Vacation rentals in Simsbury

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Top-rated vacation rentals in Simsbury

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Guest favorite

Guesthouse in Glastonbury

4.96 out of 5 average rating, 133 reviews

Unique luxurious private building in historic area

Unique private space for sophisticated adult(s). Located just 7 miles from downtown Hartford, 1 mile from Route 2 & 84/91 interchange. Guests may relax in this completely renovated historic Barn, with covered parking, away from street view. Enjoy this luxurious space and the private gym which includes treadmill, eliptical, bike, free weights, boxing bags, and yoga space. Upstairs, walk the catwalk between spacious bedroom and full sized Office / Loft over looking historic Main Street.

Aug 13 – 20

G$27,807 GYD per night

Superhost

Apartment in West Granby

4.89 out of 5 average rating, 115 reviews

Majestic Farmhouse Private & Peaceful Guest Apt.

Welcome to the Joab Griffin House. We are a beautiful historic farmhouse set on a private hill tucked away in the foothills of the Berkshires, surrounded by gorgeous farmland and hundreds of acres of land trust and game refuge trails, streams, and waterfalls within a five-minute walk from your door. Enjoy a private apartment in this lovely farmhouse. Here, you'll find cool summer breezes, cozy, warm, sun-filled days, and star-filled skies with the sounds of the brook outside your window.

Jul 15 – 22

G$28,789 GYD per night

Guest favorite

Vacation home in Torrington

4.97 out of 5 average rating, 131 reviews

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

Enjoy the comfort and tranquility of this modern apt. A lovely space to relax after a busy day. This clean and bright apt offers a tranquil residential vibe alongside quick, easy access to the Torrington downtown areas, restaurants, stores and bars. It features an open-concept layout, a neutral color scheme, wood surfaces, tasteful furnishings and decor. Designed comfortably for your stay offering WiFi, Netflix, laundry, queen bed, well equipped kitchen, and clean fresh white bed sheets.

Sep 23 – 30

G$33,076 GYD per night

Guest favorite

Home in New Hartford

4.89 out of 5 average rating, 133 reviews

Modern Farmhouse

This is a quaint, sun-filled farmhouse in the Farmington valley of Connecticut. Convenient to great antique shopping, Ski Sundown, farm stands, Farmington river inner-tubing and biking trails, kayak and canoe rentals, the sweet towns of Collinsville and New Hartford, and a 30 minute straight shot to Hartford itself. The house is also convenient to Torrington, Simsbury, Avon, Winsted, and a beautiful drive to Hartford-Bradley International Airport.

Apr 27 – May 4

G$31,115 GYD per night

Guest favorite

Home in Manchester

4.94 out of 5 average rating, 174 reviews

Paradise On The Hill Luxury Apartment.

Enjoy your own special and separated section of this beautiful, modern colonial home. This beautiful home includes an oversize living room with a comfortable Queen Size sectional sleeper sofa, oversize Master Bedroom and very large bathroom with spa like jets. His and hers closets. Beautiful kitchenette. 50 inch T.V., Free WiFi. , comfortable dining and more, all for the comfort and convenience of our guests.

Aug 19 – 26

G$20,591 GYD per night

Guest favorite

Guest suite in East Granby

4.84 out of 5 average rating, 273 reviews

Staying at Ten Hillcrest

What I’ve always thought of as the perfect location! Private enough to see trees and birds and yet close enough to jump on the highway to anywhere. Conveniently located on a dead end street with no through traffic. On your way out take a left and head towards farm and eateries or take a right and head to the city of Hartford or Springfield. Just minutes from Bradley International Airport

Jun 21 – 28

G$25,849 GYD per night

Guest favorite

Guesthouse in Granby

4.9 out of 5 average rating, 191 reviews

The Loft @ Lost Acres ~ A Peaceful Rural Escape!

The Loft @ Lost Acres Vineyard is a wonderfully private, rural getaway! This bright and comfortable space is located on the upper floor of a Lost Acres Vineyard barn. Originally intended for the caretaker, the owners are now offering it to the public to enjoy the beauty of the vines & the stunning rural scenery of North Granby. Oh, and stop by the tasting barn, the wine is AMAZING!

Sep 5 – 12

G$31,150 GYD per night

Guest favorite

Guest suite in Morris

4.99 out of 5 average rating, 340 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own private lounging/dining area. Separate entrance and parking space. Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing and just 10 minutes to Washington Depot.

Nov 19 – 26

G$19,579 GYD per night

Guest favorite

Cottage in Granby

4.87 out of 5 average rating, 137 reviews

The Little Red Schoolhouse ~ Circa 1877

This wonderful old building is listed on the National Register of Historic Places and operated as the District 9 schoolhouse until 1948. Now, this beautiful piece of history is available for you to enjoy! Located in the picturesque West Granby, Connecticut, this little schoolhouse directly abuts hundreds of acres of open space, Granby Land Trust property, and several organic farms.

Jan 31 – Feb 7

G$29,754 GYD per night

Guest favorite

Farm stay in Granby

4.89 out of 5 average rating, 237 reviews

The Farmhouse at Maple View Farm

Sunny, vintage 1936 farmhouse in the center of a quintessential New England farm town. Maple View Farm is a working livestock farm with horses, ponies, pigs and chickens plus a big garden. Wake up to the sounds of the rooster and step outside to pet the horses and ponies. Our on-farm Brewery (check hours) uses local ingredients. Window A/C units in bedrooms.

Dec 24 – 31

G$32,675 GYD per night

Guest favorite

Cottage in Collinsville

4.96 out of 5 average rating, 111 reviews

The Carriage House

Newly built contemporary light filled spacious 700 ft carriage house/Loft. It is walking distance to the Farmington river and downtown historic Collinsville. Just off the cycling "rails to trails" river trail, you'll find places to also kayak, fish and swim. Skiing nearby. Conveniently close to Farmington, Avon, Simsbury, West Hartford and 84 highway.

Sep 12 – 19

G$35,173 GYD per night

Guest favorite

Apartment in Enfield

4.99 out of 5 average rating, 140 reviews

FROG Suite Apartment

Welcome to the FROG Suite apartment, the prefect place in a comfy private space. Be it for work, pleasure, travel or leisure, this alluring updated space is located upstairs over the garage in a quiet residential neighborhood and includes a private keyless entry door lock. Apartment is located upstairs over the garage and is attached to the house.

Aug 31 – Sep 7

G$22,470 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Simsbury vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Simsbury's top sights

Abigail's Grille and Wine Bar14 locals recommend

Flamig Farm9 locals recommend

Simsbury Commons5 locals recommend

Heublein Tower37 locals recommend

Plan B Burger Bar - Simsbury11 locals recommend

Millwright's Restaurant and Tavern15 locals recommend

Other great vacation rentals in Simsbury

Guest favorite

Apartment in Winchester

4.91 out of 5 average rating, 340 reviews

Gateway to the Berkshires

Oct 29 – Nov 5

G$20,510 GYD per night

Guest favorite

Barn in Bloomfield

4.97 out of 5 average rating, 111 reviews

Mountaintop Horse Farm with Heated Pool

Sep 21 – 28

G$63,452 GYD per night

Guest favorite

Home in Simsbury

4.98 out of 5 average rating, 87 reviews

Nature House, water view, gazebo. 2 large decks

Nov 17 – 24

G$41,318 GYD per night

Guest favorite

Guest suite in Bloomfield

4.91 out of 5 average rating, 68 reviews

Private Cozy Suite - Zero Fees - EV Charger

Nov 14 – 21

G$21,342 GYD per night

Guest favorite

Guest suite in Bloomfield

5.0 out of 5 average rating, 71 reviews

Guest Suite with Private Entrance & View

Jan 29 – Feb 5

G$30,353 GYD per night

Superhost

Farm stay in Bloomfield

4.8 out of 5 average rating, 10 reviews

Auerfarm Farmstay Baldwin Cottage (169)

Sep 24 – Oct 1

G$26,653 GYD per night

Guest favorite

Guest suite in Avon

4.86 out of 5 average rating, 58 reviews

Sprawling, Light Filled Studio Apt. with Patio

Mar 1 – 8

G$31,173 GYD per night

Superhost

Apartment in Windsor Locks

4.86 out of 5 average rating, 92 reviews

Apt near Bradley airport Six Flags with parking

May 23 – 30

G$20,525 GYD per night

Show all

Quick stats about vacation rentals in Simsbury

Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
2.1K reviews

Frequently Asked Questions

Are there pet-friendly vacation rentals in Simsbury?
Four-legged friends are welcome in Simsbury. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Simsbury?
Yes! Work meets play with ease at over 20 vacation rentals in Simsbury featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Simsbury have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Simsbury. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Simsbury?
Simsbury has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Simsbury?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 20 homes with wifi, over 10 homes with a kitchen, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Simsbury have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Simsbury. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Simsbury have wifi?
Absolutely! We offer over 20 house rentals with wifi in Simsbury. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Simsbury have free parking?
Absolutely! We offer over 20 house rentals with free parking in Simsbury. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Simsbury

Top-rated vacation rentals in Simsbury

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Simsbury vacation rentals

Stay near Simsbury's top sights

Other great vacation rentals in Simsbury

Apartment in Winchester

Barn in Bloomfield

Home in Simsbury

Guest suite in Bloomfield

Guest suite in Bloomfield

Farm stay in Bloomfield

Guest suite in Avon

Apartment in Windsor Locks

Quick stats about vacation rentals in Simsbury

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there pet-friendly vacation rentals in Simsbury?

Are there vacation rentals with a dedicated workspace in Simsbury?

Do house rentals in Simsbury have air conditioning?

Are there family-friendly vacation rentals in Simsbury?

What are the most popular amenities for House Rentals in Simsbury?

Do house rentals in Simsbury have a kitchen?

Do house rentals in Simsbury have wifi?

Do house rentals in Simsbury have free parking?

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