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Holiday houses 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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Top Guest favourite
A welcoming sign crafted from green wire rests on a wooden base, displayed on a glass table. In the background, a spacious bed with decorative bedding and large windows allows natural light to illuminate the room.
Apartment in West Hartford
5 out of 5 average rating, 97 reviews

Cozy Studio Near Schools, Restaurants, and Shops

Cozy and private studio apartment in West Hartford. Location only a few minutes away from local restaurants and retail community. Off street parking. Queen size bed, small couch, small kitchen area with an island and seating for two, and small washer and dryer in the unit. This is a ground floor unit with some common hallways - noise is possible. Convenient and wonderful space for a simple, quiet, and comfortable stay. No pets allowed. Unit not suitable for children. Background check mandatory.

Superhost
A modern exterior view of the loft/studio features gray shingle siding and large windows. A flight of wooden stairs leads to a private upper entrance. Surrounding greenery and a landscaped path enhance the inviting atmosphere of the space.
Guest suite in Avon
4.83 out of 5 average rating, 104 reviews

Sprawling, Light Filled Studio Loft with Patio

Large, light filled, spacious loft that is a converted artist studio. Floor to ceiling windows! Loft/studio is located on beautifully landscaped grounds in carriage house adjacent to main house with its own separate private entrance. Close to shopping, restaurants, canoeing, kayaking, fishing; all are very nearby. A great place to stay while visiting Avon Old Farms or Fisher Meadows Park. Conveniently close to Avon Town Center, Whole Foods, West Hartford nightlife, Farmington and 84 highway.

Top Guest favourite
A private deck is shown overlooking the Farmington River, framed by colorful autumn foliage. Two wicker chairs with orange cushions are positioned beside a small table, all under a large blue umbrella. The tranquil water and nearby landscape are visible in the background.
Apartment in Collinsville
4.98 out of 5 average rating, 98 reviews

River Overlook - Collinsville, CT

Spotless new 1 BR apt (with additional pullout couch in LR)in downtown Collinsville, perched across the street from Farmington River and Rails to Trails. Steps to Collinsville - restaurants, antiques, concerts, walking, biking, fishing, canoe/kayaking. Sleeping for 4 (queen bed in BR, and pullout couch in LR). Relax on your private deck overlooking the river. See if you can spot our local Bald Eagle family! Voted one of "America's 10 Coolest Small Towns" by Frommer's Budget Travel Magazine!

Superhost
A bright workspace features a wooden desk with a black chair, positioned against a light-colored wall. Two framed botanical prints are displayed above the desk, complemented by a standing lamp. A mirror reflects the scene, while a potted plant adds a touch of greenery.
Apartment in Windsor Locks
4.85 out of 5 average rating, 177 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

Guest favourite
The living area features comfortable blue sofas arranged around a central coffee table. A dark wood media console holds a large TV displaying the Netflix logo. A modern kitchen is visible in the background, equipped with white cabinetry and stainless-steel appliances.
Apartment in Simsbury
4.86 out of 5 average rating, 29 reviews

Newly Renovated Apartment

Welcome to Center Street Stay, your charming retreat in Simsbury, CT. This fully renovated, first-floor one-bedroom apartment blends modern comfort with convenience. The kitchen is equipped with modern appliances, perfect for culinary endeavors. Relax in the cozy living area with a smart TV or get some rest on the memory foam queen mattress. The renovated bathroom offers sleek fixtures and a rejuvenating shower. Enjoy amenities like in-unit washer/dryer, high-speed Wi-Fi, and free parking.

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
4.92 out of 5 average rating, 113 reviews

Private Cozy Suite, 0 Fees, Easy CheckIn, EV Plug

A private cozy suite for you! Better than a hotel or private room & less than an entire house. We do not charge extra fees! Sizable discounts for medium- to long-term stays. Your guest suite includes newly furnished living room, apartment kitchenette, large bedroom with full bathroom. Heating, cooling and hot water are all-electric. Despite many renovations, we kept the vintage & cozy charm. Separate Wifi for remote work. Less than 20 minutes to the airport and Hartford metro. EV charger!

Top Guest favourite
A spacious outdoor area features a lush green meadow framed by trees under a partly cloudy sky. A single Adirondack chair is positioned on the grass, inviting relaxation. Natural light illuminates the open space, creating a serene environment.
Guesthouse in Granby
4.98 out of 5 average rating, 46 reviews

Peaceful Meadow Retreat

Unwind at Meadow's Edge, a serene and cozy refuge where you can come to relax and recharge! Looking out on our peaceful meadow and abutting 125 acres of corn fields, this is a perfect spot to enjoy a book on the shaded back patio, a yoga or meditation session, or a quiet walk through the fields & woods. Take in the view from inside the southern facing windows, where it is not uncommon to see wildlife at dawn or dusk. This is the tranquil getaway that you have been waiting for!

Top Guest favourite
A stone exterior corner of the home presents a covered porch with white railings. The adjacent grassy area leads to a serene river view, where trees surround the water's edge, reflecting the soft light of the sky.
Home in Windsor
4.97 out of 5 average rating, 63 reviews

Relax By The Water

Take it easy at this unique and tranquil getaway. Just 20 minutes from downtown Hartford, 5 minutes from Bradley airport, and conveniently close to the Loomis Chaffee school, you’ll have our entire two bedroom, two bath riverfront home to enjoy. Take in the views from the expansive balcony, enjoy a meal in the waterside dining room, or work from home in the dedicated office space. Two queen beds and a sleeper sofa sleep six comfortably. Don’t miss it!

Guest favourite
The inviting living area features a door leading to the patio, allowing natural light to fill the space. A wall clock and TV are positioned on gray walls, complemented by a coffee table and cozy seating. Views of the green outdoors can be seen through the windows.
Guest suite in Bloomfield
4.98 out of 5 average rating, 124 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
A daybed with intricate black detailing is adorned with an array of decorative pillows in various patterns. A colorful piece of wall art complements the space. Natural light streams through the window, which is fitted with light-filtering shades, illuminating a soft area rug beneath.
Apartment in Bloomfield
5 out of 5 average rating, 29 reviews

Bloomfield Bungalow

This is a unique apartment that was once a dentist office. It features a stylish décor and it is well appointed with everything needed to make your stay comfortable! Bloomfield is a quintessential New England small town. This apartment is located steps away from the Bloomfield Town Hall and the town green. The area is perfect for peaceful walks. There are fantastic restaurants in walking distance in this beautiful community.

Top Guest favourite
A modern coffee table is positioned in front of a decorative area with built-in shelving. A framed television displays a vibrant floral image. A candle and a magazine are placed on the table, accompanied by a round decorative mat, enhancing the living space's functionality.
Apartment in Collinsville
5 out of 5 average rating, 21 reviews

Collinsville Overlook at LaSalle

Stay in the heart of Collinsville, above the historic Lasalle Market. Just steps to the Farmington River, Rails to Trails, restaurants, shopping, antiquing, concerts, walking, biking, fishing, canoeing and kayaking. Sleeping for 4 (including a queen bedroom and a queen air mattress). Enjoy breakfast in your private nook overlooking the village. Voted one of America's 10 Coolest Small Towns by Frommer's Budget Travel Magazine!

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.
Guesthouse in Granby
4.98 out of 5 average rating, 859 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!

Popular amenities for Simsbury holiday rentals

When is the best time to visit Simsbury?

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Avg. price$229 AUD$201 AUD$213 AUD$192 AUD$213 AUD$213 AUD$236 AUD$227 AUD$232 AUD$229 AUD$229 AUD$215 AUD
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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 $76 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,760 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Simsbury holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Simsbury rentals

  • 4.8 Average rating

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