Simsbury Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Simsbury

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 1.996.467 ₫ per night from 24 Aug to 25 Aug
1.996.467 ₫
2.295.937 ₫ total
24 Aug - 25 Aug
includes taxes & fees
7.4/10 Good! (1,020 reviews)
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Reviewed on 6 Aug 2025

The Capitol Hotel
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way, Springfield, MA
The price is 3.644.719 ₫ per night from 25 Aug to 26 Aug
3.644.719 ₫
4.729.886 ₫ total
25 Aug - 26 Aug
includes taxes & fees
8.8/10 Excellent! (1,390 reviews)
"Best casino vibe ever"

Reviewed on 5 Aug 2025

MGM Springfield
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

2 out of 5
185 Ella Grasso Turnpike, Windsor Locks, CT
Fully refundableReserve now, pay when you stay
The price is 1.760.136 ₫ per night from 14 Aug to 15 Aug
1.760.136 ₫
2.024.156 ₫ total
14 Aug - 15 Aug
includes taxes & fees
6.6/10 (1,514 reviews)
"We stood the night it did what it was supposed to do but wasnt updated. I did really like the convenience of the shuttle from hotel to airport. A+ for that"

Reviewed on 6 Aug 2025

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
See all 651 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.

Popular places to visit

Performing Arts Center at Simsbury Meadows

Enjoy a performance at Performing Arts Center at Simsbury Meadows, a theatre with a story to tell in Simsbury. You can attend a sporting event while in the area.

Performing Arts Center at Simsbury Meadows

Rosedale Farms & Vineyards

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.

Rosedale Farms & Vineyards

Penwood State Park

You can take time to visit Penwood State Park during your travels to Simsbury. Experience the area's great live music and acclaimed theatre scene.

Penwood State Park

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.