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 3 – 10

G$27,825 GYD per night

Guest favorite

Apartment in West Granby

4.89 out of 5 average rating, 116 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.

Mar 10 – 17

G$28,730 GYD per night

Guest favorite

Vacation home in Torrington

4.96 out of 5 average rating, 134 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.

Jan 25 – Feb 1

G$33,201 GYD per night

Guest favorite

Barn in Bloomfield

4.97 out of 5 average rating, 111 reviews

Mountaintop Horse Farm with Heated Pool

Come sleep above the horses at Bloombury Hill Farm. With stunning mountaintop views, this immaculate 2 BR apartment is spacious and boasts over 2000 square feet. Basque in the sunshine at the pool (open Memorial Day through Labor Day from 11a-5pm.) Close to thriving West Hartford Center with loads of restaurants and shopping. Hiking trails, local breweries and wineries, and farm stands are all located close by. All the ingredients for a magical weekend getaway.

Jan 28 – Feb 4

G$59,921 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.

Jul 12 – 19

G$32,979 GYD per night

Guest favorite

Home in Manchester

4.94 out of 5 average rating, 176 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.

Sep 23 – 30

G$20,611 GYD per night

Guest favorite

Home in Southwick

4.99 out of 5 average rating, 181 reviews

Linny's Lakeview Cottage

Linny's lakeview cottage is updated with beautiful hardwood floors. The kitchen is finished in white shaker cabinets, granite counter tops & new ss appliances. The counter joins the kitchen/living room & comfortably sits 6. This is a renovated 650 sq ft home. Access our online guidebook (a few day before your stay) for; house rules, local attractions, maps, and more, ensuring you make the most of your stay.

Dec 3 – 10

G$29,096 GYD per night

Guest favorite

Guest suite in East Granby

4.84 out of 5 average rating, 277 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

Dec 20 – 27

G$20,869 GYD per night

Guest favorite

Guesthouse in Granby

4.99 out of 5 average rating, 706 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Apr 7 – 14

G$33,742 GYD per night

Guest favorite

Guest suite in Morris

4.99 out of 5 average rating, 342 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.

Oct 1 – 8

G$19,539 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.

Oct 3 – 10

G$29,693 GYD per night

Guest favorite

Farm stay in Granby

4.9 out of 5 average rating, 239 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 26 – Jan 2

G$32,792 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

Guest suite in Wethersfield

4.99 out of 5 average rating, 252 reviews

Bright, clean studio in charming Old Wethersfield

Dec 20 – 27

G$24,883 GYD per night

Guest favorite

Apartment in Winchester

4.91 out of 5 average rating, 340 reviews

Gateway to the Berkshires

Feb 28 – Mar 7

G$20,468 GYD per night

Superhost

Guest suite in Windsor

4.84 out of 5 average rating, 119 reviews

Rustic Loft Apartment

Jan 2 – 9

G$19,747 GYD per night

Guest favorite

Home in Granby

4.95 out of 5 average rating, 219 reviews

FULLY stocked Ranch Home, * Gardens* Gameroom

Dec 5 – 12

G$40,353 GYD per night

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 184 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Sep 4 – 11

G$25,314 GYD per night

Guest favorite

Guest suite in Bethlehem

4.99 out of 5 average rating, 200 reviews

Breezy Crest private & restful w/antique charm

Oct 10 – 17

G$35,312 GYD per night

Guest favorite

Apartment in Middletown

4.98 out of 5 average rating, 147 reviews

Apartment Near Wesleyan, Downtown, Wedding Venues!

Sep 3 – 10

G$26,959 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

Dec 3 – 10

G$21,407 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 10 homes with air conditioning, over 10 homes with a kitchen, over 20 homes with wifi, 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

Guest suite in Wethersfield

Apartment in Winchester

Guest suite in Windsor

Home in Granby

Apartment in Brookfield

Guest suite in Bethlehem

Apartment in Middletown

Guest suite in Bloomfield

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?

Destinations to explore