Holiday rentals in Simsbury

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Top-rated holiday rentals in Simsbury

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
Flat in Windsor Locks
4.85 out of 5 average rating, 184 reviews

Apt near Big E, Six Flags, Bradley airport

Welcome to our charming and stylish upstairs apartment, perfect for a cozy retreat! Enjoy the privacy of having the entire space to yourself. Access the apartment directly through the back entrance, up the outdoor staircase. We're conveniently located just a 10-minute drive from Bradley International Airport. Inside, you'll find: - A comfortable bedroom with a Queen-sized bed, complete with fresh linens - A fully stocked kitchen, equipped: Pots, pans, baking dishes, etc Washer and dryer

Top guest favourite
An open living area showcases high wooden ceilings with skylights, allowing natural light to fill the space. A simple seating arrangement includes a dark sofa and stylish chairs, while a light rug anchors a coffee table. Modern decor complements the neutral color palette.
Flat in Torrington
4.96 out of 5 average rating, 259 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.

Top guest favourite
Cottage in Windsor
4.9 out of 5 average rating, 198 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.

Guest favourite
The bedroom features a spacious bed with white bedding, complemented by a wooden desk and chair. Two windows with light-filtering shades allow natural light to enter, while a world map adorns the walls. Built-in storage and warm hardwood flooring add to the room's charm.
Guest suite in Bloomfield
4.93 out of 5 average rating, 121 reviews

Private Cozy Suite, 0 Fees, Pets Allowed, EV Plug

A private cozy suite for you! Better than a hotel or private room & less than an entire house. Pets welcome with no fees :) Generous discounts for medium- to long-term stays. Your guest suite includes newly furnished living room, apartment kitchenette, large bedroom with full bathroom. Despite many renovations, we kept the vintage & cozy charm. Separate Wifi for remote work. Less than 20 minutes to the airport and Hartford metro. No cost EV charger on site. No cleaning fees!

Top guest favourite
An elegant Arts & Crafts bungalow showcases a blend of architectural styles under a clear blue sky. The inviting façade features a distinctive porch, a brick chimney, and a nearby garage. Lush gardens adorned with vibrant plants enhance the home’s outdoor appeal.
Guest suite in Wallingford
5 out of 5 average rating, 640 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. I am not responsible for wifi.

Top guest favourite
Two blue Adirondack chairs are positioned on a stone patio, facing a lush green lawn. The background features trees and a colorful sky at dusk, with scattered clouds reflecting the softer tones of the sunset.
Guest suite in Bloomfield
4.98 out of 5 average rating, 126 reviews

Guest Suite with Private Entrance & View

Relax at our Guest Suite Apartment with a private walk-out entrance on the lower level of our home. Nestled at the end of a quiet neighborhood road our space is just 15 minutes from Bradley Airport & less than an 8-mile drive from Hartford. Have fun with the local bike path, hiking, wineries, and breweries. Afterward, kick up your feet on the queen mattress or unwind on the patio in our peaceful backyard often visited by deer.

Top guest favourite
Flat in New Britain
4.96 out of 5 average rating, 250 reviews

Spacious Cozy Guest Suite

This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

Top guest favourite
The renovated home is nestled among vibrant autumn foliage, showcasing an array of orange, red, and yellow leaves. A serene lake reflects the colorful trees, creating a picturesque backdrop for the property. The area appears tranquil and is surrounded by natural beauty.
Home in West Suffield
4.97 out of 5 average rating, 121 reviews

Linny’s Lake House - with dock

Linny’s Lake House & Dock Access 🌲🌳 Charming Lakeside Home on South Pond Welcome to our newly renovated lake house tucked into a peaceful 3/4-acre wooded lot, naturally treated to keep mosquitoes and ticks to a minimum. The setting feels calm and restorative, with gentle breezes, shaded trees, and the charm of nearby tobacco fields adding to the sense of being away without being remote.

Top guest favourite
Guest suite in East Granby
4.85 out of 5 average rating, 405 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

Top guest favourite
The charming stone cottage features a vibrant blue door and flower boxes filled with colorful plants. Lush greenery surrounds the entrance, and original brick walkways lead to the home. Sunlight filters through the trees, creating a welcoming atmosphere outside.
Guest house in Granby
4.98 out of 5 average rating, 885 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!

Superhost
The exterior of a charming red schoolhouse and accessory building is surrounded by vibrant foliage. A white wooden fence outlines the property, leading to a gravel pathway. The buildings feature classic architectural details, with windows framed in white and a backdrop of lush trees.
Cottage in Granby
4.87 out of 5 average rating, 238 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.

Superhost
Flat in Winsted
4.88 out of 5 average rating, 141 reviews

Haven at Highland lake

Kick back and relax in this calm, stylish space. This studio apartment offers fast internet, TV , a comfortable couch , a stylish new bathroom, a lovely kitchenette, as well as black out curtains in the bedroom. And a cozy warm fireplace. This apartment comfortably sleeps 1 adult or a couple. The couch folds out into a bed and there is bedding in a tote stored Under the bed.

Popular amenities for Simsbury holiday rentals

When is the best time to visit Simsbury?

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Frequently Asked Questions

  • Are there pet-friendly house rentals in Simsbury?

    Four-legged friends are welcome in Simsbury. Choose from more than 10 house rentals for guests traveling with pets.

  • Are there house rentals with a dedicated workspace in Simsbury?

    Yes! Work meets play with ease at over 10 house 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 20 house rentals with air conditioning in Simsbury. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Simsbury?

    Simsbury has more than 10 family-friendly house rentals. 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 20 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.

  • Where should I stay in Simsbury?

    Make yourself at home in Simsbury by choosing from our most frequently booked neighborhoods. We have over 10 vacation rentals in Tariffville, and over 90 vacation rentals in East Weatogue.

  • How much does it cost to stay in house rentals in Simsbury?

    Experience the best of Simsbury with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Quick stats about holiday rentals in Simsbury

  • Total holiday rentals

    Explore 30 holiday rentals in Simsbury

  • Nightly prices starting at

    Simsbury holiday rentals start at £37 per night before taxes and fees

  • Verified guest reviews

    Over 2,950 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Simsbury holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Simsbury rentals

  • 4.8 Average rating

    Simsbury stays are highly rated by guests – averaging 4.8 out of 5!