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Simsbury Vacation Rentals

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Check prices for these dates

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

Our top choices for Simsbury vacation 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)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
The price is CA $102
CA $377 total
includes taxes & fees
Sep 23 - Sep 24
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 CA $131
CA $260 total
includes taxes & fees
Oct 5 - Oct 6
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)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is CA $119
CA $400 total
includes taxes & fees
Sep 24 - Sep 25
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 CA $102
CA $380 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $266
CA $531 total
includes taxes & fees
Oct 14 - Oct 15
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 CA $250
CA $471 total
includes taxes & fees
Sep 27 - Sep 28
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 CA $378
CA $767 total
includes taxes & fees
Sep 23 - Sep 24
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 CA $246
CA $636 total
includes taxes & fees
Sep 23 - Sep 24
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 CA $121
CA $168 total
includes taxes & fees
Sep 29 - Sep 30
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 CA $182
CA $485 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $160
CA $500 total
includes taxes & fees
Oct 14 - Oct 15
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 CA $362
CA $649 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $368
CA $848 total
includes taxes & fees
Sep 23 - Sep 24
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 CA $438
CA $735 total
includes taxes & fees
Sep 29 - Sep 30
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 CA $343
CA $655 total
includes taxes & fees
Sep 23 - Sep 24
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 CA $127
CA $258 total
includes taxes & fees
Sep 23 - Sep 24
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 CA $367
CA $656 total
includes taxes & fees
Sep 23 - Sep 24
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 CA $316
CA $475 total
includes taxes & fees
Sep 27 - Sep 28
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)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The price is CA $97
CA $353 total
includes taxes & fees
Sep 23 - Sep 24
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 CA $373
CA $693 total
includes taxes & fees
Sep 23 - Sep 24
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

Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent
"Excellent services"
Edi 1-night trip
Posted less than an hour ago
Blue A Modern Hotel, an Ascend Collection Hotel

Find out more about Simsbury

Everything you need to know about Simsbury vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simsbury vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Simsbury vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simsbury vacation rentals we have selected for you start as low as CA $121 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 vacation 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 vacation.

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 vacation rentals in Simsbury?

Yes, you can find vacation rentals in Simsbury near Performing Arts Center at Simsbury Meadows, or you can select a more remote option if you want a relaxing stay. Our travelers say Simsbury has a good selection of restaurants. Make sure you have time to check out the forests and riverfront during your trip.

What's the top vacation rental in Simsbury?

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

How many vacation rentals will I find in Simsbury?

With 4 Expedia vacation rentals, you're sure 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 vacation rental in Simsbury like?

Vacation rentals are private properties you can stay in for a couple of days or more in Simsbury. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for families.