A metal bridge with a sign that reads 'Thank You' and a birdhouse on the right.

Simsbury Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Simsbury holiday rentals

A red door with a wicker basket hanging on it, leading to a laundry area with a brick wall and two large speakers.

1. The Historic Hideaway

The Historic Hideaway
Avon
6.0 out of 10, (4 reviews)
The price is HK$573
HK$2,099 total
includes taxes & fees
7 Oct - 8 Oct
The Historic Hideaway
A square fire pit with flames, surrounded by a grassy field and a green chair.

2. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (24 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
The price is HK$734
HK$1,452 total
includes taxes & fees
5 Oct - 6 Oct
Peaceful Meadow Retreat
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

3. Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.6 out of 10, (4 reviews)
The price is HK$714
HK$2,286 total
includes taxes & fees
26 Oct - 27 Oct
Sun Filled Lake House Living
A historic building with red brick architecture, snow-covered roofs, and a prominent chimney.

4. The Old Avon Village

The Old Avon Village
Avon
6.2 out of 10, (10 reviews)
"Great location. Alexander was very responsive to any requests. Met our needs. "
United States
Deborah S.
The price is HK$573
HK$2,138 total
includes taxes & fees
28 Sept - 29 Sept
The Old Avon Village
A spacious kitchen with a large island, wooden beams, and pendant lighting.

5. Linny's - Private Dock - Lake Access - Firepit

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (43 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
The price is HK$1,489
HK$2,983 total
includes taxes & fees
14 Oct - 15 Oct
Linny's - Private Dock - Lake Access - Firepit
A balcony with a view of a lake, white railings, and outdoor furniture.

6. River Overlook - What a view from your deck!

River Overlook - What a view from your deck!
Collinsville
10.0 out of 10, Exceptional, (27 reviews)
"I only did a short stay (2 nights) but it was super adorable! I will definitely stay again when I'm back in the area."
United States
Mary S.
The price is HK$1,256
HK$2,462 total
includes taxes & fees
27 Sept - 28 Sept
River Overlook - What a view from your deck!
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove. There is a dining table with chairs and a coffee maker on the table.

7. Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Windsor Locks
10.0 out of 10, Exceptional, (11 reviews)
"Great stay, home was comfortable and communication w owner was very smooth!"
United States
Stacey P.
The price is HK$2,141
HK$4,368 total
includes taxes & fees
26 Oct - 27 Oct
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
A patio area with wicker furniture and a brick floor.

8. The Old Avon 1800 Manor

The Old Avon 1800 Manor
Avon
7.0 out of 10, Good, (2 reviews)
"Wonderful place and host very responsive and friendly!"
United States
Anonymous traveller
The price is HK$1,372
HK$3,524 total
includes taxes & fees
28 Sept - 29 Sept
The Old Avon 1800 Manor
A modern living room with a sofa, a coffee table, and a rug.

9. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
9.8 out of 10, Exceptional, (10 reviews)
"Good location"
United States
Arthur
The price is HK$678
HK$936 total
includes taxes & fees
29 Sept - 30 Sept
Entire guest suite in South Windsor, Connecticut
A room with a large potted tree, a wooden cabinet, a round table, and a sofa with a cushion.

10. The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (16 reviews)
"The property was clean and inviting. The basement game room was amazing"
United States
Michael P.
The price is HK$1,004
HK$2,677 total
includes taxes & fees
5 Oct - 6 Oct
The Serene Skyway Retreat
A covered porch with wicker furniture, a potted plant, and a small table.

11. The Blue Back Bungalow

The Blue Back Bungalow
West Hartford
9.4 out of 10, Exceptional, (20 reviews)
"The bungalow is in a great location - close to I84 and West Hartford center. The kitchen had a lot of great appliances to make cooking easy. The coffee pot was a Keurig/carafe combo - which we really liked. We enjoyed drinking our morning coffee on the front porch. We would definitely stay her again!"
United States
Ben
The price is HK$878
HK$2,807 total
includes taxes & fees
14 Oct - 15 Oct
The Blue Back Bungalow
A porch with a table and chairs, an American flag, and a hanging flower basket.

12. West Hartford Center: Cozy New England Apartment

West Hartford Center: Cozy New England Apartment
West Hartford
10.0 out of 10, Exceptional, (12 reviews)
"Great comfortable spot- great location!"
United States
Sara H.
The price is HK$1,736
HK$3,327 total
includes taxes & fees
28 Sept - 29 Sept
West Hartford Center: Cozy New England Apartment
A spacious kitchen with wooden cabinets, a large island, and a dining area with chairs and a rug.

13. Spacious Yard w/ Gazebo: Charming Windsor Retreat

Spacious Yard w/ Gazebo: Charming Windsor Retreat
Windsor
9.4 out of 10, Exceptional, (12 reviews)
"The place is easy to locate. It is as beautiful as the photo. Clean and spacious.I definitely would stay there again."
United States
Delores N.
The price is HK$2,572
HK$5,460 total
includes taxes & fees
28 Sept - 29 Sept
Spacious Yard w/ Gazebo: Charming Windsor Retreat
A patio with a table and chairs, a grill, and a view of a lake.

14. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (72 reviews)
"Wow! What a great place! The house is lovely, very clean, comfy beds and cozy seating. Amazing view and an unbeatable location!"
United States
Kristi M.
The price is HK$2,447
HK$3,981 total
includes taxes & fees
29 Sept - 30 Sept
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A living room with a blue sofa, a round coffee table, and a staircase.

15. The Game House Arcade – West Hartford

The Game House Arcade – West Hartford
West Hartford
10.0 out of 10, Exceptional, (1 review)
"Great location and well equipped. We will be back"
United States
Mike W.
The price is HK$1,779
HK$3,550 total
includes taxes & fees
28 Sept - 29 Sept
The Game House Arcade – West Hartford
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

16. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (52 reviews)
"Quaint very nice loved the space very cozy the hot tub was a nice touch I did use that a few times helped my sore back LOL everything went as expected I would stay here again"
United States
paul
The price is HK$988
HK$1,866 total
includes taxes & fees
30 Sept - 1 Oct
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A spacious living room with hardwood flooring, a grey sofa, a coffee table, and a chandelier.

17. West Hartford Center: Charming New England Apt

West Hartford Center: Charming New England Apt
West Hartford
10.0 out of 10, Exceptional, (9 reviews)
"Immaculate, nice decor, very comfortable beds, every detail is well thought out. "
United States
Cathryna B.
The price is HK$1,872
HK$3,503 total
includes taxes & fees
28 Sept - 29 Sept
West Hartford Center: Charming New England Apt
A bedroom with a bed, a round table, a grey sofa, a window with a view of buildings, and a wooden wardrobe.

18. Trumbull Apartments

Trumbull Apartments
3.0 star property
Downtown Hartford
2.0 out of 10, (1 review)
"Terrible, worst stay ever . It was such a hassle to get in no clear instructions… never again"
United States
Nicolas
The price is HK$1,765
HK$2,657 total
includes taxes & fees
27 Sept - 28 Sept
Trumbull Apartments
A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

19. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
The price is HK$541
HK$1,966 total
includes taxes & fees
7 Oct - 8 Oct
The Sun Filled Cozy Creamery
A covered porch with white rocking chairs and a table, a blue ceiling, and a view of the garden.

20. Charming New England Home in West Hartford Center

Charming New England Home in West Hartford Center
West Hartford
10.0 out of 10, Exceptional, (32 reviews)
"Great location. Beautiful, comfortable home."
United States
karen
The price is HK$2,135
HK$4,009 total
includes taxes & fees
28 Sept - 29 Sept
Charming New England Home in West Hartford Center
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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Top Simsbury Hotel Reviews

Motel 6 Enfield, CT - Hartford

Motel 6 Enfield, CT - Hartford

10/10 Excellent
"Lugar renovado muy limpio"
Angel 3-night trip
Posted 10 hours ago
Motel 6 Enfield, CT - Hartford

Find out more about Simsbury

Search for holiday rentals in Simsbury on Expedia! You can easily find your home rentals, villas, holiday apartments in Simsbury using one of the methods below:

  • View our selection of featured holiday rentals in Simsbury
  • Use the map to find apartments and other holiday homes in the Simsbury neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Simsbury while they last

Look no further and take a look at our great range of rental properties in Simsbury!

Frequently asked questions

Can I find holiday rentals in Simsbury?

Yes, there are holiday rentals in Simsbury close to Performing Arts Center at Simsbury Meadows, 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?

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!: This holiday home rental outside of Simsbury has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals will I find in Simsbury?

With 4 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?

Farmington River and Pinchot Sycamore Tree are a couple of lovely local spots to get outside and enjoy nature. While here, Performing Arts Center at Simsbury Meadows 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.