Simsbury Holiday Rentals

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Holiday Rentals in Simsbury

Fridge, microwave, oven, stovetop
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
10.0 out of 10, Exceptional, (2)
"It was wonderful! Enough room for everyone and everything was cozy and working. Appreciate the stay!"
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
Fridge, microwave, oven, stovetop
PICON COZY
8.0 out of 10, Very good, (43)
"Fidelis demonstrated exceptional professionalism throughout our interaction. He was remarkably accommodating, consistently honest, and promptly addressed any inquiries I had, usually within minutes. On the rare occasion that he couldn't respond immediately, he took the time to provide an explanation and offer his apologies. Recently, my son relocated to this area for work, and thanks to Fidelis, I can now rest assured that my 24-year-old son, who has yet to experience living on his own, is safe...
The price is NZ$277
includes taxes & fees
30 May - 31 May
PICON COZY
Paper towels
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
9.0 out of 10, Wonderful, (2)
"This was easily accessible to many places and the check-in process and communications with the owner were exceptional. Great place to stay."
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
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Dining
Fun Downtown Location
9.8 out of 10, Exceptional, (48)
"Host was amazing 5 star all the way ... we walked right down the street and had some pizza everything we needed was just around the corner."
Fun Downtown Location
Property grounds
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (120)
"Wonderful place! Thoughtfully decorated, clean and incredibly comfortable. Would rent again."
The price is NZ$589
includes taxes & fees
24 Jun - 25 Jun
Big farmhouse in the foothills of the Berkshires
Pool
lakefront estate
3.8 out of 10, (8)
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate
Outdoor pool, a heated pool
Mountaintop Horse Farm with Heated Pool
10.0 out of 10, Exceptional, (15)
"Thank you for a lovely home to stay in during our family funeral weekend!"
Mountaintop Horse Farm with Heated Pool
Property grounds
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (20)
"We were in area from Uk visiting friends who live not far away. So this little home was just ideal for us. Weather improved on the day we left so we didnt sit outside by the lake but we did enjoy watching the birds and fish."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
1 bedroom, iron/ironing board, WiFi, bed sheets
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
Fridge, microwave, oven, stovetop
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
9.0 out of 10, Wonderful, (18)
"The property is as advertised. If you have a lot of people that just needs a place to sleep and collect yourseves, this is a wonderful place fir the price. The owner is a pleasure to work with and very responsive. Also met some of the neighbors and it is reassuring that they all watch out for one another."
The price is NZ$948
includes taxes & fees
9 Jun - 10 Jun
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Fridge, microwave, oven, stovetop
Lovely Family sized 3 bedroom Colonial home, close to restaurant.
8.6 out of 10, Excellent, (10)
"Nice house..Good area.."
Lovely Family sized 3 bedroom Colonial home, close to restaurant.
Fridge, microwave, oven, stovetop
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
9.8 out of 10, Exceptional, (7)
"Beautiful, quiet, private yet convenient setting, perfect room setup and accommodations/amenities, along with a gracious and helpful host. Based on my stay experience, I would recommend this property unconditionally and look forward to a longer stay in the future. Thanks!"
The price is NZ$497
includes taxes & fees
30 May - 31 May
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
Dining
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
9.6 out of 10, Exceptional, (28)
"It was nice stay!"
The price is NZ$511
includes taxes & fees
2 Jun - 3 Jun
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Fridge, microwave, oven, stovetop
comfortable home away from home
9.2 out of 10, Wonderful, (5)
"This little house is tucked behind some bigger neighbors. It was comfortable and quiet! We had a ball watching the antics of a family of squirrels. It fit our needs perfectly!"
comfortable home away from home
Interior
River Overlook - Check the view from your deck!
10.0 out of 10, Exceptional, (8)
"The location was just as promised. The view on the deck is beautiful and the apartment was clean and well stocked with anything you might need. The location is also walking distance to various shops, pizza, restaurants and bars. The river walk across the street is also great if you want to take a stroll. Carol was also great to work with. We’ll be back."
River Overlook - Check the view from your deck!
Property grounds
Nature House Water View Large Deck 2 story Gazebo 2 bed 2 bath
10.0 out of 10, Exceptional, (6)
"excellent"
Nature House Water View Large Deck 2 story Gazebo 2 bed 2 bath
Aerial view
Beautiful retreat to the woods to enjoy the winter season.
10.0 out of 10, Exceptional, (31)
"Very nice, well stocked and away from the hustle and bustle of city life. We had a great time."
Beautiful retreat to the woods to enjoy the winter season.
Smart TV
Thomas's Cozy Duplex - Centrally Located
8.0 out of 10, Very good, (5)
"Enjoyed our weekend. Check in was easy, plenty of room for 4 adults. Good location near MGM/downtown Springfield."
The price is NZ$439
includes taxes & fees
3 Jun - 4 Jun
Thomas's Cozy Duplex - Centrally Located
Fridge, microwave, oven, stovetop
Trout Brook Trail 2 · Sprawling Classic New England Home
10.0 out of 10, Exceptional, (10)
"The location was amazing! Although on a busy street, it was quiet and still a perfect walking distance from everything. Plenty of bars and restaurants just a few blocks away. The host was super easy to reach and the home was clean and well stocked with essentials."
Trout Brook Trail 2 · Sprawling Classic New England Home
TV, DVD player, books, video library
Lakeview Cottage, 5 minute walk to the beach. Southwick, MA
9.8 out of 10, Exceptional, (44)
"Great experience over all. Would definitely recommend this cottage on the lake. Communication, check in, over all experience was great! Highly recommend!"
Lakeview Cottage, 5 minute walk to the beach. Southwick, MA
Don't see what you're looking for?
See all available 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.

Other types of properties in Simsbury you may be interested in

Exterior
Holiday Inn Express Southington, an IHG Hotel
2.5 star property
8.4 out of 10, Very good, (1001)
"The property was well kept and clean"
The price is NZ$269
includes taxes & fees
30 May - 31 May
Holiday Inn Express Southington, an IHG Hotel
Lobby
Best Western Hartford Hotel & Suites
2.5 star property
8.0 out of 10, Very good, (1001)
"The staff was pleasant and efficient. The grounds were particularly well kept. The rooms looked recently painted with pleasing accent wall. The location is very convenient to highway. If you are visiting Hartford or Glastonbury, its worth a look."
The price is NZ$189
includes taxes & fees
9 Jun - 10 Jun
Best Western Hartford Hotel & Suites
8 restaurants, breakfast, lunch, dinner served; American cuisine
MGM Springfield
4.0 star property
8.8 out of 10, Excellent, (1003)
"Everyone was kind and helpful"
The price is NZ$275
includes taxes & fees
4 Jun - 5 Jun
MGM Springfield
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.

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 Rosedale Farms & Vineyards, 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.

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?

Talcott Mountain State Park and Farmington River are a couple of scenic spots to enjoy the outdoors, whereas Performing Arts Center at Simsbury Meadows is one of the cultural attractions. While here, Stratton Brook State Park and Rosedale Farms & Vineyards 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.

Recent reviews of Simsbury properties
Expedia verified reviews