Simsbury Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 16 - Dec 17
Tomorrow
Dec 17 - Dec 18
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Our top choices for Simsbury vacation rentals

Iron/ironing board, WiFi, bed sheets
Lux Boutique Large Private LOFT Pratt St Hartford

Lux Boutique Large Private LOFT Pratt St Hartford

Lux Boutique Large Private LOFT Pratt St Hartford
Downtown Hartford
8.6 out of 10, Excellent, (24)
"Great stay"
United States
Josh H.
The price is ￥15,501
￥23,600 total
includes taxes & fees
Dec 17 - Dec 18
Lux Boutique Large Private LOFT Pratt St Hartford
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
New Britain
10.0 out of 10, Exceptional, (8)
" Heck-on was smooth and the kitchen and facilities were great. "
United States
Elizabeth P.
The price is ￥17,439
￥37,417 total
includes taxes & fees
Dec 18 - Dec 19
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Interior
Experience Downtown Hartford near XL Center

Experience Downtown Hartford near XL Center

Experience Downtown Hartford near XL Center
Downtown Hartford
6.6 out of 10, (7)
"Nice place, good location. "
United States
Lacey A.
The price is ￥15,501
￥23,600 total
includes taxes & fees
Dec 17 - Dec 18
Experience Downtown Hartford near XL Center
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Private Apartment in Berlin

Private Apartment in Berlin
2.0 star property
Berlin
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
The price is ￥18,136
￥48,991 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Private Apartment in Berlin
Full-size fridge, microwave, oven, dishwasher
Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway
3.5 star property
Forest Park
The price is ￥63,046
￥94,778 total
includes taxes & fees
Dec 20 - Dec 21
Newly Renovated 2 floor Getaway
Microwave
Cozy apartment in charming Hartford with AC, WiFi

Cozy apartment in charming Hartford with AC, WiFi

Cozy apartment in charming Hartford with AC, WiFi
Downtown Hartford
8.8 out of 10, Excellent, (9)
"Very nice for one night"
United States
Jack
The price is ￥15,501
￥23,600 total
includes taxes & fees
Dec 17 - Dec 18
Cozy apartment in charming Hartford with AC, WiFi
HOMEY HOMEY

HOMEY HOMEY

HOMEY HOMEY
Sixteen Acres
2.8 out of 10, (5)
"We did not even stay. The upstairs has access to the basement door so I did not at all feel comfortable. And there is a terrible mildew smell. "
United States
Erin N.
The price is ￥11,161
￥25,851 total
includes taxes & fees
Dec 17 - Dec 18
HOMEY HOMEY
Fridge, microwave, oven, stovetop
Charming 3-Bedroom Home with Modern Comforts in West Hartford

Charming 3-Bedroom Home with Modern Comforts in West Hartford

Charming 3-Bedroom Home with Modern Comforts in West Hartford
2.0 star property
West Hartford
8.6 out of 10, Excellent, (9)
"Great house in a safe neighborhood with a fenced in yard. Amenities provided. "
United States
Ben H.
The price is ￥21,314
￥47,608 total
includes taxes & fees
Dec 18 - Dec 19
Charming 3-Bedroom Home with Modern Comforts in West Hartford
Property grounds
Humble Abode #2

Humble Abode #2

Humble Abode #2
2.0 star property
Manchester Center
10.0 out of 10, Exceptional, (1)
"the place was clean bed was nice"
United States
Jonathan
The price is ￥18,601
￥24,491 total
includes taxes & fees
Dec 17 - Dec 18
Humble Abode #2
Terrace/patio
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Barkhamsted
10.0 out of 10, Exceptional, (4)
"It's a wonderful house, lots of space to visit with family and the bed rooms were confortable and cozy. The host was very helpful and accesible at all times."
Spain
Heather A.
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Terrace/patio
Cozy Lakefront Bungalow w firepit/dock/kayaks

Cozy Lakefront Bungalow w firepit/dock/kayaks

Cozy Lakefront Bungalow w firepit/dock/kayaks
Plymouth
9.8 out of 10, Exceptional, (40)
"Our stay was so peaceful and relaxing. The property was beautiful and exactly as described in the listing. We loved having a fire outside, sitting in the screened-in porch. Will absolutely be coming back!"
United States
Jean R.
Cozy Lakefront Bungalow w firepit/dock/kayaks
Interior
Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is ￥111,607
￥144,314 total
includes taxes & fees
Dec 17 - Dec 18
Conference Room Rental no sleeping arrangements
Smart TV
PICON COZY

PICON COZY

PICON COZY
Sixteen Acres
7.4 out of 10, Good, (69)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
United States
Linda W.
The price is ￥11,781
￥26,555 total
includes taxes & fees
Dec 23 - Dec 24
PICON COZY
Fridge, microwave, oven, stovetop
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Forest Park
9.0 out of 10, Wonderful, (28)
"This home was great. It had everything our large group needed and was as advertised. The owner was great to communicate with. We enjoyed our stay and would definitely come back again. "
United States
Matthew C.
The price is ￥40,496
￥81,290 total
includes taxes & fees
Dec 17 - Dec 18
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
WiFi, bed sheets
Totally Private Cozy studio in awesome Hartford with WiFi, AC

Totally Private Cozy studio in awesome Hartford with WiFi, AC

Totally Private Cozy studio in awesome Hartford with WiFi, AC
Downtown Hartford
8.6 out of 10, Excellent, (11)
"Great location, very nice and clean. "
United States
Manuel M.
The price is ￥15,501
￥23,600 total
includes taxes & fees
Dec 18 - Dec 19
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Dining
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Northwest Harwinton
8.8 out of 10, Excellent, (28)
"Great little place, beutiful view to enjoy your coffee."
United States
Shaun H.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Interior
Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Modern Family Retreat | Near Downtown Hartford | Sleeps 10
2.0 star property
Bloomfield
9.4 out of 10, Exceptional, (3)
"There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! "
United States
Joslynn T.
The price is ￥47,743
￥109,235 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Fridge, microwave, oven, stovetop
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT

Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT

Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
Manchester
9.8 out of 10, Exceptional, (7)
"Property fit our needs well. Clean, convenient location, easy to access the places around town we needed to get to, and a helpful and responsive host."
United States
Brian H.
The price is ￥18,446
￥43,379 total
includes taxes & fees
Dec 17 - Dec 18
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
Microwave, oven, stovetop
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Spacious 4-bedroom condo with AC and WiFi in charming Enfield
Enfield
10.0 out of 10, Exceptional, (2)
"I had a family event in the area and needed a place for 8 people that was of better value than hotel rooms. This location was the perfect option."
United States
Logan M.
The price is ￥19,476
￥65,557 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Spacious 4-bedroom condo with AC and WiFi in charming Enfield
Smart TV, fireplace, video games, books
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Forest Park
9.8 out of 10, Exceptional, (36)
"His home was great. It had everything our group needed and was as advertised. We enjoyed our stay and would definitely come back again. "
United States
Matthew C.
The price is ￥27,243
￥46,736 total
includes taxes & fees
Dec 17 - Dec 18
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Simsbury Hotel Reviews

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"Clean room. Great location. Very nice staff."
William 2-night trip
Posted 2 days ago
Holiday Inn Express Southington by IHG

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 vacation rentals in Simsbury?

Yes, you can find vacation rentals near top attractions in Simsbury, or you can go with a more secluded option if you're looking for relaxation. 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?

Private Apartment in Berlin: This vacation home rental outside of Simsbury is equipped with a balcony, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Simsbury?

With 3 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?

Cultural attractions include Performing Arts Center at Simsbury Meadows, whereas Farmington River is a spot to enjoy nature. While here, Talcott Mountain State Park and Stratton Brook 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.