Simsbury Vacations from $294

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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.
DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport

4 out of 5
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Hartford (BDL)
8/10 Very Good! (1,004 reviews)
People made the difference in a very good way.

Reviewed on Jul 15, 2025

Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Hartford (BDL)
8.6/10 Excellent! (1,005 reviews)
Clean and good breakfast.

Reviewed on Jul 18, 2025

Hilton Garden Inn Hartford South/Glastonbury

Hilton Garden Inn Hartford South/Glastonbury

3 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Hartford (BDL)
8.6/10 Excellent! (951 reviews)
Very welcoming staff. Enjoyed the pool and hot tub too.

Reviewed on Jul 18, 2025

DoubleTree by Hilton Hartford Downtown

DoubleTree by Hilton Hartford Downtown

4 out of 5
Downtown Hartford
Save 100% on your flight
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Hartford (BDL)
7.6/10 Good! (1,001 reviews)
Its was good experience

Reviewed on Jul 14, 2025

Delamar West Hartford

Delamar West Hartford

4 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Hartford (BDL)
9.8/10 Exceptional! (993 reviews)
Love the coffee machine! Love the staff! Loved my stay!

Reviewed on Jul 13, 2025

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Discover the most popular places to visit in Simsbury

Performing Arts Center at Simsbury Meadows

1/5(1 review)

Enjoy a show at Performing Arts Center at Simsbury Meadows, a storied theater 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 theater scene.

Penwood State Park

Simsbury Hotel Deals

The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $118 total per night from Jul 27 to Jul 28
$118 total
Jul 27 - Jul 28
Total includes taxes and fees
7.4/10 Good! (1,035 reviews)
"They have nice room"

Reviewed on Jul 13, 2025

The Capitol Hotel
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
$72 nightly
The price is $83 total per night from Jul 21 to Jul 22
$83 total
Jul 21 - Jul 22
Total includes taxes and fees
6.6/10 (1,494 reviews)
"We have been going to this hotel for 5 years when we travel because its so close to the airport. When we went to our room one of the beds was broken and we informed the front desk and she was so nice about it not like other places that the front desk employees get mad about changing our rooms. A ..."

Reviewed on Jul 10, 2025

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

MGM Springfield

4 out of 5
One MGM Way, Springfield, MA
$169 nightly
The price is $192 total per night from Aug 11 to Aug 12
$192 total
Aug 11 - Aug 12
Total includes taxes and fees
8.8/10 Excellent! (1,382 reviews)
"Great stay. Room was very updated and clean. Easy access and safe."

Reviewed on Jul 14, 2025

MGM Springfield
See all 663 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.

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 $294 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.