A metal bridge with a sign that reads 'Thank You' and a birdhouse on the right.

Simsbury Holiday Rentals

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Our top choices for Simsbury holiday rentals

1. Trumbull Apartments

Trumbull Apartments
3.0 star property
Downtown Hartford
2.0 out of 10, (1 review)
"Terrible, worst stay ever . It was such a hassle to get in no clear instructions… never again"
United States
Nicolas
The price is NZ$546
includes taxes & fees
27 Nov - 28 Nov
Trumbull Apartments

2. Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway
3.5 star property
Forest Park
The price is NZ$1,208
includes taxes & fees
15 Nov - 16 Nov
Newly Renovated 2 floor Getaway
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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Top Simsbury Hotel Reviews

Find out more about Simsbury

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Simsbury holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Simsbury. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Simsbury. Seeing all the best attractions is bound to make you fall in love with Simsbury. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Simsbury short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Simsbury?

Yes, there are holiday rentals in Simsbury close to Performing Arts Center at Simsbury Meadows, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Simsbury has a good selection of restaurants. Make sure you have time to check out the forests and riverfront during your trip.

What are some of the best holiday rentals that Simsbury has to offer?

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!: This holiday home rental outside of Simsbury has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals will I find in Simsbury?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Simsbury stay.

What’s there to see and do in Simsbury?

Farmington River and Pinchot Sycamore Tree are a couple of lovely local spots to get outside and enjoy nature. While here, Performing Arts Center at Simsbury Meadows and Talcott Mountain State Park are other places worth a visit.

What’s a holiday rental in Simsbury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Simsbury. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family getaway.