Simsbury Vacations from $372

Book a Hotel + Flight or Car together to unlock savings

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.
Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
per person
Oct 10 - Oct 12
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
8.6/10 Excellent! (1,007 reviews)
Mon seul point négatif est au sujet de la cafétéria. Elle est plutôt petite et il n’y avait aucun fruit au déjeuner.

Reviewed on Aug 18, 2025

Hilton Garden Inn Hartford South/Glastonbury

Hilton Garden Inn Hartford South/Glastonbury

3 out of 5
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
8.6/10 Excellent! (965 reviews)
We enjoyed a King Suite with separate bedroom. Fantastic! Excellent staff from front desk to kitchen & bar & excellent service on 6th floor.

Reviewed on Aug 9, 2025

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
per person
Oct 20 - Oct 24
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Hartford (BDL)
10/10 Exceptional! (114 reviews)
Viking Villages Resort was absolutely incredible in every way! My husband and I were blown away by the details, quality and overall uniqueness of this resort! We will definitely be back.

Reviewed on Aug 18, 2025

Holiday Inn Express Hartford South - Rocky Hill by IHG

Holiday Inn Express Hartford South - Rocky Hill by IHG

2.5 out of 5
per person
Oct 10 - Oct 12
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
8.6/10 Excellent! (1,000 reviews)
It was wonderful. I needed a room last minute and they were able to accommodate. The guest service was excellent and very resourceful.

Reviewed on Aug 15, 2025

Green River Bridge Inn

Green River Bridge Inn

3 out of 5
per person
Oct 20 - Oct 24
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Hartford (BDL)
8.4/10 Very Good! (7 reviews)
Wonderful host. Breakfast was delicious. Great place for a peaceful retreat.

Reviewed on Aug 2, 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
$84 nightly
The price is $97 total per night from Aug 31 to Sep 1
$97 total
Aug 31 - Sep 1
Total includes taxes and fees
7.4/10 Good! (1,007 reviews)
"Quiet downtown area. Ubers to other area like the Parkville Market, cheap rates."

Reviewed on Aug 16, 2025

The Capitol Hotel
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way, Springfield, MA
$179 nightly
The price is $203 total per night from Sep 2 to Sep 3
$203 total
Sep 2 - Sep 3
Total includes taxes and fees
8.8/10 Excellent! (1,393 reviews)
"We had fun at the MGM Springfield, their is a lot to do. They have a movie theater, a lot of restaurants to pick from to eat. Staff are nice and informative. Fun place to go"

Reviewed on Aug 16, 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
$80 nightly
The price is $92 total per night from Aug 19 to Aug 20
$92 total
Aug 19 - Aug 20
Total includes taxes and fees
6.6/10 (1,530 reviews)
"Next to airport so planes taking off"

Reviewed on Aug 14, 2025

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
See all 652 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.

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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 $372 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.