Simsbury Holidays

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Top hotels in Simsbury

Simsbury 1820 House

Simsbury 1820 House

731 Hopmeadow St Simsbury CT
Fully refundableReserve now, pay when you stay
S$297
27 Sept - 28 Sept
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"We had a lovely room on the second floor. Staff was friendly and helpful. Some friends stayed in a third floor room and were not happy with the room. The ceiling was low. There was a roof line over the bed and they kept knocking their heads. We also noted a 400 series of rooms that were on the other ..."

Reviewed on 13 Sept, 2026

Simsbury 1820 House
The Capitol Hotel

The Capitol Hotel

440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
S$147
28 Sept - 29 Sept
includes taxes & fees
The Capitol Hotel
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

149 Ella Grasso Turnpike Windsor Locks CT
Fully refundable
S$172
11 Oct - 12 Oct
includes taxes & fees
8.4/10 Very good! (1,120 reviews)
"I arrived with a $200. gift certificate. I was unable to use on booking or arriving. Nobody seems to know what or how to use this item. Very disturbing. The front desk staff was helpful. The facility was clean but we did not know you had to request a cleaning. Trash was full, bed unmade. Asked night ..."

Reviewed on 15 Sept, 2026

Candlewood Suites Windsor Locks Bradley Arpt by IHG
See all 745 properties in Simsbury
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.
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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.
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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.
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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.
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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.
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Phelps Tavern Museum

9.6/10 (4 reviews)
Step back in time at this 1771 colonial tavern where the Phelps family hosted travellers for over 60 years. Explore period-furnished rooms that reveal daily life in early America through guided afternoon tours.
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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.
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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.
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What to do in Simsbury

Connecticut Coloured Regiment Parade Route: An Audio Tour

Connecticut Coloured Regiment Parade Route: An Audio Tour

S$13
per adult
Connecticut Coloured Regiment Parade Route: An Audio Tour
See all activities in Simsbury

Frequently asked questions

How much does a Simsbury holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. But how much your holiday to Simsbury costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Simsbury?
If you're hoping to snag a cheap Simsbury holiday package, consider travelling in January, February and March. You'll usually find lower prices on hotels and airfares during these months — perfect for a budget-friendly getaway.
How many days is enough for Simsbury?
With about 2 days, you'll have enough time to experience popular neighbourhoods like Simsbury Centre and Tariffville during your Simsbury holiday. Remember to also add Performing Arts Centre at Simsbury Meadows and Rosedale Farms & Vineyards to your sightseeing list. In the mood for more adventures? Consider exploring outside of Simsbury on tours and day trips.
How to find the best Simsbury package deals?
Bagging a cheap Simsbury package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply a few filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Simsbury package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Simsbury holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customised Simsbury holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Simsbury?
Score amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Simsbury break.
How to plan a trip to Simsbury?
  1. Choose when to go: Check your diary and get packing. Your favourite time of year and the activities available will also help you decide when to visit Simsbury.
  2. Budget wisely: As well as the price of your stay, you should consider other expenses. These include flights, food and transportation. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Simsbury.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Simsbury. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Simsbury holiday package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.