Title: Weston Vacation Packages 2026 from $593 | Expedia.com [Weston Travel Guide](https://expedia.com/Weston.dx3000430603)[Hotels in Weston](https://expedia.com/Weston-Hotels.d3000430603.Travel-Guide-Hotels)[Vacation Rentals in Weston](https://expedia.com/Weston-Vacation-Rentals.d3000430603.Travel-Guide-VacationRentals)[Flights to Weston](https://expedia.com/Cheap-Flights-To-Weston.d3000430603.Travel-Guide-Flights)[Car Rentals in Weston](https://expedia.com/Car-Rentals-In-Weston.d3000430603.Car-Rental-Guide) ![](https://images.trvl-media.com/place/3000430603/061ea7d0-3e5b-4862-b746-93728a1c3870.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Weston Vacations from $593 ## Book a Hotel + Flight or Car together to unlock savings - ## 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 Weston Vacation When you organize a vacation package to Weston, you can relax and enjoy your escape knowing that all your travel plans have been made in advance. Discover the charms of this amazing city while based in a neighborhood like Cranbury, which is great for nature. A trip to Weston is a great opportunity to do some sightseeing. Be sure to look around renowned attractions like [Westport Country Playhouse](https://www.expedia.com/Westport-Country-Playhouse-Westport.d6089813.Vacation-Attraction), [Westport Farmers Market](https://www.expedia.com/Westport-Farmers-Market-Westport.d553248621561886375.Vacation-Attraction) and [Silvermine Arts Center](https://www.expedia.com/Silvermine-Arts-Center-New-Canaan.d553248621561886372.Vacation-Attraction). Check out Expedia's extensive range of travel options and book your ultimate vacation to Weston now. ## The Latest Weston vacation packages Price found within the past 48 hours. Click for updated prices. ![Sheraton New York Times Square Hotel](https://images.trvl-media.com/lodging/1000000/10000/100/87/2bf1f7f9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sheraton New York Times Square Hotel Manhattan Save 100% on your flight $593 per person May 9 - May 13 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 7.4/10 Good! (7,403 reviews) Like many others mentioned, the property IS dated. Not only does the loud water /pipe sounds wake you up. But our shower was not working properly, sink was leaking, and overall the unit was not well cleaned. We put a towel on the floor to catch water, and it was filthy when we lifted it to put in the tub, the floor was not dusted well under the sink. The pricing on Expedia is not correct, the hotel adds on a bunch of extra charges when you check in, including their "bar" that we had 0 interest in using. Reviewed on Apr 5, 2026 ![Topping Rose House](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Topping Rose House $3,600 per person Jun 22 - Jun 26 found 22 hours ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 9/10 Wonderful! (145 reviews) Overall it was a great stay! Best part of the cottage was the bathroom with its deep big tub and walk in shower. But the room itself lacked visual appeal & some conveniences usually associated with booking a cottage which is more private and removed from the house. Could use more and better art in the room. I would also trade all the storage space for a mini fridge, tea kettle or coffee maker. Also the only full-size mirror is hidden far back in the bathroom which isn’t terrible but very inconvenient to check the outfit before heading out the door. It’s little odd things that just made it not feel like a luxury stay. And no one mentioned to us beforehand that the sauna, gym, pool area (even though in off season) was under renovation and not available to use. The restaurant was amazing though, room service was wonderful. And staff were adorable. But I don’t know if we would book again tbh. Reviewed on Mar 24, 2026 ![Park Central Hotel New York](https://images.trvl-media.com/lodging/1000000/10000/4200/4164/cb48c512_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Central Hotel New York Manhattan Save 100% on your flight $1,180 per person May 13 - May 20 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 7.6/10 Good! (4,012 reviews) Ideal location! Nice room sizes by NYC standards. Staff was so helpful and friendly. We loved our stay here. Reviewed on Apr 2, 2026 ![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/b1e6b86c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Brooklyn Bridge $1,640 per person Jun 19 - Jun 22 found 1 hour ago Roundtrip flight included Dallas (DFW) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,000 reviews) Fantastic staycation! The spa was awesome and experience overall was solid. Would definitely stay here again! Reviewed on Mar 31, 2026 ![1 Hotel Central Park](https://images.trvl-media.com/lodging/10000000/9220000/9215600/9215515/26ae58cd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Central Park Manhattan $1,471 per person May 18 - May 22 found 1 day ago Roundtrip non-stop flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 9/10 Wonderful! (1,003 reviews) You book this hotel for the location. Amenities, service are ok. People are friendly and willing to help but some thing are just the way they are. AC don’t work all the time, when it did it produced a high pitched noise, there was this flashing light right above the bed that was seemingly random in its blinking pattern sometimes really bright other times not noticeable. Our first room had a view of construction equipment, second room on floor 10 was a lot better. TV stopped working after first night, two asks to fix nothing changed. It was really nice to be able to drink from the taps in the bathroom. Reviewed on Mar 31, 2026 Don't see what you're looking for? See all available trips from Columbus to Weston [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-05/2026-05-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HPN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Weston #### Lucius Pond Ordway / Devil's Den Preserve Explore the great outdoors at Lucius Pond Ordway / Devil's Den Preserve, a lovely green space in Weston. While you're here, you can savor the top-notch restaurants. [](https://expedia.com/Lucius-Pond-Ordway-Devils-Den-Preserve-Weston.d553248621532664590.Vacation-Attraction) ## Weston Hotel Deals ![Motel 6 Milford, CT](https://images.trvl-media.com/lodging/1000000/10000/300/291/1144278e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Motel 6 Milford, CT 111 Schoolhouse Road Milford CT Fully refundableReserve now, pay when you stay $65 nightly $75 total Apr 26 - Apr 27 Total with taxes and fees 6.2/10 (1,003 reviews) Everything went as smooth as possible with my stay. My reservation was ready for me when I walked in the door. Parking was well lit and plenty of it complementary coffee in the morning. Reviewed on Apr 2, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F26%2F2026&endDate=4%2F27%2F2026&selected=291&PinnedHotelID=291&HadPinnedHotel=true®ionId=3000430603) ![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/80833193_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Place Milford / New Haven 190 Old Gate Lane Milford CT Fully refundableReserve now, pay when you stay $118 nightly $136 total Apr 12 - Apr 13 Total with taxes and fees 8.6/10 Excellent! (1,290 reviews) Outdated, felt like a renovated motel Reviewed on Apr 4, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=1562702&PinnedHotelID=1562702&HadPinnedHotel=true®ionId=3000430603) ![Trumbull Marriott Shelton](https://images.trvl-media.com/lodging/1000000/10000/1200/1166/b3c487eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Trumbull Marriott Shelton 180 Hawley Ln Trumbull CT Fully refundableReserve now, pay when you stay $152 nightly $175 total Apr 12 - Apr 13 Total with taxes and fees 8/10 Very Good! (1,004 reviews) The property is old and run down. For example they had three elevators and two of them didn’t work. The room was pretty clean but the rest of the property was pretty old and not that clean. Reviewed on Apr 3, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=1166&PinnedHotelID=1166&HadPinnedHotel=true®ionId=3000430603) [See all 1,114 properties in Weston](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F6%2F2026&endDate=4%2F7%2F2026®ionId=3000430603) 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. ## Find the Best Weston Vacation Packages ### Things to do near Weston Weston, Connecticut is perfect for outdoor enthusiasts and couples seeking scenic getaways. Visitors can enjoy a variety of activities including educational experiences, theater performances, and recreational areas. Nearby attractions and day trips enhance your stay, while resort activities provide relaxation and fun. Discover the charm of Weston as you explore its natural beauty and engaging amenities. **Shopping** For local shopping, visit [Gateway Shopping Center](https://www.expedia.com/Gateway-Shopping-Center-Wilton.d553248621557920173.Vacation-Attraction), 3 miles away, for a lively atmosphere. [Caldor Shopping Center](https://www.expedia.com/Caldor-Shopping-Center-Norwalk.d553248621557920172.Vacation-Attraction), 4 miles away, offers a mix of shops perfect for families. If you're up for a drive, check out the [Westport Farmers Market](https://www.expedia.com/Westport-Farmers-Market-Westport.d553248621561886375.Vacation-Attraction), 5 miles away, for fresh produce and local goods. **Recreation** Experience the [Hartford HealthCare Amphitheater](https://www.expedia.com/Hartford-HealthCare-Amphitheater-Downtown-Bridgeport.d6178252.Vacation-Attraction) for thrilling sports events and vibrant energy, just 10 miles from Weston. Enjoy live music at [Levitt Pavilion](https://www.expedia.com/Levitt-Pavilion-Westport.d6248410.Vacation-Attraction), only 4 miles away, or unwind at [Seaside Park](https://www.expedia.com/Seaside-Park-South-End.d6347889.Vacation-Attraction), a serene spot for wellness and relaxation, also 10 miles from Weston. **Adventure** [The Adventure Park at Discovery Museum](https://www.expedia.com/The-Adventure-Park-At-Discovery-Museum-North-End.d553248621587477416.Vacation-Attraction), 8 miles from Weston, offers thrilling zipline and ropes courses amidst beautiful outdoor scenery. [Ives Trail](https://www.expedia.com/Ives-Trail-Danbury.d901029281241845760.Vacation-Attraction), located 11 miles away, provides a scenic hiking experience, while Wolfe Park Tennis Center, also 11 miles from Weston, is perfect for tennis enthusiasts looking for adventure. **Nightlife** Weston, Connecticut, offers a charming nightlife with cozy bars and local eateries. Check out the nearby towns like Westport for vibrant nightlife spots, including trendy bars and live music venues, where you can unwind and mingle with locals after a day of exploring. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions in and around Weston Weston, Connecticut, is perfect for outdoor and romantic getaways, offering beautiful scenery and a range of activities. Explore popular attractions such as local beaches, urban parks, and modern colleges that cater to travelers seeking outdoor adventures, cultural experiences, and family-friendly fun. Don't forget to check out nearby Cancun hotels for a unique vacation enhancement. - **[Historic South Norwalk: ](https://www.expedia.com/Historic-South-Norwalk-Norwalk.d6129062.Vacation-Attraction)** Just 7 miles from Weston, this charming historic district offers a vibrant cultural experience with its well-preserved architecture, art galleries, and trendy dining options. Stroll along the waterfront and immerse yourself in the rich history of the area. - **[Compo Beach: ](https://www.expedia.com/Compo-Beach-Westport.d553248621532664563.Vacation-Attraction)** Located 7 miles away, Compo Beach is a picturesque destination perfect for sunbathing, picnicking, and enjoying water activities. With its soft sand and scenic views, it's an ideal spot to relax and soak up beach vibes. - **[Lucius Pond Ordway / Devil's Den Preserve: ](https://www.expedia.com/Lucius-Pond-Ordway-Devils-Den-Preserve-Weston.d553248621532664590.Vacation-Attraction)** Situated within Weston, this beautiful nature reserve features miles of hiking trails surrounded by lush forests and serene ponds. It’s a great place to connect with friendly locals and enjoy the tranquility of nature. ### Best time to go to Weston The best time to visit Weston is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 30.6°F (-0.8°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | February | 32.0°F (0.0°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | March | 38.7°F (3.7°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | April | 48.9°F (9.4°C) | Light Rain | Mostly Sunny | Average | Average | | May | 59.0°F (15.0°C) | Light Rain | Mostly Sunny | Average | Average | | June | 67.8°F (19.9°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | July | 74.7°F (23.7°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | August | 73.4°F (23.0°C) | Light Rain | Mostly Sunny | Average | Average | | September | 66.7°F (19.3°C) | Light Rain | Mostly Sunny | Slightly High | Average | | October | 56.7°F (13.7°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 45.3°F (7.4°C) | Light Rain | Mostly Sunny | Average | Average | | December | 36.9°F (2.7°C) | Light Rain | Mostly Sunny | Slightly Low | Average | ### Tips to save on your trip to Weston - Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Weston. - Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Weston. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Weston Essential Information | Language | English | | --------------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Westchester County Airport (HPN) | | Top Sights | [Jennings Beach](https://www.expedia.com/Jennings-Beach-Fairfield.d553248621582621431.Vacation-Attraction), [Norwalk Maritime Aquarium](https://www.expedia.com/Norwalk-Maritime-Aquarium-Norwalk.d6071501.Vacation-Attraction) and [Compo Beach](https://www.expedia.com/Compo-Beach-Westport.d553248621532664563.Vacation-Attraction) | ## More vacations you might like 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[](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) ## Frequently asked questions ### How much does a Weston vacation package cost? ### What are the cheapest months to go to Weston? ### How many days is enough for Weston? ### How to find the best Weston package deals? ### Is it cheaper to book a Weston vacation as a package? ### When to book a vacation package to Weston? ### Does Expedia offer Book Now, Pay Later Weston vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [Hotels near Wilton Historical Society ](https://www.expedia.com/Wilton-Historical-Society-Hotels.0-l553248621561886373-0.Travel-Guide-Filter-Hotels) - 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