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Compare 210 Vacation Homes in Simsbury with updated reviews, rates, and availability.

Stylish & Luxurious 3 BDR Home with Play Station

9.4 out of 10, Exceptional, (9)
"We needed a place for our family of 6 to stay while visiting family in the area. This place was exactly what we needed, as advertised, and the owner was quick with communications. We would definitely stay here again!"
Stylish & Luxurious 3 BDR Home with Play Station

Owl's Nest - Cozy Westfield Home w/ Fire Pit

9.4 out of 10, Exceptional, (3)
"We were really only at the house for the late evenings, nights, and mornings. We found the kitchen well stocked to make breakfast (we bought the groceries). The beds were comfortable. Only a couple minor issues that we just handled. The temperature control was preprogrammed to go to 50 degrees in the evening and overnight. We couldn't seem to reprogram it; however, did get it to kick up warmer about midnight or so. The shower in the main floor bathroom was hard to get turned off so the...
Owl's Nest - Cozy Westfield Home w/ Fire Pit

Cozy 2 Bedroom Family Stay

9.8 out of 10, Exceptional, (7)
"The property was within a few miles to my family who we were visiting. It was very across the street from a very good pub and a couple of minutes to the town’s downtown with several good restaurants to choose from.The apartment was clean with a very comfortable bed and nice furnishings. The kitchen was well equipped with dining and cooking tools. It’s nice to have a good smart tv as well to watch football games. "
Cozy 2 Bedroom Family Stay

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

10.0 out of 10, Exceptional, (7)
"It was a great house to host our family for Thanksgiving dinner! "
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Cozy Lakefront Cottage - Hot Tub, Game Room & Lake Views

10.0 out of 10, Exceptional, (1)
"Beautiful view from the upstairs window. I enjoyed the pellet stove on the cold days."
The price is AED 661
AED 1,216 total
includes taxes & fees
26 Mar - 27 Mar
Cozy Lakefront Cottage - Hot Tub, Game Room & Lake Views

PICON COZY

7.8 out of 10, Good, (60)
"Peaceful everything just as listed "
The price is AED 275
AED 625 total
includes taxes & fees
29 Mar - 30 Mar
PICON COZY

Historic Farmhouse Near Mountains & Colleges!

10.0 out of 10, Exceptional, (6)
"We loved everything about this home! It fit us perfectly and we would love to rent it again!"
Historic Farmhouse Near Mountains & Colleges!

Charming Farmhouse w/ Pool & Fishing Pond!

10.0 out of 10, Exceptional, (9)
"Everything about the house and property was exactly as described. We had the best time there with plenty of space to spread out. It was very clean and comfortable. The kids had so much fun exploring and they visited the ice cream shop everyday that it was open.We will definitely stay here again."
Charming Farmhouse w/ Pool & Fishing Pond!

Prime West Hartford Center: Timeless Charm

10.0 out of 10, Exceptional, (14)
"Super clean, nice little touches like bottled water, & bathroom supplies. Great location. "
Prime West Hartford Center: Timeless Charm

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

2.0 star property
10.0 out of 10, Exceptional, (2)
"Same day check in info, not provided the day before like most hosts "
The price is AED 1,090
AED 2,567 total
includes taxes & fees
8 Apr - 9 Apr
Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Spacious Tolland Home w/ Deck + Screened Porch!

9.6 out of 10, Exceptional, (5)
"The property was the perfect cozy place for my friends and I for our reading retreat weekend. The the only drawback to the otherwise beautiful location is that it is a little bit remote with the nearest town center about 35 minutes away. The property manager was very prompt in her communication and incredibly friendly and accommodating. The privacy and serenity of the house were perfect I absolutely recommended this property "
Spacious Tolland Home w/ Deck + Screened Porch!

Tranquil Litchfield Connecticut Retreat".

9.4 out of 10, Exceptional, (9)
"This is a neat, clean and lovely little place that perfectly suited our needs. It had all the amenities we needed for our short stay. Jose was a gracious host, answering all of my questions promptly - even the one about the mattresses which were incredibly comfortable! "
The price is AED 808
AED 1,149 total
includes taxes & fees
26 Mar - 27 Mar
Tranquil Litchfield Connecticut Retreat".

A “Wow” Experience everywhere there is something to stimulate your mind Interest

9.4 out of 10, Exceptional, (3)
"Tasteful decor. Very clean. Not too far from the city. Quiet, safe neighborhood. Host was very friendly and super responsive! Would definitely recommend!"
A “Wow” Experience everywhere there is something to stimulate your mind Interest

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (10)
"Can’t beat proximity to downtown and other CT locations.Unfortunately we were hit with icy conditions so we could not enjoy all it has to offer. Owner checked in on us and kept driveway safe and clear. We really appreciated his hospitality.The rental was well equipped with everything you need. I LOVED the sunny kitchen to enjoy my morning coffee.We’ll definitely come back when it is warmer!"
NEW-Another Fun Downtown Location 1st floor

The Skyway

10.0 out of 10, Exceptional, (3)
"Very well staged. Smart TV’s in every room. Quiet, safe area. Comfortable bed. It was perfect for my short stay"
The price is AED 529
AED 1,356 total
includes taxes & fees
1 Apr - 2 Apr
The Skyway

Thomas's Cozy Duplex - Centrally Located

8.6 out of 10, Excellent, (10)
"The duplex was clean and quiet. The kitchen was stocked well enough for us to make dinner, although there was no kitchen towel for drying hands and dishes (very minor). Three bedrooms, two with a double/queen, one with a single, and it looked like the couch in the living room was a pull out. Beds were comfortable with plenty of bedding. Wi-fi worked well. Couldn't ask for anything more. I would stay here again if in the area. "
The price is AED 477
AED 1,079 total
includes taxes & fees
27 Mar - 28 Mar
Thomas's Cozy Duplex - Centrally Located

Mountaintop Horse Farm with Heated Pool

10.0 out of 10, Exceptional, (22)
"Serene and peaceful, this weekend getaway was so good for the soul. The horses and donkeys in the lower level of the barn each had their own unique personalities that enhanced the festivities. Walking around the property accompanied by three happy dogs while hearing the goats bleating and the chickens crowing in the background only added to the quiet winter magic. A huge thank you to our wonderful hosts. "
Mountaintop Horse Farm with Heated Pool

The Jefferson House, Charming, Exceptional, Spacious Home, Estate in Litchfield

10.0 out of 10, Exceptional, (1)
"The lighting is warm and inviting as you step up the stairs into a large open concept room. Every detail is beyond modern from the giant marble counter equipped with the comfiest and largest leather barstools, to the kitchen whose colors and appliances are so beautifully designed; cabinets stocked with every item you need to cook a homemade meal.The king size bed was like a cloud, swallowing us in the fluffiest duvets and sheets, comfortable pillows, making it an easy switch to use the TV in the...
The price is AED 918
AED 1,357 total
includes taxes & fees
26 Mar - 27 Mar
The Jefferson House, Charming, Exceptional, Spacious Home, Estate in Litchfield

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

9.6 out of 10, Exceptional, (7)
"This property was exactly what we needed. Perfect location beautiful house very clean and very comfortable. We will definitely return "
The price is AED 588
AED 1,205 total
includes taxes & fees
31 Mar - 1 Apr
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
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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Other property types in Simsbury

PICON COZY

7.8 out of 10, Good, (60)
"Peaceful everything just as listed "
The price is AED 275
AED 625 total
includes taxes & fees
29 Mar - 30 Mar
PICON COZY

Lux Boutique Large Private LOFT Pratt St Hartford

9.2 out of 10, Wonderful, (12)
"Super nice location/convenient "
The price is AED 459
AED 665 total
includes taxes & fees
26 Mar - 27 Mar
Lux Boutique Large Private LOFT Pratt St Hartford

Charming Farmhouse w/ Pool & Fishing Pond!

10.0 out of 10, Exceptional, (9)
"Everything about the house and property was exactly as described. We had the best time there with plenty of space to spread out. It was very clean and comfortable. The kids had so much fun exploring and they visited the ice cream shop everyday that it was open.We will definitely stay here again."
Charming Farmhouse w/ Pool & Fishing Pond!
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.