Simsbury Holiday Rentals

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Holiday Rentals in Simsbury

PICON COZY
8.0 out of 10, Very good, (44)
"Perfect little house 20 minutes from six flags. Bathroom looks like it was recently updated as well as kitchen appliances. it's a little dated but who cares the price was right. Much more relaxing and comfy than a hotel room."
The price is AU$259
per night
18 June - 19 June
PICON COZY
Fun Downtown Location 2nd flr
9.8 out of 10, Exceptional, (51)
"Great property for our family trip. We had lots of fun. Owner was responsive and communicative. Hope to be back some day!"
Fun Downtown Location 2nd flr
Spacious three bedroom house with pool and hot tub near Historic Suffield Center
10.0 out of 10, Exceptional, (3)
"It was wonderful! Enough room for everyone and everything was cozy and working. Appreciate the stay!"
Spacious three bedroom house with pool and hot tub near Historic Suffield Center
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Mountaintop Horse Farm with Heated Pool
10.0 out of 10, Exceptional, (16)
"How fun to stay above a hose barn in such a spectaular spot. The apartment was much more spacious than we expected and really fun! As we sat poolside for a little bit we watched Frank driving his tractor, heard animals chatting and played with the dogs. It was the perfect spot to call home during our high school reunion. Loved it and hope to return again some day!"
Mountaintop Horse Farm with Heated 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
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.
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.
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 AU$413
per night
17 June - 18 June
Thomas's Cozy Duplex - Centrally Located
Trout Brook Trail 2 · Sprawling Classic New England Home
10.0 out of 10, Exceptional, (11)
"In town for our daughters graduation. The home was perfect in every way! Clean, all rooms are a good size, nicely situated kitchen, beautiful deck for socializing, our guests did not feel like we were on top of each other. Plenty of blankets, towels, kitchen supplies. Everything in good working condition. The home has antique charm with updated benefits. The host Mark was easy to communicate with. We walked to town and loved every part of our weekend! Its a must! Thank you Mark for sharing Trout...
The price is AU$807
per night
16 June - 17 June
Trout Brook Trail 2 · Sprawling Classic New England Home
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
9.8 out of 10, Exceptional, (8)
"This is an immaculate guest suite with incredible views in a gorgeous setting. The owners were extremely responsive and communicative, enhancing our stay. The bed is very comfortable and the appliances and just about everything looks brand new. The grounds, pool area and views are amazing. If you’re looking for a comfortable and peaceful stay in a relaxing setting, this is the place! Your hosts will make sure you are well taken care of."
The price is AU$449
per night
8 July - 9 July
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
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!
The getaway! Located in the downtown area.
10.0 out of 10, Exceptional, (7)
"This home was very nicely updated with new pillows, comfy bed and well stocked kitchen. Perfect location near the hospital"
The price is AU$412
per night
9 July - 10 July
The getaway! Located in the downtown area.
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
9.4 out of 10, Exceptional, (6)
"Cute cabin in a beautiful private setting. Very peaceful and surrounded by nature."
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
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
Massive 5 Bedrooms: 3King 2Queen
The price is AU$1,263
per night
9 July - 10 July
Massive 5 Bedrooms: 3King 2Queen
Upscaled Quiet Neighborhood- Modern 3 BDRM
10.0 out of 10, Exceptional, (22)
"Entire experience was great just a couple of suggestions. I stayed with my mother in the room with the twin beds. Wished we had a dresser or a closet and maybe another night stand. Other than that great stay also the water and snacks were a great hit. Thank You both very much!!!!"
Upscaled Quiet Neighborhood- Modern 3 BDRM
Minimalist Downtown Homestay
The price is AU$332
per night
16 June - 17 June
Minimalist Downtown Homestay
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 AU$787
per night
3 July - 4 July
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
10.0 out of 10, Exceptional, (85)
"We had a wonderful time. The house has everything you need, and the view is very beautiful. We enjoyed our stay, and will definitely be back again."
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
9.6 out of 10, Exceptional, (29)
"It was nice stay!"
The price is AU$463
per night
19 June - 20 June
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
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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.

Simsbury Holiday Home Travel Info

Other types of properties in Simsbury you may be interested in

MGM Springfield
4.0 star property
8.8 out of 10, Excellent, (1018)
"The attention to detail particularly in the hotel lobby was impressive. The location was great, staff excellent. The rooms were clean, quiet and very comfortable. Easy access in and out to the highway. Overall, very well laid out and a pleasant experience."
The price is AU$238
per night
17 June - 18 June
MGM Springfield
Fairfield Inn & Suites by Marriott Springfield Enfield
2.5 star property
8.8 out of 10, Excellent, (821)
"Area well maintained. Staff especially Marion was the best."
The price is AU$191
per night
7 July - 8 July
Fairfield Inn & Suites by Marriott Springfield Enfield
DoubleTree by Hilton Hartford - Bradley Airport
4.0 star property
8.0 out of 10, Very good, (1002)
"Great experience in all areas! Thank you so much. "
The price is AU$233
per night
3 July - 4 July
DoubleTree by Hilton Hartford - Bradley Airport
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.

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, 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 favourite 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 depend 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 AU$259 per night. Entering your travel dates in the search wizard might find you 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. 

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.

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