Holiday rentals in Simsbury

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Top-rated holiday rentals in Simsbury

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Guest favourite

Guest house 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.

4–11 Sep

$181 SGD per night

Guest favourite

Holiday home in Torrington

4.97 out of 5 average rating, 130 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.

21–28 Sep

$213 SGD per night

Guest favourite

Cottage in Windsor

4.89 out of 5 average rating, 162 reviews

In-law apartment in Farmington River Cottage

If you are craving a getaway with a special someone, this space is meticulously clean and an opportunity to practice social distancing while relaxing and enjoying the Farmington River. Only 15 minutes from Bradley airport, 5 minutes from the train and I91. Nature, dining, all within a comfortable drive. You get it all here! Private space with its own entrance, one bedroom and newly updated bathroom, a cozy living room with fireplace in a Garden Level Unit. Off street parking available.

7–14 May

$118 SGD per night

Guest favourite

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.

30 Jan – 6 Feb

$392 SGD per night

Guest favourite

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.

29 Apr – 6 May

$203 SGD per night

Guest favourite

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.

11–18 Oct

$134 SGD per night

Guest favourite

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

10–17 Jan

$136 SGD per night

Guest favourite

Guest house in Granby

4.99 out of 5 average rating, 703 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!

22–29 Jan

$221 SGD per night

Guest favourite

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.

21–28 Oct

$194 SGD per night

Guest favourite

Flat in Winchester

4.91 out of 5 average rating, 340 reviews

Gateway to the Berkshires

Remodeled apartment on 2nd floor of a 1910 Victorian house near the center of Winsted, CT. The apartment is unique and cozy, with large windows, some stained glass, tin ceilings, hand painted kitchen cabinets, and plants. Close proximity to all Litchfield County and the Berkshires have to offer, in all seasons. It's an easy drive from NYC or Boston. Great weekend get-away.

2–9 Dec

$134 SGD per night

Guest favourite

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.

3–10 Mar

$213 SGD per night

Guest favourite

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.

7–14 Oct

$225 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Simsbury holiday 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 holiday rentals in Simsbury

Guest favourite

Guest suite in Morris

4.99 out of 5 average rating, 340 reviews

Lakeside Private Guest Suite

24–31 Mar

$128 SGD per night

Guest favourite

Guest suite in Coventry

4.93 out of 5 average rating, 214 reviews

Country retreat 25min to Hartford/15min to UCONN

30 Sep – 7 Oct

$108 SGD per night

Guest favourite

Home in Granby

4.95 out of 5 average rating, 219 reviews

FULLY stocked Ranch Home, * Gardens* Gameroom

28 Jun – 5 Jul

$225 SGD per night

Guest favourite

Home in Simsbury

4.98 out of 5 average rating, 86 reviews

Nature House, water view, gazebo. 2 large decks

22–29 Oct

$274 SGD per night

Guest favourite

Guest suite in Bloomfield

4.91 out of 5 average rating, 68 reviews

Private Cozy Suite - Zero Fees - EV Charger

29 Jan – 5 Feb

$139 SGD per night

Guest favourite

Guest suite in Bloomfield

5.0 out of 5 average rating, 71 reviews

Guest Suite with Private Entrance & View

28 Nov – 5 Dec

$198 SGD per night

Guest favourite

Guest suite in Avon

4.86 out of 5 average rating, 58 reviews

Sprawling, Light Filled Studio Apt. with Patio

15–22 Jul

$203 SGD per night

Guest favourite

Home in Simsbury

4.89 out of 5 average rating, 57 reviews

Simsbury Ranch in a quiet neighborhood!

13–20 Dec

$358 SGD per night

Show all

Quick stats about holiday 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

Holiday rentals in Simsbury

Top-rated holiday rentals in Simsbury

Guest house in Glastonbury

Holiday home in Torrington

Cottage in Windsor

Barn in Bloomfield

Home in New Hartford

Home in Manchester

Guest suite in East Granby

Guest house in Granby

Cottage in Granby

Flat in Winchester

Farm stay in Granby

Cottage in Collinsville

Holiday rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Simsbury holiday rentals

Stay near Simsbury's top sights

Other great holiday rentals in Simsbury

Guest suite in Morris

Guest suite in Coventry

Home in Granby

Home in Simsbury

Guest suite in Bloomfield

Guest suite in Bloomfield

Guest suite in Avon

Home in Simsbury

Quick stats about holiday rentals in Simsbury

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore