Simsbury Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Simsbury

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Manchester CT

$279 nightly

$316 total

Apr 22 - Apr 23

Total with taxes and fees

Located in Manchester, this vacation home is within a 5-minute drive of Cheney Homestead Museum and Rockville General Hospital.

Kitchen

Washer

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

Manchester CT

With a stay at this vacation home in Manchester, you'll be within a 5-minute drive of Manchester Memorial Hospital and Cheney Homestead Museum.

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

Windsor CT

With a stay at this vacation home in Windsor, you'll be within a 5-minute drive of Keney Park and Loomis Chaffee School.

Kitchen

Air conditioning

Stylish & Luxurious 3 BDR Home with Play Station

Bristol CT

With a stay at this vacation home in Bristol, you'll be within a 5-minute drive of Seymour Park and Bristol Commons Shopping Center.

Kitchen

Washer

Welcoming 3-bedroom house- Gardner home

Chicopee MA

With a stay at this vacation home in Chicopee, you'll be within a 10-minute drive of MGM Springfield and Naismith Memorial Basketball Hall of Fame.

Big farmhouse in the foothills of the Berkshires

Russell MA

$347 nightly

$367 total

Apr 23 - Apr 24

Total with taxes and fees

Located in Russell, this vacation home is within a 10-minute drive of Westfield River and Strathmore Park.

Kitchen

Washer

Lakefront Cottage in CT with Hot Tub Pet Friendly

Plymouth CT

Located in Terryville, this vacation home is on the waterfront, within a 10-minute drive of Cedar Lake and Bracket Park.

Tranquil 3-bedroom house with AC in Hartford

Hartford CT

Located in Hartford (Blue Hills), this vacation home is within a 5-minute drive of Saint Francis Hospital and Medical Center - Mount Sinai Campus and Keney Park.

Washer

Dryer

Cozy Lakefront Bungalow w firepit/dock/kayaks

Plymouth CT

Located in Plymouth, this vacation home is on the waterfront, within a 15-minute drive of Black Rock State Park and Rockwell Park.

Charming 3-Bedroom Home with Modern Comforts in West Hartford

West Hartford CT

$235 nightly

$267 total

Apr 22 - Apr 23

Total with taxes and fees

Located in West Hartford, this vacation home is within a 5-minute drive of Wolcott Park and Noah Webster House.

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

Springfield MA

$319 nightly

$362 total

Apr 22 - Apr 23

Total with taxes and fees

With a stay at this vacation home in Springfield (Forest Park), you'll be within a 5-minute drive of MGM Springfield and Naismith Memorial Basketball Hall of Fame.

Kitchen

Washer

Charming 3BR Hilltop House, Newly Remodeled with Arcade

Plymouth CT

Located in Terryville, this vacation home is a 5-minute drive from Witch's Dungeon Classic Movie Museum and 5 minutes from Muzzy Field.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Simsbury

View all properties

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.