Simsbury Holiday Rentals from €141: Search Short-Term Rentals

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

Mountaintop Horse Farm with Heated Pool : This holiday home rental outside of Simsbury is located in the mountains, and has an outdoor pool, a balcony and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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Holiday Rentals in Simsbury

"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."

"The house and location were perfect. Comfortable beds! Would definitely stay again"

includes taxes & fees

13 Jul - 14 Jul

"This was a much needed haven! Frank was very helpful and hospitable. All of the animals were a definite plus! "

"I am impressed with the Lux Private Loft. Absolutely Gorgeous!!. I hope to return. The kitchen area, enormous shower, large screen t.v. I will book again as soon as possible."

includes taxes & fees

1 Aug - 2 Aug

"Peaceful "

includes taxes & fees

13 Jul - 14 Jul

"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "

includes taxes & fees

31 Jul - 1 Aug

"This was the perfect place to stay while we visited family in Massachusetts. The place was kept beautifully and had all of the amenities to make our visit comfortable. We will definitely book this place in the future."

includes taxes & fees

10 Jul - 11 Jul

"We checked out early. The place had mold/mildew. Power went out and the place was dark. Not suitable for human use without major renovations and updates."

includes taxes & fees

9 Jul - 10 Jul

"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"

"Had a great time. Ive stayed here multiplt times and keep coming back. Jessica is an amazing host. Very easy to talk to... but they leave you alone. Just an absolutely phenomenal stay"

"My friends and stayed for a night. The house is nice and the owners is very communicative. "

includes taxes & fees

26 Jul - 27 Jul

"This is such a great property, I spent a whole month with three separate stays adjacent due to travel planning and the host was wonderful. The house is really beautiful and in a great neighborhood and it’s very comfortable and super clean. This will be a regular for me in the Hartford area. I’m looking forward to seeing what the beautiful landscaping is like in the spring and summer too."

"Beautiful lake, traditional charming cottage- great get-away"

Microwave, electric kettle, cookware/dishes/utensils, paper towels

"Great place in a very nice part of the city. Walkable and lots to do around, and a reasonable parking garage right across the street. Apartment was clean, comfy and easily accessible."

includes taxes & fees

13 Jul - 14 Jul

"We stayed at the property for 2 nights and it was just what we had hoped. We enjoyed the lake, the fall colors and the house thoroughly. Would love to come back someday. "

"What a lovely studio!! Checking in and out was so easy. The studio looks just like the pictures. The hosts had everything there that one would need except an iron/board. Quaint little town with limited dining choices but many options near by. We will definitely use this place again."

includes taxes & fees

16 Jul - 17 Jul

"The location was fantastic.Check-In, Parking and Check-Out easy.The images of the condo were misleading.- cockroaches were present- Floors were not swept- sofa bed sheets were still on bed and unwashed- makeup on the pillow cases from the pullout couch and the hair dryer bag- bedside furniture had broken drawers- one kitchen chair was extremely wobbly- kitchen table light did not workWe will not staying here again."

includes taxes & fees

9 Jul - 10 Jul

"As advertised, great communication, would stay there again!"

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Find out more about Simsbury

Everything you need to know about Simsbury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Simsbury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simsbury holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Simsbury holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simsbury. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simsbury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simsbury holiday rentals we have selected for you start as low as €141 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Simsbury rentals

At Expedia, we put the best Simsbury holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Simsbury rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simsbury holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simsbury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Simsbury properties

5/5 Excellent

"This was my second time staying at this hotel in Southington, and it was just as great as I remembered from my visit back in December 2024. The property is exceptionally quiet, which made it easy to relax and get a good night’s sleep. And even though it’s conveniently located near restaurants, shops, and major roads. It strikes the perfect balance between peaceful and practical. One thing that really stood out to me again was the beautiful view of the surrounding nature. Waking up to greenery and open space just outside my window gave the stay a calm, refreshing feel, a rare treat for a hotel that’s so close to everything. I also want to give a special mention to the young lady at the front desk. I recognised her from my last visit, and even though I unfortunately don’t recall her name, her warm, welcoming energy made a lasting impression both times. She was kind, helpful, and made the check-in process smooth and personal. The room was also spotless, the bed was incredibly comfortable, and the whole place felt well cared for. I’ll definitely be back the next time I’m in town. It’s become a go-to spot for me!"

A verified traveller stayed at Holiday Inn Express Southington by IHG

Posted 14 hours ago

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

5/5 Excellent

"The staff is always very helpful. Lizzie, at the front desk was very nice and made my stay very enjoyable. The manager on call is also a treat to approach and makes sure to ensure I have what I need in order to enjoy my stay at the hotel. "

A verified traveller stayed at Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Posted 22 hours ago

5/5 Excellent

Clean Room, great value, and comfortable!

"Recently stayed two nights at the Quality Inn at the end of June. Check in was quick, staff was friendly, and I got my room request, towards the back of the building on a higher floor. I had room 423, it was clean, fairly good condition, everything worked, although fridge took a few hours to cool my drinks, and beds were comfortable. Each queen bed had 3 pillows and I couldn't remember if they used to have 4 each, but I think they did. The room was a great value and there were improvements since my last stay in April. They no longer start clearing breakfast before it ends at 9am, and it was well stocked especially Tuesday morning. Monday morning things were running out and I didn't see staff at all for the last 20 minutes. There was still plenty to eat though. Tuesday, staff kept things full and cleaned the serving area. The AC worked great, decent water pressure, bathroom was clean, and plenty of towels. I overall enjoyed my stay and had no issues. After check out, staff later called as they believed I had left an item behind, and they wanted to figure out how to return it to me, however it wasn't one of my items, but a nice gesture nonetheless! My go to hotel when visiting the area for Six Flags and will continue visiting! Glad to see some improvements! Wish I had more time to take a swim and pool closes at 10pm! Try Tokyo restaurant next door or Wood N Tap down the street for some great dinners! "

A verified traveller stayed at Quality Inn West Springfield

Posted 6 days ago

Frequently asked questions

Can I find holiday rentals in Simsbury?

Yes, there are holiday rentals close to the most popular sights in Simsbury, 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?

Mountaintop Horse Farm with Heated Pool: This holiday home rental outside of Simsbury is located in the mountains, and has an outdoor pool, a balcony and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Simsbury?

With 3 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?

Cultural attractions include Performing Arts Center at Simsbury Meadows, whereas Farmington River is a spot to enjoy nature. While here, Rosedale Farms & Vineyards 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.

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Holiday Rentals in Simsbury

Check prices for these dates

Holiday Rentals in Simsbury

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Bring Your Pet & Visit Springfield: Westfield Home

Cozy apartment in charming Hartford with AC, WiFi

Mountaintop Horse Farm with Heated Pool

Lux Boutique Large Private LOFT Pratt St Hartford

PICON COZY

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Big farmhouse in the foothills of the Berkshires

HOMEY HOMEY

Cozy Lakefront Bungalow w firepit/dock/kayaks

Charming Boutique Studio suite with everything you need for a getaway

Tranquil Litchfield Connecticut Retreat".

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi

Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.

Modern Condo|DWNTN Hartord| XL Center| GYM

5 bedroom in the center of Springfield .

Find out more about Simsbury

Recent reviews of Simsbury properties

Holiday Inn Express Southington by IHG

Best Western Manchester

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

MGM Springfield

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Springfield/Downtown

The Capitol Hotel

Holiday Inn Express & Suites Bradley Airport by IHG

Quality Inn West Springfield

Frequently asked questions