Vacation rentals in Simsbury

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Top-rated vacation rentals in Simsbury

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

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Guest favorite
Cabin in Bloomfield
4.96 out of 5 average rating, 146 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 favorite
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, 104 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.

Top guest favorite
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, 101 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, 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 favorite
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
4.89 out of 5 average rating, 36 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 favorite
A spacious living area features high wooden ceilings and large windows allowing natural light to fill the room. A black sofa and stylish chairs surround a round dining table. A television is positioned on the wall, accompanied by decorative plants and neutral-toned artwork.
Apartment in Torrington
4.96 out of 5 average rating, 253 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 favorite
A cozy living room features a stone fireplace surrounded by purple walls. A wooden table sits at the center, adorned with a decorative bowl. A comfortable sofa and a wooden chair are positioned near the fireplace, complementing the warm ambiance.
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 favorite
Guest suite in Bloomfield
4.92 out of 5 average rating, 118 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 favorite
Home in West Suffield
4.97 out of 5 average rating, 120 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 favorite
A brick patio area is seen with two rocking chairs positioned beside vibrant orange and yellow flower pots. A welcoming wreath adorns the double doors, and a pumpkin is placed on the ground, enhancing the seasonal decor.
Guest suite in East Granby
4.85 out of 5 average rating, 404 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 favorite
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, 881 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
4.86 out of 5 average rating, 237 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.

Popular amenities for Simsbury vacation rentals

When is the best time to visit Simsbury?

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Avg. priceG$31,374 GYDG$27,609 GYDG$29,283 GYDG$26,354 GYDG$29,283 GYDG$29,283 GYDG$30,328 GYDG$32,420 GYDG$30,119 GYDG$31,374 GYDG$31,374 GYDG$29,492 GYD
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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 vacation rentals in Simsbury

  • Total vacation rentals

    Explore 30 vacation rentals in Simsbury

  • Nightly prices starting at

    Simsbury vacation rentals start at G$10,458 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,950 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Simsbury vacation rentals include wi-fi 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!