Simsbury Vacations from $433
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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.
The Latest Simsbury vacation packages
Price found within the past 48 hours. Click for updated prices.
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.
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.
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.
What to do in Simsbury
Connecticut Coloured Regiment Parade Route: An Audio Tour
$10
per adult
Simsbury Hotel Deals
Simsbury 1820 House
731 Hopmeadow St Simsbury CT
Fully refundableReserve now, pay when you stay
$184 nightly
$212 total
Aug 31 - Sep 1
Total with taxes and fees
9.4/10 Exceptional! (1,000 reviews)
"The staff at Simsbury 1820 were the highlight of the stay. They were expecially friendly and very helpful. They had some suggestions of things to do that were interesting and area specific. Understandably but a bit disappointing was the inadquacy of the plumbing. It's a very old building but toilets ..."
Reviewed on Aug 23, 2026
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
$99 nightly
$114 total
Sep 3 - Sep 4
Total with taxes and fees
MGM Springfield
One MGM Way Springfield MA
$179 nightly
$203 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (1,550 reviews)
"We stayed 1 night & had a relaxing enjoyable experience. Beautiful hotel & we felt safe. The outdoor park is very clean & nicely maintained. The casino area was just enough. Many slots & tables. The restaurants were awesome too!"
Reviewed on Aug 29, 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.
Find the Best Simsbury Vacation Packages
Simsbury Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Bradley Intl. Airport (BDL) |
Population | 5,800 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Xfinity Theatre, Connecticut Science Center and Talcott Mountain State Park |
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Frequently asked questions
How much does a Simsbury vacation package cost?
You can snap up a vacation package to this popular destination from $433 on Expedia. But how much your vacation 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'd like to score a cheap Simsbury vacation package, consider traveling in May, November and December. You'll typically find better rates on flights and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Simsbury?
When planning your Simsbury vacation, a handful of days will be enough to see all the highlights. Be sure to check out Rosedale Farms & Vineyards — it's one of the main sights in this destination. If you're looking for more adventure, consider basing yourself here and going on some day trips from Simsbury.
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 vacation as a package?
Expedia vacation 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 customized Simsbury vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation 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?
- Choose when to travel: Check your calendar and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Simsbury.
- Work out your budget: Make sure you have enough money to pay for everything from transportation and dining out to flights and activities. Your hotel will likely be the largest expense during your trip to Simsbury.
- Use our trip planning tool to discover Simsbury: Research every part of your trip to Simsbury with this handy planner. Invite family or friends to collaborate on a group getaway, search for hotels or things to do and make bookings.
- Work out your trip length: Think about how long you'd like to spend exploring Simsbury. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Simsbury vacation package.
- Book any activities or excursions: Here's the fun part — organizing everything you want to see and do. Browse some of the best things to do in Simsbury and reserve your tickets in advance to save time (and maybe some dollars too!).
Does Expedia offer Book Now, Pay Later Simsbury vacation packages?
Your Simsbury getaway is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you a bit more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
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- Countryside Park
- Connecticut Science Center
- Windsor Locks Vacations
- Rosedale Farms & Vineyards
- Bushnell Center for the Performing Arts
- Visit Hartford
- Hartford State Armory
- Wintonbury Hills Playground
- Saint Francis Hospital and Medical Center
- American School for Deaf
- Windsor Vacations
- Mark Twain House & Museum
- Canton Green Shopping Center
- Dunkin' Donuts Park
- Ski Sundown
- Nomads Adventure Quest
- Satan's Kingdom State Recreation Area
- Talcott Mountain State Park
- Elizabeth Park
- Connecticut State Capital
- Visit Connecticut
- Bushnell Park
- Hartford Vacations
- Mortensen Riverfront Plaza
- Yale University
- Connecticut Vacations
- New England Air Museum
- Blue Hills Vacations
- Sycamore Hills Recreation Area
- Riverside Park
- Flamig Farm
- Wadsworth Atheneum Museum of Art
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.