Search Vacation Homes in Simsbury

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 210 Vacation Homes in Simsbury with updated reviews, rates, and availability.

Stylish & Luxurious 3 BDR Home with Play Station
Fridge, microwave, oven, stovetop

Stylish & Luxurious 3 BDR Home with Play Station

9.4 out of 10, Exceptional, (10)
"We needed a place for our family of 6 to stay while visiting family in the area. This place was exactly what we needed, as advertised, and the owner was quick with communications. We would definitely stay here again!"
Stylish & Luxurious 3 BDR Home with Play Station
PICON COZY
Fridge, microwave, oven, stovetop

PICON COZY

7.6 out of 10, Good, (64)
"Picon Cozy was a great place to rest our weary heads. The neighborhood was quiet and the lodging/amenities met our needs very nicely. We'll definitely consider this place for future visits to the Springfield area 😊."
The price is AED 275
AED 625 total
includes taxes & fees
4 May - 5 May
PICON COZY
Lakefront Retreat w Hot Tub, Game Room & Peaceful Views - Fall Mountain Lake
Outdoor spa tub

Lakefront Retreat w Hot Tub, Game Room & Peaceful Views - Fall Mountain Lake

10.0 out of 10, Exceptional, (3)
"Everything was great. "
Lakefront Retreat w Hot Tub, Game Room & Peaceful Views - Fall Mountain Lake
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Living area

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

9.4 out of 10, Exceptional, (15)
"It was a very comfortable house! We were only there 2 days for the Mizzou game. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Tranquil Litchfield Connecticut Retreat".
Property grounds

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (11)
"This is a neat, clean and lovely little place that perfectly suited our needs. It had all the amenities we needed for our short stay. Jose was a gracious host, answering all of my questions promptly - even the one about the mattresses which were incredibly comfortable! "
The price is AED 808
AED 1,141 total
includes taxes & fees
4 May - 5 May
Tranquil Litchfield Connecticut Retreat".
Thomas's Cozy Duplex - Centrally Located
Smart TV

Thomas's Cozy Duplex - Centrally Located

8.4 out of 10, Very Good, (11)
"Quiet and comfy "
Thomas's Cozy Duplex - Centrally Located
Owl's Nest - Cozy Westfield Home w/ Fire Pit
Fridge, microwave, oven, stovetop

Owl's Nest - Cozy Westfield Home w/ Fire Pit

9.0 out of 10, Wonderful, (4)
"Property worked well for us "
Owl's Nest - Cozy Westfield Home w/ Fire Pit
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Outdoor pool

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

10.0 out of 10, Exceptional, (7)
"It was a great house to host our family for Thanksgiving dinner! "
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Interior

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (19)
"Very nice clean house. Felt like coming home after work"
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Interior

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

2.0 star property
10.0 out of 10, Exceptional, (2)
"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!! "
The price is AED 1,440
AED 3,046 total
includes taxes & fees
20 May - 21 May
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
WeHa Oak Haven
Private kitchen

WeHa Oak Haven

10.0 out of 10, Exceptional, (5)
"Lovely property in a great area of West Hartford. Will definitely stay again!"
WeHa Oak Haven
Historic Farmhouse Near Mountains & Colleges!
Fridge, microwave, stovetop, dishwasher

Historic Farmhouse Near Mountains & Colleges!

10.0 out of 10, Exceptional, (7)
"Loved our stay at this adorable ranch home. Cute and comfy and clean. "
Historic Farmhouse Near Mountains & Colleges!
Charming Farmhouse w/ Pool & Fishing Pond!
Fridge, microwave, stovetop, dishwasher

Charming Farmhouse w/ Pool & Fishing Pond!

10.0 out of 10, Exceptional, (9)
"Very classy, unique, well taken care of home. I would highly recommend this for anyone."
Charming Farmhouse w/ Pool & Fishing Pond!
Cozy 4 Bedroom West Hartford House
Smart TV, fireplace

Cozy 4 Bedroom West Hartford House

2.0 star property
9.0 out of 10, Wonderful, (4)
"This was the best property for our large family. The host was very attentive to our family. Thank again for everything."
Cozy 4 Bedroom West Hartford House
Cozy 2 Bedroom Family Stay
Private kitchen

Cozy 2 Bedroom Family Stay

9.8 out of 10, Exceptional, (8)
"We had a great stay in Manchester! Quick walk to stores, restaurants, and Main St Manchester. The apartment was clean and spacious. Would definitely recommend & stay here again!"
Cozy 2 Bedroom Family Stay
Upscaled Quiet Neighborhood- Modern 3 BDRM
Fridge, microwave, oven, stovetop

Upscaled Quiet Neighborhood- Modern 3 BDRM

10.0 out of 10, Exceptional, (24)
"Nice place to stay"
Upscaled Quiet Neighborhood- Modern 3 BDRM
Blue Back Bungalow
Exterior

Blue Back Bungalow

2.0 star property
9.6 out of 10, Exceptional, (10)
"Seamless check in, beautiful quaint home with excellent water pressure and hot water!Location is excellent, thank you to our hosts "
The price is AED 459
AED 1,410 total
includes taxes & fees
4 May - 5 May
Blue Back Bungalow
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Smart TV, fireplace, video games, books

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

9.6 out of 10, Exceptional, (31)
"It was nice stay!"
The price is AED 680
AED 1,167 total
includes taxes & fees
5 May - 6 May
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Island Vibes Home
Interior

Island Vibes Home

9.4 out of 10, Exceptional, (17)
"House was just as described. Clean and well stocked. Communication and instructions were clear. Great location. "
Island Vibes Home
The Skyway
Private kitchen

The Skyway

10.0 out of 10, Exceptional, (5)
"Very well staged. Smart TV’s in every room. Quiet, safe area. Comfortable bed. It was perfect for my short stay"
The price is AED 489
AED 1,339 total
includes taxes & fees
5 May - 6 May
The Skyway
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
Sign in
Sign up, it's free

Other property types in Simsbury

Blue Back Bungalow
Exterior

Blue Back Bungalow

2.0 star property
9.6 out of 10, Exceptional, (10)
"Seamless check in, beautiful quaint home with excellent water pressure and hot water!Location is excellent, thank you to our hosts "
The price is AED 459
AED 1,410 total
includes taxes & fees
4 May - 5 May
Blue Back Bungalow
PICON COZY
Fridge, microwave, oven, stovetop

PICON COZY

7.6 out of 10, Good, (64)
"Picon Cozy was a great place to rest our weary heads. The neighborhood was quiet and the lodging/amenities met our needs very nicely. We'll definitely consider this place for future visits to the Springfield area 😊."
The price is AED 275
AED 625 total
includes taxes & fees
4 May - 5 May
PICON COZY
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Living area

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

9.4 out of 10, Exceptional, (15)
"It was a very comfortable house! We were only there 2 days for the Mizzou game. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
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.