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Holiday rentals in Simsbury

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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 $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,000 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!

Top-rated holiday rentals in Simsbury

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

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Superhost
A serene brook meanders through a wooded area, reflecting the clear blue sky above. A wooden deck extends over the water, surrounded by fresh greenery and trees in early spring bloom. The peaceful setting invites relaxation and exploration of nature.
Cabin in Bloomfield
4.95 out of 5 average rating, 153 reviews

Hidden Cozy Waterfront Eco Cabin Nature Sanctuary

Welcome to Otter Falls Inn! Nestled in the trees directly above the brook and hidden off the main road sits our cozy, vintage eco cottage. Just 8 minutes from all major conveniences, our property is a hidden oasis- an urban nature sanctuary where we are restoring native habitat and the waterway. We lovingly restored and updated the cottage to offer a unique, relaxing, romantic getaway where guests can slow down and enjoy connecting to each other and nature in this stylish, eco conscious home.

Top guest favourite
A living room is depicted with a light-toned couch and matching ottoman, positioned on a patterned area rug. Natural light enters through large front windows with minimalist window coverings, offering views of the outdoors while maintaining a sense of openness and tranquility.
Home in Avon
4.97 out of 5 average rating, 71 reviews

Easy Living Modern Ranch-Garage & Central Air

This one floor easy living, peaceful, ranch home has an updated kitchen with an induction cooktop, new appliances +(all cookware etc.). The freshly remodeled modern master bathroom has a curb-less shower & overhead heat (to keep you warm) pristine hardwood floors are throughout the entire space, and the use of a 2 car garage for your safety and convenience. The home has new Central Air Conditioning. The The shops at Farmington Valley, The Fresh Market and Whole Foods are around the corner.

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.
Flat in Simsbury
4.88 out of 5 average rating, 42 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.

Top guest favourite
The spacious loft features a sloped ceiling with exposed beams, accommodating a king-size bed and a cozy sofa. A work table is positioned beside a large window that allows natural light to fill the room. A flat-screen TV is mounted on the opposite wall.
Cottage in Collinsville
4.96 out of 5 average rating, 166 reviews

The Carriage House Wine Vineyards nearby

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, SUP, fish and swim. CT Wine Trail and Brignole Vineyards nearby where you'll find food trucks and live music along with award winning wine! Skiing nearby. Conveniently close to Farmington, Avon, Simsbury, West Hartford and 84 highway.

Top guest favourite
A large farmhouse is depicted in the background, featuring a broad balcony and distinctive architectural details. Sunflowers are prominently featured in the foreground, with bright yellow petals and green leaves, surrounded by lush grass and trees providing a serene atmosphere.
Barn in Bloomfield
4.97 out of 5 average rating, 136 reviews

Farm Stay with Horses & Pool | Mountaintop Views

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. Bask 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.

Top guest favourite
A charming house is visible along the riverbank, surrounded by lush greenery and blooming trees. The landscape features the calm waters of the river, reflecting the clear blue sky dotted with soft clouds, providing a scenic backdrop to the quaint property.
Home in Canton
4.99 out of 5 average rating, 135 reviews

Best River View, on Rail Trail in Collinsville!

This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

Guest favourite
A bright living room features a cozy arrangement with a gray sofa and two wooden chairs. A simple coffee table displays decorative items and a potted plant. Natural light streams through two windows, adorned with bamboo shades, creating a warm and inviting space.
Home in New Hartford
4.89 out of 5 average rating, 156 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.

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, 915 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!

Guest favourite
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, 251 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.

Top guest favourite
A rustic farmhouse exterior showcases a wooden façade with red double doors and a welcoming balcony adorned with potted flowers. The balcony is accessed by wooden steps, leading to a charming outdoor seating area. Seasonal foliage decorates the surrounding landscape.
Farm stay in West Simsbury
4.96 out of 5 average rating, 551 reviews

Flamig Farm Staycation

Very charming private farmhouse tastefully decorated situated in rural West Simsbury CT. Learn every day farm life from helping gather the 200 eggs daily and morning chores of caring for and feeding the petting zoo animals. Please note you are welcome to help the farmer as a family, but please do not leave children unsupervised.

Top guest favourite
The living area features a large leather sectional sofa arranged around a wooden coffee table, with a cozy area rug beneath. Natural light pours in through multiple windows, highlighting the exposed log beams on the ceiling and the warm wooden walls.
Cabin in Harwinton
4.97 out of 5 average rating, 107 reviews

Beautiful Brook-side Log Cabin on 3 Private Acres

Fall asleep to the sound of the rushing brook in this beautifully restored log home. The cabin sits in the middle of three wooded acres overlooking Catlin Brook as it cascades through the gorge below. It seems like wilderness, yet all the amenities of Harwinton are just a few minutes away.

Top guest favourite
Home in West Suffield
4.97 out of 5 average rating, 132 reviews

Linny's | Private Dock | Lake Access | Firepit

✓ Relax, swim, or watch the sunset. ✓ Private dock and lake access on-site. ✓ Fire pit and backyard for evenings. ✓ Fully equipped renovated kitchen. ✓ Self check-in, fast WiFi, free parking. ✓ Family-friendly and clean throughout.

Popular amenities for Simsbury holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Simsbury's top sights

Talcott Mountain State Park

50 locals recommend

The Shoppes At Farmington Valley

25 locals recommend

Millwright's

27 locals recommend

Other great holiday rentals in Simsbury

Top guest favourite
A dining area features a round wooden table surrounded by six gray chairs. A white vase filled with fresh flowers is placed center stage. A staircase with a black railing leads to an upper level, while an open kitchen is visible in the background.
Home in Bloomfield
4.89 out of 5 average rating, 38 reviews

The Majestic View | Luxury Stay Golf Views

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
4.96 out of 5 average rating, 74 reviews

Relax By The Water

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.
Flat in Bloomfield
4.98 out of 5 average rating, 51 reviews

Bloomfield Bungalow

Top guest favourite
Home in Tolland
4.98 out of 5 average rating, 66 reviews

Backyard Tiny House in the Woods

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.
Flat in Canton
5 out of 5 average rating, 50 reviews

Collinsville Overlook at LaSalle

A row of colorful canoes is stored on wooden racks beside a tranquil lake. A concrete path leads to the water's edge, where several chairs are positioned for relaxation. The sun casts a gentle glow over the serene landscape, enhancing the calm atmosphere.
Home in Avon
4.63 out of 5 average rating, 38 reviews

Lake House Living

Guest favourite
A charming house is set amid lush greenery, featuring a large driveway and an inviting porch with white railings. The front door is painted bright red, creating a warm focal point. A two-car garage is positioned on the right side of the property.
Home in Bloomfield
5 out of 5 average rating, 10 reviews

Classic Country Home

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
4.84 out of 5 average rating, 110 reviews

Sprawling, Light Filled Studio Loft with Patio

When is the best time to visit Simsbury?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$175 SGD$177 SGD$175 SGD$163 SGD$181 SGD$181 SGD$188 SGD$200 SGD$186 SGD$213 SGD$185 SGD$175 SGD
Avg. temp-3°C-1°C3°C10°C16°C20°C24°C23°C18°C12°C6°C0°C

Frequently Asked Questions

  • What are the best places to stay in Simsbury?

    Accommodations in Simsbury range from historic homes near downtown, stays surrounded by nature, and family-friendly rentals around the Farmington River area. Many guests choose neighborhoods with walkable access to parks or shops.

  • What are the best things to do in Simsbury with kids?

    Families can explore playgrounds at Simsbury Meadows, walk nature trails at Stratton Brook State Park, or visit the Simsbury Farms Recreation Complex for seasonal activities. Educational museums and riverside picnics are also popular.

  • What are some of the best things to do in Simsbury?

    Explore Talcott Mountain State Park, stroll downtown to enjoy local shops and galleries, or take a walk along the Farmington River Trail. Community concerts, outdoor markets, and historical tours are frequently suggested.

  • How is the weather in Simsbury?

    Simsbury has cold, snowy winters around 19–35°F (-7–2°C) and warm, humid summers near 64–85°F (18–30°C). Spring and fall bring mild temperatures and frequent rain, so packing layers is recommended.

  • When is the best time to visit Simsbury?

    Late spring through early autumn is often recommended, with mild temperatures and lush landscapes. Fall brings vibrant foliage, while summer is popular for local festivals and outdoor activities.

  • What are the best places to visit in Simsbury?

    Visit Talcott Mountain State Park for panoramic views, stroll the Simsbury Meadows, or tour local historical sites such as the Simsbury Free Library. Gardens, river walks, and art spaces are frequently suggested.

  • What are some hiking trails in Simsbury?

    Explore trails in Talcott Mountain State Park, wander the Farmington River Trail, or enjoy forest paths at Stratton Brook State Park. These routes showcase local scenery and are frequently suggested for hikers of varied skill levels.

  • What are some family activities we can do in Simsbury?

    Families can walk nature trails at Stratton Brook State Park, play at Simsbury Meadows, or join seasonal community events. The local recreation complex provides swimming, skating, and youth programs.

  • What are some of the best day trip ideas from Simsbury?

    Explore nearby cultural and outdoor attractions, including traditional New England villages, local museums, or state parks for hiking and biking. The region is known for historic sites and scenic countryside escapes.

  • Are there any pet friendly accommodations available in Simsbury?

    Simsbury has pet-friendly vacation rentals and some local inns that welcome pets. Parks such as Stratton Brook State Park make it easy to get outside with your dog.

  • What are some local tips for visiting Simsbury?

    Locals suggest checking the town’s event calendar, arriving early for hiking routes like Talcott Mountain, and supporting small businesses in the historic center. Many enjoy scenic river walks and the area’s vibrant community music scene.

  • What is Simsbury known for?

    Simsbury has charming historic neighborhoods, scenic landscapes along the Farmington River, and locally rooted arts and music traditions. The area is frequently suggested for outdoor activities, classic New England architecture, and a welcoming community atmosphere.

  • What are the best hidden gems to explore in Simsbury?

    Discover unique spots like historic barns, quiet riverbank paths, and locally run art studios. Some visitors find the Heublein Tower in Talcott Mountain State Park a favorite for panoramic views and history.

  • What are the best foods to try in Simsbury?

    Locally rooted flavors include farm-fresh produce, classic New England baked goods, and small-batch ice cream. Many visitors also enjoy locally sourced maple products and seasonal dishes at area cafes.

  • What should I bring for a trip to Simsbury?

    Pack comfortable walking shoes, layered clothing for changing temperatures, and a waterproof jacket for frequent rain. Outdoor gear is recommended for hiking or cycling, and reusable water bottles are popular among visitors.

  • What is the nightlife in Simsbury like?

    Simsbury has a low-key nightlife scene, with friendly pubs, relaxed wine bars, and occasional live music at local venues. Nightlife here is often centered around community events and casual gatherings.

  • What are the most popular events or festivals in Simsbury?

    Simsbury has recurring community events like the Simsbury Fly-In, music festivals in summer, and art fairs, often held in parks or downtown. Seasonal celebrations and food-focused gatherings are frequently suggested for visitors.

  • Are there family friendly vacation rentals in Simsbury?

    Family-friendly rentals are available throughout Simsbury, especially near parks and the downtown area. Many homes provide access to playgrounds, hiking trails, and seasonal recreation facilities.

Destinations to explore