Simsbury Vacation Rentals

April 2025

SundayMondayTuesdayWednesdayThursdayFridaySaturday

May 2025

SundayMondayTuesdayWednesdayThursdayFridaySaturday
  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Vacation Rentals in Simsbury

PICON COZY

7.8 out of 10, Good, (61)
"Peaceful everything just as listed "
The price is CA $106
CA $240 total
includes taxes & fees
Apr 13 - Apr 14
PICON COZY

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.4 out of 10, Exceptional, (15)
"This is such a great property, I spent a whole month with three separate stays adjacent due to travel planning and the host was wonderful. The house is really beautiful and in a great neighborhood and it’s very comfortable and super clean. This will be a regular for me in the Hartford area. I’m looking forward to seeing what the beautiful landscaping is like in the spring and summer too."
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Blue Back Bungalow

2.0 star property
9.8 out of 10, Exceptional, (11)
"Great location and pleasant area to walk to area restaurants and shops. Prompt and friendly communication with host who was very accommodating to our needs. We enjoyed our stay."
The price is CA $176
CA $549 total
includes taxes & fees
Apr 13 - Apr 14
Blue Back Bungalow

Lux Boutique Large Private LOFT Pratt St Hartford

9.2 out of 10, Wonderful, (14)
"Super nice location/convenient "
The price is CA $204
CA $290 total
includes taxes & fees
Apr 14 - Apr 15
Lux Boutique Large Private LOFT Pratt St Hartford

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (10)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is CA $310
CA $442 total
includes taxes & fees
Apr 11 - Apr 12
Tranquil Litchfield Connecticut Retreat".

Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.

2.0 star property
10.0 out of 10, Exceptional, (5)
"This place was perfect for my daughter and I while we waited for our new home to be ready. The owners are easy to communicate with and the description of the property was spot on! Definitely a nice and cozy spot! "
The price is CA $162
CA $257 total
includes taxes & fees
Apr 19 - Apr 20
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.

Bring Your Pet & Visit Springfield: Westfield Home

2.0 star property
6.6 out of 10, (4)
"The house and location were perfect. Comfortable beds! Would definitely stay again"
Bring Your Pet & Visit Springfield: Westfield Home

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (130)
"Cozy, historic experience from great owners. Nice trail and brook right behind the house as well. "
The price is CA $282
CA $513 total
includes taxes & fees
Apr 13 - Apr 14
Big farmhouse in the foothills of the Berkshires

New!Quaint & Convenient Hideaway: Great Location

10.0 out of 10, Exceptional, (6)
"Very comfortable house for our stay to visit with family. It was conveniently located near highway and Glastonbury shopping. Owner was extremely communicative and helpful."
New!Quaint & Convenient Hideaway: Great Location

Thomas's Cozy Duplex - Centrally Located

8.4 out of 10, Very good, (11)
"The duplex was clean and quiet. The kitchen was stocked well enough for us to make dinner, although there was no kitchen towel for drying hands and dishes (very minor). Three bedrooms, two with a double/queen, one with a single, and it looked like the couch in the living room was a pull out. Beds were comfortable with plenty of bedding. Wi-fi worked well. Couldn't ask for anything more. I would stay here again if in the area. "
Thomas's Cozy Duplex - Centrally Located

Lakefront Home, Close to Mt Southington!

10.0 out of 10, Exceptional, (16)
"Beautiful lakefront home. Tastefully furnished. Spotless with all the little touches included. Loved ir"
Lakefront Home, Close to Mt Southington!

The Skyway

10.0 out of 10, Exceptional, (3)
"Very well staged. Smart TV’s in every room. Quiet, safe area. Comfortable bed. It was perfect for my short stay"
The price is CA $134
CA $434 total
includes taxes & fees
Apr 28 - Apr 29
The Skyway

Cozy BoHo pet & family friendly near downtown & hospitals

8.6 out of 10, Excellent, (8)
"The property was very clean and relaxing. "
The price is CA $148
CA $410 total
includes taxes & fees
Apr 21 - Apr 22
Cozy BoHo pet & family friendly near downtown & hospitals

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

9.0 out of 10, Wonderful, (12)
"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

Exquisite Downtown Loft Apartment

8.6 out of 10, Excellent, (8)
"We loved having this home to return to each night during a whirlwind college tour. Extremely clean, comfortable, and pleasantly decorated. "
Exquisite Downtown Loft Apartment

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

9.6 out of 10, Exceptional, (30)
"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "
The price is CA $261
CA $440 total
includes taxes & fees
Apr 13 - Apr 14
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Mins from MGM, Downtown springfield, Mercy and Baystate Medical center.

7.0 out of 10, Good, (6)
"We had a wonderful stay at this property and it was the perfect location and size for us while we were vendors at the Big E. The condo itself is large and spacious with comfortable beds, tvs in the living room and two bedrooms, a fully stocked bathroom with laundry, a beautiful kitchen with a fridge with ice maker and water capability. The entry is by code, which made it very convenient to access. Hana, the hostess was extremely attentive and helpful every step of the way. The drawbacks were...
The price is CA $169
CA $437 total
includes taxes & fees
Apr 15 - Apr 16
Mins from MGM, Downtown springfield, Mercy and Baystate Medical center.

Lakefront Granby Escape w/ Private Dock & Kayaks!

9.2 out of 10, Wonderful, (11)
"Enjoyed our stay"
Lakefront Granby Escape w/ Private Dock & Kayaks!

Peaceful Lakefront Cottage with Hot Tub - 2BR 2BA - Sleeps 4

10.0 out of 10, Exceptional, (1)
"Beautiful view from the upstairs window. I enjoyed the pellet stove on the cold days."
The price is CA $367
CA $653 total
includes taxes & fees
Apr 13 - Apr 14
Peaceful Lakefront Cottage with Hot Tub - 2BR 2BA - Sleeps 4
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.
Don't see what you're looking for?
See all available properties in Simsbury
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Simsbury you may be interested in

Holiday Inn Express Southington by IHG

2.5 star property
8.8 out of 10, Excellent, (1004)
"Great location"
The price is CA $134
CA $154 total
includes taxes & fees
Apr 20 - Apr 21
Holiday Inn Express Southington by IHG

MGM Springfield

4.0 star property
8.8 out of 10, Excellent, (1339)
"To many add on taxes after hotel fee is quoted. Casino room is to fenced off."
The price is CA $238
CA $302 total
includes taxes & fees
Apr 13 - Apr 14
MGM Springfield

DoubleTree by Hilton Hartford Downtown

4.0 star property
7.6 out of 10, Good, (1003)
"Easy off the highway. Friendly staff. Easy check in."
The price is CA $214
CA $247 total
includes taxes & fees
Apr 18 - Apr 19
DoubleTree by Hilton Hartford Downtown
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.

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?

PICON COZY: This vacation home rental outside of Simsbury has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. 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.