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Vacation rentals in Simsbury

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Quick stats about vacation rentals in Simsbury

  • Total vacation rentals

    Explore 30 vacation rentals in Simsbury

  • Nightly prices starting at

    Simsbury vacation rentals start at $99 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,170 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Simsbury vacation 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 vacation rentals in Simsbury

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

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Top guest favourite
A jetted swim spa is positioned on a deck overlooking Lake Garda at sunset. The water's surface reflects soft hues of orange and pink, with serene trees framing the view. The spa displays an illuminated edge, enhancing the tranquil atmosphere of the lakeside setting.
Cottage in Burlington
4.99 out of 5 average rating, 185 reviews

Lakefront Cozy - SwimSpa, Firepit, Ski 20 min away

Discover a charming 1080 sqft lakefront cottage offering modern comfort and tranquility. Wake up to peaceful Lake Garda waterfront views while staying near Farmington Valley’s conveniences. This newly remodeled retreat features a large jetted swim spa, stone patio with fire pit and grill, and direct lake access for kayaking or pedal boating perfect for relaxation. Enjoy a private getaway with nature’s beauty at your doorstep, all while being minutes from dining, shopping, and outdoor adventures.

Top guest favourite
Guest suite in Bloomfield
4.93 out of 5 average rating, 136 reviews

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

A private cozy suite for you powered by solar! Better than a hotel & 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. Keurig machine. Separate Wifi for remote work. Powered by solar! Less than 20 minutes to the airport and Hartford. No cost EV charger. No cleaning fees!

Guest favourite
The exterior of a newly renovated schoolhouse is depicted, showcasing a welcoming entrance with a red door. Surrounding greenery includes well-maintained lawns and established trees. A carriage house is visible on the left, complementing the charming architecture of the main house.
Home in Collinsville
4.95 out of 5 average rating, 123 reviews

Nature Lovers Retreat-Wine Vineyards nearby

Sleeps 6! Newly renovated 1910 schoolhouse. You'll love 2-3 bdr, clean, bright well appointed home. Volume ceilings, and a well stocked kitchen for long stays. Walk to nearby historic downtown Collinsville, where you'll find antique stores, restaurants and beautiful New England scenery. The CT wine trail and Brignole Vinyards nearby, where you will find food trucks and live music. Walk or cycle the Farmington River Trail. You will also find hiking, fishing, skiing, SUP , canoeing kayak rentals

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.

Guest favourite
A spacious living area features high ceilings with exposed beams and wooden flooring. Comfortable seating includes sofas and chairs arranged around a central coffee table. A large television is set against one wall, and plants add a touch of greenery to the room.
Home in Windsor
4.91 out of 5 average rating, 104 reviews

Island Vibes

Come and enjoy a tranquil stay with an island vibe. This 3 bedroom, 2 bath home will comfortably accommodate up to 8 persons. Large kitchen and living space for everyone. Situated in a quiet suburb on the outskirts of downtown Hartford, it is 12 minutes from Bradley International Airport, 20 minutes from the Basketball Hall of Fame and Springfield Museums Quadrangle. In the region is the Connecticut Science Museum, The Mark Twain House, Wadsworth Atheneum Museum of Art, and much more.

Guest favourite
A modern kitchen and dining area showcase contemporary cabinetry and stainless steel appliances. A round table with four chairs is set for meals, complemented by decorative placemats. Natural light enters through the entryway, which features a glass door, enhancing the bright atmosphere of the space.
Apartment in Simsbury
4.91 out of 5 average rating, 33 reviews

Newly Renovated 2 Bedroom in Heart of Tariffville

Welcome to Center Street Stay, a second story charming retreat in Simsbury, CT. This fully renovated two-bedroom apartment blends modern comfort with convenience. The kitchen is equipped with modern appliances, perfect for culinary endeavors. Relax in the living area with a smart TV or get some rest on the memory foam mattresses. The renovated bathrooms offers sleek fixtures and a rejuvenating shower. Enjoy amenities like a dedicated workspace, in-unit washer/dryer, high-speed Wi-Fi.

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, 138 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, 136 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!

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 Canton
5 out of 5 average rating, 52 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, 921 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, 254 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, 554 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.

Popular amenities for Simsbury vacation 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 vacation rentals in Simsbury

Top guest favourite
An outdoor firepit area is surrounded by natural scenery, featuring light-colored chairs and a wooden swing suspended from a pergola. The ground is covered in white gravel, with scattered leaves from nearby trees, creating a peaceful spot for gatherings.
Home in Barkhamsted
4.87 out of 5 average rating, 47 reviews

Woodland Sanctuary-hot tub|fireplace|hikes|fishing

Guest favourite
A cozy living area features a gray sofa facing a wooden coffee table, complemented by two lamps on matching side tables. Windows allow natural light to illuminate the space, with a comfortable armchair placed nearby. A decorative rug adds warmth to the wooden floor.
Farm stay in Bloomfield
4.9 out of 5 average rating, 62 reviews

Auerfarm Farmstay Crispin Cottage (173)

Top guest favourite
A cozy studio space features a comfortable bed with striped bedding and soft pillows. A reading nook with multiple cushions and a window offers natural light and views. A small television sits on a wooden table, while a potted plant adds a touch of greenery.
Apartment in Canton
5 out of 5 average rating, 63 reviews

Charming Main Street Studio in Collinsville!

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.
Apartment in Bloomfield
4.98 out of 5 average rating, 52 reviews

Bloomfield Bungalow

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 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, 112 reviews

Sprawling, Light Filled Studio Loft with Patio

When is the best time to visit Simsbury?

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Avg. price$190 CAD$193 CAD$190 CAD$177 CAD$197 CAD$197 CAD$204 CAD$218 CAD$203 CAD$232 CAD$201 CAD$190 CAD
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