Simsbury Vacation Packages
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Your Simsbury Vacation
When a fun city getaway is calling, answer it with a Simsbury vacation package. The neighborhood of Downtown Hartford, which is good for shopping, families and festivals, makes a wonderful base for your adventures. If taking in sights is on the to-do list during your trip to Simsbury, stop by big attractions like Talcott Mountain State Park, Northwest Park and Wintonbury Hills Golf Course. Don't delay your visit to this destination any longer. The perfect Simsbury vacation is a few quick clicks away with Expedia.
Top Simsbury Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Landing in Downtown Hartford Near Dunkin' Park
Downtown Hartford
CA $1,600
per person
Oct 1 - Oct 8
found 10 hours ago
Roundtrip flight included
Vancouver (YVR) to Hartford (BDL)
6/10 (2 reviews)
It says parking is included but I had to pay for parking every day. Front desk couldn’t fix it, the people she called didn’t fix it. Missed a work meeting because of the whole ordeal. Just the night is $24.
Reviewed on May 3, 2026
Two Trees Inn
CA $977
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Hartford (BDL)
8.4/10 Very good! (126 reviews)
Check in was at 4pm. We arrived at 3:50pm and was told they had no time frame when our room would be ready. They said it was because they were busy the night prior…..not an excuse when I have a reservation booked and plans to attend. Didn’t get a room for almost 2 hours after the check in time. That was with me going to the desk again and asking. They were never going to contact me when a room was ready. Very disappointed with the process.
Reviewed on Aug 10, 2026
Ready to book your vacation to Simsbury?
Simsbury Hotel Deals
Simsbury 1820 House
731 Hopmeadow St Simsbury CT
Fully refundableReserve now, pay when you stay
CA $227
CA $285 total
Aug 12 - Aug 13
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"The room was very clean and spacious. Bathroom a little dated. Room was very comfortable. We stayed in the carriage house, which we like very much. The breakfast was very good for a continental breakfast. We appreciated the bottled water provided each day. Thank you for a nice stay."
Reviewed on Aug 10, 2026
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
CA $128
CA $147 total
Aug 30 - Aug 31
includes taxes & fees
8.6/10 Excellent! (1,413 reviews)
"Clean room friendly and helpful staff. Decent Breakfast offerings"
Reviewed on Aug 9, 2026
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
CA $143
CA $165 total
Aug 12 - Aug 13
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 Simsbury attractions
Performing Arts Center at Simsbury Meadows
8.4/10 (5 reviews)
Enjoy an outing to Performing Arts Center at Simsbury Meadows during your stay in Simsbury. You can attend a sporting event while in the area.
Rosedale Farms & Vineyards
10.0/10 (5 reviews)
You can take time to visit Rosedale Farms & Vineyards during your travels to Simsbury. Experience the area's great live music or attend a sporting event.
Phelps Tavern Museum
9.6/10 (4 reviews)
You can study the exhibits at Phelps Tavern Museum, a museum with a storied past, during your travels to Simsbury. You can attend a sporting event while in the area.
Penwood State Park
10.0/10 (3 reviews)
You can take time to visit Penwood State Park during your travels to Simsbury. Experience the area's acclaimed theater scene and great live music.
Apex Go Karting
You can take time to visit Apex Go Karting during your travels to Simsbury. While in this family-friendly area, you can enjoy the restaurants.
What to do in Simsbury
Connecticut Coloured Regiment Parade Route: An Audio Tour
CA $14
per adult
Frequently asked questions
How much does a Simsbury vacation package cost?
Offering great value package deals from CA $721 on Expedia, you'll be pleasantly surprised at how much a vacation to Simsbury costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Simsbury?
January, February and March are great times to search for cheap Simsbury vacation packages. Travelling in less busy periods means you can typically find better prices on hotels and flights.
How many days is enough for Simsbury?
We suggest planning a Simsbury vacation for around 2 days. This will allow you plenty of time to check off top sights including Enders State Forest and Rosedale Farms & Vineyards, and check out neighbourhoods like Simsbury Centre and Tariffville. You could even make time for a day trip (or two) from Simsbury.
How to find the best Simsbury package deals?
Use Expedia's handy filters to help you find some great Simsbury package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Simsbury package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Simsbury vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels separately. Better still, you can personalize your Simsbury escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Simsbury?
If you have your Simsbury vacation dates finalized, book early to bag some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Simsbury?
- Choose the best time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Simsbury.
- Plan your budget wisely: In addition to the price of your stay, you'll need to factor in other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected costs that may arise during your trip to Simsbury.
- Decide how long to go for: Now that you're more familiar with Simsbury, you can figure out the ideal length of your vacation. Pull together a rough itinerary and give yourself enough time to cover everything you want to do.
- Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Simsbury vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
