff was very friendly Reviewed on Feb 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F02%2F2026&endDate=17%2F02%2F2026&selected=12143&PinnedHotelID=12143&HadPinnedHotel=true®ionId=553248635976431666) [See all 3,440 properties in Middlesex County](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=16%2F02%2F2026&endDate=17%2F02%2F2026®ionId=553248635976431666) 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 ### How much does a Middlesex County vacation package cost? ### How do I get a cheap travel package to Middlesex County? ### What are the top hotels in Middlesex County? ### How far in advance should I book my Middlesex County vacation? ### What does an Expedia Middlesex County travel package include? ### What should I know before booking a Middlesex County travel package? ### Can I choose my airline with a Middlesex County Expedia vacation package? ### If I'm not able to travel, can I cancel my Middlesex County vacation package? \* 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