Simsbury Holidays

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    Save up to €900 when you book a flight and hotel together*

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Top hotels in Simsbury

Simsbury 1820 House

Simsbury 1820 House

4 out of 5
731 Hopmeadow St Simsbury CT
Fully refundableReserve now, pay when you stay
The price is €168 per night from 15 Nov to 16 Nov
€168
15 Nov - 16 Nov
includes taxes & fees
Simsbury 1820 House
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
The price is €101 per night from 12 Nov to 13 Nov
€101
12 Nov - 13 Nov
includes taxes & fees
The Capitol Hotel
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way Springfield MA
The price is €148 per night from 23 Nov to 24 Nov
€148
23 Nov - 24 Nov
includes taxes & fees
9/10 Wonderful! (1,546 reviews)
"Friendly staff"

Reviewed on 11 Nov 2026

MGM Springfield
See all 790 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.
See properties

What to do in Simsbury

Connecticut Coloured Regiment Parade Route: An Audio Tour

Connecticut Coloured Regiment Parade Route: An Audio Tour

€9
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.