West Simsbury Vacation Packages

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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.

Top West Simsbury Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

2 out of 5
per person
Aug 28 - Sep 4
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
7.2/10 Good! (433 reviews)
Really nice property and very helpful staff. Area around the hotel is pretty, with lots of places to sit and watch the geese. Rooms are okay--be sure to get a "suite" or a double, as the single rooms are very small. Bathing facilities are pretty rudimentary--could use a shower seat or a bathtub. "Breakfast" is weak coffee and orange or apple juice.

Reviewed on Jun. 13, 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
Save 100% on your flight
per person
Aug 28 - Sep 4
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
9.4/10 Exceptional! (1,003 reviews)
Great staff and service

Reviewed on Jul. 14, 2025

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4 out of 5
Old Saybrook Center
Save 100% on your flight
per person
Aug 28 - Sep 4
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
9.4/10 Exceptional! (16 reviews)
We loved the convenient location and beautiful historic building, but we were very disappointed in the level of cleanliness (a layer of dust on shelves and fireplace, cobwebs under furniture). There were some other issues (loose shower head, broken coffee maker). There's no one on site to address in person. It's a lovely place, but needs some attention. For the price, it should be better! :(

Reviewed on May 1, 2025

Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
per person
Aug 28 - Sep 4
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
7/10 Good! (880 reviews)
A simple, affordable, conveniently located, and pleasant stay.

Reviewed on Jun. 23, 2025

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
per person
Aug 28 - Sep 4
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
7.8/10 Good! (987 reviews)
Overall was Good Bed was Comfortable Room had musty smell

Reviewed on Jul. 13, 2025

Ready to book your vacation to West Simsbury?

 

Choose your dates

West 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
The price is CA $126 per night from Jul 28 to Jul 29
CA $126
CA $145 total
Jul 28 - Jul 29
includes taxes & fees
7.4/10 Good! (1,030 reviews)
"Love that the venue overlooked the Festival Venue. Easy walk to restaurants & bars. Near the Capital and other cool historic places."

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
The price is CA $92 per night from Jul 21 to Jul 22
CA $92
CA $106 total
Jul 21 - Jul 22
includes taxes & fees
6.6/10 (1,499 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
The price is CA $204 per night from Aug 11 to Aug 12
CA $204
CA $263 total
Aug 11 - Aug 12
includes taxes & fees
8.8/10 Excellent! (1,387 reviews)
"Great stsy"

Reviewed on Jul. 11, 2025

MGM Springfield
See all 598 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.

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Frequently asked questions

How much does a West Simsbury vacation package cost?
You'll find cheap prices from CA $813 on Expedia for your West Simsbury break. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to West Simsbury costs.
What are the cheapest months to go to West Simsbury?
You're likely to find lower rates and better availability in January, February and March. Explore our cheap West Simsbury vacation packages and you could land some great off-season deals.
How many days is enough for West Simsbury?
West Simsbury vacations come in all shapes and sizes, but to really get a feel for this place, we think 18 days is a good ballpark. This will mean you can visit top attractions like Ski Sundown and Enders State Forest and track down some lesser-known gems. Don't miss out on cool areas such as Simsbury Centre and Tariffville either. If you're clever with your time, you may even be able to take a day trip from West Simsbury too.
How to find the best West Simsbury package deals?
Begin your search for a West Simsbury package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal West Simsbury package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your West Simsbury escape underway.
Is it cheaper to book a West Simsbury vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still get the flexibility to create a customized West Simsbury vacation by choosing your preferred accommodation type, airline and car class.
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 terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for quick escapes.
How to plan a trip to West Simsbury?

  1. Choose your dates: The things you'd like to do in West Simsbury and your preferred season can help you decide when to go.
  2. Work out your budget: Ensure you have enough money to cover everything from meals and transportation to experiences and flights. Your accommodations will probably be the biggest expense during your trip to West Simsbury.
  3. Work out your trip length: Consider how much time you want to spend exploring West Simsbury. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your accommodations and airfare: Once you've nailed down your dates and duration, book the right West Simsbury vacation package for you.

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