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

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.
$252 nightly
The price is $268
Sep 23 - Sep 24
Total with taxes and fees
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.
$164 nightly
The price is $185
Oct 5 - Oct 6
Total with taxes and fees
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.
$265 nightly
The price is $283
Sep 24 - Sep 25
Total with taxes and fees
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.
$257 nightly
The price is $273
Sep 28 - Sep 29
Total with taxes and fees
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.
$360 nightly
The price is $380
Oct 14 - Oct 15
Total with taxes and fees
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.
$297 nightly
The price is $336
Sep 27 - Sep 28
Total with taxes and fees
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.
$487 nightly
The price is $551
Sep 23 - Sep 24
Total with taxes and fees
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 traveler
$412 nightly
The price is $449
Sep 23 - Sep 24
Total with taxes and fees
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
$106 nightly
The price is $119
Sep 29 - Sep 30
Total with taxes and fees
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.
$318 nightly
The price is $346
Oct 5 - Oct 6
Total with taxes and fees
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
$336 nightly
The price is $360
Oct 14 - Oct 15
Total with taxes and fees
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.
$475 nightly
The price is $517
Sep 27 - Sep 28
Total with taxes and fees
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.
$536 nightly
The price is $610
Sep 23 - Sep 24
Total with taxes and fees
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.
$446 nightly
The price is $508
Sep 29 - Sep 30
Total with taxes and fees
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.
$434 nightly
The price is $471
Sep 23 - Sep 24
Total with taxes and fees
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
$163 nightly
The price is $186
Sep 23 - Sep 24
Total with taxes and fees
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.
$413 nightly
The price is $450
Sep 23 - Sep 24
Total with taxes and fees
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
$295 nightly
The price is $339
Sep 27 - Sep 28
Total with taxes and fees
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.
$236 nightly
The price is $251
Sep 23 - Sep 24
Total with taxes and fees
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
$463 nightly
The price is $503
Sep 23 - Sep 24
Total with taxes and fees
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

Fairfield Inn & Suites by Marriott Springfield Enfield

Fairfield Inn & Suites by Marriott Springfield Enfield

8/10 Good
"Hotel is nice and in a good location for what we need. Fridge wasn’t up to temp on arrival, had to pull it out of cubby to turn up. Lighting in the bathroom could be brighter. Ice machines on floors 4-6 did not work, that’s was a bit frustrating. Overall plus is cleanliness and check in process."
Jennifer 2-night trip
Posted 1 hour ago
Fairfield Inn & Suites by Marriott Springfield Enfield

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Simsbury in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $86 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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.