Sharon Vacation Packages
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Your Sharon Vacation
From its highlights to its hidden delights, this city is best explored with a Sharon vacation package. Look for places to stay in Cornwall, which is great for history, nature and skiing. You'll want to do a little exploring during your trip to Sharon. Carve out some time for leading attractions such as Housatonic Meadows State Park, Sharon Audubon Center and TriArts Sharon Playhouse. Check out Expedia's wide range of travel options and begin planning your perfect vacation to Sharon today.
Top Sharon Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Cheshire Welcome Inn
CA $1,009
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
8.4/10 Very good! (860 reviews)
First and foremost, the room was exceptionally clean. Kudos to the housekeeping staff. The room wasn’t fancy, but pleasant and for the most part well maintained. Bed was comfortable however pillows were as hard as rocks. It would have been nice to have options. There were plenty of towels which appeared to be brand new. The room offered the use of a coffeemaker, refrigerator and microwave. Our tv remote didn’t work but we operated the television manually as it was most likely a matter of needing new batteries.
The seemingly only drawback was the three o’clock check in time. Arriving around 1:00 we acknowledged that we were early but would just like the key as we were attending a reunion and would be returning quite late. We didn’t need to enter a room at that time since they were being cleaned. The receptionist was initially reluctant to accommodate but eventually made a concession and gave us the keycard. There was also a computer problem at check-in, which caused a minor delay, but all in all would recommend the accommodations for the price.
Reviewed on Aug 15, 2026
The Scranton Seahorse Inn
Madison Center
CA $1,343
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
9/10 Wonderful! (245 reviews)
Excellent B&B. Great breakfast. Lovely area. Walk around to local stores and restaurants. And beach is nearby.
Reviewed on Aug 1, 2026
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
CA $1,133
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
8/10 Very good! (1,009 reviews)
Very nice family-owned inn and the WiFi is getting an uograde. Beautiful view of the water on the backside of the inn. It’s located close to everything. Good cost.
Reviewed on Aug 15, 2026
Madison Beach Hotel
Madison Center
CA $2,599
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
9.4/10 Exceptional! (379 reviews)
The whole experience was fantastic. Very relaxed atmosphere.with a gorgeous beach view from the hotel room .
Reviewed on Aug 13, 2026
Ready to book your vacation to Sharon?
Sharon Hotel Deals
Lakefront Summer Stunner in New England Just 2 Hours From NYC
Sharon CT
10/10 Exceptional! (96 reviews)
"This was our second consecutive year staying here for a week in July. The cottage is very comfortable, and we enjoyed boating, biking, hiking, and exploring Sharon and Millerton. The amazing views of the water and the hills never get old!"
Reviewed on Jul 27, 2026
Mayflower Inn & Spa, Auberge Collection
118 Woodbury Rd. Washington CT
CA $1,871
CA $2,232 total
Aug 17 - Aug 18
includes taxes & fees
9.4/10 Exceptional! (62 reviews)
"The best"
Reviewed on Aug 2, 2026
Americas Best Value Inn Torrington CT
395 Winsted Rd Torrington CT
Fully refundableReserve now, pay when you stay
CA $166
CA $191 total
Aug 17 - Aug 18
includes taxes & fees
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.
Stay near popular Sharon attractions
TriArts Sharon Playhouse
You can make plans for a show at TriArts Sharon Playhouse during your stay in Sharon. While you're in the area, wander around the natural setting.
Bodhi Tree Gallery
You can spend time studying the exhibits at Bodhi Tree Gallery during your travels in Sharon. While you're in the area, wander around the natural setting.
Veterans Field
Explore the great outdoors at Veterans Field, a lovely green space in Sharon. Wander the forest and gardens while you're in the area.
Frequently asked questions
How much does a Sharon vacation package cost?
You can pick up a vacation package to this top destination from CA $1,009 on Expedia. However, how much your vacation to Sharon costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Sharon?
Plan your getaway for the off-season and you're likely to get cheap Sharon vacation packages. Remember that school vacation periods and local festivals and events can have an impact on prices, so do a little research before you go.
How many days is enough for Sharon?
Usually, a handful of days is enough to check out the main sights during your Sharon vacation. But if you prefer to have more time to kick back or take day trips, consider extending your itinerary.
Is it worth booking a vacation package to Sharon?
During your Sharon vacation, you can look forward to experiencing some top-notch history and nature. Leave enough room in your itinerary to explore leading sights like Sharon Audubon Centre and TriArts Sharon Playhouse.
How to find the best Sharon package deals?
Landing a cheap Sharon package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most economical Sharon package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Sharon vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Sharon vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Sharon?
Score amazing discounts by booking your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Sharon getaway.
How to plan a trip to Sharon?
- Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Sharon.
- Set your budget: Factor in expenses such as food, flights and transportation when working out how much to set aside for your trip to Sharon. Then, choose a property that fits your budget, whether that's a low-cost stay or a high-end retreat.
- Set the duration of your trip: Start by making a list of all the attractions you'd like to experience in Sharon. Then, estimate how long you'll need for each, as well as any travel time.
- Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose a Sharon vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
