Simsbury Vacations from $535

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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.
Best Western Manchester

Best Western Manchester

2.5 out of 5
Price was $705, price is now $535 per person
$535
per person
Nov 24 - Nov 30
found 6 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hartford (BDL)
8.6/10 Excellent! (239 reviews)
The property was nice and it was very quiet but there was a weird smell coming from our sink

Reviewed on Sep 14, 2025

Delamar West Hartford

Delamar West Hartford

4 out of 5
Save 100% on your flight
Price was $2,001, price is now $1,445 per person
$1,445
per person
Nov 24 - Nov 30
found 6 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hartford (BDL)
9.8/10 Exceptional! (1,004 reviews)
Our stay at the Delamar West Hartford was absolutely wonderful from start to finish. The staff was warm, attentive, and genuinely welcoming, making us feel right at home. The rooms were beautifully designed—modern, clean, and incredibly comfortable. We especially appreciated the thoughtful touches throughout the hotel, from the complimentary breakfast to the cozy outdoor spaces. Its location is perfect for exploring West Hartford, with great dining and shopping just steps away. We’ll definitely be returning—highly recommended!

Reviewed on Sep 9, 2025

Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
Price was $745, price is now $552 per person
$552
per person
Nov 24 - Nov 30
found 6 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hartford (BDL)
8.6/10 Excellent! (1,014 reviews)
Beds were very comfortable and room and bath were clean and updated. Thank you for a nice stay.

Reviewed on Sep 15, 2025

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Save 100% on your flight
Price was $936, price is now $704 per person
$704
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
10/10 Exceptional! (124 reviews)
Such a unique stay on our road trip up North. The owner was so lovely and approachable. We will definitely stay again.

Reviewed on Aug 30, 2025

DoubleTree by Hilton Hartford Downtown

DoubleTree by Hilton Hartford Downtown

4 out of 5
Downtown Hartford
Price was $995, price is now $759 per person
$759
per person
Nov 24 - Nov 30
found 6 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hartford (BDL)
7.6/10 Good! (1,002 reviews)
It was walking distance to the concert we where going to. Along with I think that all hotels should have parking for their guest. Why should we have to pay for parking when we are already paying to stay at hotel just greedy for money.

Reviewed on Aug 9, 2025

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Discover the most popular places to visit in Simsbury

Performing Arts Center at Simsbury Meadows

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 acclaimed theater scene and great live music.

Penwood State Park

Simsbury Hotel Deals

Simsbury 1820 House

Simsbury 1820 House

4 out of 5
731 Hopmeadow St, Simsbury, CT
$204 nightly
The price is $235 total per night from Sep 18 to Sep 19
$235 total
Sep 18 - Sep 19
Total with taxes and fees
9.2/10 Wonderful! (988 reviews)
"Beautiful place, great staff, needs a little updating"

Reviewed on Sep 10, 2025

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
$92 nightly
The price is $106 total per night from Sep 21 to Sep 22
$106 total
Sep 21 - Sep 22
Total with taxes and fees
7.4/10 Good! (1,033 reviews)
Overnight stay
"The staff is very polite and helpful. Breakfast was very good. I would recommend"

Reviewed on Sep 14, 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 Oct 1 to Oct 2
$203 total
Oct 1 - Oct 2
Total with taxes and fees
8.8/10 Excellent! (1,417 reviews)
"Room was clean. The only thing that was not great was the position of the TV in the room. On side of the bed instead of adjacent to the wall. Was hard to watch while in bed. But loved the shower"

Reviewed on Sep 16, 2025

MGM Springfield
See all 670 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 $535 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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