West Simsbury Vacations from $527

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Your West Simsbury Vacation

When a getaway to the city is calling, answer it with a West Simsbury vacation package. The neighborhood of Downtown Hartford, which is good for shopping, families and festivals, makes a terrific base for your adventures. If your trip to West Simsbury includes a little sightseeing, check out much-loved attractions like Ski Sundown, Talcott Mountain State Park and Wintonbury Hills Golf Course. Whoever you're going away with and whatever you plan to spend, your ultimate West Simsbury vacation is just clicks away with Expedia.

The Latest West Simsbury vacation packages

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $686, price is now $527 per person
$527
per person
Sep 24 - Sep 28
found 4 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8/10 Very Good! (1,001 reviews)

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Save 100% on your flight
Price was $1,167, price is now $855 per person
$855
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Price was $1,132, price is now $944 per person
$944
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.2/10 Wonderful! (31 reviews)
the room and amenities are well maintained, clean and convenient, the customer service is awesome , answering requests fast and responsive.

Reviewed on Jul 5, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Price was $1,114, price is now $929 per person
$929
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.6/10 Exceptional! (85 reviews)
I had an amazing stay at the Hyatus. The property was exceptionally clean and well maintained, which made me feel comfortable from the moment I arrived. The location was perfect—convenient to everything I needed while still being quiet and peaceful, making it easy to relax after a busy week. Overall, it was a wonderful experience, and I would absolutely stay here again. Highly recommend!

Reviewed on Jul 6, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $679, price is now $569 per person
$569
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.2/10 Wonderful! (1,005 reviews)
-

Reviewed on Jul 17, 2026

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Stay near popular West Simsbury attractions

Meadow Pond

You can take time to visit Meadow Pond during your travels to West Simsbury. Wander the forest and riverfront while you're in the area.
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West Simsbury Hotel Deals

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
$91 nightly
The price is $104 total per night from Aug 2 to Aug 3
$104 total
Aug 2 - Aug 3
Total with taxes and fees
Holiday Inn Express Southington by IHG
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $124 total per night from Jul 19 to Jul 20
$124 total
Jul 19 - Jul 20
Total with taxes and fees
The Capitol Hotel
Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

2.5 out of 5
185 Brainard Rd Hartford CT
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $123 total per night from Aug 2 to Aug 3
$123 total
Aug 2 - Aug 3
Total with taxes and fees
Best Western Hartford Hotel & Suites
See all 681 properties in West 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 West Simsbury Vacation Packages

West Simsbury Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
2,400
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Xfinity Theatre, Connecticut Science Center and Connecticut Valley Winery

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Frequently asked questions

How much does a West Simsbury vacation package cost?
You can pick up a vacation package to this top destination from $527 on Expedia. However, how much your vacation to West Simsbury costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to West Simsbury?
If you're hoping to score a cheap West Simsbury vacation package, consider visiting in December, January and February. You'll typically find lower rates on hotels and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for West Simsbury?
The ideal duration for your West Simsbury vacation depends on what you'd like to do and see. Usually, a few days to a week will give you plenty of time to hit all the major sights and explore some hidden gems along the way.
Is it worth booking a vacation package to West Simsbury?
Known for its golfing, nature and a host of other highlights, you can be assured West Simsbury is a good vacation destination. Some of the most popular attractions to stick on your to-do list? Visit Flamig Farm and Stratton Brook State Park during your West Simsbury vacation.
How to find the best West Simsbury package deals?
Bagging a cheap West Simsbury package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most economical West Simsbury package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a West Simsbury vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging hotels and flights individually. Better still, you can customize your West Simsbury escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to West Simsbury?
If you've got your West Simsbury vacation dates locked in, book as early as you can to snap up some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for traveling on a whim.
Does Expedia offer Book Now, Pay Later West Simsbury vacation packages?
Secure your perfect trip to West Simsbury with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next paycheck — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no late payment fees or extra charges, you can easily budget for your trip and snag great deals while they last.

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.