Simsbury Vacations
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- Plan, book, travel with confidence
- Better togetherSave up to SAR 5,400 when you book a flight and hotel together*
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Find the Best Simsbury Vacation Packages
Simsbury Hotel Deals
Simsbury 1820 House
731 Hopmeadow St Simsbury CT
Fully refundableReserve now, pay when you stay
SAR 635
SAR 794 total
3 Sep - 4 Sep
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Quaint Inn in a scienic location."
Reviewed on 31 August 2026
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
SAR 380
SAR 437 total
3 Sep - 4 Sep
includes taxes & fees
7.4/10 Good! (1,512 reviews)
"Room was dirty. To"
Reviewed on 31 August 2026
MGM Springfield
One MGM Way Springfield MA
SAR 537
SAR 695 total
28 Sep - 29 Sep
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)
This open-air venue hosts exceptional performances from local artists to the Hartford Symphony Orchestra. Bring lawn chairs for summer concerts at the Talcott Mountain Music Festival, where picturesque evenings await.
Rosedale Farms & Vineyards
10.0/10 (5 reviews)
This fifth-generation family farm offers award-winning wines and seasonal agritourism in a picturesque Connecticut setting. Explore vineyards, enjoy wine tastings, and discover the sunflower stroll during summer months.
Old Drake Hill Flower Bridge
After visiting Old Drake Hill Flower Bridge, make a plan to see the other sights and activities in Simsbury. While in this family-friendly area, you can enjoy the restaurants.
Pinchot Sycamore Tree
Commune with nature and explore the great outdoors at Pinchot Sycamore Tree during your travels in Simsbury. While in this family-friendly area, you can enjoy the restaurants.
Phelps Tavern Museum
9.6/10 (4 reviews)
Step back in time at this 1771 colonial tavern where the Phelps family hosted travelers for over 60 years. Explore period-furnished rooms that reveal daily life in early America through guided afternoon tours.
Heublein Tower
After visiting Heublein Tower, make a plan to see the other sights and activities in Simsbury. While in this family-friendly area, you can enjoy the restaurants.
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.
Penwood State Park
10.0/10 (3 reviews)
Hike through 800 acres of woodland trails offering panoramic views of the Farmington River Valley. The Metacomet Trail section is especially magnificent during fall's vibrant foliage display.
Frequently asked questions
How much does a Simsbury vacation package cost?
Offering great value package deals 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. Traveling in less busy periods means you can typically find better prices on hotels and flights.
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, favorite 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.
