Simsbury Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Avon Old Farms Hotel
CA $1,126
per person
Sep 26 - Sep 29
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hartford (BDL)
8.4/10 Very good! (1,004 reviews)
This is our fourth time staying there. The rooms are clean and quiet. The bed is comfortable.
The free breakfast is the selling point. Best free breakfast I have ever had.
I will be back
Reviewed on Aug 6, 2026
Sheraton Hartford Hotel at Bradley Airport
CA $1,351
per person
Sep 26 - Sep 29
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hartford (BDL)
9.2/10 Wonderful! (1,014 reviews)
After a late arrival and no food all day it was great having the restaurant open and able to grab food. Thanks!!
Reviewed on Aug 8, 2026
Homewood Suites by Hilton Hartford-Farmington
CA $1,008
per person
Sep 26 - Sep 29
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hartford (BDL)
8.4/10 Very good! (1,007 reviews)
The property is a bit run down. The walls and ceilings are paper thin so you hear everything around and above you. The electrical is finicky - lights blink and struggle to turn on, some outlets don’t work, living room furniture is not clean, bathroom door doesn’t close. The pool is dingy and uninviting, the water is not heated as advertised. Breakfast was okay.
The guests above us flooded their toilet and it poured into our bathroom through the ceiling fan and light fixture, none of the three phones worked to notify the front desk , staff was limited so the front desk attendant offered me extra towels to clean up the bathroom. I refused and had to wait an hour at midnight before he was able to get there to clean and disinfect the bathroom.
Reviewed on Aug 7, 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 $224
CA $282 total
Aug 9 - Aug 10
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"We very much enjoyed our weekend at the simsbury 1820. The rooms are decorated in the manner of a luxurious early 20th century; poster bed; spacious; full bath; on site good quality restaurant; extremely helpful staff; electric charging stations for my vehicle; and access to amenities at a sister ..."
Reviewed on Aug 7, 2026
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
CA $128
CA $147 total
Sep 7 - Sep 8
includes taxes & fees
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
CA $123
CA $142 total
Aug 9 - Aug 10
includes taxes & fees
7.4/10 Good! (1,472 reviews)
"They have German roaches"
Reviewed on Aug 7, 2026
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 great live music and acclaimed theater scene.
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 $780 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.
