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Top Holiday Rentals in Simsbury

Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
10.0 out of 10, Exceptional, (2)
"My family and I enjoyed our stay here. We had lots of space for my 4yo to run around and each of my 3 kids had their own room. The house was very clean and the host was easily able to contact if I had questions or concerns. We would def. stay here again"
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
Newly Renovated Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (17)
"The property was perfect for our needs. Instructions for everything was provided fabulous rental. "
Newly Renovated Family House On Highland Lake with Dock
Upscaled Quiet Neighborhood- Modern 3 BDRM
10.0 out of 10, Exceptional, (20)
"Enjoyed our stay very much. We definitely recommend and stay again in near future. Management was quick with response and very helpful and kind."
Upscaled Quiet Neighborhood- Modern 3 BDRM
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Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
10.0 out of 10, Exceptional, (5)
"From the very beginning the hosts were fantastic. There was great communication and offered support. The property was super clean , well organized, and perfect for what we needed. I will be staying here again and truly recommend it !"
The price is £193
includes taxes & fees
6 May - 7 May
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table
10.0 out of 10, Exceptional, (56)
"The place was nice and is clean. I knew it was a downstairs of a house. The owner does have a dog that barks from time to time in the evening and you can hear people above, but was not too much to handle. Overall was a nice place in a nice town."
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (119)
"My wife and I and our daughter and dog spent the week. Everything we needed was provided. Nice quiet and relaxing time. Great location down the street from the AMC Noble View trails. We all had a wonderful hike and a wonderful week."
The price is £299
includes taxes & fees
5 May - 6 May
Big farmhouse in the foothills of the Berkshires
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (17)
"Well appointed and modern. A great quiet spot for the family."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Mountaintop Horse Farm with Heated Pool
10.0 out of 10, Exceptional, (14)
"Beautiful, spacious house on top of the horse staples.literally the horses & donkey were sleeping downstairs of our place. What a beautiful experience! Frank & Julliane gave us nice tour of the farm. Also nice hiking trail close by."
Mountaintop Horse Farm with Heated Pool
Nature House Water View Large Deck 2 story Gazebo 2 bed 2 bath
10.0 out of 10, Exceptional, (5)
"My second time staying with Ed and Milly. Always very comfortable and welcoming. The house is super cozy and has everything you need. Thank you!!"
Nature House Water View Large Deck 2 story Gazebo 2 bed 2 bath
Trout Brook Trail 2 · Sprawling Classic New England Home
10.0 out of 10, Exceptional, (9)
"Awesome! Check in was smooth, property was super clean and spacious. We will definitely be back!"
Trout Brook Trail 2 · Sprawling Classic New England Home
Fun Downtown Location
9.8 out of 10, Exceptional, (46)
"Clean, comfortable, convenient. Gracious host."
Fun Downtown Location
Cheerful 4 bedroom residential country home
9.8 out of 10, Exceptional, (38)
"We enjoyed our stay at this cottage/cape /modern-style home. With several windows, including skylights, and two sets of French doors, there was tons of natural light. The area is quiet and peaceful. It was nice that we could see some of the lake across the street from inside the home. The location was about 15 minutes from Bradley, so perfect. Also, close enough to the highway and other towns but nestled away from everything so you don't hear any street noises. We were there for a funeral so we...
Cheerful 4 bedroom residential country home
Cozy Lakefront Bungalow w firepit/dock/kayaks
9.8 out of 10, Exceptional, (19)
"Words cannot describe how beautiful and peaceful this place was I did not wanna leave and I’m already looking forward to my next stay! Owners were wonderful to communicate, and exceeded my expectations. Thank you for giving me blissful place to spend my birthday."
Cozy Lakefront Bungalow w firepit/dock/kayaks
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
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 £245
includes taxes & fees
5 May - 6 May
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Clean, Comfy and Spacious Bedroom
9.6 out of 10, Exceptional, (4)
"It was exactly what we needed. long hours volunteering so, a place to rest our head, clean up and fuel our bodies. great host"
The price is £109
includes taxes & fees
6 May - 7 May
Clean, Comfy and Spacious Bedroom
Bungalow House - Free Parking - 10 mins to Hartford & Airport
9.0 out of 10, Wonderful, (17)
"We were able to stay @ this location for several days just before the holidays. The space was perfect for the running around we needed to do and was a solid base of operation. The kitchen, bedroom, and bathroom are well-appointed. We did not spend any time in the living room or outside areas. The water pressure in the shower is amazing and I could spend hours there. :) The home is on a busy road at commute times so take the owner's advice and K turn in the driveway to make exiting the home...
The price is £183
includes taxes & fees
14 May - 15 May
Bungalow House - Free Parking - 10 mins to Hartford & Airport
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 £468
includes taxes & fees
5 May - 6 May
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
9.0 out of 10, Wonderful, (4)
"My wife and I enjoyed getting some peace and quiet for our vacation. It wasn’t clear how remote the entire area was for things like dining. Everything was 45 minutes away which was unexpected. Also, It should be clearer that there are no beds larger than double in the property. That was a surprise. We did relax which was the plan."
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
PICON COZY
8.0 out of 10, Very good, (42)
"Very clean, lots of space. Super quiet neighborhood."
The price is £139
includes taxes & fees
9 May - 10 May
PICON COZY
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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 Rental 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, (1004)
"👍"
The price is £133
includes taxes & fees
20 May - 21 May
MGM Springfield
Fairfield Inn & Suites by Marriott Springfield Enfield
2.5 star property
8.8 out of 10, Excellent, (777)
"Very clean and staff was super friendly. Would definitely stay again."
The price is £101
includes taxes & fees
5 May - 6 May
Fairfield Inn & Suites by Marriott Springfield Enfield
Best Western Hartford Hotel & Suites
2.5 star property
8.0 out of 10, Very good, (1002)
"The staff was exceptional"
The price is £93
includes taxes & fees
20 May - 21 May
Best Western Hartford Hotel & Suites
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, 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 £109 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. 

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.

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

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!: This holiday home rental outside of Simsbury is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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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