Title: Middlesex County Vacation Packages 2026 from $349 | Expedia.com [Middlesex County Hotels](https://expedia.com/Destinations-In-Middlesex-County.d553248635976431666.Hotel-Destinations)[Vacation Rentals in Middlesex County](https://expedia.com/Destinations-In-Middlesex-County.d553248635976431666.Vacation-Rental-Destinations)[Middlesex County Flights](https://expedia.com/Destinations-In-Middlesex-County.d553248635976431666.Flight-Destinations)[Car Rentals in Middlesex County](https://expedia.com/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 Vacations & Trips from $349 ## Book a Hotel + Flight or Car together to unlock savings Photo by Dawn Johnson - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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.com/Old-Saybrook.d6057199.Destination-Travel-Guides) visiting popular sights like Westbrook Town Beach and Clinton Crossing Premium Outlets. [East Hampton](https://www.expedia.com/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 destinations in Middlesex County ![This photo was taken during a nice fall weekend. The water level was low enough to cross to the other side to capture the falls from a different angle than most. Best time however is early morning before most people get there.](https://mediaim.expedia.com/destination/2/6f9a0e2222ff440d9a1af81a42bdbc0f.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Middletown [](https://expedia.com/Middletown.d8862.Destination-Travel-Guides) ![Essex featuring 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.com/Essex.d183061.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/45fbf80ef7607317ec353a8a0058ef75.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Old Saybrook [](https://expedia.com/Old-Saybrook.d6057199.Destination-Travel-Guides) ![School built 1801 ](https://mediaim.expedia.com/destination/2/d0ac3e710d2b9e1eda1f101101c46f4e.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Clinton [](https://expedia.com/Clinton.d90508.Destination-Travel-Guides) ![Wadsworth Falls State Park](https://mediaim.expedia.com/destination/2/20278228da4f02f8cf69337b57d70698.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Middlefield [](https://expedia.com/Middlefield.d6003940.Destination-Travel-Guides) ![Lake life #4thofjuly2019](https://mediaim.expedia.com/destination/2/a63b7b2166957e79a94bff7e89c48b79.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Moodus [](https://expedia.com/Moodus.d183066.Destination-Travel-Guides) ## The Latest Middlesex County Vacation Packages Price found within the past 48 hours. Click for updated prices. ![The Westin New York Grand Central](https://images.trvl-media.com/lodging/6000000/5450000/5445500/5445478/02061152_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin New York Grand Central Manhattan Save 100% on your flight $349 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to New York (JFK) 9/10 Wonderful! (3,569 reviews) I had a wonderful time at the Westin Grand Central. The rooms were clean and neat. The service was amazing. The breakfast buffet was a little overpriced, but The quality was excellent. To make it even more amazing, Eve Melendez and her team had a wonderful gift and a card my daughter when we arrived. She was amazing throughout our trip to New York City. Jose from concierge went above and beyond to help us get to where we need to be! Especially some last-minute pizza from uncle Paul’s. Thank you so much to the rockstar team at the Westin!! we will be back! Reviewed on Feb 6, 2026 ![Hotel St. James](https://images.trvl-media.com/lodging/2000000/1150000/1144500/1144474/ecd19bcc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel St. James Manhattan $394 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to New York (JFK) 8.8/10 Excellent! (6,546 reviews) The best place to stay on a budget if you’re planning to see Broadway shows. I’ve already reserved The St. James for my trip in April. Reviewed on Feb 6, 2026 ![Hotel Riu Plaza Manhattan Times Square](https://images.trvl-media.com/lodging/61000000/60680000/60677500/60677495/0bd08347_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Manhattan Times Square Manhattan $487 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to New York (JFK) 9.2/10 Wonderful! (3,348 reviews) The staff was nice and the rooms were clean! Great place! Reviewed on Feb 6, 2026 ![The Inn At Fox Hollow Hotel](https://images.trvl-media.com/lodging/1000000/880000/871900/871849/9f9215cb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn At Fox Hollow Hotel $481 per person Apr 9 - Apr 12 found 1 day ago Roundtrip flight included Atlanta (ATL) to New York (JFK) 9.2/10 Wonderful! (1,002 reviews) Rooms Property were Fantastic ! Reviewed on Feb 6, 2026 ![Mountain Springs Lake Resort](https://images.trvl-media.com/lodging/34000000/33270000/33260600/33260524/3c4b3304_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Mountain Springs Lake Resort $413 per person Mar 15 - Mar 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 9.6/10 Exceptional! (234 reviews) The staff was friendly and helpful. They were great! Reviewed on Feb 2, 2026 ## Find the Best Middlesex County Vacation Packages ## Middlesex County Essential Information | Language | English | | --------------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Bradley Intl. Airport (BDL) | | Top Sights | [Harveys Beach](https://www.expedia.com/Harveys-Beach-Old-Saybrook.d6224621.Vacation-Attraction), [Devils Hopyard State Park](https://www.expedia.com/Devils-Hopyard-State-Park-East-Haddam.d6341056.Vacation-Attraction) and [Clinton Town Beach](https://www.expedia.com/Clinton-Town-Beach-Old-Saybrook.d553248635983994778.Vacation-Attraction) | ## 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 $175 nightly $198 total Feb 9 - Feb 10 Total with taxes and fees 8.8/10 Excellent! (550 reviews) The hotel staff and accommodations were great. I would highly recommend it. Reviewed on Jan 17, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F9%2F2026&endDate=2%2F10%2F2026&selected=6747876&PinnedHotelID=6747876&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 $79 nightly $91 total Feb 8 - Feb 9 Total with taxes and fees 7.8/10 Good! (1,002 reviews) Room was clean and warm and the staff was very friendly Reviewed on Feb 1, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F8%2F2026&endDate=2%2F9%2F2026&selected=12143&PinnedHotelID=12143&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 $244 nightly $281 total Feb 8 - Feb 9 Total with taxes and fees 8.8/10 Excellent! (1,000 reviews) Great room and staff Reviewed on Jan 14, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F8%2F2026&endDate=2%2F9%2F2026&selected=9679841&PinnedHotelID=9679841&HadPinnedHotel=true®ionId=553248635976431666) [See all 3,426 properties in Middlesex County](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F8%2F2026&endDate=2%2F9%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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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.com/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.com/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.com/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.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) Explore a world of travel with Expedia ## Other vacations you might like - Top cities in Middlesex County - Vacations and getaways similar to Middlesex County - Best vacation destinations by month - [Westbrook Vacations ](https://expedia.com/Westbrook.d173488.Destination-Travel-Guides) - [Old Saybrook Vacations ](https://expedia.com/Old-Saybrook.d6057199.Destination-Travel-Guides) - [Middletown Vacations ](https://expedia.com/Middletown.d8862.Destination-Travel-Guides) - [Cromwell Vacations ](https://expedia.com/Cromwell.d6635.Destination-Travel-Guides) - [Clinton Vacations ](https://expedia.com/Clinton.d90508.Destination-Travel-Guides) - [Essex Vacations ](https://expedia.com/Essex.d183061.Destination-Travel-Guides) - [East Hampton Vacations ](https://expedia.com/East-Hampton.d6341064.Destination-Travel-Guides) - [Middlefield Vacations ](https://expedia.com/Middlefield.d6003940.Destination-Travel-Guides) - [Killingworth Vacations ](https://expedia.com/Killingworth.d180682.Destination-Travel-Guides) - [Chester Vacations ](https://expedia.com/Chester.d183058.Destination-Travel-Guides) - [Haddam Vacations ](https://expedia.com/Haddam.d6341057.Destination-Travel-Guides) - [Deep River Vacations ](https://expedia.com/Deep-River.d6004513.Destination-Travel-Guides) - [Massachusetts Vacations ](https://expedia.com/Massachusetts.d223.Destination-Travel-Guides) - [New York Vacations ](https://expedia.com/New-York.d234.Destination-Travel-Guides) - [Rhode Island Vacations ](https://expedia.com/Rhode-Island.d241.Destination-Travel-Guides) - [January Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-january) - [February Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-february) - [March Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-march) - [April Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-april) - [May Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-may) - [June Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-june) - [July Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-july) - [August Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-august) - [September Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-september) - [October Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-october) - [November Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-november) - [December Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-december) \* 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 even more - get up to 20% on select hotels 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