Simsbury Vacations from $358

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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.
Hampton Inn & Suites Rocky Hill - Hartford South

Hampton Inn & Suites Rocky Hill - Hartford South

2.5 out of 5
Price was $412, price is now $358 per person
$358
per person
Jan 10 - Jan 13
found 11 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Hartford (BDL)
18.4/10 Exceptional! (759 reviews)
Very clean hotel, amazing customer service, great breakfast

Reviewed on Nov 6, 2025

Delamar West Hartford

Delamar West Hartford

4 out of 5
Price was $1,807, price is now $1,519 per person
$1,519
per person
Dec 23 - Dec 27
found 3 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Hartford (BDL)
19.6/10 Exceptional! (1,001 reviews)
Everything was excellent as usual.

Reviewed on Nov 2, 2025

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

4 out of 5
Price was $483, price is now $427 per person
$427
per person
Jan 10 - Jan 13
found 11 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Hartford (BDL)
18/10 Exceptional! (1,002 reviews)
Everything and everyone

Reviewed on Nov 11, 2025

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

3 out of 5
Price was $450, price is now $400 per person
$400
per person
Jan 10 - Jan 13
found 11 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Hartford (BDL)
9.4/10 Exceptional! (143 reviews)
The kids enjoyed the pool. It was wonderful.

Reviewed on Nov 13, 2025

Fairfield Inn & Suites Hartford Manchester

Fairfield Inn & Suites Hartford Manchester

2.5 out of 5
Price was $782, price is now $712 per person
$712
per person
Dec 29 - Jan 2
found 3 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Hartford (BDL)
8.6/10 Excellent! (1,007 reviews)
The service was quick and friendly. The pool area was nice. No issues with our room. Beds were comfortable. No issues with our stay

Reviewed on Oct 26, 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

Simsbury 1820 House

Simsbury 1820 House

4 out of 5
731 Hopmeadow St Simsbury CT
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $223 total per night from Nov 17 to Nov 18
$223 total
Nov 17 - Nov 18
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
Adorable bed and breakfast with a nice bar/restaurant. The staff were very accommodating.

Reviewed on Nov 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
$89 nightly
The price is $102 total per night from Dec 14 to Dec 15
$102 total
Dec 14 - Dec 15
Total with taxes and fees
7.4/10 Good! (1,072 reviews)
It is such a fantastic view from my room, super clean, great amenities, comfy bed. The only mild criticism is they are out of regular coffee. Many people are coffee addicts and rely on regular coffee to wake up! Luckily I travel with some instant, so I poured a little into the delicious decaf Starbucks ...

Reviewed on Nov 13, 2025

The Capitol Hotel
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
$83 nightly
The price is $95 total per night from Nov 23 to Nov 24
$95 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (1,149 reviews)
The room was great and the staff was really helpful...

Reviewed on Nov 7, 2025

Holiday Inn Express Southington by IHG
See all 697 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 $358 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

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