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

Simsbury Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Simsbury vacation rentals

A square fire pit with flames, surrounded by a grassy field and a green chair.

1. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (26 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
$152 nightly
The price is $173
Nov 9 - Nov 10
Total with taxes and fees
Peaceful Meadow Retreat
A historic building with red brick architecture, snow-covered roofs, and a prominent chimney.

2. 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.
$236 nightly
The price is $252
Nov 8 - Nov 9
Total with taxes and fees
The Old Avon Village
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.
$230 nightly
The price is $245
Nov 16 - Nov 17
Total with taxes and fees
Sun Filled Lake House Living
A balcony with a view of a lake, white railings, and outdoor furniture.

4. 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.
$257 nightly
The price is $294
Nov 9 - Nov 10
Total with taxes and fees
River Overlook - What a view from your deck!
A reception area with a counter, a plant, and an exit sign.

5. 1 Queen Bed | Micfridge

1 Queen Bed | Micfridge
Windsor Locks
10.0 out of 10, Exceptional, (51 reviews)
"Near the airport, this place made for a quick and easy stay."
United States
Anonymous traveler
$78 nightly
The price is $90
Nov 8 - Nov 9
Total with taxes and fees
1 Queen Bed | Micfridge
A reception area with a counter, a plant, and an exit sign.

6. 1 Queen Bed | ADA/Tub/Micfridge

1 Queen Bed | ADA/Tub/Micfridge
Windsor Locks
10.0 out of 10, Exceptional, (53 reviews)
"The pool area was clean and relaxing, perfect for unwinding after a busy day."
United States
Anonymous traveler
$78 nightly
The price is $90
Nov 8 - Nov 9
Total with taxes and fees
1 Queen Bed | ADA/Tub/Micfridge
A modern kitchen with blue cabinets, a central island, and a dining area with a glass table and chairs.

7. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
9.6 out of 10, Exceptional, (4 reviews)
"Cute and cozy home away from home! We loved our stay and all the nice features there were!! Everything was neat and clean and host was super amazing and helpful! We definitely will choose this place again if we’re ever in the area."
United States
Leah H.
$120 nightly
The price is $136
Nov 11 - Nov 12
Total with taxes and fees
Collinsville River Escape / Fall Foliage, Deck & Yard
A modern bedroom with a large bed, a wooden wardrobe, a small round table, and a window with blinds.

8. Modern Private Furnished Studio Downtown Hartford

Modern Private Furnished Studio Downtown Hartford
Downtown Hartford
7.4 out of 10, Good, (3 reviews)
"I had wondered about the amenities. the coffee pot was not cleaned , actually had mold in it , and the carpet was lifting at one corner, where i kept tripping on it. I certainly appreciated the rest ! As it was during the turkey holiday and easy to find through downtown Hartford "
United States
Lynnett
$167 nightly
The price is $190
Nov 9 - Nov 10
Total with taxes and fees
Modern Private Furnished Studio Downtown Hartford
A lakeside view with a row of beach chairs and umbrellas.

9. Waterfront Lake Cottage - Lake Access -Kayaks

Waterfront Lake Cottage - Lake Access -Kayaks
Avon
10.0 out of 10, Exceptional, (1 review)
"The cottage is very cozy, private, and in a beatiful setting. We really appreciated the upgrades that made our stay comfortable. The fenced-in yard was great for our dog. Take a note of a stone floor on the lower level. We had to cover it to be not too cold for the dog to lie on (in late October). The location is right on the water for kayaking and close to some well maintained trails for biking and hiking."
United States
Victoria F.
$497 nightly
The price is $568
Nov 7 - Nov 8
Total with taxes and fees
Waterfront Lake Cottage - Lake Access -Kayaks
A reception area with a counter, a plant, and an exit sign.

10. 1 Queen Bed | Deluxe, Micfridge

1 Queen Bed | Deluxe, Micfridge
Windsor Locks
10.0 out of 10, Exceptional, (53 reviews)
"Good location near the airport, clean rooms, straightforward setup for travelers."
United States
Anonymous traveler
$78 nightly
The price is $90
Nov 8 - Nov 9
Total with taxes and fees
1 Queen Bed | Deluxe, Micfridge
A multi-story building with a brick facade, large windows, and a street lamp.

11. Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Downtown Hartford
9.0 out of 10, Wonderful, (8 reviews)
"Nice place"
United States
Bonita T.
$176 nightly
The price is $202
Nov 8 - Nov 9
Total with taxes and fees
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
A reception area with a counter, a plant, and an exit sign.

12. 2 Queen Beds | Deluxe, Micfridge

2 Queen Beds | Deluxe, Micfridge
Windsor Locks
10.0 out of 10, Exceptional, (51 reviews)
"This spot made for an easy stopover with smooth check-in and check-out processes."
United States
Anonymous traveler
$88 nightly
The price is $101
Nov 8 - Nov 9
Total with taxes and fees
2 Queen Beds | Deluxe, Micfridge
A covered porch with wicker furniture, a potted plant, and a small table.

13. The Blue Back Bungalow

The Blue Back Bungalow
West Hartford
9.4 out of 10, Exceptional, (22 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
$273 nightly
The price is $290
Nov 19 - Nov 20
Total with taxes and fees
The Blue Back Bungalow
A reception area with a counter, a plant, and an exit sign.

14. 2 Full Beds | Micfridge

2 Full Beds | Micfridge
Windsor Locks
10.0 out of 10, Exceptional, (51 reviews)
"Close to airport, very handy for quick stays."
United States
Anonymous traveler
$88 nightly
The price is $101
Nov 8 - Nov 9
Total with taxes and fees
2 Full Beds | Micfridge
A patio with a table and chairs, a grill, and a view of a lake.

15. 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, (76 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
$394 nightly
The price is $451
Nov 8 - Nov 9
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A room with a large potted tree, a wooden cabinet, a round table, and a sofa with a cushion.

16. The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (18 reviews)
"The property was clean and inviting. The basement game room was amazing"
United States
Michael P.
$257 nightly
The price is $276
Nov 30 - Dec 1
Total with taxes and fees
The Serene Skyway Retreat
A modern reception area with a counter, two chairs, a small table, and a carpeted floor.

17. 1 King Bed|Smoking, Micfridge

1 King Bed|Smoking, Micfridge
Enfield
10.0 out of 10, Exceptional, (5 reviews)
$68 nightly
The price is $79
Nov 8 - Nov 9
Total with taxes and fees
1 King Bed|Smoking, Micfridge
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.

18. 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, (12 reviews)
"Great location for our six flags visit (about 15 minutes away)."
United States
Stacey B.
$365 nightly
The price is $417
Nov 15 - Nov 16
Total with taxes and fees
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
A modern kitchen with a central island, stainless steel appliances, and black cabinets.

19. Fully Furnished Private Apartment, Elevator, Wi-Fi A/C

Fully Furnished Private Apartment, Elevator, Wi-Fi A/C
Downtown Hartford
9.0 out of 10, Wonderful, (2 reviews)
"Great place downtown Hartford! Clean and quiet and minutes from everything! My only issue was that it claims to be fully furnished but there is no iron or steamer. Guests are often traveling in for events so having that on hand is essential. Other than that all was wonderful!"
United States
Shea O.
$194 nightly
The price is $221
Nov 9 - Nov 10
Total with taxes and fees
Fully Furnished Private Apartment, Elevator, Wi-Fi A/C
A modern kitchen with black cabinets, a white countertop, and a built-in oven.

20. Lux Boutique Large Private LOFT Pratt St Hartford

Lux Boutique Large Private LOFT Pratt St Hartford
Downtown Hartford
8.4 out of 10, Very good, (30 reviews)
"Great stay"
United States
Josh H.
$223 nightly
The price is $255
Nov 8 - Nov 9
Total with taxes and fees
Lux Boutique Large Private LOFT Pratt St 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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Top Simsbury Hotel Reviews

Holiday Inn Express Springfield Downtown by IHG

Holiday Inn Express Springfield Downtown by IHG

8/10 Good
"Staff is superb, front desk was so kind and welcoming. The breakfast was tasty, the room was very spacious and well equipped, loved the mini fridge and microwave. Parking is free but you have to walk to the garage, the walk is not the worst."
Alexandra 3-night trip
Posted 1 hour ago
Holiday Inn Express Springfield Downtown by IHG

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 $219 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.